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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 23:54:04 UTC
Update Date2022-03-07 02:55:49 UTC
HMDB IDHMDB0038577
Secondary Accession Numbers
  • HMDB38577
Metabolite Identification
Common Name(Z)-N-Coumaroyl-5-hydroxyanthranilic acid
Description(Z)-N-Coumaroyl-5-hydroxyanthranilic acid belongs to the class of organic compounds known as avenanthramides. These are a group of phenolic alkaloids consisting of conjugate of three phenylpropanoids (ferulic, caffeic, or p-coumaric acid) and anthranilic acid (Z)-N-Coumaroyl-5-hydroxyanthranilic acid is found, on average, in the highest concentration within oats (Avena sativa). This could make (Z)-N-coumaroyl-5-hydroxyanthranilic acid a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (Z)-N-Coumaroyl-5-hydroxyanthranilic acid.
Structure
Data?1563863221
Synonyms
ValueSource
5-Hydroxy-2-[(2E)-3-(4-hydroxyphenyl)prop-2-enamido]benzoateKegg
5-Hydroxy-2-[(2E)-3-(4-hydroxyphenyl)prop-2-enamido]benzoic acidGenerator
(Z)-N-Coumaroyl-5-hydroxyanthranilateGenerator
5-Hydroxy-N-(4-hydroxycinnamoyl)anthranilic acidHMDB
Avenalumin IHMDB
Avenanthramide aHMDB
Chemical FormulaC16H13NO5
Average Molecular Weight299.2781
Monoisotopic Molecular Weight299.079372531
IUPAC Name5-hydroxy-2-[(2E)-3-(4-hydroxyphenyl)prop-2-enamido]benzoic acid
Traditional Name5-hydroxy-2-[(2E)-3-(4-hydroxyphenyl)prop-2-enamido]benzoic acid
CAS Registry Number108605-70-5
SMILES
OC(=O)C1=CC(O)=CC=C1NC(=O)\C=C\C1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C16H13NO5/c18-11-4-1-10(2-5-11)3-8-15(20)17-14-7-6-12(19)9-13(14)16(21)22/h1-9,18-19H,(H,17,20)(H,21,22)/b8-3+
InChI KeyQGUMNWHANDITDB-FPYGCLRLSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as avenanthramides. These are a group of phenolic alkaloids consisting of conjugate of three phenylpropanoids (ferulic, caffeic, or p-coumaric acid) and anthranilic acid.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassHydroxycinnamic acids and derivatives
Direct ParentAvenanthramides
Alternative Parents
Substituents
  • Avenanthramide
  • N-cinnamoylanthranilic acid
  • Acylaminobenzoic acid or derivatives
  • Coumaric acid or derivatives
  • Cinnamic acid amide
  • Hydroxybenzoic acid
  • Benzoic acid or derivatives
  • Anilide
  • Benzoic acid
  • N-arylamide
  • Styrene
  • Benzoyl
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Vinylogous amide
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point277 °CNot Available
Boiling Point644.00 to 645.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility249.8 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.910 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.045 g/LALOGPS
logP2.96ALOGPS
logP3.27ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)3.31ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area106.86 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity82.56 m³·mol⁻¹ChemAxon
Polarizability30.33 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+168.05630932474
DeepCCS[M-H]-165.69830932474
DeepCCS[M-2H]-199.18430932474
DeepCCS[M+Na]+174.41130932474
AllCCS[M+H]+168.932859911
AllCCS[M+H-H2O]+165.532859911
AllCCS[M+NH4]+172.132859911
AllCCS[M+Na]+173.132859911
AllCCS[M-H]-169.332859911
AllCCS[M+Na-2H]-168.932859911
AllCCS[M+HCOO]-168.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(Z)-N-Coumaroyl-5-hydroxyanthranilic acidOC(=O)C1=CC(O)=CC=C1NC(=O)\C=C\C1=CC=C(O)C=C15205.0Standard polar33892256
(Z)-N-Coumaroyl-5-hydroxyanthranilic acidOC(=O)C1=CC(O)=CC=C1NC(=O)\C=C\C1=CC=C(O)C=C12913.2Standard non polar33892256
(Z)-N-Coumaroyl-5-hydroxyanthranilic acidOC(=O)C1=CC(O)=CC=C1NC(=O)\C=C\C1=CC=C(O)C=C13493.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(Z)-N-Coumaroyl-5-hydroxyanthranilic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC(O)=CC=C1NC(=O)/C=C/C1=CC=C(O)C=C13265.4Semi standard non polar33892256
(Z)-N-Coumaroyl-5-hydroxyanthranilic acid,1TMS,isomer #2C[Si](C)(C)OC1=CC=C(NC(=O)/C=C/C2=CC=C(O)C=C2)C(C(=O)O)=C13257.8Semi standard non polar33892256
(Z)-N-Coumaroyl-5-hydroxyanthranilic acid,1TMS,isomer #3C[Si](C)(C)OC1=CC=C(/C=C/C(=O)NC2=CC=C(O)C=C2C(=O)O)C=C13249.2Semi standard non polar33892256
