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Grape Seed Extract

Grape Seed Extract

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Also known as: 84929-27-1, (2r,3s,4s)-2-(3,4-dihydroxyphenyl)-4-[(2r,3r)-2-(3,4-dihydroxyphenyl)-3,7-dihydroxy-3,5-dimethyl-2,4-dihydrochromen-8-yl]-3,4-dihydro-2h-chromene-3,5,7-triol, Grape seed p.e., Grape,red, ext., Ccg-270162, As-83774

Molecular Formula

C₃₂H₃₀O₁₁

Molecular Weight

590.6 g/mol

InChI Key

VWKAFYWVDIOMSL-PMFFMQSYSA-N

Exudate from seeds of the grape plant Vitis vinifera, composed of oils and secondary plant metabolites (BIOFLAVONOIDS and polyphenols) credited with important medicinal properties.

1 2D Structure

Grape Seed Extract

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2R,3S,4S)-2-(3,4-dihydroxyphenyl)-4-[(2R,3R)-2-(3,4-dihydroxyphenyl)-3,7-dihydroxy-3,5-dimethyl-2,4-dihydrochromen-8-yl]-3,4-dihydro-2H-chromene-3,5,7-triol

2.1.2 InChI

InChI=1S/C32H30O11/c1-13-7-22(38)26(30-17(13)12-32(2,41)31(43-30)15-4-6-19(35)21(37)9-15)27-25-23(39)10-16(33)11-24(25)42-29(28(27)40)14-3-5-18(34)20(36)8-14/h3-11,27-29,31,33-41H,12H2,1-2H3/t27-,28-,29+,31+,32+/m0/s1

2.1.3 InChI Key

VWKAFYWVDIOMSL-PMFFMQSYSA-N

2.1.4 Canonical SMILES

CC1=CC(=C(C2=C1CC(C(O2)C3=CC(=C(C=C3)O)O)(C)O)C4C(C(OC5=CC(=CC(=C45)O)O)C6=CC(=C(C=C6)O)O)O)O

2.1.5 Isomeric SMILES

CC1=CC(=C(C2=C1C[C@@]([C@H](O2)C3=CC(=C(C=C3)O)O)(C)O)[C@H]4[C@@H]([C@H](OC5=CC(=CC(=C45)O)O)C6=CC(=C(C=C6)O)O)O)O

2.2 Synonyms

2.2.1 MeSH Synonyms

1. Extract, Grape Seed

2. Seed Extract, Grape

2.2.2 Depositor-Supplied Synonyms

1. 84929-27-1

2. (2r,3s,4s)-2-(3,4-dihydroxyphenyl)-4-[(2r,3r)-2-(3,4-dihydroxyphenyl)-3,7-dihydroxy-3,5-dimethyl-2,4-dihydrochromen-8-yl]-3,4-dihydro-2h-chromene-3,5,7-triol

3. Grape Seed P.e.

4. Grape,red, Ext.

5. Ccg-270162

6. As-83774

2.3 Create Date

2014-10-15

3 Chemical and Physical Properties

Molecular Formula	C₃₂H₃₀O₁₁
Molecular Weight	590.6 g/mol
XLogP3	3.3
Hydrogen Bond Donor Count	9
Hydrogen Bond Acceptor Count	11
Rotatable Bond Count	3
Exact Mass	590.17881177 g/mol
Monoisotopic Mass	590.17881177 g/mol
Topological Polar Surface Area	201 Å²
Heavy Atom Count	43
Formal Charge	0
Complexity	970
Isotope Atom Count	0
Defined Atom Stereocenter Count	5
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Antineoplastic Agents, Phytogenic

Agents obtained from higher plants that have demonstrable cytostatic or antineoplastic activity. (See all compounds classified as Antineoplastic Agents, Phytogenic.)

Antioxidants

Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues. (See all compounds classified as Antioxidants.)