Human Metabolome Database Version 3.5

Showing metabocard for 3-O-Caffeoylshikimic acid (HMDB30654)

Record Information
Version 3.5
Creation Date 2012-09-11 11:38:12 -0600
Update Date 2013-06-29 23:27:35 -0600
HMDB ID HMDB30654
Secondary Accession Numbers None
Metabolite Identification
Common Name 3-O-Caffeoylshikimic acid
Description 3-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
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Display: 2D Structure | 3D Structure
Synonyms
  1. 3-Caffeoylshikimic acid
  2. 3-O-Caffeoylshikimic acid
  3. Neodactylifric acid
  4. Neodattelic acid
Chemical Formula C16H16O8
Average Molecular Weight 336.2934
Monoisotopic Molecular Weight 336.084517488
IUPAC Name 5-{[(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,4-dihydroxycyclohex-1-ene-1-carboxylic acid
Traditional IUPAC Name 5-{[(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,4-dihydroxycyclohex-1-ene-1-carboxylic acid
CAS Registry Number 6082-44-6
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 Key QMPHZIPNNJOWQI-RQOWECAXNA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Homomonocyclic Compounds
Class Cinnamic Acid Derivatives
Sub Class Hydroxycinnamic 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 Parent Coumaric Acid Esters
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction Not Available
Application
  • Nutrient
Cellular locations
  • Cytoplasm
  • Extracellular
Physical Properties
State Not Available
Experimental Properties
Property Value Reference
Melting Point 224 - 225 °C Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 1.01 g/L ALOGPS
LogP 1.17 ALOGPS
LogP 0.79 ChemAxon
LogS -2.52 ALOGPS
pKa (strongest acidic) 3.94 ChemAxon
pKa (strongest basic) -3.4 ChemAxon
Hydrogen Acceptor Count 7 ChemAxon
Hydrogen Donor Count 5 ChemAxon
Polar Surface Area 144.52 A2 ChemAxon
Rotatable Bond Count 5 ChemAxon
Refractivity 82.49 ChemAxon
Polarizability 32.18 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB002563
KNApSAcK ID Not Available
Chemspider ID Not Available
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB30654 Link_out
Metagene Link HMDB30654 Link_out
METLIN ID Not Available
PubChem Compound Not Available
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Not 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.