Showing metabocard for trans-Cinnamic acid (BMDB0000930)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:38:44 UTC
Update Date2020-04-22 15:06:00 UTC
BMDB IDBMDB0000930
Secondary Accession Numbers
  • BMDB00930
Metabolite Identification
Common Nametrans-Cinnamic acid
Descriptiontrans-Cinnamic acid, also known as (2E)-3-phenylacrylate or (e)-cinnamate, belongs to the class of organic compounds known as cinnamic acids. These are organic aromatic compounds containing a benzene and a carboxylic acid group forming 3-phenylprop-2-enoic acid. trans-Cinnamic acid exists as a solid, possibly soluble (in water), and a weakly acidic compound (based on its pKa) molecule. trans-Cinnamic acid exists in all living species, ranging from bacteria to humans. trans-Cinnamic acid is a potentially toxic compound.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2E)-3-Phenyl-2-propenoic acidChEBI
(2E)-3-Phenylacrylic acidChEBI
(e)-3-Phenyl-2-propenoic acidChEBI
(e)-CinnamateChEBI
(e)-Cinnamic acidChEBI
Benzeneacrylic acidChEBI
PHENYLETHYLENECARBOXYLIC ACIDChEBI
trans-3-Phenylacrylic acidChEBI
trans-beta-CarboxystyreneChEBI
trans-CinnamateChEBI
trans-ZimtsaeureChEBI
(2E)-3-Phenyl-2-propenoateGenerator
(2E)-3-PhenylacrylateGenerator
(e)-3-Phenyl-2-propenoateGenerator
BenzeneacrylateGenerator
PHENYLETHYLENECARBOXYLateGenerator
trans-3-PhenylacrylateGenerator
trans-b-CarboxystyreneGenerator
trans-Β-carboxystyreneGenerator
(2E)-2-Phenyl-2-propenoateHMDB
(2E)-2-Phenyl-2-propenoic acidHMDB
(e)-3-PhenylacrylateHMDB
(e)-3-Phenylacrylic acidHMDB
(e)-3-Phenylprop-2-enoateHMDB
(e)-3-Phenylprop-2-enoic acidHMDB
trans-3-Phenyl-2-propenoateHMDB
trans-3-Phenyl-2-propenoic acidHMDB
Cinnamic acid, 14C-labeled CPDHMDB
Cinnamic acid, 2-(14)C-labeled CPDHMDB
Cinnamic acid, 3-(14)C-labeled CPDHMDB
Cinnamic acid, (Z)-isomerHMDB
Cinnamic acid, 2-(13)C-labeled CPDHMDB
Cinnamic acid, 3H-labeled CPD (e)-isomerHMDB
Cinnamic acid, 3H-labeled CPD (Z)-isomerHMDB
Cinnamic acid, ion(1-)-(e)-isomerHMDB
Cinnamic acid, sodium saltHMDB
Cinnamic acid, sodium salt(e)-isomerHMDB
Cinnamic acid, sodium salt(Z)-isomerHMDB
Cinnamic acid, (trans)-(e)-isomerHMDB
Cinnamic acid, 14C-labeled CPD (e)-isomerHMDB
Cinnamic acid, ion(1-)HMDB
Cinnamic acid, nickel (+2) saltHMDB
Cinnamic acid, potassium saltHMDB
Cinnamic acid, zinc salt(e)-isomerHMDB
Cinnamic acid, 13C-labeled CPDHMDB
Cinnamic acidHMDB
(2E)-3-Phenylprop-2-enoic acidHMDB
(2E)-Cinnamic acidHMDB
3-Phenyl-(e)-2-propenoic acidHMDB
3-Phenyl-2-propenoic acidHMDB
3-Phenylacrylic acidHMDB
Phenylacrylic acidHMDB
beta-Phenylacrylic acidHMDB
Β-phenylacrylic acidHMDB
trans-Cinnamic acidHMDB
Chemical FormulaC9H8O2
Average Molecular Weight148.1586
Monoisotopic Molecular Weight148.0524295
IUPAC Name(2E)-3-phenylprop-2-enoic acid
Traditional Namecinnamic acid
CAS Registry Number140-10-3
SMILES
OC(=O)\C=C\C1=CC=CC=C1
InChI Identifier
InChI=1S/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6+
InChI KeyWBYWAXJHAXSJNI-VOTSOKGWSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as cinnamic acids. These are organic aromatic compounds containing a benzene and a carboxylic acid group forming 3-phenylprop-2-enoic acid.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassCinnamic acids
Direct ParentCinnamic acids
Alternative Parents
Substituents
  • Cinnamic acid
  • Styrene
  • Benzenoid
  • Monocyclic benzene moiety
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point133 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.546 mg/mLNot Available
LogP2.13HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
logP2.38ALOGPS
logP2.14ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)4.51ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity43.06 m³·mol⁻¹ChemAxon
Polarizability15.43 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cell membrane
  • Membrane
Biospecimen Locations
  • Milk
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000930
DrugBank IDNot Available
Phenol Explorer Compound ID549
FooDB IDFDB012052
KNApSAcK IDC00000170
Chemspider ID392447
KEGG Compound IDC10438
BioCyc IDCPD-674
BiGG IDNot Available
Wikipedia LinkCinnamic_acid
METLIN ID5880
PubChem Compound444539
PDB IDNot Available
ChEBI ID35697
References
Synthesis ReferenceZhu, Min; Shentu, Chao; Zhou, Zhong Shi. Microwave-assisted base-free synthesis of trans-cinnamic acids using hypervalent iodonium salts. Chinese Chemical Letters (2007), 18(3), 272-274.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Hagi T, Kobayashi M, Nomura M: Metabolome analysis of milk fermented by gamma-aminobutyric acid-producing Lactococcus lactis. J Dairy Sci. 2016 Feb;99(2):994-1001. doi: 10.3168/jds.2015-9945. Epub 2015 Dec 10. [PubMed:26686724 ]