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Analytical chemistry Published methods and open data Proposed capability

Targeted methods measure the constituents you expect, non-targeted screening looks for the ones you did not

How a botanical laboratory would combine validated assays with high-resolution mass spectrometry, molecular networking and natural-product databases. Every chart uses a published method or an open dataset.

Status. EUTECNIQ is pre-operational: it has no laboratory, instruments, methods or data. The workflows here describe what it would do.

695,133unique natural-product structures in COCONUT 2.0, September 2024 release
7biosynthetic pathways in NPClassifier, with 70 superclasses and 672 classes
802LEAFBOT reference spectra of plant metabolites networked on this page
6molecular formulas still fit curcumin's mass at 1 ppm (CHNOPS, Kind & Fiehn rules)

Sources: COCONUT 2.0 (Chandrasekhar et al., Nucleic Acids Res 2025); NPClassifier (Kim et al., J Nat Prod 2021); GNPS LEAFBOT library, downloaded October 24, 2026; formula count computed on this page.

Workflow

One high-resolution LC-MS run can answer three different questions

One raw data file, three analyses: targeted, suspect and non-targetedSchematic
One LC-HRMS run of a botanical extract can feed three analyses: targeted quantitation against reference standards, suspect screening against a list of expected compounds, and non-targeted screening of every detected feature, which ends in ranked hypotheses with a confidence levelExtractLC pumpColumn (separates by RT)Ion sourceESI, + and − modeHigh-resolution MSOrbitrap or Q-TOFRaw dataMS1 scans + MS/MS spectraTargetedReference standardCalibration line for each listed analyteQuantify known analytesExact m/z, retention time, MS/MStransitionsConcentration ± uncertaintyProcedure validated for its purpose(ICH Q2(R2))SuspectList of expected compoundsFormula and m/z from literature or adatabaseMatch mass, isotopes, RT,MS/MSWithin a stated mass toleranceTentative identityConfidence level 2 or 3 until a standardconfirms itNon-targetedFeature finding and alignmentEvery m/z × RT signal across allsamplesAnnotateSpectral libraries, in silico tools,molecular networkingRanked hypothesesEach with a confidence level (1–5)The same raw file can be processed three waysSchematic, not to scale. RT = retention time; ESI = electrospray ionization.One LC-HRMS run feeds targeted, suspect and non-targeted analyses1 · One LC-HRMS runExtract → LC pump → columnSeparates constituents by retention time (RT)Ion source → high-resolution MSESI in + and − mode; Orbitrap or Q-TOFRaw dataFull-scan MS1 + data-dependent MS/MS2 · TargetedReference standardCalibration line for each listed analyteQuantify known analytesExact m/z, retention time, MS/MS transitionsConcentration ± uncertaintyProcedure validated for its purpose (ICH Q2(R2))3 · SuspectList of expected compoundsFormula and m/z from literature or a databaseMatch mass, isotopes, RT, MS/MSWithin a stated mass toleranceTentative identityConfidence level 2 or 3 until a standard confirms it4 · Non-targetedFeature finding and alignmentEvery m/z × RT signal across all samplesAnnotateSpectral libraries, in silico tools, molecular networkingRanked hypothesesEach with a confidence level (1–5)Schematic, not to scale. The same raw file can be processedthree ways.
Workflow terms: NORMAN guidance on suspect and non-target screening (Hollender et al. 2023); ICH Q2(R2) (2023). Schematic, not to scale.

The same raw file can support a validated assay, a check against a suspect list and an open search for unknowns; the certainty of each answer differs.

Explanation, details and sources

Liquid chromatography (LC) separates the constituents of an extract by retention time; electrospray ionization (ESI) charges them; a high-resolution mass spectrometer (HRMS, such as an Orbitrap or a quadrupole time-of-flight) records their mass-to-charge ratio (m/z) to within a few parts per million and fragments selected ions (MS/MS).

Targeted analysis measures a short list of named analytes against reference standards and is validated for its purpose. Suspect screening searches the data for compounds on a prepared list (formula, m/z, sometimes MS/MS) without a standard for each. Non-targeted screening treats every detected signal as a possible compound. The NORMAN guidance notes that screening allows detection "without upfront selection and purchase of standards" and that target methods "are typically optimised for a small set of compounds".

Hollender J, Schymanski EL, Ahrens L, et al. NORMAN guidance on suspect and non-target screening in environmental monitoring. Environ Sci Eur. 2023;35:75. ICH Q2(R2), adopted November 1, 2023.

Compare

Only targeted methods report concentrations; screening reports candidates with a stated confidence

What each approach needs before the run, and what it can claim afterSummary of cited guidance
Targeted analysis fixes the analytes and needs a reference standard for each, so it can report a validated concentration; suspect screening checks a predefined list; non-targeted screening can reveal unexpected compounds but reports hypotheses, and blanks are essential to itTargetedSuspect screeningNon-targeted screeningAnalytes chosen before the runAnalytes chosen before the run · Targeted: highAnalytes chosen before the run · Suspect screening: mediumReference standard for each analyteReference standard for each analyte · Targeted: highReference standard for each analyte · Suspect screening: lowReference standard for each analyte · Non-targeted screening: lowAbsolute concentration reportedAbsolute concentration reported · Targeted: highAbsolute concentration reported · Suspect screening: lowAbsolute concentration reported · Non-targeted screening: lowCan reveal unexpected compoundsCan reveal unexpected compounds · Suspect screening: lowCan reveal unexpected compounds · Non-targeted screening: highHarmonized validation frameworkHarmonized validation framework · Targeted: highHarmonized validation framework · Suspect screening: lowHarmonized validation framework · Non-targeted screening: lowBlanks and pooled QC essentialBlanks and pooled QC essential · Targeted: mediumBlanks and pooled QC essential · Suspect screening: mediumBlanks and pooled QC essential · Non-targeted screening: highTypical outputNumber with uncertaintyCandidate listFeature table + hypothesesStandard practicePartlyOnly to confirm, or limitedNo
ICH Q2(R2) (2023) for validation of targeted procedures; NORMAN guidance (Hollender et al. 2023) for screening, including blanks; Schymanski et al. (2014) for confidence levels.

Targeted methods, calibrated with reference standards and validated under ICH Q2(R2), report concentrations. Screening results are hypotheses until a standard confirms them.

Explanation, details and sources

ICH Q2(R2) covers procedures for identity, assay, purity and impurity testing and sets out the performance characteristics to demonstrate (specificity or selectivity, working range, accuracy and precision, and detection or quantitation limits where relevant); the method-development page shows them by test type. Non-targeted screening has no equivalent harmonized validation guideline; the NORMAN guidance sets out quality assurance and states that "blanks are a requirement for NTS", because features present in blanks must be removed.

The symbols are EUTECNIQ's summary of these documents, not a ranking from any one source. Absolute quantitation without a reference standard is possible only as an estimate; NORMAN treats quantification without standards as a separate topic.

