5-[1-(3'-adamantan-1-yl-2-chloro-4'-hydroxy-biphenyl-4-yl)-meth-(Z)-ylidene]-thiazolidine-2,4-dione

ID: ALA376571

Chembl Id: CHEMBL376571

PubChem CID: 44423905

Max Phase: Preclinical

Molecular Formula: C26H24ClNO3S

Molecular Weight: 466.00

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1NC(=O)/C(=C/c2ccc(-c3ccc(O)c(C45CC6CC(CC(C6)C4)C5)c3)c(Cl)c2)S1

Standard InChI:  InChI=1S/C26H24ClNO3S/c27-21-8-14(9-23-24(30)28-25(31)32-23)1-3-19(21)18-2-4-22(29)20(10-18)26-11-15-5-16(12-26)7-17(6-15)13-26/h1-4,8-10,15-17,29H,5-7,11-13H2,(H,28,30,31)/b23-9-

Standard InChI Key:  CLYLAPYROSOQCD-AQHIEDMUSA-N

Alternative Forms

1. Parent:

   

   ALA376571

   (5Z)-5-[[4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-chlorophenyl]methylidene]-1,3-thiazolidine-2,4-dione

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: 466.00

Molecular Weight (Monoisotopic): 465.1165

AlogP: 6.50

#Rotatable Bonds: 3

Polar Surface Area: 66.40

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 6.35

CX Basic pKa: ┄

CX LogP: 6.15

CX LogD: 5.11

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.51

Np Likeness Score: -0.43

References

1. Dawson MI, Xia Z, Liu G, Ye M, Fontana JA, Farhana L, Patel BB, Arumugarajah S, Bhuiyan M, Zhang XK, Han YH, Stallcup WB, Fukushi J, Mustelin T, Tautz L, Su Y, Harris DL, Waleh N, Hobbs PD, Jong L, Chao WR, Schiff LJ, Sani BP..  (2007)  An adamantyl-substituted retinoid-derived molecule that inhibits cancer cell growth and angiogenesis by inducing apoptosis and binds to small heterodimer partner nuclear receptor: effects of modifying its carboxylate group on apoptosis, proliferation, and protein-tyrosine phosphatase activity.,  50  (11): [PMID:17489579] [10.1021/jm0613323]

Source

Source(1):

• Scientific Literature