| Common Name |
Caffeoylmalic acid
| Description |
Caffeoylmalic acid is found in common bean. Caffeoylmalic acid is isolated from leaves of French bean (Phaseolus vligaris) and from Trifolium pratense (red clover) Caffeoylmalic acid belongs to the family of Coumaric Acid Esters. These are aromatic compounds containing an ester derivative of coumaric acid.
| Structure |
MOLSDFPDBSMILESInChI
Structure for HMDB29318 (Caffeoylmalic acid)
| Synonyms |
| Value |
Source |
(S)-Phaselic acidHMDB
Phaseolic acid?HMDB
| Chemical Formlia |
C13H12O8
| Average Molecliar Weight |
296.2296
| Monoisotopic Molecliar Weight |
296.05321736
| IUPAC Name |
2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}butanedioic acid
| Traditional Name |
2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}butanedioic acid
| CAS Registry Number |
53755-04-7
| SMILES |
OC(=O)CC(OC(=O)C=CC1=CC=C(O)C(O)=C1)C(O)=O
| InChI Identifier |
InChI=1S/C13H12O8/c14-8-3-1-7(5-9(8)15)2-4-12(18)21-10(13(19)20)6-11(16)17/h1-5,10,14-15H,6H2,(H,16,17)(H,19,20)/b4-2+
| InChI Key |
PMKQSEYPLQIEAY-DUXPYHPUSA-N
| Chemical Taxonomy |
| Description |
This 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.
| Kingdom |
Organic compounds
| Super Class |
Phenylpropanoids and polyketides
| Class |
Cinnamic acids and derivatives
| Sub Class |
Hydroxycinnamic acids and derivatives
| Direct Parent |
Coumaric acids and derivatives
| Alternative Parents |
Cinnamic acid esters
Tricarboxylic acids and derivatives
Phenylpropenes
Styrenes
Catechols
Fatty acid esters
Enoate esters
Carboxylic acids
Hydrocarbon derivatives
Carbonyl compounds
| Substituents |
Cinnamic acid ester
Coumaric acid or derivatives
Tricarboxylic acid or derivatives
Phenylpropene
Styrene
1,2-diphenol
Phenol
Fatty acid ester
Fatty acyl
Benzenoid
Monocyclic benzene moiety
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic homomonocyclic compound
| Molecliar Framework |
Aromatic homomonocyclic compounds
| External Descriptors |
Not Available
| Ontology |
| Status |
Expected but not Quantified
| Origin |
Endogenous
Food
| Biofunction |
Not Available
| Application |
Nutrient
| Cellliar locations |
Cytoplasm
Extracellliar
| Physical Properties |
| State |
Not Available
| Experimental Properties |
| Property |
Value |
Reference |
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility0.33 mg/mLALOGPS
logP1.87ALOGPS
logP1.31ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)3.07ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area141.36 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity68.4 m3·mol-1ChemAxon
Polarizability26.85 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available
| Biological Properties |
| Cellliar Locations |
Cytoplasm
Extracellliar
| 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
| External Links |
| DrugBank ID |
Not Available
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
FDB000379
| KNApSAcK ID |
C00002765
| Chemspider ID |
4816367
| KEGG Compound ID |
Not Available
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB29318
| Metagene Link |
HMDB29318
| METLIN ID |
Not Available
| PubChem Compound |
6124299
| PDB ID |
Not Available
| ChEBI ID |
493262
Product: IC87201
References |
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
- (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
|
PMID: 8321323