ICH Q2(R2) Validation of Analytical Procedures (2023); see analytical method development. Hollender et al. 2023 (NORMAN). Schymanski EL, et al. Environ Sci Technol. 2014;48(4):2097–2098.

Mass accuracy

Mass accuracy narrows the candidate formulas, but rarely to one

Mass error and rings plus double bondsppm = 106(mf − m)/m
RDBE = C − H/2 + N/2 + P/2 + 1
Neutral mass used
Tolerance window
Candidate formulas
The true formula

Candidate formulas at five mass tolerances, and the closest at the chosen oneComputed
Closest candidates (up to 8)
FormulaMass (Da)Error (ppm)RDBE

Exact masses: NIST atomic weights and isotopic compositions; electron mass: CODATA. Rules: Kind & Fiehn, BMC Bioinformatics 2007;8:105. Marker masses: PubChem.
Method, assumptions and limits

What it calculates. Every molecular formula made of the allowed elements whose monoisotopic mass lies within the tolerance of the neutral mass, after the filters below. An [M+H]+ or [M−H]− m/z is converted with the proton mass (1.00727646 Da).

Equations and constants. Monoisotopic masses 1H 1.00782503223, 12C 12, 14N 14.00307400443, 16O 15.99491461957, 31P 30.97376199842, 32S 31.9720711744 u (NIST); electron 5.485799090441 × 10−4 u (CODATA). Error in ppm and RDBE as shown above.

Filters (Kind & Fiehn 2007). Rule 1, element limits from their Table 1, taking the higher of the DNP and Wiley counts (below 500 Da: C 39, H 72, N 20, O 20, P 9, S 10; 500–1,000 Da: C 78, H 126, N 25, O 27, P 9, S 14). Rule 2, LEWIS (integer, non-negative RDBE for a neutral even-electron molecule) and SENIOR conditions with maximum valences C 4, H 1, N 5, O 2, P 5, S 6. Rules 4 and 5 (optional): common ranges covering 99.7% of the Wiley library, H/C 0.2–3.1, N/C ≤ 1.3, O/C ≤ 1.2, P/C ≤ 0.3, S/C ≤ 0.8.

Valid range. Neutral masses 50–1,000 Da, tolerances 0.5–20 ppm; outside this range the tool shows a warning and no result.

What it does not establish. It omits rule 3 (isotope pattern), rule 6 (element probabilities) and halogens, so real software that scores isotope patterns and fragments ranks far fewer candidates. A formula is not a structure: each formula still has many isomers.

References. Kind T, Fiehn O. BMC Bioinformatics. 2007;8:105 and 2006;7:234. NIST Atomic Weights and Isotopic Compositions. CODATA electron mass in u (NIST).

Verification. An independent numpy brute-force implementation (tests/numerics/ref/ana_formula.py) reproduces the counts; for example 6, 10, 16, 37 and 70 candidates for curcumin at 1, 2, 5, 10 and 20 ppm.

Candidate formulas grow with mass tolerance and with massComputed
The number of molecular formulas that fit a measured mass grows with the mass tolerance and with the mass: at 5 ppm, 64 CHNOPS formulas fit the mass of epigallocatechin gallate and 2 fit caffeine; even at 1 ppm, 9 and 1 remain131030100300Candidate formulas1251020Mass tolerance (ppm)EGCG, 458.085 DaEGCG, 458.085 Da: 1, 9EGCG, 458.085 Da: 2, 25EGCG, 458.085 Da: 5, 64EGCG, 458.085 Da: 10, 125EGCG, 458.085 Da: 20, 245EGCG, 458.085 DaGinkgolide B, 424.137 DaGinkgolide B, 424.137 Da: 1, 4Ginkgolide B, 424.137 Da: 2, 10Ginkgolide B, 424.137 Da: 5, 31Ginkgolide B, 424.137 Da: 10, 66Ginkgolide B, 424.137 Da: 20, 135Ginkgolide B, 424.137 DaCurcumin, 368.126 DaCurcumin, 368.126 Da: 1, 6Curcumin, 368.126 Da: 2, 10Curcumin, 368.126 Da: 5, 16Curcumin, 368.126 Da: 10, 37Curcumin, 368.126 Da: 20, 70Curcumin, 368.126 DaCaffeine, 194.080 DaCaffeine, 194.080 Da: 1, 1Caffeine, 194.080 Da: 2, 1Caffeine, 194.080 Da: 5, 2Caffeine, 194.080 Da: 10, 4Caffeine, 194.080 Da: 20, 6Caffeine, 194.080 DaComputed: CHNOPS formulas passing the Kind & Fiehn (2007) element limits, LEWIS and SENIOR rules and common element ratios.
Computed with the rules above (CHNOPS, common ratios). Marker masses from PubChem (checked October 24, 2026).
Data table
Candidate CHNOPS formulas within each tolerance
CompoundNeutral mass (Da)1 ppm2 ppm5 ppm10 ppm20 ppm
Curcumin368.12599610163770
Quercetin302.0426534132347
Epigallocatechin gallate458.0849192564125245
Hyperforin536.3865659194077
Ginkgolide B424.136954103166135
Caffeine194.0803811246

At 5 ppm, 16 formulas fit curcumin's mass and 64 fit EGCG's; isotope patterns, fragments and retention time are needed to choose among them.

Explanation, details and sources

Kind and Fiehn showed that "mass accuracy is insufficient even at less than 1 ppm" to give a unique formula in higher mass ranges, and proposed seven heuristic rules to remove chemically impossible or improbable formulas. Of their rules, isotope-pattern scoring was the most efficient filter; it needs the measured abundances of the M+1 and M+2 isotopologues, which this teaching tool does not use.

Kind T, Fiehn O. Metabolomic database annotations via query of elemental compositions: mass accuracy is insufficient even at less than 1 ppm. BMC Bioinformatics. 2006;7:234. Kind T, Fiehn O. Seven Golden Rules for heuristic filtering of molecular formulas obtained by accurate mass spectrometry. BMC Bioinformatics. 2007;8:105.

