(S)-1-(fluoromethyl)-4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(2-(4-hydroxy-1-(methylsulfonyl)piperidin-4-yl)ethylamino)-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-1H-cyclopenta[a]chrysen-9-yl)cyclohex-3-enecarboxylic acid

ID: ALA5271451

Chembl Id: CHEMBL5271451

Max Phase: Preclinical

Molecular Formula: C45H71FN2O5S

Molecular Weight: 771.14

Names and Identifiers

Canonical SMILES:  C=C(C)[C@@H]1CC[C@]2(NCCC3(O)CCN(S(C)(=O)=O)CC3)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC=C(C6=CC[C@](CF)(C(=O)O)CC6)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]12

Standard InChI:  InChI=1S/C45H71FN2O5S/c1-30(2)32-13-20-45(47-26-23-44(51)24-27-48(28-25-44)54(8,52)53)22-21-41(6)34(37(32)45)9-10-36-40(5)16-14-33(39(3,4)35(40)15-17-42(36,41)7)31-11-18-43(29-46,19-12-31)38(49)50/h11,14,32,34-37,47,51H,1,9-10,12-13,15-29H2,2-8H3,(H,49,50)/t32-,34+,35-,36+,37+,40-,41+,42+,43-,45-/m0/s1

Standard InChI Key:  VNJDWPYWLXHZHK-USONSBQLSA-N

Alternative Forms

1. Parent:

   

   ALA5271451

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 771.14

Molecular Weight (Monoisotopic): 770.5068

AlogP: 8.85

#Rotatable Bonds: 9

Polar Surface Area: 106.94

Molecular Species: ZWITTERION

HBA: 5

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 4.33

CX Basic pKa: 10.88

CX LogP: 3.50

CX LogD: 3.50

Aromatic Rings: ┄

Heavy Atoms: 54

QED Weighted: 0.20

Np Likeness Score: 1.39

References

1. 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(1):

• Scientific Literature