Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:29:25 UTC
Update Date2022-03-07 02:52:06 UTC
HMDB IDHMDB0029282
Secondary Accession Numbers
  • HMDB29282
Metabolite Identification
Common NameAvenanthramide 1p
DescriptionAvenanthramide 1p 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. Based on a literature review very few articles have been published on Avenanthramide 1p.
Structure
Data?1582753397
Synonyms
ValueSource
Avenanthramide DHMDB
N-[4-Hydroxy-(e)-cinnamoyl]-anthranilic acidHMDB
2-{[(2E)-1-hydroxy-3-(4-hydroxyphenyl)prop-2-en-1-ylidene]amino}benzoateHMDB
Chemical FormulaC16H13NO4
Average Molecular Weight283.2787
Monoisotopic Molecular Weight283.084457909
IUPAC Name2-[(2E)-3-(4-hydroxyphenyl)prop-2-enamido]benzoic acid
Traditional Name2-[(2E)-3-(4-hydroxyphenyl)prop-2-enamido]benzoic acid
CAS Registry Number115610-36-1
SMILES
OC(=O)C1=C(NC(=O)\C=C\C2=CC=C(O)C=C2)C=CC=C1
InChI Identifier
InChI=1S/C16H13NO4/c18-12-8-5-11(6-9-12)7-10-15(19)17-14-4-2-1-3-13(14)16(20)21/h1-10,18H,(H,17,19)(H,20,21)/b10-7+
InChI KeyINBHLTYBRKASIZ-JXMROGBWSA-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
  • Benzoic acid or derivatives
  • Benzoic acid
  • Anilide
  • Styrene
  • N-arylamide
  • 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 DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility60.31 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.015 g/LALOGPS
logP3.17ALOGPS
logP3.57ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)3.55ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.63 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity80.57 m³·mol⁻¹ChemAxon
Polarizability29.16 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]+165.74830932474
DeepCCS[M-H]-163.3930932474
DeepCCS[M-2H]-197.11930932474
DeepCCS[M+Na]+172.34630932474
AllCCS[M+H]+165.432859911
AllCCS[M+H-H2O]+161.732859911
AllCCS[M+NH4]+168.732859911
AllCCS[M+Na]+169.732859911
AllCCS[M-H]-166.532859911
AllCCS[M+Na-2H]-166.032859911
AllCCS[M+HCOO]-165.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Avenanthramide 1pOC(=O)C1=C(NC(=O)\C=C\C2=CC=C(O)C=C2)C=CC=C14670.3Standard polar33892256
Avenanthramide 1pOC(=O)C1=C(NC(=O)\C=C\C2=CC=C(O)C=C2)C=CC=C12696.2Standard non polar33892256
Avenanthramide 1pOC(=O)C1=C(NC(=O)\C=C\C2=CC=C(O)C=C2)C=CC=C13158.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Avenanthramide 1p,1TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC=CC=C1NC(=O)/C=C/C1=CC=C(O)C=C12986.9Semi standard non polar33892256
Avenanthramide 1p,1TMS,isomer #2C[Si](C)(C)OC1=CC=C(/C=C/C(=O)NC2=CC=CC=C2C(=O)O)C=C12985.1Semi standard non polar33892256
Avenanthramide 1p,1TMS,isomer #3C[Si](C)(C)N(C(=O)/C=C/C1=CC=C(O)C=C1)C1=CC=CC=C1C(=O)O2829.6Semi standard non polar33892256
Avenanthramide 1p,2TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC=CC=C1NC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C=C12978.0Semi standard non polar33892256
Avenanthramide 1p,2TMS,isomer #2C[Si](C)(C)OC(=O)C1=CC=CC=C1N(C(=O)/C=C/C1=CC=C(O)C=C1)[Si](C)(C)C2778.1Semi standard non polar33892256
Avenanthramide 1p,2TMS,isomer #3C[Si](C)(C)OC1=CC=C(/C=C/C(=O)N(C2=CC=CC=C2C(=O)O)[Si](C)(C)C)C=C12826.6Semi standard non polar33892256
Avenanthramide 1p,3TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC=CC=C1N(C(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C=C1)[Si](C)(C)C2838.8Semi standard non polar33892256
Avenanthramide 1p,3TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC=CC=C1N(C(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C=C1)[Si](C)(C)C2808.2Standard non polar33892256
Avenanthramide 1p,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC=C1NC(=O)/C=C/C1=CC=C(O)C=C13245.9Semi standard non polar33892256