Data processing

Eight processing steps turn raw scans into a feature table

From raw LC-HRMS scans to a feature table with MS/MS spectraSchematic
Non-targeted data processing converts raw LC-HRMS scans into a feature table in eight steps, from mass detection through alignment, gap filling and blank filtering to an exported table with MS/MS spectra1 · Mass detectionCentroid each scan; set a noiselevel2 · Chromatogram buildingTrace each m/z through retentiontime3 · Peak pickingResolve co-eluting peaks; a feature= m/z × RT × area4 · Isotopes and adductsGroup ¹³C isotopes and [M+H]⁺,[M+Na]⁺ of one compound5 · AlignmentCorrect RT drift; match featuresacross samples6 · Gap fillingRe-read raw data where a featurewas missed7 · Blank and QC filterDrop features in blanks or unstablein pooled QC8 · Feature table + MS/MSExport for statistics, annotation,networkingOpen implementations include MZmine 3, XCMS and MS-DIAL; each step has parameters that change the result and must be reported.Eight processing steps turn raw scans into a feature tableRaw LC-HRMS data1 · Mass detectionCentroid each scan; set a noise level2 · Chromatogram buildingTrace each m/z through retention time3 · Peak pickingResolve co-eluting peaks; a feature = m/z × RT × area4 · Isotopes and adductsGroup ¹³C isotopes and [M+H]⁺, [M+Na]⁺ of onecompound5 · AlignmentCorrect RT drift; match features across samples6 · Gap fillingRe-read raw data where a feature was missed7 · Blank and QC filterDrop features in blanks or unstable in pooled QC8 · Feature table + MS/MSExport for statistics, annotation, networkingOpen implementations include MZmine 3, XCMS andMS-DIAL; parameters change the result and must bereported.
Steps as implemented in open software: MZmine 3 (Schmid et al. 2023), XCMS (Smith et al. 2006), MS-DIAL (Tsugawa et al. 2015).

Each step has parameters, so two laboratories can produce different feature tables from the same raw files unless every setting is reported.

Explanation, details and sources

A feature is a detected signal defined by its m/z, retention time and intensity in each sample. Feature finding, alignment across samples and gap filling are implemented, for example, in MZmine 3, XCMS (nonlinear retention-time alignment, matched filtration, peak detection and matching) and MS-DIAL (deconvolution of data-independent MS/MS). Feature-based molecular networking (FBMN) in GNPS takes such a feature table and its MS/MS spectra, which allows quantitative comparison and the separation of isomers.

Schmid R, et al. Integrative analysis of multimodal mass spectrometry data in MZmine 3. Nat Biotechnol. 2023;41(4):447–449. Smith CA, et al. XCMS. Anal Chem. 2006;78(3):779–787. Tsugawa H, et al. MS-DIAL. Nat Methods. 2015;12(6):523–526. Nothias LF, et al. Feature-based molecular networking in the GNPS analysis environment. Nat Methods. 2020;17(9):905–908.

Molecular networking
Molecular network of plant-metabolite reference spectra (LEAFBOT), computed for this pagePublished spectra, computed network

Positive mode, [M+H]+: 251 spectra, 113 edges, 26 clusters (largest 18); 99 linked spectra drawn, 152 without a partner not drawn.

Spectra: GNPS LEAFBOT library (Cech and Kellogg laboratories; downloaded October 24, 2026; CC0). Network computed by EUTECNIQ with the modified cosine score and GNPS default thresholds (cosine ≥ 0.7, ≥ 6 matched fragments, top 10 neighbors, 0.02 Da). Colors: NPClassifier pathway of the matching COCONUT 2.0 structure. Larger, labeled circles: the most connected spectrum in each cluster of three or more; hover or focus any node for its name. Edge list: leafbot-network.csv.
Data table: clusters in each ion mode
Positive mode, [M+H]+: 26 clusters of two or more spectra
ClusterSpectraCompounds (library names, normalized)Main pathways
118dulcoside A, herbacetin 3,8-diglucoside, hesperidin, hyperoside, kaempferol 4′-glucoside, naringin, pectolinarin, quercitrin, rebaudioside A, rebaudioside C, rebaudioside D, rebaudioside E, rebaudioside G, rebaudioside M, rebaudioside N, rutin, steviolbioside, steviosideTerpenoids (9); Shikimates and phenylpropanoids (8)
217chrysin, curcumin, eriodictyol, hesperetin, isoliquiritigenin, kaempferol, liquiritigenin, luteolin, myricetin, naringenin, quercetin, sakuranetinShikimates and phenylpropanoids (17)
37cannabichromene, cannabidiol, cannabigerolPolyketides (7)
46isoorientin, mangiferin, orientin, puerarin, swertisin, vitexinShikimates and phenylpropanoids (6)
54costunolide, steviol, ursolic acid, valerenic acidTerpenoids (4)
64(−)-epicatechin, (−)-epicatechin gallate, (−)-epigallocatechin, (−)-epigallocatechin gallateShikimates and phenylpropanoids (4)
742-amino-4-methylbenzothiazole, 2-amino-5-methylbenzothiazole, 2-amino-6-methylbenzothiazole, 2-amino-7-methylbenzothiazoleNot in COCONUT (3); Alkaloids (1)
8311-keto-β-boswellic acid, 18α-glycyrrhetinic acid, enoxoloneTerpenoids (3)
92aconitine, hypaconitineAlkaloids (2)
102apigenin 7-O-glucoside, baicalinShikimates and phenylpropanoids (2)
112coniferaldehydeShikimates and phenylpropanoids (2)
122astragaloside IV, cycloastragenolTerpenoids (2)
132ginkgolic acid I, ginkgolic acid IIPolyketides (2)
142ginkgolide A, ginkgolide BTerpenoids (2)
152glycyrrhizic acid, glycyrrhizic acid (ammonium salt)Terpenoids (2)
162(E)-guggulsterone, (Z)-guggulsteroneTerpenoids (2)
172lobeline, lobeline (HCl salt)Alkaloids (2)
182sinomenine, sinomenine (HCl salt)Alkaloids (2)
192corynanthine, yohimbine (HCl salt)Alkaloids (2)
202anagyrine, baptifolineAlkaloids (2)
212cannabidiolic acid, cannabigerolic acidPolyketides (2)
222cannabidiolic acid, cannabigerolic acidPolyketides (2)
232corydaline, tetrahydropalmatineAlkaloids (2)
242(+)-Isocorydine, isoboldineAlkaloids (2)
252allocryptopine, protopineAlkaloids (2)
262chelidonine, corynolineAlkaloids (2)
Negative mode, [M−H]−: 20 clusters of two or more spectra
ClusterSpectraCompounds (library names, normalized)Main pathways
112eriodictyol, isoliquiritigenin, liquiritigenin, myricetin, naringenin, quercetin, sakuranetinShikimates and phenylpropanoids (12)
29dulcoside A, rebaudioside A, rebaudioside C, rebaudioside D, rebaudioside E, rebaudioside G, rebaudioside M, rebaudioside N, steviosideTerpenoids (8); Not in COCONUT (1)
35isoorientin, mangiferin, orientin, puerarin, vitexinShikimates and phenylpropanoids (5)
45hyperoside, kaempferol 4′-glucoside, quercitrin, rutin, tilirosideShikimates and phenylpropanoids (5)
54cannabichromene, cannabigerolPolyketides (4)
63(−)-epicatechin gallate, (−)-epigallocatechin gallateShikimates and phenylpropanoids (3)
73herbacetin 3,8-diglucoside, sennoside A, sennoside BPolyketides (2); Shikimates and phenylpropanoids (1)
83hesperidin, naringin, neohesperidin dihydrochalconeShikimates and phenylpropanoids (3)
93eriodictyol, luteolin, naringeninShikimates and phenylpropanoids (3)
102apigenin 7-O-glucoside, luteolin 7-O-glucosideShikimates and phenylpropanoids (2)
112bilobalideTerpenoids (2)
122ginkgolide B, ginkgolide CTerpenoids (2)
132glycyrrhizic acid, glycyrrhizic acid (ammonium salt)Terpenoids (2)
142gentiobiose, palatinoseCarbohydrates (2)
152cannabidiol, cannabidiolic acidPolyketides (2)
162cannabidiolic acid, cannabigerolic acidPolyketides (2)
172curcuminShikimates and phenylpropanoids (2)
182rosmarinic acidShikimates and phenylpropanoids (2)
192phloretinShikimates and phenylpropanoids (2)
202glabranin, pinocembrinShikimates and phenylpropanoids (2)

