ID: ALA396176

Max Phase: Preclinical

Molecular Formula: C15H13NO8S

Molecular Weight: 367.34

Molecule Type: Small molecule

Representations

Canonical SMILES:  COc1ccc(/C=C2\SC(=O)N(CC(=O)O)C2=O)cc1OCC(=O)O

Standard InChI:  InChI=1S/C15H13NO8S/c1-23-9-3-2-8(4-10(9)24-7-13(19)20)5-11-14(21)16(6-12(17)18)15(22)25-11/h2-5H,6-7H2,1H3,(H,17,18)(H,19,20)/b11-5-

Standard InChI Key:  DLKPSHJFPIKYCB-WZUFQYTHSA-N

Molecule Features

Natural Product: No

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

Properties

Molecular Weight: 367.34

Molecular Weight (Monoisotopic): 367.0362

AlogP: 1.28

#Rotatable Bonds: 7

Polar Surface Area: 130.44

Molecular Species: ACID

HBA: 7

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 2.75

CX Basic pKa:

CX LogP: 0.71

CX LogD: -6.22

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.68

Np Likeness Score: -1.23

References

1. Maccari R, Ottanà R, Ciurleo R, Vigorita MG, Rakowitz D, Steindl T, Langer T..  (2007)  Evaluation of in vitro aldose redutase inhibitory activity of 5-arylidene-2,4-thiazolidinediones.,  17  (14): [PMID:17512196] [10.1016/j.bmcl.2007.04.109]

2. Carbone V, Giglio M, Chung R, Huyton T, Adams J, Maccari R, Ottana R, Hara A, El-Kabbani O..  (2010)  Structure of aldehyde reductase in ternary complex with a 5-arylidene-2,4-thiazolidinedione aldose reductase inhibitor.,  45  (3): [PMID:20036445] [10.1016/j.ejmech.2009.12.019]

Source

Source(1):

• Scientific Literature