(1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-9-(4-Hydroxyphenyl)-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]chrysene-3a-carboxylic acid

ID: ALA3774938

Chembl Id: CHEMBL3774938

PubChem CID: 54759387

Max Phase: Preclinical

Molecular Formula: C36H50O3

Molecular Weight: 530.79

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C36H50O3/c1-22(2)25-14-19-36(31(38)39)21-20-34(6)27(30(25)36)12-13-29-33(5)17-15-26(23-8-10-24(37)11-9-23)32(3,4)28(33)16-18-35(29,34)7/h8-11,15,25,27-30,37H,1,12-14,16-21H2,2-7H3,(H,38,39)/t25-,27+,28-,29+,30+,33-,34+,35+,36-/m0/s1

Standard InChI Key:  ZVGBPYAQHAAOIJ-PDVPNEPJSA-N

Alternative Forms

1. Parent:

   

   ALA3774938

   (1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-9-(4-hydroxyphenyl)-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-1,2,3,4,5,6,7,7a,11,11b,12,13,13a,13b-tetradecahydrocyclopenta[a]chrysene-3a-carboxylic acid

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: 530.79

Molecular Weight (Monoisotopic): 530.3760

AlogP: 9.13

#Rotatable Bonds: 3

Polar Surface Area: 57.53

Molecular Species: ACID

HBA: 2

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 4.78

CX Basic pKa: ┄

CX LogP: 8.72

CX LogD: 6.14

Aromatic Rings: 1

Heavy Atoms: 39

QED Weighted: 0.38

Np Likeness Score: 2.60

References

1. Liu Z, Swidorski JJ, Nowicka-Sans B, Terry B, Protack T, Lin Z, Samanta H, Zhang S, Li Z, Parker DD, Rahematpura S, Jenkins S, Beno BR, Krystal M, Meanwell NA, Dicker IB, Regueiro-Ren A..  (2016)  C-3 benzoic acid derivatives of C-3 deoxybetulinic acid and deoxybetulin as HIV-1 maturation inhibitors.,  24  (8): [PMID:26968652] [10.1016/j.bmc.2016.03.001]

2. Borková L, Frydrych I, Vránová B, Jakubcová N, Lišková B, Gurská S, Džubák P, Pavliš P, Hajdúch M, Urban M..  (2022)  Lupane derivatives containing various aryl substituents in the position 3 have selective cytostatic effect in leukemic cancer cells including resistant phenotypes.,  244  [PMID:36283179] [10.1016/j.ejmech.2022.114850]

Source

Source(1):

• Scientific Literature