Flavonoids, steviol glycosides, cannabinoids and aconitine-type alkaloids each form their own clusters; 152 of 251 positive-mode spectra have no partner.

Mirror plot: matched fragments line up directly or after a shift equal to the precursor mass differencePublished spectra
Direct matchShifted matchNo partner
Modified cosine0.86
Matched fragments9
Of which shifted6 (Δ 15.995 Da)
LEAFBOT spectra CCMSLIB00011427951, CCMSLIB00011427952, CCMSLIB00011428723, CCMSLIB00011428750, CCMSLIB00011427934, CCMSLIB00011427937 after GNPS peak filtering; intensities relative to the largest remaining fragment.
Data table: matched fragments for each pair
ginkgolide A (m/z 409.1490) versus ginkgolide B (m/z 425.1440): modified cosine 0.859, 9 matched
m/z, top%m/z, bottom%Match
57.0709257.07074direct
59.0501259.04992direct
113.096316113.096111direct
299.127226315.121230shifted (Δ 15.995 Da)
327.122134343.117142shifted (Δ 15.995 Da)
345.1327100361.1274100shifted (Δ 15.995 Da)
363.143145379.138175shifted (Δ 15.995 Da)
373.127730389.122234shifted (Δ 15.995 Da)
391.138118407.133021shifted (Δ 15.995 Da)
kaempferol (m/z 287.0550) versus quercetin (m/z 303.0500): modified cosine 0.849, 11 matched
m/z, top%m/z, bottom%Match
68.99711268.997011direct
111.007515111.007518direct
121.028360137.023168shifted (Δ 15.995 Da)
153.0180100153.017998direct
165.017941165.017939direct
183.028517183.028414direct
213.054333229.0490100shifted (Δ 15.995 Da)
231.064717247.059413shifted (Δ 15.995 Da)
241.049319257.043958shifted (Δ 15.995 Da)
258.051830274.046819shifted (Δ 15.995 Da)
269.04365285.038924shifted (Δ 15.995 Da)
(−)-epicatechin gallate (m/z 443.0970) versus (−)-epigallocatechin gallate (m/z 459.0920): modified cosine 0.938, 9 matched
m/z, top%m/z, bottom%Match
123.0442100139.0388100shifted (Δ 15.995 Da)
147.04392163.03873shifted (Δ 15.995 Da)
151.038817151.038818direct
153.018129153.018120direct
165.054310181.04945shifted (Δ 15.995 Da)
231.06452247.06061shifted (Δ 15.995 Da)
255.06562271.06021shifted (Δ 15.995 Da)
273.07547289.07037shifted (Δ 15.995 Da)
291.085715307.08112shifted (Δ 15.995 Da)

Ginkgolide A and B differ by one oxygen atom (15.995 Da); 6 of their 9 matched fragments line up only after that shift.

Explanation, details and sources

Molecular networking (Watrous et al. 2012; Wang et al. 2016) compares every MS/MS spectrum with every other. The modified cosine score counts a fragment pair as matched if the two m/z values agree, or if they agree after adding the difference between the two precursor masses, so a methylation or an extra hydroxyl does not break the match. Spectra above a score threshold are joined by an edge; clusters of related structures emerge.

For this page EUTECNIQ downloaded the 802 spectra of the LEAFBOT library and wrote its own implementation, using the defaults in the GNPS documentation: peaks within ±17 Da of the precursor removed; only the 6 most intense peaks kept in any ±50 Da window; spectra with fewer than 5 fragments left unconnected; an edge where cosine ≥ 0.7 with at least 6 matched fragments; each node keeps at most its 10 best neighbors (mutual); clusters are capped at 100 nodes; fragment tolerance 0.02 Da, the documented value for high-resolution data. Intensities were not transformed. Only [M+H]+ (positive) or [M−H]− (negative) spectra were used.

Edges reflect shared fragments, not shared biosynthesis. In positive mode, steviol glycosides and flavonoid glycosides fall in one cluster, connected through sugar-related fragments; in negative mode they separate. Library names were normalized for display (lower case, obvious misspellings corrected); the edge list keeps the original names.

Watrous J, et al. Mass spectral molecular networking of living microbial colonies. Proc Natl Acad Sci USA. 2012;109(26):E1743–E1752. Wang M, et al. Sharing and community curation of mass spectrometry data with Global Natural Products Social Molecular Networking. Nat Biotechnol. 2016;34(8):828–837. GNPS documentation, molecular networking parameters (accessed October 24, 2026). LEAFBOT library page, GNPS (accessed October 24, 2026).

Confidence

Every annotation should carry a confidence level, from exact mass to confirmed structure

Identification confidence levels for high-resolution MS (Schymanski et al. 2014)Peer-reviewed framework
Identification confidence levels from Schymanski et al. (2014): level 1 confirmed structure with a reference standard, 2a library spectrum match, 2b diagnostic evidence, 3 tentative candidates, 4 unequivocal molecular formula, 5 exact mass of interestLevelIdentificationMinimum dataExample (illustrative)Level 1Confirmed structureby reference standardMS, MS², RT, reference standardQuercetin: same RT and MS/MS as an authenticstandard run under the same methodLevel 2aProbable structureby library spectrum matchMS, MS², library or literature MS²MS/MS matches a reference library spectrum suchas LEAFBOT; no standard runLevel 2bProbable structureby diagnostic evidenceMS, MS², experimental data or contextNo library spectrum, but fragments and context leaveone structureLevel 3Tentative candidate(s)structure, substituent or classMS, MS², experimental dataA quercetin hexoside, with the sugar and its positionunknownLevel 4Unequivocal molecular formulaMS isotope or adduct pattern (MS²helps)C₂₁H₂₀O₁₂, from exact mass and isotope patternLevel 5Exact mass of interestMSm/z 465.1028 is higher in one lot than in the othersConfidence rises toward level 1. Examples are illustrative, not EUTECNIQ results.Identification confidence levels (Schymanski et al. 2014)Higher confidence ↑Level 1 · Confirmed structure, by referencestandardNeeds: MS, MS², RT, reference standard. Example:Quercetin: same RT and MS/MS as an authenticstandard run under the same methodLevel 2a · Probable structure, by libraryspectrum matchNeeds: MS, MS², library or literature MS². Example:MS/MS matches a reference library spectrum such asLEAFBOT; no standard runLevel 2b · Probable structure, by diagnosticevidenceNeeds: MS, MS², experimental data or context.Example: No library spectrum, but fragments andcontext leave one structureLevel 3 · Tentative candidate(s), structure,substituent or classNeeds: MS, MS², experimental data. Example: Aquercetin hexoside, with the sugar and its positionunknownLevel 4 · Unequivocal molecular formulaNeeds: MS isotope or adduct pattern (MS² helps).Example: C₂₁H₂₀O₁₂, from exact mass and isotopepatternLevel 5 · Exact mass of interestNeeds: MS. Example: m/z 465.1028 is higher in one lotthan in the othersExamples are illustrative, not EUTECNIQ results.
Schymanski EL, et al. Environ Sci Technol. 2014;48(4):2097–2098; level names and minimum data as reproduced in the NORMAN guidance (Hollender et al. 2023, Table 7). Examples are illustrative.