(Z)-N-Coumaroyl-5-hydroxyanthranilic acid,1TMS,isomer #4C[Si](C)(C)N(C(=O)/C=C/C1=CC=C(O)C=C1)C1=CC=C(O)C=C1C(=O)O3171.2Semi standard non polar33892256
(Z)-N-Coumaroyl-5-hydroxyanthranilic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C)=CC=C1NC(=O)/C=C/C1=CC=C(O)C=C13276.7Semi standard non polar33892256
(Z)-N-Coumaroyl-5-hydroxyanthranilic acid,2TMS,isomer #2C[Si](C)(C)OC(=O)C1=CC(O)=CC=C1NC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C=C13273.0Semi standard non polar33892256
(Z)-N-Coumaroyl-5-hydroxyanthranilic acid,2TMS,isomer #3C[Si](C)(C)OC(=O)C1=CC(O)=CC=C1N(C(=O)/C=C/C1=CC=C(O)C=C1)[Si](C)(C)C3117.0Semi standard non polar33892256
(Z)-N-Coumaroyl-5-hydroxyanthranilic acid,2TMS,isomer #4C[Si](C)(C)OC1=CC=C(/C=C/C(=O)NC2=CC=C(O[Si](C)(C)C)C=C2C(=O)O)C=C13272.0Semi standard non polar33892256
(Z)-N-Coumaroyl-5-hydroxyanthranilic acid,2TMS,isomer #5C[Si](C)(C)OC1=CC=C(N(C(=O)/C=C/C2=CC=C(O)C=C2)[Si](C)(C)C)C(C(=O)O)=C13136.5Semi standard non polar33892256
(Z)-N-Coumaroyl-5-hydroxyanthranilic acid,2TMS,isomer #6C[Si](C)(C)OC1=CC=C(/C=C/C(=O)N(C2=CC=C(O)C=C2C(=O)O)[Si](C)(C)C)C=C13109.6Semi standard non polar33892256
(Z)-N-Coumaroyl-5-hydroxyanthranilic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C)=CC=C1NC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C=C13285.8Semi standard non polar33892256
(Z)-N-Coumaroyl-5-hydroxyanthranilic acid,3TMS,isomer #2C[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C)=CC=C1N(C(=O)/C=C/C1=CC=C(O)C=C1)[Si](C)(C)C3071.8Semi standard non polar33892256
(Z)-N-Coumaroyl-5-hydroxyanthranilic acid,3TMS,isomer #3C[Si](C)(C)OC(=O)C1=CC(O)=CC=C1N(C(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C=C1)[Si](C)(C)C3068.7Semi standard non polar33892256
(Z)-N-Coumaroyl-5-hydroxyanthranilic acid,3TMS,isomer #4C[Si](C)(C)OC1=CC=C(/C=C/C(=O)N(C2=CC=C(O[Si](C)(C)C)C=C2C(=O)O)[Si](C)(C)C)C=C13117.4Semi standard non polar33892256
(Z)-N-Coumaroyl-5-hydroxyanthranilic acid,4TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C)=CC=C1N(C(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C=C1)[Si](C)(C)C3141.6Semi standard non polar33892256
(Z)-N-Coumaroyl-5-hydroxyanthranilic acid,4TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C)=CC=C1N(C(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C=C1)[Si](C)(C)C3024.2Standard non polar33892256
(Z)-N-Coumaroyl-5-hydroxyanthranilic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O)=CC=C1NC(=O)/C=C/C1=CC=C(O)C=C13554.7Semi standard non polar33892256
(Z)-N-Coumaroyl-5-hydroxyanthranilic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C(NC(=O)/C=C/C2=CC=C(O)C=C2)C(C(=O)O)=C13557.7Semi standard non polar33892256
(Z)-N-Coumaroyl-5-hydroxyanthranilic acid,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)NC2=CC=C(O)C=C2C(=O)O)C=C13574.2Semi standard non polar33892256
(Z)-N-Coumaroyl-5-hydroxyanthranilic acid,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)N(C(=O)/C=C/C1=CC=C(O)C=C1)C1=CC=C(O)C=C1C(=O)O3479.7Semi standard non polar33892256
(Z)-N-Coumaroyl-5-hydroxyanthranilic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C(C)(C)C)=CC=C1NC(=O)/C=C/C1=CC=C(O)C=C13819.0Semi standard non polar33892256
(Z)-N-Coumaroyl-5-hydroxyanthranilic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O)=CC=C1NC(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C13845.6Semi standard non polar33892256
(Z)-N-Coumaroyl-5-hydroxyanthranilic acid,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O)=CC=C1N(C(=O)/C=C/C1=CC=C(O)C=C1)[Si](C)(C)C(C)(C)C3705.6Semi standard non polar33892256
(Z)-N-Coumaroyl-5-hydroxyanthranilic acid,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)NC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2C(=O)O)C=C13880.0Semi standard non polar33892256
(Z)-N-Coumaroyl-5-hydroxyanthranilic acid,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC1=CC=C(N(C(=O)/C=C/C2=CC=C(O)C=C2)[Si](C)(C)C(C)(C)C)C(C(=O)O)=C13703.8Semi standard non polar33892256
(Z)-N-Coumaroyl-5-hydroxyanthranilic acid,2TBDMS,isomer #6CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)N(C2=CC=C(O)C=C2C(=O)O)[Si](C)(C)C(C)(C)C)C=C13724.1Semi standard non polar33892256
(Z)-N-Coumaroyl-5-hydroxyanthranilic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C(C)(C)C)=CC=C1NC(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C14061.0Semi standard non polar33892256
