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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 IDHMDB0029284
Secondary Accession Numbers
  • HMDB29284
Metabolite Identification
Common NameAvenanthramide 1c
DescriptionAvenanthramide 1c 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 1c.
Structure
Data?1582753397
Synonyms
ValueSource
N-[3,4-Dihydroxy-(e)-cinnamoyl]-anthranilic acidHMDB
2-{[(2E)-3-(3,4-dihydroxyphenyl)-1-hydroxyprop-2-en-1-ylidene]amino}benzoateHMDB
Chemical FormulaC16H13NO5
Average Molecular Weight299.2781
Monoisotopic Molecular Weight299.079372531
IUPAC Name2-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enamido]benzoic acid
Traditional Name2-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enamido]benzoic acid
CAS Registry NumberNot Available
SMILES
OC(=O)C1=CC=CC=C1NC(=O)\C=C\C1=CC(O)=C(O)C=C1
InChI Identifier
InChI=1S/C16H13NO5/c18-13-7-5-10(9-14(13)19)6-8-15(20)17-12-4-2-1-3-11(12)16(21)22/h1-9,18-19H,(H,17,20)(H,21,22)/b8-6+
InChI KeyLLPIRWBXMYKFQM-SOFGYWHQSA-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
  • Cinnamic acid amide
  • Anilide
  • Benzoic acid or derivatives
  • Benzoic acid
  • Catechol
  • Styrene
  • N-arylamide
  • Benzoyl
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Monocyclic benzene moiety
  • Vinylogous amide
  • Carboxamide group
  • Secondary carboxylic acid amide
  • 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 SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.044 g/LALOGPS
logP3.01ALOGPS
logP3.27ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)3.55ChemAxon
pKa (Strongest Basic)-2.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area106.86 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity82.56 m³·mol⁻¹ChemAxon
Polarizability30.05 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]+168.80830932474
DeepCCS[M-H]-166.4530932474
DeepCCS[M-2H]-200.05530932474
DeepCCS[M+Na]+175.28230932474
AllCCS[M+H]+168.832859911
AllCCS[M+H-H2O]+165.332859911
AllCCS[M+NH4]+172.032859911
AllCCS[M+Na]+173.032859911
AllCCS[M-H]-168.832859911
AllCCS[M+Na-2H]-168.332859911
AllCCS[M+HCOO]-168.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Avenanthramide 1cOC(=O)C1=CC=CC=C1NC(=O)\C=C\C1=CC(O)=C(O)C=C14917.9Standard polar33892256
Avenanthramide 1cOC(=O)C1=CC=CC=C1NC(=O)\C=C\C1=CC(O)=C(O)C=C12970.4Standard non polar33892256
Avenanthramide 1cOC(=O)C1=CC=CC=C1NC(=O)\C=C\C1=CC(O)=C(O)C=C13257.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Avenanthramide 1c,1TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC=CC=C1NC(=O)/C=C/C1=CC=C(O)C(O)=C13162.3Semi standard non polar33892256
Avenanthramide 1c,1TMS,isomer #2C[Si](C)(C)OC1=CC(/C=C/C(=O)NC2=CC=CC=C2C(=O)O)=CC=C1O3142.6Semi standard non polar33892256
Avenanthramide 1c,1TMS,isomer #3C[Si](C)(C)OC1=CC=C(/C=C/C(=O)NC2=CC=CC=C2C(=O)O)C=C1O3153.6Semi standard non polar33892256
Avenanthramide 1c,1TMS,isomer #4C[Si](C)(C)N(C(=O)/C=C/C1=CC=C(O)C(O)=C1)C1=CC=CC=C1C(=O)O3024.5Semi standard non polar33892256
Avenanthramide 1c,2TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC=CC=C1NC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C(O)=C13110.7Semi standard non polar33892256
Avenanthramide 1c,2TMS,isomer #2C[Si](C)(C)OC(=O)C1=CC=CC=C1NC(=O)/C=C/C1=CC=C(O)C(O[Si](C)(C)C)=C13102.7Semi standard non polar33892256
Avenanthramide 1c,2TMS,isomer #3C[Si](C)(C)OC(=O)C1=CC=CC=C1N(C(=O)/C=C/C1=CC=C(O)C(O)=C1)[Si](C)(C)C2900.6Semi standard non polar33892256
Avenanthramide 1c,2TMS,isomer #4C[Si](C)(C)OC1=CC=C(/C=C/C(=O)NC2=CC=CC=C2C(=O)O)C=C1O[Si](C)(C)C3150.4Semi standard non polar33892256
Avenanthramide 1c,2TMS,isomer #5C[Si](C)(C)OC1=CC(/C=C/C(=O)N(C2=CC=CC=C2C(=O)O)[Si](C)(C)C)=CC=C1O2923.5Semi standard non polar33892256
Avenanthramide 1c,2TMS,isomer #6C[Si](C)(C)OC1=CC=C(/C=C/C(=O)N(C2=CC=CC=C2C(=O)O)[Si](C)(C)C)C=C1O2923.1Semi standard non polar33892256
Avenanthramide 1c,3TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC=CC=C1NC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C13153.3Semi standard non polar33892256
Avenanthramide 1c,3TMS,isomer #2C[Si](C)(C)OC(=O)C1=CC=CC=C1N(C(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C(O)=C1)[Si](C)(C)C2909.1Semi standard non polar33892256
Avenanthramide 1c,3TMS,isomer #3C[Si](C)(C)OC(=O)C1=CC=CC=C1N(C(=O)/C=C/C1=CC=C(O)C(O[Si](C)(C)C)=C1)[Si](C)(C)C2922.1Semi standard non polar33892256
Avenanthramide 1c,3TMS,isomer #4C[Si](C)(C)OC1=CC=C(/C=C/C(=O)N(C2=CC=CC=C2C(=O)O)[Si](C)(C)C)C=C1O[Si](C)(C)C2968.6Semi standard non polar33892256
Avenanthramide 1c,4TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC=CC=C1N(C(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)[Si](C)(C)C2998.1Semi standard non polar33892256
Avenanthramide 1c,4TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC=CC=C1N(C(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)[Si](C)(C)C2896.4Standard non polar33892256
Avenanthramide 1c,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC=C1NC(=O)/C=C/C1=CC=C(O)C(O)=C13413.0Semi standard non polar33892256