A library match reaches level 2a; only a run against an authentic reference standard under the same method reaches level 1.

Explanation, details and sources

The five levels separate what was measured from what was inferred. A level-4 formula comes from exact mass with isotope or adduct evidence; a level-3 annotation names a candidate structure, substituent or class; level 2 needs a library spectrum match (2a) or diagnostic evidence (2b); level 1 requires a reference standard measured with MS, MS/MS and retention time. The example m/z 465.1028 is the [M+H]+ ion of C21H20O12 (for example hyperoside, a quercetin hexoside), computed from NIST masses.

Schymanski EL, Jeon J, Gulde R, Fenner K, Ruff M, Singer HP, Hollender J. Identifying small molecules via high resolution mass spectrometry: communicating confidence. Environ Sci Technol. 2014;48(4):2097–2098. Hollender et al. 2023, Table 7.

Dereplication

Dereplication checks each spectrum against what is already known before anything is called new

Where 257 LEAFBOT [M+H]+ spectra go: COCONUT match, NPClassifier pathway, network partnerOpen data, computed
LEAFBOT (GNPS) spectra; structures matched to the COCONUT October 2026 dump by the InChIKey connectivity block (RDKit InChIKey of the library SMILES); pathways from the dump's NPClassifier fields; network as above.
Data table
Flows (number of spectra)
FromToSpectra
LEAFBOT [M+H]+ spectraIn COCONUT 2.0245
In COCONUT 2.0Shikimates and phenylpropanoids86
In COCONUT 2.0Alkaloids85
AlkaloidsNo partner (singleton)66
Shikimates and phenylpropanoidsNo partner (singleton)47
In COCONUT 2.0Terpenoids44
Shikimates and phenylpropanoidsLinked in the network39
TerpenoidsLinked in the network24
In COCONUT 2.0Polyketides22
TerpenoidsNo partner (singleton)20
AlkaloidsLinked in the network19
PolyketidesLinked in the network13
PolyketidesNo partner (singleton)9
LEAFBOT [M+H]+ spectraNot in COCONUT6
In COCONUT 2.0Amino acids and peptides5
Amino acids and peptidesNo partner (singleton)5
Not in COCONUTLinked in the network4
Not in COCONUTNo partner (singleton)2
In COCONUT 2.0Fatty acids2
Fatty acidsNo partner (singleton)2
In COCONUT 2.0Carbohydrates1
CarbohydratesNo partner (singleton)1
LEAFBOT [M+H]+ spectraFewer than 5 fragments6

245 of 257 positive-mode reference spectra belong to structures already in COCONUT 2.0, which is why dereplication comes before any claim of novelty.

Explanation, details and sources

Dereplication means recognizing known compounds early, so that effort goes to the unknowns. Structure databases answer "is this structure known, and from which organism?"; spectral libraries answer "does this spectrum match a measured reference?"; in silico tools rank candidates when no reference spectrum exists.

  • COCONUT 2.0: an open collection of natural products from 63 data collections; 695,133 unique structures in the September 2024 release. Stereoisomers are kept as separate molecules under one identifier with a suffix. Data released under CC0. The October 2026 dump used here has 738,794 entries and 479,690 unique 2D structures.
  • LOTUS: an open resource of more than 750,000 referenced structure–organism pairs.
  • GNPS spectral libraries: community reference MS/MS spectra; spectra contributed directly to GNPS carry a CC0 license by default.
  • SIRIUS 4 with CSI:FingerID searches structure databases from MS/MS when no library spectrum exists; CANOPUS predicts 2,497 compound classes from fragmentation spectra; NPClassifier assigns structures to 7 pathways, 70 superclasses and 672 classes.

Six LEAFBOT [M+H]+ spectra had fewer than 5 fragments after filtering and were not networked. Five of the six spectra without a COCONUT match are of three aminomethylbenzothiazoles, synthetic reference compounds; the sixth is rebaudioside M, a steviol glycoside whose structure had no connectivity match in the October 2026 dump.

Chandrasekhar V, et al. COCONUT 2.0: a comprehensive overhaul and curation of the collection of open natural products database. Nucleic Acids Res. 2025;53(D1):D634–D643. COCONUT download page (October 2026 release; CC0). Rutz A, et al. The LOTUS initiative for open knowledge management in natural products research. eLife. 2022;11:e70780. GNPS documentation, library license. Dührkop K, et al. SIRIUS 4. Nat Methods. 2019;16(4):299–302. Dührkop K, et al. CANOPUS. Nat Biotechnol. 2021;39(4):462–471. Kim HW, et al. NPClassifier. J Nat Prod. 2021;84(11):2795–2807.

