Acetic acid (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bS)-3a-acetoxymethyl-1-(1-bromomethyl-vinyl)-5a,5b,8,8,11a-pentamethyl-icosahydro-cyclopenta[a]chrysen-9-yl ester

ID: ALA342970

Chembl Id: CHEMBL342970

PubChem CID: 10769974

Max Phase: Preclinical

Molecular Formula: C34H53BrO4

Molecular Weight: 605.70

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C34H53BrO4/c1-21(19-35)24-11-16-34(20-38-22(2)36)18-17-32(7)25(29(24)34)9-10-27-31(6)14-13-28(39-23(3)37)30(4,5)26(31)12-15-33(27,32)8/h24-29H,1,9-20H2,2-8H3/t24-,25+,26-,27+,28-,29+,31-,32+,33+,34+/m0/s1

Standard InChI Key:  ARLHMKGOWJBLNG-MQXQNARFSA-N

Alternative Forms

1. Parent:

   

   ALA342970

   3,28-Diacetoxy-29-bromobetulin

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: 605.70

Molecular Weight (Monoisotopic): 604.3127

AlogP: 8.51

#Rotatable Bonds: 5

Polar Surface Area: 52.60

Molecular Species: NEUTRAL

HBA: 4

HBD: 0

#RO5 Violations: 2

HBA (Lipinski): 4

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 2

CX Acidic pKa:

CX Basic pKa:

CX LogP: 7.31

CX LogD: 7.31

Aromatic Rings: 0

Heavy Atoms: 39

QED Weighted: 0.18

Np Likeness Score: 2.83

References

1. Sun IC, Wang HK, Kashiwada Y, Shen JK, Cosentino LM, Chen CH, Yang LM, Lee KH..  (1998)  Anti-AIDS agents. 34. Synthesis and structure-activity relationships of betulin derivatives as anti-HIV agents.,  41  (23): [PMID:9804704] [10.1021/jm980391g]

2. Pettit GR, Melody N, Chapuis JC..  (2018)  Antineoplastic Agents. 606. The Betulastatins.,  81  (3): [PMID:29303263] [10.1021/acs.jnatprod.7b00536]

Source

Source(1):

• Scientific Literature