Quinoline-2-carboxylic acid [(S)-[(1S,2R)-1-benzyl-3-((3S,4aS,8aS)-3-tert-butylcarbamoyl-octahydro-isoquinolin-2-yl)-2-hydroxy-propylcarbamoyl]-(tetrahydro-furan-3-yl)-methyl]-amide

ID: ALA17612

Chembl Id: CHEMBL17612

PubChem CID: 44271787

Max Phase: Preclinical

Molecular Formula: C40H53N5O5

Molecular Weight: 683.89

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C)NC(=O)[C@@H]1C[C@@H]2CCCC[C@@H]2CN1C[C@@H](O)[C@H](Cc1ccccc1)NC(=O)[C@@H](NC(=O)c1ccc2ccccc2n1)C1CCOC1

Standard InChI:  InChI=1S/C40H53N5O5/c1-40(2,3)44-38(48)34-22-28-14-7-8-15-29(28)23-45(34)24-35(46)33(21-26-11-5-4-6-12-26)42-39(49)36(30-19-20-50-25-30)43-37(47)32-18-17-27-13-9-10-16-31(27)41-32/h4-6,9-13,16-18,28-30,33-36,46H,7-8,14-15,19-25H2,1-3H3,(H,42,49)(H,43,47)(H,44,48)/t28-,29+,30?,33-,34-,35+,36-/m0/s1

Standard InChI Key:  JPWJMZNJZWAWDA-JPRBTODASA-N

Alternative Forms

1. Parent:

   

   ALA17612

   N-[(1S)-2-[[(2S,3R)-4-[(3S,4aS,8aS)-3-(tert-butylcarbamoyl)-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinolin-2-yl]-3-hydroxy-1-phenylbutan-2-yl]amino]-2-oxo-1-(oxolan-3-yl)ethyl]quinoline-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: 683.89

Molecular Weight (Monoisotopic): 683.4047

AlogP: 4.25

#Rotatable Bonds: 11

Polar Surface Area: 132.89

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.64

CX Basic pKa: 8.47

CX LogP: 4.27

CX LogD: 3.16

Aromatic Rings: 3

Heavy Atoms: 50

QED Weighted: 0.24

Np Likeness Score: -0.07

References

1. Ghosh AK, Lee HY, Thompson WJ, Culberson C, Holloway MK, McKee SP, Munson PM, Duong TT, Smith AM, Darke PL..  (1994)  The development of cyclic sulfolanes as novel and high-affinity P2 ligands for HIV-1 protease inhibitors.,  37  (8): [PMID:8164260] [10.1021/jm00034a016]

2. 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]

3. Holloway MK, Wai JM, Halgren TA, Fitzgerald PM, Vacca JP, Dorsey BD, Levin RB, Thompson WJ, Chen LJ, deSolms SJ..  (1995)  A priori prediction of activity for HIV-1 protease inhibitors employing energy minimization in the active site.,  38  (2): [PMID:7830273] [10.1021/jm00002a012]

4. Pérez C, Pastor M, Ortiz AR, Gago F..  (1998)  Comparative binding energy analysis of HIV-1 protease inhibitors: incorporation of solvent effects and validation as a powerful tool in receptor-based drug design.,  41  (6): [PMID:9526559] [10.1021/jm970535b]

5. Kumari S,Carmona AV,Tiwari AK,Trippier PC.  (2020)  Amide Bond Bioisosteres: Strategies, Synthesis, and Successes.,  63  (21.0): [PMID:32686940] [10.1021/acs.jmedchem.0c00530]

Source

Source(1):

• Scientific Literature