3,5-dihydroxy-1,4-di(3,4,5-trihydroxyphenylcarbonyloxy)-1-cyclohexanecarboxylic acid

ID: ALA39530

Chembl Id: CHEMBL39530

PubChem CID: 475264

Max Phase: Preclinical

Molecular Formula: C21H20O14

Molecular Weight: 496.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O[C@H]1[C@H](O)C[C@](OC(=O)c2cc(O)c(O)c(O)c2)(C(=O)O)C[C@H]1O)c1cc(O)c(O)c(O)c1

Standard InChI:  InChI=1S/C21H20O14/c22-9-1-7(2-10(23)15(9)28)18(30)34-17-13(26)5-21(20(32)33,6-14(17)27)35-19(31)8-3-11(24)16(29)12(25)4-8/h1-4,13-14,17,22-29H,5-6H2,(H,32,33)/t13-,14-,17-,21+/m1/s1

Standard InChI Key:  UTNZIIOILCFURH-YQMRLJPGSA-N

Alternative Forms

1. Parent:

   

   ALA39530

   (3R,5R)-3,5-dihydroxy-1,4-bis[(3,4,5-trihydroxybenzoyl)oxy]cyclohexanecarboxylic 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: 496.38

Molecular Weight (Monoisotopic): 496.0853

AlogP: -0.36

#Rotatable Bonds: 5

Polar Surface Area: 251.74

Molecular Species: ACID

HBA: 13

HBD: 9

#RO5 Violations: 2

HBA (Lipinski): 14

HBD (Lipinski): 9

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 2.62

CX Basic pKa: ┄

CX LogP: 0.47

CX LogD: -3.19

Aromatic Rings: 2

Heavy Atoms: 35

QED Weighted: 0.19

Np Likeness Score: 1.39

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]

Source

Source(1):

• Scientific Literature