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Record Information
Version3.6
Creation Date2012-09-12 03:17:09 UTC
Update Date2016-02-11 03:54:49 UTC
HMDB IDHMDB41592
Secondary Accession NumbersNone
Metabolite Identification
Common NameCoumaric acid
DescriptionCoumarinic acid is found in pomegranate. Coumaric acid is a hydroxycinnamic acid, an organic compound that is a hydroxy derivative of cinnamic acid. There are three isomers, o-coumaric acid, m-coumaric acid, and p-coumaric acid, that differ by the position of the hydroxy substitution of the phenyl group. p-Coumaric acid is the most abundant isomer of the three in nature. (Wikipedia).
Structure
Thumb
Synonyms
ValueSource
(2Z)-3-(2-Hydroxyphenyl)acrylic acidChEBI
2-CoumarinateChEBI
cis-2-Hydroxy cinnamateChEBI
cis-2-Hydroxycinnamic acidChEBI
(2Z)-3-(2-Hydroxyphenyl)acrylateGenerator
CoumarateGenerator
2-Coumarinic acidGenerator
cis-2-Hydroxy cinnamic acidGenerator
cis-2-HydroxycinnamateGenerator
(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
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=CC=CC=C1O
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 KeyInChIKey=PMOWTIHVNWZYFI-WAYWQWQTSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as hydroxycinnamic acids. These 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
  • Hydroxycinnamic acid
  • Coumaric acid or derivatives
  • Coumaric acid
  • Cinnamic acid
  • Phenylpropene
  • Styrene
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Food
Biofunction
  • Nutrient
Application
  • Nutrient
Cellular locations
  • Cytoplasm
  • Extracellular
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 mg/mLALOGPS
logP1.9ALOGPS
logP1.83ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)3.54ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity45.04 m3·mol-1ChemAxon
Polarizability16.17 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-01ox-1941000000-85dd77bfea7f6b8125b7View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.904 +/- 0.337 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.188 +/- 0.059 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.339 +/- 0.088 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.366 +/- 0.164 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.521 +/- 0.278 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.58 +/- 0.184 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.6 +/- 0.253 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified3.528 +/- 3.295 uMAdult (>18 years old)Male
Normal
details
UrineDetected and Quantified0.213 +/- 0.099 umol/mmol creatinineAdult (>18 years old)Male
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB021703
KNApSAcK IDNot Available
Chemspider ID4444389
KEGG Compound IDC05838
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCoumaric_acid
NuGOwiki LinkHMDB41592
Metagene LinkHMDB41592
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.

Enzymes

General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
Glycosidase probably involved in the intestinal absorption and metabolism of dietary flavonoid glycosides. Able to hydrolyze a broad variety of glycosides including phytoestrogens, flavonols, flavones, flavanones and cyanogens. Possesses beta-glycosylceramidase activity and may be involved in a nonlysosomal catabolic pathway of glycosylceramide.
Gene Name:
GBA3
Uniprot ID:
Q9H227
Molecular weight:
Not Available
Reactions
cis-beta-D-Glucosyl-2-hydroxycinnamate + Water → Coumaric acid + D-Glucosedetails