5-[3,4-dihydroxy-5-(3,4,5-trihydroxyphenylcarbonyloxy)phenylcarbonyloxy]-3,4-dihydroxy-1-cyclohexene-1-carboxylic acid

ID: ALA39413

Chembl Id: CHEMBL39413

Cas Number: 95719-52-1

PubChem CID: 475266

Max Phase: Preclinical

Molecular Formula: C21H18O13

Molecular Weight: 478.36

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 3-O-Digalloylshikimic Acid | 3-O-Digalloylshikimic acid|95719-52-1|CHEMBL39413|(3R,4R,5R)-5-({3,4-Dihydroxy-5-[(3,4,5-trihydroxybenzoyl)oxy]benzoyl}oxy)-3,4-dihydroxycyclohex-1-ene-1-carboxylic acid|DTXSID70914842|BDBM50260543|(3R,4R,5R)-5-[3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyl)oxy-benzoyl]oxy-3,4-dihydroxy-cyclohexene-1-carboxylic acid|5-({3,4-Dihydroxy-5-[(3,4,5-trihydroxybenzoyl)oxy]benzoyl}oxy)-3,4-dihydroxycyclohex-1-ene-1-carboxylic acid|Benzoic acid, 3,4(or 3,5)-dihydroxy-5(or 4)-[(3,4Show More⌵

Canonical SMILES:  O=C(O)C1=C[C@@H](O)[C@@H](O)[C@H](OC(=O)c2cc(O)c(O)c(OC(=O)c3cc(O)c(O)c(O)c3)c2)C1

Standard InChI:  InChI=1S/C21H18O13/c22-10-2-8(3-11(23)16(10)26)20(31)34-15-6-9(4-13(25)18(15)28)21(32)33-14-5-7(19(29)30)1-12(24)17(14)27/h1-4,6,12,14,17,22-28H,5H2,(H,29,30)/t12-,14-,17-/m1/s1

Standard InChI Key:  PKRKPJWPNZPNCK-SUYBPPKGSA-N

Alternative Forms

1. Parent:

   

   ALA39413

   3-O-Digalloylshikimic acid

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 478.36

Molecular Weight (Monoisotopic): 478.0747

AlogP: 0.10

#Rotatable Bonds: 5

Polar Surface Area: 231.51

Molecular Species: ACID

HBA: 12

HBD: 8

#RO5 Violations: 2

HBA (Lipinski): 13

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.04

CX Basic pKa: ┄

CX LogP: 1.65

CX LogD: -1.92

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.16

Np Likeness Score: 1.41

References

1. Kilkuskie RE, Kashiwada Y, Nonaka G, Nishioka I, Bodner AJ, Cheng Y, Lee K.  (1992)  HIV and reverse transcriptase inhibition by tannins,  2  (12): [10.1016/S0960-894X(00)80422-9]

2. Kashiwada Y, Nonaka G, Nishioka I, Ballas LM, Jiang JB, Janzen WP, Lee K.  (1992)  Tannins as selective inhibitors of protein kinase C,  2  (3): [10.1016/S0960-894X(01)81072-6]

3. Kashiwada Y, Nonaka G, Nishioka I, Chang JJ, Lee KH..  (1992)  Antitumor agents, 129. Tannins and related compounds as selective cytotoxic agents.,  55  (8): [PMID:1431932] [10.1021/np50086a002]

Source

Source(1):

• Scientific Literature