4-[(1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-[[2-(1,1-dioxido-4-thiomorpholinyl)ethyl]amino]-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13boctadecahydro-5a,5b,8,8,11a-pentamethyl-1-(1-methylethenyl)-1H-cyclopenta[a]chrysen-9-yl]-benzoic acid

ID: ALA3827379

Chembl Id: CHEMBL3827379

Cas Number: 1392312-45-6

PubChem CID: 60152109

Max Phase: Phase

Molecular Formula: C42H62N2O4S

Molecular Weight: 691.04

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Bms-955176 | BMS-955176 | GSK-3532795 | BMS-955176|1392312-45-6|GSK3532795|BMS-955176 free base|4CA9IAU7RJ|GSK-3532795|1392312-45-6 (free base)|BMS-955176 TFA|Benzoic acid, 4-(17-((2-(1,1-dioxido-4-thiomorpholinyl)ethyl)amino)-28-norlupa-2,20(29)-dien-3-yl)-|2097784-79-5|UNII-4CA9IAU7RJ|CHEMBL3827379|SCHEMBL12697862|XDMUFNNPLXHNKA-ZTESCHFWSA-N|DTXSID401336145|EX-A3677|BDBM50450015|BMS955176|AKOS040733323|DB15193|BMS-955176?|AC-36687|MS-31132|HY-112714|CS-0062829|4((1R,3aS,5aR,5bR,7aR,11aS,11bR,1Show More⌵

Canonical SMILES:  C=C(C)[C@@H]1CC[C@]2(NCCN3CCS(=O)(=O)CC3)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC=C(c6ccc(C(=O)O)cc6)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]12

Standard InChI:  InChI=1S/C42H62N2O4S/c1-28(2)31-14-19-42(43-22-23-44-24-26-49(47,48)27-25-44)21-20-40(6)33(36(31)42)12-13-35-39(5)17-15-32(29-8-10-30(11-9-29)37(45)46)38(3,4)34(39)16-18-41(35,40)7/h8-11,15,31,33-36,43H,1,12-14,16-27H2,2-7H3,(H,45,46)/t31-,33+,34-,35+,36+,39-,40+,41+,42-/m0/s1

Standard InChI Key:  XDMUFNNPLXHNKA-ZTESCHFWSA-N

Alternative Forms

1. Parent:

   

   ALA3827379

   BMS-955176

2. Alternative Forms:

   

   ALA3827379

   ---

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: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 691.04

Molecular Weight (Monoisotopic): 690.4430

AlogP: 8.11

#Rotatable Bonds: 7

Polar Surface Area: 86.71

Molecular Species: ZWITTERION

HBA: 5

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 4.10

CX Basic pKa: 10.55

CX LogP: 4.49

CX LogD: 4.49

Aromatic Rings: 1

Heavy Atoms: 49

QED Weighted: 0.28

Np Likeness Score: 1.22

References

1. Regueiro-Ren A, Liu Z, Chen Y, Sin N, Sit SY, Swidorski JJ, Chen J, Venables BL, Zhu J, Nowicka-Sans B, Protack T, Lin Z, Terry B, Samanta H, Zhang S, Li Z, Beno BR, Huang XS, Rahematpura S, Parker DD, Haskell R, Jenkins S, Santone KS, Cockett MI, Krystal M, Meanwell NA, Hanumegowda U, Dicker IB..  (2016)  Discovery of BMS-955176, a Second Generation HIV-1 Maturation Inhibitor with Broad Spectrum Antiviral Activity.,  7  (6): [PMID:27326328] [10.1021/acsmedchemlett.6b00010]

2. Regueiro-Ren A, Swidorski JJ, Liu Z, Chen Y, Sin N, Sit SY, Chen J, Venables BL, Zhu J, Nowicka-Sans B, Protack T, Lin Z, Terry B, Samanta H, Zhang S, Li Z, Easter J, Beno BR, Arora V, Huang XS, Rahematpura S, Parker DD, Haskell R, Santone KS, Cockett MI, Krystal M, Meanwell NA, Jenkins S, Hanumegowda U, Dicker IB..  (2018)  Design, Synthesis, and SAR of C-3 Benzoic Acid, C-17 Triterpenoid Derivatives. Identification of the HIV-1 Maturation Inhibitor 4-((1 R,3a S,5a R,5b R,7a R,11a S,11b R,13a R,13b R)-3a-((2-(1,1-Dioxidothiomorpholino)ethyl)amino)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1 H-cyclopenta[ a]chrysen-9-yl)benzoic Acid (GSK3532795, BMS-955176).,  61  (16): [PMID:30067361] [10.1021/acs.jmedchem.8b00854]

3. Unpublished dataset, 

4. Regueiro-Ren A,Dicker IB,Hanumegowda U,Meanwell NA.  (2019)  Second Generation Inhibitors of HIV-1 Maturation.,  10  (3.0): [PMID:30891128] [10.1021/acsmedchemlett.8b00656]

5. Swidorski JJ,Jenkins S,Hanumegowda U,Parker DD,Beno BR,Protack T,Ng A,Gupta A,Shanmugam Y,Dicker IB,Krystal M,Meanwell NA,Regueiro-Ren A.  (2021)  Design and exploration of C-3 benzoic acid bioisosteres and alkyl replacements in the context of GSK3532795 (BMS-955176) that exhibit broad spectrum HIV-1 maturation inhibition.,  36  [PMID:33508465] [10.1016/j.bmcl.2021.127823]

6. Regueiro-Ren A, Sit SY, Chen Y, Chen J, Swidorski JJ, Liu Z, Venables BL, Sin N, Hartz RA, Protack T, Lin Z, Zhang S, Li Z, Wu DR, Li P, Kempson J, Hou X, Gupta A, Rampulla R, Mathur A, Park H, Sarjeant A, Benitex Y, Rahematpura S, Parker D, Phillips T, Haskell R, Jenkins S, Santone KS, Cockett M, Hanumegowda U, Dicker I, Meanwell NA, Krystal M..  (2022)  The Discovery of GSK3640254, a Next-Generation Inhibitor of HIV-1 Maturation.,  65  (18.0): [PMID:36044257] [10.1021/acs.jmedchem.2c00879]

7. Hartz RA, Xu L, Sit SY, Chen J, Venables BL, Lin Z, Zhang S, Li Z, Parker D, Simmons TS, Jenkins S, Hanumegowda UM, Dicker I, Krystal M, Meanwell NA, Regueiro-Ren A..  (2022)  Synthesis, Structure-Activity Relationships, and In Vivo Evaluation of Novel C-17 Amine Derivatives Based on GSK3640254 as HIV-1 Maturation Inhibitors with Broad Spectrum Activity.,  65  (23.0): [PMID:36441509] [10.1021/acs.jmedchem.2c01618]

Source

Source(2):

• Scientific Literature
• Clinical Candidates