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Record Information
Version3.6
Creation Date2012-09-11 17:38:12 UTC
Update Date2013-06-30 05:27:35 UTC
HMDB IDHMDB30654
Secondary Accession NumbersNone
Metabolite Identification
Common Name3-O-Caffeoylshikimic acid
Description3-O-Caffeoylshikimic acid is found in date. 3-O-Caffeoylshikimic acid is a constituent of dates (Phoenix dactylifera). 3-o-caffeoylshikimic acid belongs to the family of Coumaric Acid Esters. These are aromatic compounds containing an ester derivative of coumaric acid.
Structure
Thumb
Synonyms
  1. 3-Caffeoylshikimic acid
  2. 3-O-Caffeoylshikimic acid
  3. Neodactylifric acid
  4. Neodattelic acid
Chemical FormulaC16H16O8
Average Molecular Weight336.2934
Monoisotopic Molecular Weight336.084517488
IUPAC Name5-{[(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,4-dihydroxycyclohex-1-ene-1-carboxylic acid
Traditional Name5-{[(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,4-dihydroxycyclohex-1-ene-1-carboxylic acid
CAS Registry Number6082-44-6
SMILES
OC1C=C(CC(OC(=O)\C=C/C2=CC(O)=C(O)C=C2)C1O)C(O)=O
InChI Identifier
InChI=1/C16H16O8/c17-10-3-1-8(5-11(10)18)2-4-14(20)24-13-7-9(16(22)23)6-12(19)15(13)21/h1-6,12-13,15,17-19,21H,7H2,(H,22,23)/b4-2-
InChI KeyQMPHZIPNNJOWQI-RQOWECAXNA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAromatic Homomonocyclic Compounds
ClassCinnamic Acid Derivatives
Sub ClassHydroxycinnamic Acid Derivatives
Other Descriptors
  • Aromatic Homopolycyclic Compounds
  • Hydroxycinnamic Acid Derivatives
  • Organic Compounds
Substituents
  • 1,2 Diol
  • 1,2 Diphenol
  • Carboxylic Acid
  • Carboxylic Acid Ester
  • Cyclic Alcohol
  • Cyclohexene
  • Dicarboxylic Acid Derivative
  • Enone
  • Fatty Acid Ester
  • Phenol
  • Phenol Derivative
  • Phenylpropene
  • Secondary Alcohol
  • Styrene
Direct ParentCoumaric Acid Esters
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
  • Food
BiofunctionNot Available
Application
  • Nutrient
Cellular locations
  • Cytoplasm
  • Extracellular
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting Point224 - 225 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.01 g/LALOGPS
logP1.17ALOGPS
logP0.79ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)3.94ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area144.52ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity82.49ChemAxon
Polarizability32.18ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
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 IDFDB002563
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB30654
Metagene LinkHMDB30654
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
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.