Avenanthramide 1p,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)NC2=CC=CC=C2C(=O)O)C=C13280.2Semi standard non polar33892256
Avenanthramide 1p,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N(C(=O)/C=C/C1=CC=C(O)C=C1)C1=CC=CC=C1C(=O)O3117.6Semi standard non polar33892256
Avenanthramide 1p,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC=C1NC(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C13498.7Semi standard non polar33892256
Avenanthramide 1p,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC=C1N(C(=O)/C=C/C1=CC=C(O)C=C1)[Si](C)(C)C(C)(C)C3307.3Semi standard non polar33892256
Avenanthramide 1p,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)N(C2=CC=CC=C2C(=O)O)[Si](C)(C)C(C)(C)C)C=C13373.1Semi standard non polar33892256
Avenanthramide 1p,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC=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)C3548.5Semi standard non polar33892256
Avenanthramide 1p,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC=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)C3380.7Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Avenanthramide 1p GC-MS (Non-derivatized) - 70eV, Positivesplash10-014s-0970000000-a566f728fa7183881de42017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Avenanthramide 1p GC-MS (2 TMS) - 70eV, Positivesplash10-0072-6839200000-233811b6b290dbe57d6c2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Avenanthramide 1p GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Avenanthramide 1p 10V, Positive-QTOFsplash10-0019-0890000000-04ad40c92e259a7d11d62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Avenanthramide 1p 20V, Positive-QTOFsplash10-000i-1920000000-44906bb2b5721bdec1ff2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Avenanthramide 1p 40V, Positive-QTOFsplash10-0f79-9800000000-ad6fc6f94bf65f268a8c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Avenanthramide 1p 10V, Negative-QTOFsplash10-001r-0190000000-4ee1473cdcf98c48a16e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Avenanthramide 1p 20V, Negative-QTOFsplash10-000i-1490000000-f60605812a47a3f42c412016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Avenanthramide 1p 40V, Negative-QTOFsplash10-0006-8900000000-d19f83c6414c2312c7612016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Avenanthramide 1p 10V, Negative-QTOFsplash10-001i-0090000000-0786f2d6ceb295d228c42021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Avenanthramide 1p 20V, Negative-QTOFsplash10-014r-1790000000-d3cc0cd017bee4c03d712021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Avenanthramide 1p 40V, Negative-QTOFsplash10-014i-1910000000-79dcee6fd90a20fbd59a2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Avenanthramide 1p 10V, Positive-QTOFsplash10-0002-0900000000-061a828162cdf954fd232021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Avenanthramide 1p 20V, Positive-QTOFsplash10-00kb-1900000000-7a1597345127828215e42021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Avenanthramide 1p 40V, Positive-QTOFsplash10-014i-4900000000-9c1631c53579bbdd3f752021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound ID530
FooDB IDFDB000281
KNApSAcK IDNot Available
Chemspider ID4947061
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6443019
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1808141
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Neveu V, Perez-Jimenez J, Vos F, Crespy V, du Chaffaut L, Mennen L, Knox C, Eisner R, Cruz J, Wishart D, Scalbert A: Phenol-Explorer: an online comprehensive database on polyphenol contents in foods. Database (Oxford). 2010;2010:bap024. doi: 10.1093/database/bap024. Epub 2010 Jan 8. [PubMed:20428313 ]