4-[(S)-2-(3-Chloro-phenyl)-2-hydroxy-ethylamino]-3-[6-(1,4-dioxa-8-aza-spiro[4.5]dec-8-yl)-4-methyl-1H-benzoimidazol-2-yl]-1H-pyridin-2-one

ID: ALA482101

Chembl Id: CHEMBL482101

PubChem CID: 135960715

Max Phase: Preclinical

Molecular Formula: C28H30ClN5O4

Molecular Weight: 536.03

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(N2CCC3(CC2)OCCO3)cc2[nH]c(-c3c(NC[C@@H](O)c4cccc(Cl)c4)cc[nH]c3=O)nc12

Standard InChI:  InChI=1S/C28H30ClN5O4/c1-17-13-20(34-9-6-28(7-10-34)37-11-12-38-28)15-22-25(17)33-26(32-22)24-21(5-8-30-27(24)36)31-16-23(35)18-3-2-4-19(29)14-18/h2-5,8,13-15,23,35H,6-7,9-12,16H2,1H3,(H,32,33)(H2,30,31,36)/t23-/m1/s1

Standard InChI Key:  OQEBLEZRSCIFJK-HSZRJFAPSA-N

Alternative Forms

1. Parent:

   

   ALA482101

   ---

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: 536.03

Molecular Weight (Monoisotopic): 535.1986

AlogP: 4.37

#Rotatable Bonds: 6

Polar Surface Area: 115.50

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.58

CX Basic pKa: 3.79

CX LogP: 3.73

CX LogD: 3.73

Aromatic Rings: 4

Heavy Atoms: 38

QED Weighted: 0.29

Np Likeness Score: -0.95

References

1. Zimmermann K, Wittman MD, Saulnier MG, Velaparthi U, Langley DR, Sang X, Frennesson D, Carboni J, Li A, Greer A, Gottardis M, Attar RM, Yang Z, Balimane P, Discenza LN, Vyas D..  (2008)  Balancing oral exposure with Cyp3A4 inhibition in benzimidazole-based IGF-IR inhibitors.,  18  (14): [PMID:18572407] [10.1016/j.bmcl.2008.05.104]

2. Zimmermann K, Wittman MD, Saulnier MG, Velaparthi U, Sang X, Frennesson DB, Struzynski C, Seitz SP, He L, Carboni JM, Li A, Greer AF, Gottardis M, Attar RM, Yang Z, Balimane P, Discenza LN, Lee FY, Sinz M, Kim S, Vyas D..  (2010)  SAR of PXR transactivation in benzimidazole-based IGF-1R kinase inhibitors.,  20  (5): [PMID:20153189] [10.1016/j.bmcl.2010.01.087]

Source

Source(1):

• Scientific Literature