(Z)-N-Coumaroyl-5-hydroxyanthranilic acid,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C(C)(C)C)=CC=C1N(C(=O)/C=C/C1=CC=C(O)C=C1)[Si](C)(C)C(C)(C)C3840.2Semi standard non polar33892256
(Z)-N-Coumaroyl-5-hydroxyanthranilic acid,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O)=CC=C1N(C(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C3879.8Semi standard non polar33892256
(Z)-N-Coumaroyl-5-hydroxyanthranilic acid,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)N(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2C(=O)O)[Si](C)(C)C(C)(C)C)C=C13970.8Semi standard non polar33892256
(Z)-N-Coumaroyl-5-hydroxyanthranilic acid,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C(C)(C)C)=CC=C1N(C(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C4102.7Semi standard non polar33892256
(Z)-N-Coumaroyl-5-hydroxyanthranilic acid,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C(C)(C)C)=CC=C1N(C(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C3740.5Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (Z)-N-Coumaroyl-5-hydroxyanthranilic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ue9-0980000000-5ff674d142cf4aef9af42017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (Z)-N-Coumaroyl-5-hydroxyanthranilic acid GC-MS (3 TMS) - 70eV, Positivesplash10-0udi-4040970000-1cc5a65d02b8330e143c2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (Z)-N-Coumaroyl-5-hydroxyanthranilic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - (Z)-N-Coumaroyl-5-hydroxyanthranilic acid LC-ESI-qToF , Positive-QTOFsplash10-0002-0900000000-6f538a3ee4a8f4537cc22017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (Z)-N-Coumaroyl-5-hydroxyanthranilic acid , positive-QTOFsplash10-0002-0900000000-6f538a3ee4a8f4537cc22017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (Z)-N-Coumaroyl-5-hydroxyanthranilic acid , positive-QTOFsplash10-0002-1900000000-9558a527d5becfe510a02017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-N-Coumaroyl-5-hydroxyanthranilic acid 10V, Positive-QTOFsplash10-0udi-0944000000-e4bf26fe5a3717ab4f602016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-N-Coumaroyl-5-hydroxyanthranilic acid 20V, Positive-QTOFsplash10-0udi-0920000000-4fdb81cd65ed4d4fc5f42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-N-Coumaroyl-5-hydroxyanthranilic acid 40V, Positive-QTOFsplash10-100r-4900000000-b64973d21c9e8333fdc32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-N-Coumaroyl-5-hydroxyanthranilic acid 10V, Negative-QTOFsplash10-0f6t-0190000000-5c1d411b255629965b772016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-N-Coumaroyl-5-hydroxyanthranilic acid 20V, Negative-QTOFsplash10-0udj-0690000000-dd4c217c818be429dd842016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-N-Coumaroyl-5-hydroxyanthranilic acid 40V, Negative-QTOFsplash10-0a4i-1900000000-89daf2d6294feb8ca7e62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-N-Coumaroyl-5-hydroxyanthranilic acid 10V, Positive-QTOFsplash10-0002-0932000000-41d35e197bc1bd76d45f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-N-Coumaroyl-5-hydroxyanthranilic acid 20V, Positive-QTOFsplash10-01ot-0910000000-3899a82200af21e97ff12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-N-Coumaroyl-5-hydroxyanthranilic acid 40V, Positive-QTOFsplash10-066r-1920000000-57726dd7b1b33db7fd4c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-N-Coumaroyl-5-hydroxyanthranilic acid 10V, Negative-QTOFsplash10-0udi-0290000000-438c4dcba155df8662342021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-N-Coumaroyl-5-hydroxyanthranilic acid 20V, Negative-QTOFsplash10-014i-0930000000-27770e34f1baac3196752021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-N-Coumaroyl-5-hydroxyanthranilic acid 40V, Negative-QTOFsplash10-014i-2900000000-f25c88dc5bddd9a01af12021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound ID532
FooDB IDFDB000283
KNApSAcK IDC00001527
Chemspider ID4444597
KEGG Compound IDC08472
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5281157
PDB IDNot Available
ChEBI ID2939
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1646571
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .