1-Hydroxy-6-phenyl-4-trifluoromethyl-1H-indole-2-carboxylic Acid

ID: ALA1688790

Chembl Id: CHEMBL1688790

Cas Number: 1269802-68-7

PubChem CID: 46893144

Max Phase: Preclinical

Molecular Formula: C16H10F3NO3

Molecular Weight: 321.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1cc2c(C(F)(F)F)cc(-c3ccccc3)cc2n1O

Standard InChI:  InChI=1S/C16H10F3NO3/c17-16(18,19)12-6-10(9-4-2-1-3-5-9)7-13-11(12)8-14(15(21)22)20(13)23/h1-8,23H,(H,21,22)

Standard InChI Key:  KGXDBNBXAPVUIM-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA1688790

   1-Hydroxy-4-(trifluoromethyl)-6-phenyl-1H-indole-2-carboxylic acid

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

Calculated Properties

Molecular Weight: 321.25

Molecular Weight (Monoisotopic): 321.0613

AlogP: 4.26

#Rotatable Bonds: 2

Polar Surface Area: 62.46

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.43

CX Basic pKa: ┄

CX LogP: 3.50

CX LogD: 0.11

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.69

Np Likeness Score: -0.55

References

1. Granchi C, Roy S, Giacomelli C, Macchia M, Tuccinardi T, Martinelli A, Lanza M, Betti L, Giannaccini G, Lucacchini A, Funel N, León LG, Giovannetti E, Peters GJ, Palchaudhuri R, Calvaresi EC, Hergenrother PJ, Minutolo F..  (2011)  Discovery of N-hydroxyindole-based inhibitors of human lactate dehydrogenase isoform A (LDH-A) as starvation agents against cancer cells.,  54  (6): [PMID:21332213] [10.1021/jm101007q]

2. Ward RA, Brassington C, Breeze AL, Caputo A, Critchlow S, Davies G, Goodwin L, Hassall G, Greenwood R, Holdgate GA, Mrosek M, Norman RA, Pearson S, Tart J, Tucker JA, Vogtherr M, Whittaker D, Wingfield J, Winter J, Hudson K..  (2012)  Design and synthesis of novel lactate dehydrogenase A inhibitors by fragment-based lead generation.,  55  (7): [PMID:22417091] [10.1021/jm201734r]

Source

Source(1):

• Scientific Literature