3-Amino-5-{[[1-benzyl-3-(3-tert-butylcarbamoyl-octahydro-isoquinolin-2-yl)-2-hydroxy-propylcarbamoyl]-(tetrahydro-furan-3-yl)-methyl]-amino}-6-chloro-pyrazine-2-carboxylic acid methyl ester

ID: ALA306974

Chembl Id: CHEMBL306974

PubChem CID: 515895

Max Phase: Preclinical

Molecular Formula: C36H52ClN7O6

Molecular Weight: 714.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)c1nc(Cl)c(N[C@H](C(=O)N[C@@H](Cc2ccccc2)[C@H](O)CN2C[C@H]3CCCC[C@H]3C[C@H]2C(=O)NC(C)(C)C)[C@H]2CCOC2)nc1N

Standard InChI:  InChI=1S/C36H52ClN7O6/c1-36(2,3)43-33(46)26-17-22-12-8-9-13-23(22)18-44(26)19-27(45)25(16-21-10-6-5-7-11-21)39-34(47)28(24-14-15-50-20-24)41-32-30(37)40-29(31(38)42-32)35(48)49-4/h5-7,10-11,22-28,45H,8-9,12-20H2,1-4H3,(H,39,47)(H,43,46)(H3,38,41,42)/t22-,23+,24-,25-,26-,27+,28-/m0/s1

Standard InChI Key:  LCKITJOWWCXRAD-DCZJRQIWSA-N

Alternative Forms

1. Parent:

   

   ALA306974

   methyl 5-{[(S)-{[(2S,3R)-4-[(3S,4aS,8aS)-3-(tert-butylcarbamoyl)-decahydroisoquinolin-2-yl]-3-hydroxy-1-phenylbutan-2-yl]carbamoyl}(3R)-oxolan-3-ylmethyl]amino}-3-amino-6-chloropyrazine-2-carboxylate

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: 714.31

Molecular Weight (Monoisotopic): 713.3668

AlogP: 3.20

#Rotatable Bonds: 12

Polar Surface Area: 181.03

Molecular Species: NEUTRAL

HBA: 11

HBD: 5

#RO5 Violations: 2

HBA (Lipinski): 13

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 12.00

CX Basic pKa: 8.47

CX LogP: 3.71

CX LogD: 2.60

Aromatic Rings: 2

Heavy Atoms: 50

QED Weighted: 0.20

Np Likeness Score: 0.00

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]

Source

Source(1):

• Scientific Literature