Building blocks

Natural products are assembled from a handful of biosynthetic building blocks

Building blocks, the routes that use them and the NPClassifier pathways they feedTextbook biosynthesis, open data
Natural products are assembled from a few building blocks: acetate units give fatty acids and polyketides, shikimate gives phenylpropanoids and flavonoids, isoprene units give terpenoids and steroids, amino acids give alkaloids and peptides, and sugars attach to all of them; counts are unique 2D structures in COCONUT, October 2026Building blockRoute (Dewick 2009)Pathway: COCONUT countMarker on this pageAcetyl-CoA, malonyl-CoA (C₂ units)Acetate pathwayFatty acids: 55,560Polyketides: 40,174Hyperforin (meroterpenoid)Shikimic acid (C₆C₃, C₆C₁ units)Shikimate pathwayShikimates andphenylpropanoids: 81,918Quercetin, EGCG, curcuminMevalonate or MEP (C₅ isopreneunits)Terpenoid pathwaysTerpenoids: 111,860Ginkgolide B (C₂₀)Amino acids, purinesAmino-acid-derived routesAlkaloids: 126,597Amino acids and peptides:20,253Caffeine (purine alkaloid)SugarsCarbohydrate metabolismCarbohydrates: 4,696Glycosides of all classesMixed origins are common: flavonoids combine a shikimate-derived C₆C₃ unit with acetate-derived units.Building blocks, routes and pathwaysBuilding block → route → pathway (COCONUT count)Acetyl-CoA, malonyl-CoA (C₂ units) → AcetatepathwayFatty acids: 55,560; Polyketides: 40,174. Example:Hyperforin (meroterpenoid)Shikimic acid (C₆C₃, C₆C₁ units) → ShikimatepathwayShikimates and phenylpropanoids: 81,918. Example:Quercetin, EGCG, curcuminMevalonate or MEP (C₅ isoprene units) →Terpenoid pathwaysTerpenoids: 111,860. Example: Ginkgolide B (C₂₀)Amino acids, purines → Amino-acid-derivedroutesAlkaloids: 126,597; Amino acids and peptides: 20,253.Example: Caffeine (purine alkaloid)Sugars → Carbohydrate metabolismCarbohydrates: 4,696. Example: Glycosides of allclassesFlavonoids combine a shikimate-derived C₆C₃ unit withacetate-derived units.
Routes: Dewick PM, Medicinal Natural Products: A Biosynthetic Approach, 3rd ed. (Wiley, 2009), chapters 2–8. Counts: unique 2D structures in the COCONUT October 2026 dump by NPClassifier pathway.
COCONUT structures by NPClassifier pathway and superclass (select a ring to zoom)Open data
COCONUT October 2026 dump (CC0): 479,690 unique 2D structures (InChIKey connectivity block), pathway and superclass from the dump's NPClassifier fields; superclasses under 2% of their pathway are grouped; the 38,632 structures with no pathway assigned are in the table only.
Data table
Unique 2D structures by pathway and superclass
PathwaySuperclassStructuresShare of pathway
TerpenoidsDiterpenoids25,43722.7%
TerpenoidsTriterpenoids24,65222.0%
TerpenoidsSesquiterpenoids23,14120.7%
TerpenoidsSteroids17,93216.0%
TerpenoidsMonoterpenoids6,6535.9%
TerpenoidsMeroterpenoids2,5212.3%
TerpenoidsOther or none (11 groups)11,52410.3%
AlkaloidsTryptophan alkaloids22,31117.6%
AlkaloidsLysine alkaloids13,20510.4%
AlkaloidsTyrosine alkaloids10,9568.7%
AlkaloidsPseudoalkaloids9,0097.1%
AlkaloidsNicotinic acid alkaloids8,7276.9%
AlkaloidsAnthranilic acid alkaloids8,0126.3%
AlkaloidsOrnithine alkaloids4,5083.6%
AlkaloidsPeptide alkaloids2,7992.2%
AlkaloidsOther or none (43 groups)47,07037.2%
Shikimates and phenylpropanoidsFlavonoids24,16729.5%
Shikimates and phenylpropanoidsCoumarins20,92525.5%
Shikimates and phenylpropanoidsIsoflavonoids6,0687.4%
Shikimates and phenylpropanoidsLignans4,6885.7%
Shikimates and phenylpropanoidsPhenolic acids (C6-C1)3,7714.6%
Shikimates and phenylpropanoidsPhenylpropanoids (C6-C3)3,0513.7%
Shikimates and phenylpropanoidsStilbenoids1,6672.0%
Shikimates and phenylpropanoidsXanthones1,6442.0%
Shikimates and phenylpropanoidsOther or none (18 groups)15,93719.5%
Fatty acidsGlycerolipids30,84355.5%
Fatty acidsGlycerophospholipids6,08711.0%
Fatty acidsFatty acyls5,4259.8%
Fatty acidsFatty Acids and Conjugates3,9727.1%
Fatty acidsFatty esters3,2335.8%
Fatty acidsSphingolipids1,8193.3%
Fatty acidsOther or none (16 groups)4,1817.5%
PolyketidesPolycyclic aromatic polyketides5,40413.5%
PolyketidesChromanes4,89512.2%
PolyketidesMacrolides4,12910.3%
PolyketidesAromatic polyketides3,8269.5%
PolyketidesNaphthalenes3,3548.3%
PolyketidesCyclic polyketides3,1737.9%
PolyketidesLinear polyketides2,6606.6%
PolyketidesMeroterpenoids2,0645.1%
PolyketidesPhloroglucinols1,5803.9%
PolyketidesXanthones8102.0%
PolyketidesOther or none (23 groups)8,27920.6%
Amino acids and peptidesOligopeptides8,64942.7%
Amino acids and peptidesSmall peptides7,41736.6%
Amino acids and peptidesβ-lactams5702.8%
Amino acids and peptidesMacrolides4812.4%
Amino acids and peptidesOther or none (23 groups)3,13615.5%
CarbohydratesSaccharides1,85539.5%
CarbohydratesNucleosides1,23826.4%
CarbohydratesAminosugars and aminoglycosides73315.6%
CarbohydratesPolyols4178.9%
CarbohydratesOther or none (6 groups)4539.6%

NPClassifier places 92% of the 479,690 unique 2D structures in COCONUT in a pathway; alkaloids (126,597) and terpenoids (111,860) are the largest.

Explanation, details and sources

Dewick organizes secondary metabolism by building block: the acetate pathway (fatty acids and polyketides), the shikimate pathway (aromatic amino acids and phenylpropanoids, including coumarins, flavonoids and stilbenes), the mevalonate and methylerythritol phosphate (MEP) pathways (terpenoids and steroids), alkaloids grouped by their amino-acid origin, peptides and carbohydrates. NPClassifier uses seven matching pathways. Counts here use one record per InChIKey connectivity block (stereoisomers counted once), so they are lower than the database's entry count of 738,794.

Dewick PM. Medicinal Natural Products: A Biosynthetic Approach. 3rd ed. Chichester: Wiley; 2009 (ISBN 978-0-470-74168-9). Kim HW, et al. J Nat Prod. 2021;84(11):2795–2807. COCONUT October 2026 dump.

Marker compounds

Six marker compounds in three dimensions, each computed from its PubChem structure

Curcumin, C21H20O6Computed conformer
Turmeric. NPClassifier (COCONUT): Shikimates and phenylpropanoids, Diarylheptanoids. PubChem CID 969516.
Quercetin, C15H10O7Computed conformer
Ginkgo (flavonol aglycone). NPClassifier (COCONUT): Shikimates and phenylpropanoids, Flavonoids. PubChem CID 5280343.
Ginkgolide B, C20H24O10Computed conformer
Ginkgo. NPClassifier (COCONUT): Terpenoids, Sesquiterpenoids (see note). PubChem CID 11973122.
Hyperforin, C35H52O4Computed conformer
St. John's wort. NPClassifier (COCONUT): Polyketides, Meroterpenoids. PubChem CID 441298.
Epigallocatechin gallate, C22H18O11Computed conformer
Green tea. NPClassifier (COCONUT): Shikimates and phenylpropanoids, Flavonoids. PubChem CID 65064.
Caffeine, C8H10N4O2Computed conformer
Green tea. NPClassifier (COCONUT): Alkaloids, Pseudoalkaloids. PubChem CID 2519.

