2-((3R,5R,6S)-1-((S)-1-tert-butoxy-1-oxobutan-2-yl)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methyl-2-oxopiperidin-3-yl)acetic acid

ID: ALA2059300

Chembl Id: CHEMBL2059300

PubChem CID: 56591154

Max Phase: Preclinical

Molecular Formula: C28H33Cl2NO5

Molecular Weight: 534.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC[C@@H](C(=O)OC(C)(C)C)N1C(=O)[C@@](C)(CC(=O)O)C[C@H](c2cccc(Cl)c2)[C@H]1c1ccc(Cl)cc1

Standard InChI:  InChI=1S/C28H33Cl2NO5/c1-6-22(25(34)36-27(2,3)4)31-24(17-10-12-19(29)13-11-17)21(18-8-7-9-20(30)14-18)15-28(5,26(31)35)16-23(32)33/h7-14,21-22,24H,6,15-16H2,1-5H3,(H,32,33)/t21-,22+,24-,28-/m1/s1

Standard InChI Key:  BTIJKFCQUAULPU-YEPCPMPXSA-N

Alternative Forms

1. Parent:

   

   ALA2059300

   2-((3R,5R,6S)-1-((S)-1-tert-butoxy-1-oxobutan-2-yl)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methyl-2-oxopiperidin-3-yl)acetic 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: 534.48

Molecular Weight (Monoisotopic): 533.1736

AlogP: 6.65

#Rotatable Bonds: 7

Polar Surface Area: 83.91

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 4.20

CX Basic pKa: ┄

CX LogP: 6.57

CX LogD: 3.54

Aromatic Rings: 2

Heavy Atoms: 36

QED Weighted: 0.40

Np Likeness Score: -0.21

References

1. Bernard D, Zhao Y, Wang S..  (2012)  AM-8553: a novel MDM2 inhibitor with a promising outlook for potential clinical development.,  55  (11): [PMID:22624960] [10.1021/jm3007068]

2. Rew Y, Sun D, Gonzalez-Lopez De Turiso F, Bartberger MD, Beck HP, Canon J, Chen A, Chow D, Deignan J, Fox BM, Gustin D, Huang X, Jiang M, Jiao X, Jin L, Kayser F, Kopecky DJ, Li Y, Lo MC, Long AM, Michelsen K, Oliner JD, Osgood T, Ragains M, Saiki AY, Schneider S, Toteva M, Yakowec P, Yan X, Ye Q, Yu D, Zhao X, Zhou J, Medina JC, Olson SH..  (2012)  Structure-based design of novel inhibitors of the MDM2-p53 interaction.,  55  (11): [PMID:22524527] [10.1021/jm300354j]

Source

Source(1):

• Scientific Literature