(1S,4R,5bR,7aR,9S,11aR,11bR,13bR)-9-Acetoxy-1-(1-formyl-vinyl)-5a,5b,8,8,11a-pentamethyl-icosahydro-cyclopenta[a]chrysene-3a-carboxylic acid

ID: ALA150416

Chembl Id: CHEMBL150416

PubChem CID: 44367054

Max Phase: Preclinical

Molecular Formula: C32H48O5

Molecular Weight: 512.73

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C(C=O)[C@@H]1CC[C@]2(C(=O)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)C12

Standard InChI:  InChI=1S/C32H48O5/c1-19(18-33)21-10-15-32(27(35)36)17-16-30(6)22(26(21)32)8-9-24-29(5)13-12-25(37-20(2)34)28(3,4)23(29)11-14-31(24,30)7/h18,21-26H,1,8-17H2,2-7H3,(H,35,36)/t21-,22+,23-,24+,25-,26?,29-,30+,31+,32-/m0/s1

Standard InChI Key:  QQVONFVPCJCTQB-SJGBUFNVSA-N

Alternative Forms

1. Parent:

   

   ALA150416

   (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR)-9-acetyloxy-5a,5b,8,8,11a-pentamethyl-1-(3-oxoprop-1-en-2-yl)-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[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: 512.73

Molecular Weight (Monoisotopic): 512.3502

AlogP: 6.84

#Rotatable Bonds: 4

Polar Surface Area: 80.67

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 4.58

CX Basic pKa: ┄

CX LogP: 6.11

CX LogD: 3.37

Aromatic Rings: ┄

Heavy Atoms: 37

QED Weighted: 0.25

Np Likeness Score: 3.12

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]

Source

Source(1):

• Scientific Literature