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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2012-09-12 03:17:09 UTC
Update Date2019-07-23 06:34:41 UTC
HMDB IDHMDB0041592
Secondary Accession Numbers
  • HMDB0062655
  • HMDB41592
  • HMDB62655
Metabolite Identification
Common NameCoumarinic acid
DescriptionCoumarinic acid, also known as cis-o-coumaric acid or cis-o-hydroxycinnamic acid, is a hydroxy derivative of cinnamic acid. Cinnamic acid and its derivatives are used as important components in flavours, perfumes, synthetic indigo, and pharmaceuticals. There are three isomers of coumaric acid: o-coumaric acid, m-coumaric acid, and p-coumaric acid. These isomers differ by the position of the hydroxy substitution. p-Coumaric acid is the most abundant isomer in nature (Wikipedia). Coumarinic acid is found in pomegranate.
Structure
Data?1563863681
Synonyms
ValueSource
(2Z)-3-(2-Hydroxyphenyl)acrylic acidChEBI
2-CoumarinateChEBI
cis-2-Hydroxy cinnamateChEBI
cis-2-Hydroxycinnamic acidChEBI
(2Z)-3-(2-Hydroxyphenyl)acrylateGenerator
2-Coumarinic acidGenerator
cis-2-Hydroxy cinnamic acidGenerator
cis-2-HydroxycinnamateGenerator
CoumarateGenerator
(Z)-FormHMDB
3-(2-Hydroxyphenyl)-(2Z)-2-propenoic acidHMDB
3-(2-Hydroxyphenyl)-(Z)-2-propenoic acidHMDB
3-(2-Hydroxyphenyl)-2-propenoic acid, 9ciHMDB
Cinnamic acid, O-hydroxy-, (Z)- (8ci)HMDB
cis-O-Coumaric acidHMDB
cis-O-Hydroxycinnamic acidHMDB
Coumarinic acidHMDB
cis-2-CoumarateGenerator
(2Z)-3-(2-Hydroxyphenyl)-2-propenoic acidHMDB
(Z)-2-Hydroxycinnamic acidHMDB
(Z)-3-(2-Hydroxyphenyl)acrylic acidHMDB
(Z)-o-Hydroxycinnamic acidHMDB
2-Coumaric acidHMDB
2-Hydroxycinnamic acidHMDB
3-(2-Hydroxyphenyl)-2-propenoic acidHMDB
o-Coumaric acidHMDB
o-Hydroxy-cis-cinnamic acidHMDB
o-Hydroxycinnamic acidHMDB
Chemical FormulaC9H8O3
Average Molecular Weight164.158
Monoisotopic Molecular Weight164.047344122
IUPAC Name(2Z)-3-(2-hydroxyphenyl)prop-2-enoic acid
Traditional Name2-coumarinate
CAS Registry Number495-79-4
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-WAYWQWQTSA-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
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.15 g/LALOGPS
logP1.9ALOGPS
logP1.83ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)3.54ChemAxon
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
Polarizability16.17 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-01ox-1941000000-85dd77bfea7f6b8125b7JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-01ox-1941000000-85dd77bfea7f6b8125b7JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-1910000000-73438ba0cdf6f364fa48JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-1900000000-6663bcef745d1f3aa724JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00y3-6390000000-a82ff5bd6498e3c478eaJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0900000000-ba0915b2f87da989c92bJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-2900000000-fd2da9ac5865a50fc50cJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gdu-9300000000-3baee6b4124fba79677eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-69f05779283af436427dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03xr-1900000000-0bc76f24c2abf6670fc0JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9600000000-a2981a5342a71b94ce69JSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 IDNot Available
FoodDB IDFDB021703
KNApSAcK IDNot Available
Chemspider ID4444389
KEGG Compound IDC05838
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCoumaric acid
METLIN IDNot Available
PubChem Compound5280841
PDB IDNot Available
ChEBI ID28873
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.. .