Common Name |
p-Coumaroyl vitisin A
Description |
p-Coumaroyl vitisin A is a polyphenol compound found in foods of plant origin (PMID: 20428313 ).p-Coumaroyl vitisin A belongs to the family of Anthocyanins. These are organic compounds containing a flavyliumA ion or 2-phenylchromenylium based skeleton bound to a sugar.
Structure |
MOLSDFPDBSMILESInChI
Structure for HMDB29239 (p-Coumaroyl vitisin A)
Synonyms |
Value |
Source |
Malvidin 3-(6-coumaroyl)-glucoside pyruvic acidHMDB
Malvidin 3-(6-coumaroyl)-glucoside pyruvic adductHMDB
Chemical Formlia |
C35H31O16
Average Molecliar Weight |
707.611
Monoisotopic Molecliar Weight |
707.161209944
IUPAC Name |
7-carboxy-11-hydroxy-3-(4-hydroxy-3,5-dimethoxyphenyl)-4-{[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-2λ⁴,8-dioxatricyclo[7.3.1.0⁵,¹³]trideca-1(13),2,4,6,9,11-hexaen-2-ylium
Traditional Name |
7-carboxy-11-hydroxy-3-(4-hydroxy-3,5-dimethoxyphenyl)-4-{[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-2λ⁴,8-dioxatricyclo[7.3.1.0⁵,¹³]trideca-1(13),2,4,6,9,11-hexaen-2-ylium
CAS Registry Number |
Not Available
SMILES |
COC1=CC(=CC(OC)=C1O)C1=[O+]C2=C3C(OC(=CC3=C1OC1O[C@H](COC(=O)C=CC3=CC=C(O)C=C3)[C@@H](O)[C@H](O)[C@H]1O)C(O)=O)=CC(O)=C2
InChI Identifier |
InChI=1S/C35H30O16/c1-45-22-9-16(10-23(46-2)28(22)39)32-33(19-13-24(34(43)44)48-20-11-18(37)12-21(49-32)27(19)20)51-35-31(42)30(41)29(40)25(50-35)14-47-26(38)8-5-15-3-6-17(36)7-4-15/h3-13,25,29-31,35,40-42H,14H2,1-2H3,(H3-,36,37,38,39,43,44)/p+1/t25-,29-,30+,31-,35?/m1/s1
InChI Key |
GOINLVYYMYVHAQ-CJKUAQFFSA-O
Chemical Taxonomy |
Description |
This compound belongs to the class of chemical entities known as anthocyanidin 3-o-6-p-coumaroyl glycosides. These are anthocyanidin 3-O-glycosides where the carbohydrate moiety is esterified at the C6 position with a p-coumaric acid. P-coumaric acid is an organic derivative of cinnamic acid, that carries a hydroxyl group at the 4-position of the benzene ring.
Kingdom |
Chemical entities
Super Class |
Organic compounds
Class |
Phenylpropanoids and polyketides
Sub Class |
Flavonoids
Direct Parent |
Anthocyanidin 3-O-6-p-coumaroyl glycosides
Alternative Parents |
Proanthocyanidins
Biflavonoids and polyflavonoids
Anthocyanidin-3-O-glycosides
Flavonoid-3-O-glycosides
3-O-methylated flavonoids
4-hydroxyflavonoids
7-hydroxyflavonoids
Anthocyanidins
Coumaric acid esters
Cinnamic acid esters
Coumaric acids and derivatives
O-glycosyl compounds
Methoxyphenols
Dimethoxybenzenes
1-benzopyrans
Styrenes
Anisoles
Phenoxy compounds
Fatty acid esters
1-hydroxy-2-unsubstituted benzenoids
Alkyl aryl ethers
Monosaccharides
Dicarboxylic acids and derivatives
Oxanes
Heteroaromatic compounds
Enoate esters
Secondary alcohols
Carboxylic acids
Polyols
Acetals
Oxacyclic compounds
Organic oxides
Carbonyl compounds
Hydrocarbon derivatives
Organic cations
Substituents |
Anthocyanidin 3-o-6-p-coumaroyl-glycoside
Proanthocyanidin
Bi- and polyflavonoid skeleton
Anthocyanin
Anthocyanidin-3-o-glycoside
Flavonoid-3-o-glycoside
3p-methoxyflavonoid-skeleton
Hydroxyflavonoid
4'-hydroxyflavonoid
7-hydroxyflavonoid
Anthocyanidin
Coumaric acid ester
Hydroxycinnamic acid or derivatives
Cinnamic acid or derivatives
Coumaric acid or derivatives
Cinnamic acid ester
Glycosyl compound
O-glycosyl compound
Methoxyphenol
1-benzopyran
Benzopyran
M-dimethoxybenzene
Dimethoxybenzene
Phenoxy compound
Anisole
Methoxybenzene
Styrene
Phenol ether
Fatty acid ester
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Fatty acyl
Benzenoid
Monocyclic benzene moiety
Oxane
Dicarboxylic acid or derivatives
Monosaccharide
Heteroaromatic compound
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Secondary alcohol
Carboxylic acid ester
Carboxylic acid
Ether
Acetal
Polyol
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic oxygen compound
Alcohol
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic cation
Aromatic heteropolycyclic compound
Molecliar Framework |
Aromatic heteropolycyclic compounds
External Descriptors |
Not Available
Ontology |
Status |
Expected but not Quantified
Origin |
Endogenous
Food
Biofunction |
Not Available
Application |
Nutrient
Cellliar locations |
Membrane
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 Solubility0.028 mg/mLALOGPS
logP3.19ALOGPS
logP3.8ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)2.11ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area244.27 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity183.94 m3·mol-1ChemAxon
Polarizability68.47 Å3ChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
Spectra |
Spectra |
Not Available
Biological Properties |
Cellliar Locations |
Membrane
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 |
66
Phenol Explorer Metabolite ID |
Not Available
FoodDB ID |
FDB000048
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 |
HMDB29239
Metagene Link |
HMDB29239
METLIN ID |
Not Available
PubChem Compound |
Not Available
PDB ID |
Not Available
ChEBI ID |
Not Available
Product: MK-1064
References |
Synthesis Reference |
Not Available |
Material Safety Data Sheet (MSDS) |
Not Available |
General References |
- Neveu V, Perez-Jimenez J, Vos F, Crespy V, du Chaffaut L, Mennen L, Knox C, Eisner R, Cruz J, Wishart D, Scalbert A: Phenol-Explorer: an online comprehensive database on polyphenol contents in foods. Database (Oxford). 2010;2010:bap024. doi: 10.1093/database/bap024. Epub 2010 Jan 8. [PubMed:20428313 ]
|
PMID: 9357513