NPClassifier, as distributed with COCONUT, labels ginkgolide B a sesquiterpenoid, although it is a C20 diterpene trilactone: automated class labels are predictions to check.

Explanation, details and sources

Each model is one low-energy conformer computed by EUTECNIQ with RDKit (ETKDG version 3 embedding, then MMFF94 optimization) from the PubChem SMILES; the molecular formula was checked against PubChem. It is not a crystal structure and not the only shape the molecule adopts. Drag or use the arrow keys to rotate; dashed bonds are aromatic.

Marker compounds, identifiers and NPClassifier labels (pathway / superclass / class)
CompoundPubChem CIDFormulaBotanicalCOCONUT identifierNPClassifier (COCONUT dump)
Curcumin969516C21H20O6TurmericCNP0337918.1Shikimates and phenylpropanoids / Diarylheptanoids / Linear diarylheptanoids
Quercetin5280343C15H10O7Ginkgo (flavonol aglycone)CNP0103504.0Shikimates and phenylpropanoids / Flavonoids / Flavonols
Ginkgolide B11973122C20H24O10GinkgoCNP0254856.10Terpenoids / Sesquiterpenoids / Picrotoxane sesquiterpenoids
Hyperforin441298C35H52O4St. John's wortCNP0290944.1Polyketides / Meroterpenoids / Polyprenylated cyclic polyketides (Hop meroterpenoids)
Epigallocatechin gallate65064C22H18O11Green teaCNP0258703.1Shikimates and phenylpropanoids / Flavonoids / Flavan-3-ols
Caffeine2519C8H10N4O2Green teaCNP0228556.0Alkaloids / Pseudoalkaloids / Purine alkaloids

Ginkgolides A, B, C and J are described as diterpene trilactones and bilobalide as a sesquiterpene trilactone (EFSA FEEDAP Panel 2024); the NPClassifier label in the dump is therefore wrong for ginkgolide B.

PubChem compound records (CIDs above; checked October 24, 2026). Wang S, Witek J, Landrum GA, Riniker S. J Chem Inf Model. 2020;60(4):2044–2058 (ETKDG v3). Halgren TA. J Comput Chem. 1996;17(5–6):490–519 (MMFF94). RDKit 2026.09.1. EFSA FEEDAP Panel. EFSA J. 2024;22(4):e8733. Strømgaard K, Nakanishi K. Angew Chem Int Ed. 2004;43(13):1640–1658.

Scaffolds

A dozen ring scaffolds recur thousands of times across natural products

The 12 most frequent Bemis–Murcko ring scaffolds in COCONUTOpen data, computed
The twelve most frequent ring scaffolds among 479,690 unique natural-product structures in COCONUT: benzene (13,753), tetrahydropyran (2,726), coumarin (2,686) and flavone (2,248) lead; 55,326 structures have no ringBenzeneBenzene: 13,753 structures13,753OTetrahydropyranTetrahydropyran: 2,726 structures2,726OOCoumarinCoumarin: 2,686 structures2,686OOFlavoneFlavone: 2,248 structures2,248NHIndoleIndole: 1,704 structures1,704Steroid nucleus(gonane)Steroid nucleus (gonane): 1,533 structures1,533CyclohexaneCyclohexane: 1,413 structures1,413OOAuroneAurone: 1,184 structures1,184CyclohexeneCyclohexene: 1,166 structures1,166Δ5-Steroid nucleusΔ5-Steroid nucleus: 1,146 structures1,146OOXanthoneXanthone: 1,121 structures1,121OOFlavanoneFlavanone: 1,102 structures1,102RDKit Bemis–Murcko scaffolds (side chains removed, stereochemistry ignored) of 479,690 unique 2D structures; 123,533 distinct scaffolds, 75,889 of them seen only once.
Computed by EUTECNIQ with RDKit from the COCONUT October 2026 dump (479,690 unique 2D structures). Bemis GW, Murcko MA. J Med Chem. 1996;39(15):2887–2893.
Data table
Most frequent scaffolds (SMILES) and the pathways of the structures that carry them
RankScaffold (SMILES)StructuresTop pathways
1c1ccccc113,753Shikimates and phenylpropanoids 4,206; No pathway assigned 2,379; Alkaloids 2,363
2C1CCOCC12,726Fatty acids 1,235; Carbohydrates 424; No pathway assigned 392
3O=c1ccc2ccccc2o12,686Shikimates and phenylpropanoids 2,672; Amino acids and peptides 10; No pathway assigned 3
4O=c1cc(-c2ccccc2)oc2ccccc122,248Shikimates and phenylpropanoids 2,247; No pathway assigned 1
5c1ccc2[nH]ccc2c11,704Alkaloids 1,242; Amino acids and peptides 378; No pathway assigned 41
6C1CCC2C(C1)CCC1C3CCCC3CCC211,533Terpenoids 1,520; Alkaloids 12; No pathway assigned 1
7C1CCCCC11,413Fatty acids 539; Terpenoids 479; No pathway assigned 155
8O=C1C(=Cc2ccccc2)Oc2ccccc211,184Shikimates and phenylpropanoids 1,148; No pathway assigned 31; Alkaloids 5
9C1=CCCCC11,166Terpenoids 904; No pathway assigned 131; Amino acids and peptides 33
10C1=C2CCCCC2C2CCC3CCCC3C2C11,146Terpenoids 1,129; Alkaloids 17
11O=c1c2ccccc2oc2ccccc121,121Shikimates and phenylpropanoids 714; Polyketides 407
12O=C1CC(c2ccccc2)Oc2ccccc211,102Shikimates and phenylpropanoids 1,099; Polyketides 2; No pathway assigned 1

Benzene alone is the scaffold of 13,753 structures, while 75,889 of the 123,533 distinct scaffolds occur only once.

Explanation, details and sources

A Bemis–Murcko scaffold keeps the ring systems and the linkers between them and removes side chains; RDKit keeps atoms double-bonded to the scaffold, so carbonyl groups of coumarins, flavones and xanthones remain. Stereochemistry was removed first, so stereoisomers share a scaffold. 55,326 structures (mostly fatty acids) have no ring and therefore no scaffold. Steroid ring systems appear more than once because RDKit scaffolds keep ring double bonds.

