(3aS,5aR,5bR,7aR,9S,11aR,11bR,13aS)-9-Acetoxy-1-isopropyl-5a,5b,8,8,11a-pentamethyl-2,3-dioxo-2,3,4,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a-octadecahydro-cyclopenta[a]chrysene-3a-carboxylic acid methyl ester

ID: ALA153117

Chembl Id: CHEMBL153117

PubChem CID: 9937136

Max Phase: Preclinical

Molecular Formula: C33H48O6

Molecular Weight: 540.74

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)[C@@]12CC[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)C1=C(C(C)C)C(=O)C2=O

Standard InChI:  InChI=1S/C33H48O6/c1-18(2)24-25-20-10-11-22-30(6)14-13-23(39-19(3)34)29(4,5)21(30)12-15-32(22,8)31(20,7)16-17-33(25,28(37)38-9)27(36)26(24)35/h18,20-23H,10-17H2,1-9H3/t20-,21+,22-,23+,30+,31-,32-,33+/m1/s1

Standard InChI Key:  SQNAVENFPQWCIW-YHXGQZGQSA-N

Alternative Forms

1. Parent:

   

   ALA153117

   methyl (3aS,5aR,5bR,7aR,9S,11aR,11bR,13aS)-9-acetyloxy-5a,5b,8,8,11a-pentamethyl-2,3-dioxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydrocyclopenta[a]chrysene-3a-carboxylate

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: 540.74

Molecular Weight (Monoisotopic): 540.3451

AlogP: 6.25

#Rotatable Bonds: 3

Polar Surface Area: 86.74

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 6.81

CX LogD: 6.81

Aromatic Rings: ┄

Heavy Atoms: 39

QED Weighted: 0.24

Np Likeness Score: 2.71

References

1. Sarek J, Klinot J, Dzubák P, Klinotová E, Nosková V, Krecek V, Korínková G, Thomson JO, Janost'áková A, Wang S, Parsons S, Fischer PM, Zhelev NZ, Hajdúch M..  (2003)  New lupane derived compounds with pro-apoptotic activity in cancer cells: synthesis and structure-activity relationships.,  46  (25): [PMID:14640549] [10.1021/jm020854p]

2. Urban M, Sarek J, Kvasnica M, Tislerova I, Hajduch M..  (2007)  Triterpenoid pyrazines and benzopyrazines with cytotoxic activity.,  70  (4): [PMID:17371067] [10.1021/np060436d]

Source

Source(1):

• Scientific Literature