Avenanthramide 1c,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC(/C=C/C(=O)NC2=CC=CC=C2C(=O)O)=CC=C1O3425.1Semi standard non polar33892256
Avenanthramide 1c,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)NC2=CC=CC=C2C(=O)O)C=C1O3435.2Semi standard non polar33892256
Avenanthramide 1c,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)N(C(=O)/C=C/C1=CC=C(O)C(O)=C1)C1=CC=CC=C1C(=O)O3298.3Semi standard non polar33892256
Avenanthramide 1c,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(O)=C13634.6Semi standard non polar33892256
Avenanthramide 1c,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC=C1NC(=O)/C=C/C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C13622.5Semi standard non polar33892256
Avenanthramide 1c,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC=C1N(C(=O)/C=C/C1=CC=C(O)C(O)=C1)[Si](C)(C)C(C)(C)C3429.1Semi standard non polar33892256
Avenanthramide 1c,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)NC2=CC=CC=C2C(=O)O)C=C1O[Si](C)(C)C(C)(C)C3676.4Semi standard non polar33892256
Avenanthramide 1c,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC1=CC(/C=C/C(=O)N(C2=CC=CC=C2C(=O)O)[Si](C)(C)C(C)(C)C)=CC=C1O3487.5Semi standard non polar33892256
Avenanthramide 1c,2TBDMS,isomer #6CC(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=C1O3488.4Semi standard non polar33892256
Avenanthramide 1c,3TBDMS,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(O[Si](C)(C)C(C)(C)C)=C13837.7Semi standard non polar33892256
Avenanthramide 1c,3TBDMS,isomer #2CC(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(O)=C1)[Si](C)(C)C(C)(C)C3622.1Semi standard non polar33892256
Avenanthramide 1c,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC=C1N(C(=O)/C=C/C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C3623.2Semi standard non polar33892256
Avenanthramide 1c,3TBDMS,isomer #4CC(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=C1O[Si](C)(C)C(C)(C)C3695.2Semi standard non polar33892256
Avenanthramide 1c,4TBDMS,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(O[Si](C)(C)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C3838.0Semi standard non polar33892256
Avenanthramide 1c,4TBDMS,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(O[Si](C)(C)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C3618.5Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Avenanthramide 1c GC-MS (Non-derivatized) - 70eV, Positivesplash10-03ei-0970000000-0f85089d01f3c6f013ba2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Avenanthramide 1c GC-MS (3 TMS) - 70eV, Positivesplash10-0pi3-3011930000-9f3c51403a36032bb96c2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Avenanthramide 1c 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 1c 10V, Positive-QTOFsplash10-0f79-0944000000-572f97b2d1cb962f60902016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Avenanthramide 1c 20V, Positive-QTOFsplash10-000i-1910000000-99d60d003d66b05a91742016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Avenanthramide 1c 40V, Positive-QTOFsplash10-0f79-8900000000-9a6c0c6b575ceac4051e2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Avenanthramide 1c 10V, Negative-QTOFsplash10-0f6t-0190000000-85572801e7260d0ffc482016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Avenanthramide 1c 20V, Negative-QTOFsplash10-0udr-1490000000-186ab994a2d992f6eec22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Avenanthramide 1c 40V, Negative-QTOFsplash10-0006-8900000000-a4a60e0c0ca8e12f7d502016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Avenanthramide 1c 10V, Negative-QTOFsplash10-0002-0290000000-50c6639b64e14d58aa912021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Avenanthramide 1c 20V, Negative-QTOFsplash10-000i-1930000000-d53c4ff0c45696138d0a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Avenanthramide 1c 40V, Negative-QTOFsplash10-0019-1910000000-00e62c1ff14365cf946e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Avenanthramide 1c 10V, Positive-QTOFsplash10-03di-0911000000-62cd227d3ac94469eb852021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Avenanthramide 1c 20V, Positive-QTOFsplash10-03e9-0930000000-b1f368ebae5203f688ad2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Avenanthramide 1c 40V, Positive-QTOFsplash10-000j-1910000000-d5288893d97757e538bb2021-09-22Wishart 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 ID535
FooDB IDFDB000286
KNApSAcK IDNot Available
Chemspider ID8036787
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9861088
PDB IDNot Available
ChEBI ID710546
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Bratt K, Sunnerheim K, Bryngelsson S, Fagerlund A, Engman L, Andersson RE, Dimberg LH: Avenanthramides in oats (Avena sativa L.) and structure-antioxidant activity relationships. J Agric Food Chem. 2003 Jan 29;51(3):594-600. [PubMed:12537428 ]
  2. 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 ]