(4aR,4bS,6R,10bS,12aS)-7-Hydroxy-4a,4b,6,9,10b,12a-hexamethyl-1,3,4,4a,4b,10b,11,12a-octahydro-2H,6H-chrysene-5,12-dione

ID: ALA89658

PubChem CID: 44323284

Max Phase: Preclinical

Molecular Formula: C24H32O3

Molecular Weight: 368.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(O)c2c(c1)[C@]1(C)CC(=O)[C@@]3(C)CCCC[C@@]3(C)[C@@]1(C)C(=O)[C@@H]2C

Standard InChI:  InChI=1S/C24H32O3/c1-14-11-16-19(17(25)12-14)15(2)20(27)24(6)22(16,4)13-18(26)21(3)9-7-8-10-23(21,24)5/h11-12,15,25H,7-10,13H2,1-6H3/t15-,21-,22+,23-,24+/m1/s1

Standard InChI Key:  ZENUGQHOXVHFGV-QFBKEJFNSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  1  0  0  0  0  0999 V2000
   -0.2583   -1.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9750   -1.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4667   -1.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2583   -0.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6958   -1.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4667   -2.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6958   -0.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9833    0.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2500   -2.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9708   -2.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4125    0.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4125   -1.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4542    0.0458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1250   -0.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2500   -3.6917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1250   -1.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2583   -2.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9833   -0.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4208    0.8625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4667   -0.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1917   -1.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4625   -3.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1917   -2.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9875    0.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8458   -1.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9167   -1.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9167   -2.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  1  1  0
  5  2  1  0
  6  3  1  0
  7  8  1  0
  8  4  1  0
  9  6  1  0
 10  2  1  0
 11  7  2  0
 12  5  2  0
 13  4  2  0
 14 11  1  0
 15  9  2  0
 16 12  1  0
  1 17  1  1
  2 18  1  6
 19 11  1  0
  3 20  1  1
 21  3  1  0
  6 22  1  1
 23  6  1  0
  8 24  1  1
 25 16  1  0
 26 21  1  0
 27 26  1  0
  9 10  1  0
  7  5  1  0
 27 23  1  0
 16 14  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA89658

   (4aR,4bS,6R,10bS,12aS)-7-hydroxy-4a,4b,6,9,10b,12a-hexamethyl-1,2,3,4,6,11-hexahydrochrysene-5,12-dione

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: 368.52

Molecular Weight (Monoisotopic): 368.2351

AlogP: 5.21

#Rotatable Bonds: ┄

Polar Surface Area: 54.37

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.30

CX Basic pKa: ┄

CX LogP: 6.04

CX LogD: 6.04

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.68

Np Likeness Score: 1.27

References

1. Hirai G, Oguri H, Hayashi M, Koyama K, Koizumi Y, Moharram SM, Hirama M..  (2004)  Synthesis and preliminary biological evaluation of truncated zoanthenol analogues.,  14  (10): [PMID:15109670] [10.1016/j.bmcl.2004.02.064]

Source

Source(1):

• Scientific Literature