Quinoline-2-carboxylic acid {1-[1-benzyl-3-(3-tert-butylcarbamoyl-octahydro-isoquinolin-2-yl)-2-hydroxy-propylcarbamoyl]-2-methyl-propyl}-amide

ID: ALA75082

Chembl Id: CHEMBL75082

PubChem CID: 464721

Max Phase: Preclinical

Molecular Formula: C39H53N5O4

Molecular Weight: 655.88

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)[C@H](NC(=O)c1ccc2ccccc2n1)C(=O)N[C@@H](Cc1ccccc1)[C@H](O)CN1C[C@H]2CCCC[C@H]2C[C@H]1C(=O)NC(C)(C)C

Standard InChI:  InChI=1S/C39H53N5O4/c1-25(2)35(42-36(46)31-20-19-27-15-11-12-18-30(27)40-31)38(48)41-32(21-26-13-7-6-8-14-26)34(45)24-44-23-29-17-10-9-16-28(29)22-33(44)37(47)43-39(3,4)5/h6-8,11-15,18-20,25,28-29,32-35,45H,9-10,16-17,21-24H2,1-5H3,(H,41,48)(H,42,46)(H,43,47)/t28-,29+,32-,33-,34+,35-/m0/s1

Standard InChI Key:  NIQINMSYVZRSSS-MSNCXEFOSA-N

Alternative Forms

1. Parent:

   

   ALA75082

   (3S,4aS,8aS)-N-tert-butyl-2-[(2R,3S)-2-hydroxy-3-[(2S)-3-methyl-2-(quinolin-2-ylformamido)butanamido]-4-phenylbutyl]-decahydroisoquinoline-3-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: 655.88

Molecular Weight (Monoisotopic): 655.4098

AlogP: 4.87

#Rotatable Bonds: 11

Polar Surface Area: 123.66

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.69

CX Basic pKa: 8.47

CX LogP: 5.49

CX LogD: 4.38

Aromatic Rings: 3

Heavy Atoms: 48

QED Weighted: 0.23

Np Likeness Score: -0.17

References

1. Ghosh AK, Thompson WJ, Holloway MK, McKee SP, Duong TT, Lee HY, Munson PM, Smith AM, Wai JM, Darke PL..  (1993)  Potent HIV protease inhibitors: the development of tetrahydrofuranylglycines as novel P2-ligands and pyrazine amides as P3-ligands.,  36  (16): [PMID:8360874] [10.1021/jm00068a006]

2. Park C, Choi H, Son Y, Lee CS, Choy N, Koh JS, Lee TG, Kwon YD, Kim SC, Yoon H.  (1996)  -Methanesulfonyl-L-valine as a novel, unnatural amino acid surrogate for P2 in the design of HIV protease inhibitors.,  6  (6): [10.1016/0960-894X(96)00086-8]

Source

Source(1):

• Scientific Literature