Bemis GW, Murcko MA. The properties of known drugs. 1. Molecular frameworks. J Med Chem. 1996;39(15):2887–2893. RDKit 2026.09.1 (MurckoScaffold). COCONUT October 2026 dump.

Chemical space

Each biosynthetic pathway occupies its own region of chemical space

800 COCONUT structures in three descriptors: molecular weight, lipophilicity and saturationOpen data, computed

Drag to rotate, or use the buttons. Each point is one structure; hover to see its name.

200 random unique 2D structures from each of the four largest pathways (seed 20261025), COCONUT October 2026; descriptors computed with RDKit (Crippen logP; Fsp3 = fraction of sp3 carbons).
Data table
Medians of the plotted structures
PathwaynMW (Da)Crippen logPFsp3
Terpenoids2004423.60.78
Alkaloids2003942.70.42
Shikimates and phenylpropanoids2003903.30.26
Fatty acids20083514.60.83
Chemical-space map: principal components of 12 RDKit descriptors for 2,000 random COCONUT structuresOpen data, computed
Highlighted structures
Median MW
Median Crippen logP
Median Fsp3

2,000 random unique 2D structures (seed 20261024) from the COCONUT October 2026 dump; standardized descriptors, principal components by singular value decomposition. Diamonds: the six marker compounds projected on the same axes. Data: chemspace-sample.csv.
Data tables: medians by pathway and component loadings
Medians by pathway in the 2,000-structure sample
PathwaynMWcLogPTPSAFsp3Rotatable bondsAromatic ringsStereocenters
Terpenoids4554253.6820.77407
Alkaloids5473842.7770.43422
Shikimates and phenylpropanoids3554103.3950.26531
Fatty acids22983015.8790.864401
Polyketides1623883.2960.41521
Amino acids and peptides886340.81740.571015
Carbohydrates29462-3.12310.88708
Loadings of the first two components (PC1 46.2%, PC2 21.5% of variance)
DescriptorPC1PC2
MW+0.35+0.25
cLogP-0.10+0.44
TPSA+0.41-0.04
HBD+0.39-0.08
HBA+0.41-0.01
RotB+0.10+0.51
Fsp3+0.08+0.46
Rings+0.25-0.25
AromRings+0.09-0.41
nO+0.40+0.03
nN+0.14-0.17
Stereo+0.34+0.08
Share of structures with each property, by pathway (select a column to sort)Open data
COCONUT October 2026 dump, unique 2D structures; glycoside flag, aromatic-ring count, Fsp3 and Lipinski violations as distributed in the dump; nitrogen and halogen from the molecular formula. Ro5 pass = no Lipinski rule-of-five violation; on narrow screens columns are abbreviated (Glyc, N, Hal, Arom, Fsp3, Ro5).
Data table
Share of unique 2D structures (%)
Pathway (structures)GlycosidesContain nitrogenContain halogenAromatic ringFsp3 ≥ 0.5No Lipinski violation
Terpenoids (111,860)25.8%11.2%2.3%25.1%93.7%46.1%
Alkaloids (126,597)1.6%99.6%10.5%90.1%36.9%77.8%
Shikimates and phenylpropanoids (81,918)17.2%29.7%9.0%99.6%8.4%60.9%
Fatty acids (55,560)6.3%14.2%1.5%3.0%96.3%17.7%
Polyketides (40,174)14.5%26.7%8.9%75.6%41.2%53.8%
Amino acids and peptides (20,253)5.4%99.4%6.9%66.0%65.4%42.0%
Carbohydrates (4,696)64.3%64.7%3.3%32.0%94.0%29.6%
No pathway assigned (38,632)9.7%74.9%9.6%82.3%45.2%50.3%

Fsp3 is at least 0.5 in 94% of terpenoids but 8% of phenylpropanoids, and nearly all alkaloids contain nitrogen: one extraction or method rarely suits every pathway.

Explanation, details and sources

Descriptors were computed with RDKit for each sampled structure: molecular weight, Crippen logP, topological polar surface area (TPSA), hydrogen-bond donors and acceptors, rotatable bonds, Fsp3, ring and aromatic-ring counts, oxygen and nitrogen counts and stereocenters. PC1 rises with size and polarity (molecular weight, TPSA, donors, acceptors, oxygen count); PC2 rises with flexibility and saturation (rotatable bonds, Fsp3, logP) and falls with aromatic rings. Natural products have long been noted to differ from synthetic compounds in stereocenters, aromatic rings, saturation and heteroatom ratios (Feher and Schmidt 2003). Sampling one record per connectivity block avoids weighting molecules with many recorded stereoisomers.

Feher M, Schmidt JM. Property distributions: differences between drugs, natural products, and molecules from combinatorial chemistry. J Chem Inf Comput Sci. 2003;43(1):218–227. RDKit 2026.09.1. COCONUT October 2026 dump (CC0).

EUTECNIQ's approach

How EUTECNIQ would choose between targeted and non-targeted work

Proposed decision path for an analytical questionProposed
Proposed decision path: use a validated targeted method when the analyte and its reference standard are known, suspect screening when there is a list of expected compounds, and non-targeted screening otherwise; any non-targeted finding that matters for release becomes a new targeted methodIs the question about named constituents with areference standard?Targeted method, validated for the matrixAssay, identity, contaminant limits for releaseYesNoIs there a list of expected compounds oradulterants?Suspect screening against the listFlag hits; confirm with a standard before actingYesNoOtherwise: what is in this lot that we did notexpect?Non-targeted screening with confidencelevelsCompare lots, find unknowns, guide the nexttargeted methodFinding matters forrelease?If yes, develop and validate atargeted methodYesProposed approach; EUTECNIQ has no laboratory, methods or data yet.Proposed decision pathAsk in order; the first yes decidesIs the question about named constituents with areference standard?Yes → Targeted method, validated for the matrix.Assay, identity, contaminant limits for release.Is there a list of expected compounds oradulterants?Yes → Suspect screening against the list. Flag hits;confirm with a standard before acting.Otherwise: what is in this lot that we did notexpect?Yes → Non-targeted screening with confidence levels.Compare lots, find unknowns, guide the next targetedmethod.ThenFinding matters for release?Develop and validate a targeted method for it.Proposed approach; EUTECNIQ has no laboratory, methodsor data yet.
EUTECNIQ proposal. Validation per ICH Q2(R2); confidence levels per Schymanski et al. (2014).

EUTECNIQ would screen broadly to find what matters, then develop and validate a targeted method for anything a release decision depends on.

Explanation, details and sources

In practice, release testing of a botanical ingredient under 21 CFR Part 111 relies on identity, strength and contaminant methods that are scientifically valid for the matrix. Non-targeted screening would support raw-material comparison, adulteration investigations and discovery, and its findings would be reported with a confidence level. Until EUTECNIQ has its own laboratory, such work would be placed with qualified partner laboratories.

Related pages: analytical methods by question, method development and validation, discovery and characterization.

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