(1R,2S,5S)-N-((2S,3R)-4-amino-1-cyclobutyl-3-hydroxy-4-oxobutan-2-yl)-3-((S)-2-(3-tert-butylureido)-3,3-dimethylbutanoyl)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxamide

ID: ALA3542332

Chembl Id: CHEMBL3542332

PubChem CID: 71316139

Max Phase: Preclinical

Molecular Formula: C27H47N5O5

Molecular Weight: 521.70

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C)NC(=O)N[C@H](C(=O)N1C[C@H]2[C@@H]([C@H]1C(=O)N[C@@H](CC1CCC1)[C@@H](O)C(N)=O)C2(C)C)C(C)(C)C

Standard InChI:  InChI=1S/C27H47N5O5/c1-25(2,3)20(30-24(37)31-26(4,5)6)23(36)32-13-15-17(27(15,7)8)18(32)22(35)29-16(19(33)21(28)34)12-14-10-9-11-14/h14-20,33H,9-13H2,1-8H3,(H2,28,34)(H,29,35)(H2,30,31,37)/t15-,16-,17-,18-,19+,20+/m0/s1

Standard InChI Key:  FEBWCINGHXXUCV-GFLQDLJJSA-N

Alternative Forms

1. Parent:

   

   ALA3542332

   (1R,2S,5S)-N-[(2S,3R)-4-amino-1-cyclobutyl-3-hydroxy-4-oxobutan-2-yl]-3-[N-(tert-butylcarbamoyl)-3-methyl-L-valyl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxamide

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: 521.70

Molecular Weight (Monoisotopic): 521.3577

AlogP: 1.50

#Rotatable Bonds: 8

Polar Surface Area: 153.86

Molecular Species: NEUTRAL

HBA: 5

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.54

CX Basic pKa: ┄

CX LogP: 0.86

CX LogD: 0.86

Aromatic Rings: ┄

Heavy Atoms: 37

QED Weighted: 0.33

Np Likeness Score: 0.32

References

1. Ghosal A, Yuan Y, Tong W, Su AD, Gu C, Chowdhury SK, Kishnani NS, Alton KB..  (2011)  Characterization of human liver enzymes involved in the biotransformation of boceprevir, a hepatitis C virus protease inhibitor.,  39  (3): [PMID:21123164] [10.1124/dmd.110.036996]

Source

Source(1):

• Scientific Literature