Showing metabocard for 2-Hydroxycinnamic acid (BMDB0002641)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:01:03 UTC
Update Date2020-04-22 15:11:13 UTC
BMDB IDBMDB0002641
Secondary Accession Numbers
  • BMDB02641
Metabolite Identification
Common Name2-Hydroxycinnamic acid
Description2-Hydroxycinnamic acid, also known as 2-coumarate or 2-coumaric acid, belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated. 2-Hydroxycinnamic acid exists in all living organisms, ranging from bacteria to humans. Based on a literature review very few articles have been published on 2-Hydroxycinnamic acid.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(2E)-3-(2-Hydroxyphenyl)-2-propenoic acidChEBI
(2E)-3-(2-HYDROXYPHENYL)acrylIC ACIDChEBI
(e)-2-Hydroxycinnamic acidChEBI
(e)-3-(2-Hydroxy-phenyl)-acrylic acidChEBI
(e)-3-(2-Hydroxyphenyl)-2-propenoic acidChEBI
(e)-O-Hydroxycinnamic acidChEBI
2-CoumarateChEBI
2-Coumaric acidChEBI
2-HydroxycinnamateChEBI
O-Coumaric acidChEBI
O-Hydroxy-trans-cinnamic acidChEBI
trans-2-HydroxycinnamateChEBI
trans-2-Hydroxycinnamic acidChEBI
trans-O-Hydroxycinnamic acidChEBI
(2E)-3-(2-Hydroxyphenyl)-2-propenoateGenerator
(2E)-3-(2-HYDROXYPHENYL)acrylateGenerator
(e)-2-HydroxycinnamateGenerator
(e)-3-(2-Hydroxy-phenyl)-acrylateGenerator
(e)-3-(2-Hydroxyphenyl)-2-propenoateGenerator
(e)-O-HydroxycinnamateGenerator
O-CoumarateGenerator
O-Hydroxy-trans-cinnamateGenerator
trans-O-HydroxycinnamateGenerator
2-Hydroxycinnamic acid, (e)-isomerMeSH
Ortho-hydroxycinnamic acidMeSH
2-Hydroxycinnamic acid, (Z)-isomerMeSH
3-(2-Hydroxyphenyl)prop-2-enoateHMDB
3-(2-Hydroxyphenyl)prop-2-enoic acidHMDB
O-HydroxycinnamateHMDB
O-Hydroxycinnamic acidHMDB
ortho-HydroxycinnamateHMDB
trans-O-CoumarateHMDB
trans-O-Coumaric acidHMDB
2-Hydroxycinnamic acidGenerator
trans-2-CoumarateGenerator, HMDB
(E)-3-(2-Hydroxyphenyl)acrylic acidHMDB
3-(2-Hydroxyphenyl)-2-propenoic acidHMDB
o-Hydroxycinnamic acidHMDB
trans-o-Coumaric acidHMDB
3-(2-Hydroxyphenyl)acrylic acidHMDB
trans-2-Coumaric acid HMDB
(2E)-3-(2-Hydroxyphenyl)prop-2-enoic acidHMDB
2'-Hydroxycinnamic acidHMDB
Chemical FormulaC9H8O3
Average Molecular Weight164.158
Monoisotopic Molecular Weight164.047344122
IUPAC Name(2E)-3-(2-hydroxyphenyl)prop-2-enoic acid
Traditional NameO-coumaric acid
CAS Registry Number583-17-5
SMILES
OC(=O)\C=C\C1=C(O)C=CC=C1
InChI Identifier
InChI=1S/C9H8O3/c10-8-4-2-1-3-7(8)5-6-9(11)12/h1-6,10H,(H,11,12)/b6-5+
InChI KeyPMOWTIHVNWZYFI-AATRIKPKSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassHydroxycinnamic acids and derivatives
Direct ParentHydroxycinnamic acids
Alternative Parents
Substituents
  • Cinnamic acid
  • Coumaric acid
  • Coumaric acid or derivatives
  • Hydroxycinnamic acid
  • Styrene
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.9ALOGPS
logP1.83ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)4.04ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity45.04 m³·mol⁻¹ChemAxon
Polarizability16.11 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-0002-0910000000-9e0bdbf6d6389288e318View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00dj-9710000000-829ded288e3ec8312160View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00dj-9710000000-8fb7bb39d916f7402980View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0296-2941000000-b85ebef8eb8c276f220fView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-9800000000-3650ee76a1293cba7523View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0910000000-9e0bdbf6d6389288e318View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00dj-9710000000-829ded288e3ec8312160View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00dj-9710000000-8fb7bb39d916f7402980View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0296-2941000000-b85ebef8eb8c276f220fView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0910000000-c783499d6f33717b71caView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014j-2900000000-3a06c14b7e8999427ad9View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00y3-6390000000-a82ff5bd6498e3c478eaView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-03di-0900000000-9e4823d321cfe6f5e5a4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-014i-0900000000-efd5de4e7fe4032816f6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-014i-0900000000-44e81c2c735a93efc7d7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-014l-7900000000-977a2bb08508d16be531View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-00kf-9300000000-fe9b4a0aa3b23d5c2eb5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0fdn-4900000000-dcfe2b032cf6bbee16b3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-03di-0900000000-adbaf7b04487b18191e0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03di-0900000000-d368e3c354c7b05a949fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-efd5de4e7fe4032816f6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-44e81c2c735a93efc7d7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014l-7900000000-a641b2c2528f829e8ac1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00kf-9300000000-fe9b4a0aa3b23d5c2eb5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03di-0900000000-adbaf7b04487b18191e0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-014i-0900000000-2ca69c9285dedaa2f424View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-014i-0900000000-55078e8ec591840fb594View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0fdn-4900000000-95f5386456c1c353a111View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-014i-0900000000-bf00664334bbd7d7d91dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0900000000-ba0915b2f87da989c92bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-2900000000-fd2da9ac5865a50fc50cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gdu-9300000000-3baee6b4124fba79677eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-69f05779283af436427dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03xr-1900000000-0bc76f24c2abf6670fc0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9600000000-a2981a5342a71b94ce69View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-972f865a96261dcb891aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-0900000000-dfdb5072d39445a67f3aView in MoNA
MSMass Spectrum (Electron Ionization)splash10-014j-8900000000-8e96a9ec1b9d035d3edbView in MoNA
1D NMR1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 15.09 MHz, DMSO-d6, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0002641
DrugBank IDDB01650
Phenol Explorer Compound ID462
FooDB IDFDB011258
KNApSAcK IDC00002729
Chemspider ID553146
KEGG Compound IDC01772
BioCyc ID2-COUMARATE
BiGG IDNot Available
Wikipedia LinkO-Coumaric_acid
METLIN ID6727
PubChem Compound637540
PDB IDNot Available
ChEBI ID18125
References
Synthesis ReferenceAdams, Roger; Bockstahler, Theodore E. Preparation and reactions of o-hydroxycinnamic acids and esters. Journal of the American Chemical Society (1952), 74 5346-8.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available