3,4,5-Trihydroxy-benzoic acid (1R,5R,6R)-3-carboxy-5,6-dihydroxy-cyclohex-3-enyl ester

ID: ALA289369

Chembl Id: CHEMBL289369

Cas Number: 95719-51-0

PubChem CID: 460897

Max Phase: Preclinical

Molecular Formula: C14H14O9

Molecular Weight: 326.26

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 3-O-Galloylshikimic Acid | 5-Galloylshikimic acid|9XEH2JM56J|CHEMBL289369|95719-51-0|(3R,4R,5R)-3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyl)oxycyclohexene-1-carboxylic acid|Benzoic acid, 3,4,5-trihydroxy-, (1R,5R,6R)-3-carboxy-5,6-dihydroxy-3-cyclohexen-1-yl ester|5-0-Galloylshikimicacid|UNII-9XEH2JM56J|BDBM50469569|AKOS040736337|Q27273345|(3R,4R,5R)-3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyl)oxy-cyclohexene-1-carboxylic acid|(3R,4R,5R)-3,4-Dihydroxy-5-(3,4,5-trihydroxyphenylcarbonyloxy)cyclohex-1-enShow More⌵

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

Standard InChI:  InChI=1S/C14H14O9/c15-7-2-6(3-8(16)11(7)18)14(22)23-10-4-5(13(20)21)1-9(17)12(10)19/h1-3,9-10,12,15-19H,4H2,(H,20,21)/t9-,10-,12-/m1/s1

Standard InChI Key:  NTNQTAISNHFKRA-CKYFFXLPSA-N

Alternative Forms

1. Parent:

   

   ALA289369

   5-Galloylshikimic 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: 326.26

Molecular Weight (Monoisotopic): 326.0638

AlogP: -0.53

#Rotatable Bonds: 3

Polar Surface Area: 164.75

Molecular Species: ACID

HBA: 8

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.09

CX Basic pKa: ┄

CX LogP: -0.06

CX LogD: -3.60

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.32

Np Likeness Score: 1.87

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