3'-Chloro-4-methyl-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl-5'-carboxylic acid [[1-benzyl-3-(3-tert-butylcarbamoyl-octahydro-isoquinolin-2-yl)-2-hydroxy-propylcarbamoyl]-(tetrahydro-furan-3-yl)-methyl]-amide

ID: ALA310924

Chembl Id: CHEMBL310924

PubChem CID: 515894

Max Phase: Preclinical

Molecular Formula: C40H59ClN8O5

Molecular Weight: 767.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1CCN(c2ncc(C(=O)N[C@H](C(=O)N[C@@H](Cc3ccccc3)[C@H](O)CN3C[C@H]4CCCC[C@H]4C[C@H]3C(=O)NC(C)(C)C)[C@H]3CCOC3)nc2Cl)CC1

Standard InChI:  InChI=1S/C40H59ClN8O5/c1-40(2,3)46-38(52)32-21-27-12-8-9-13-28(27)23-49(32)24-33(50)30(20-26-10-6-5-7-11-26)44-39(53)34(29-14-19-54-25-29)45-37(51)31-22-42-36(35(41)43-31)48-17-15-47(4)16-18-48/h5-7,10-11,22,27-30,32-34,50H,8-9,12-21,23-25H2,1-4H3,(H,44,53)(H,45,51)(H,46,52)/t27-,28+,29-,30-,32-,33+,34-/m0/s1

Standard InChI Key:  OEBPYTHAFYTQCV-ONKMLZBSSA-N

Alternative Forms

1. Parent:

   

   ALA310924

   (3S,4aS,8aS)-N-(tert-Butyl)-2-[(2R,3S)-3-({(2S)-2-({[6-chloro-5-(4-methylpiperazin-1-yl)pyrazin-2-yl]carbonyl}amino)-2-[(3R)-tetrahydrofuran-3-yl]acetyl}amino)-2-hydroxy-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: 767.42

Molecular Weight (Monoisotopic): 766.4297

AlogP: 2.90

#Rotatable Bonds: 12

Polar Surface Area: 152.26

Molecular Species: NEUTRAL

HBA: 10

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 13

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 13.30

CX Basic pKa: 8.47

CX LogP: 3.05

CX LogD: 1.90

Aromatic Rings: 2

Heavy Atoms: 54

QED Weighted: 0.25

Np Likeness Score: -0.32

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