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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-12 02:47:38 UTC
Update Date2019-01-11 20:00:30 UTC
HMDB IDHMDB0041140
Secondary Accession Numbers
  • HMDB41140
Metabolite Identification
Common NamePrenyl cis-caffeate
DescriptionPrenyl cis-caffeate is a constituent of Populus species Prenyl cis-caffeate is a flavouring agent.
Structure
Data?1547236830
Synonyms
ValueSource
1,1-DacaeHMDB
1,1-Dimethylallyl caffeic acid esterHMDB
3-Methyl-2-butenyl caffeateHMDB
Cinnamic acid, 3,4-dihydroxy-, 3-methyl-2-butenyl esterHMDB
Isoprenyl caffeateHMDB
Prenyl cafeateHMDB
Prenyl caffeateHMDB
3-Methyl-3-butenyl caffeateMeSH
Chemical FormulaC14H16O4
Average Molecular Weight248.2744
Monoisotopic Molecular Weight248.104859
IUPAC Name3-methylbut-2-en-1-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Traditional Nameprenyl caffeate
CAS Registry Number118971-61-2
SMILES
CC(C)=CCOC(=O)\C=C\C1=CC=C(O)C(O)=C1
InChI Identifier
InChI=1S/C14H16O4/c1-10(2)7-8-18-14(17)6-4-11-3-5-12(15)13(16)9-11/h3-7,9,15-16H,8H2,1-2H3/b6-4+
InChI KeyTTYOHMFLCXENHR-GQCTYLIASA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassHydroxycinnamic acids and derivatives
Direct ParentCoumaric acids and derivatives
Alternative Parents
Substituents
  • Coumaric acid or derivatives
  • Cinnamic acid ester
  • Catechol
  • Styrene
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Fatty acid ester
  • Fatty acyl
  • Benzenoid
  • Monocyclic benzene moiety
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Source:

Role

Industrial application:

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 Solubility0.16 g/LALOGPS
logP3.24ALOGPS
logP3.27ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)9.21ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity70.91 m³·mol⁻¹ChemAxon
Polarizability26.74 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-02ti-7900000000-3ed0c0ad01e411fd28c8JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-016r-9056000000-1dbb4b42a01fde6d0dc2JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-6790000000-ed23dd50a310cc877094JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-9510000000-7e53c3d2adbc9c894000JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-9500000000-e519c212c410c3ccd505JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01ot-3970000000-c837750f955bb0d9074fJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-2910000000-0817c9c23d196638f009JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-5900000000-d36e2881a5dd8c672b4bJSpectraViewer | MoNA
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 IDNot Available
FoodDB IDFDB021025
KNApSAcK IDC00002768
Chemspider ID4445103
KEGG Compound IDC10487
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5281790
PDB IDPWH
ChEBI ID8393
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.. .