(4aS,6aR,11aR,11bS)-4,4,6a,7,11b-pentamethyl-2,3,4,4a,5,6,6a,11,11a,11b-decahydro-1H-benzo[a]fluoren-9-ol

ID: ALA1784529

Cas Number: 1000009-73-3

PubChem CID: 23634362

Max Phase: Preclinical

Molecular Formula: C22H32O

Molecular Weight: 312.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(O)cc2c1[C@]1(C)CC[C@H]3C(C)(C)CCC[C@]3(C)[C@H]1C2

Standard InChI:  InChI=1S/C22H32O/c1-14-11-16(23)12-15-13-18-21(4)9-6-8-20(2,3)17(21)7-10-22(18,5)19(14)15/h11-12,17-18,23H,6-10,13H2,1-5H3/t17-,18+,21-,22+/m0/s1

Standard InChI Key:  ZAZRBTKHYPRONZ-GKJHBJHPSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
   -3.4417  -16.6833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4417  -17.5083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7296  -17.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7296  -16.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0176  -16.6833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0166  -17.5083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3055  -17.9176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5910  -17.5065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3076  -16.2676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5904  -16.6795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1375  -15.4583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3153  -15.3699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0218  -16.1235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8413  -16.2072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3245  -15.5381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9825  -14.7832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1641  -14.7032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4628  -14.1125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1790  -16.9599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0208  -18.3292    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4500  -18.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5208  -18.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3125  -17.0917    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0250  -15.8583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1208  -17.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  9 11  1  0
  1  2  1  0
 12 13  2  0
  1  4  1  0
 13 14  1  0
  2  3  1  0
 14 15  2  0
  5  9  1  0
 15 16  1  0
  6  7  1  0
 16 17  2  0
 17 12  1  0
  7  8  1  0
 16 18  1  0
  8 10  1  0
 14 19  1  0
  9 10  1  0
  6 20  1  6
  3  6  1  0
  3 21  1  0
  5  4  1  0
  3 22  1  0
  5  6  1  0
  9 23  1  6
 10 13  1  0
  5 24  1  1
 12 11  1  0
 10 25  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA1784529

   (4aS,6aR,11aR,11bS)-4,4,6a,7,11b-Pentamethyl-2,3,4,4a,5,6,6a,11,11a,11b-decahydro-1H-benzo[a]fluoren-9-ol

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: 312.50

Molecular Weight (Monoisotopic): 312.2453

AlogP: 5.76

#Rotatable Bonds: ┄

Polar Surface Area: 20.23

Molecular Species: NEUTRAL

HBA: 1

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 1

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.39

CX Basic pKa: ┄

CX LogP: 6.38

CX LogD: 6.38

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.65

Np Likeness Score: 2.68

References

1. Li D, Carr G, Zhang Y, Williams DE, Amlani A, Bottriell H, Mui AL, Andersen RJ..  (2011)  Turnagainolides A and B, cyclic depsipeptides produced in culture by a Bacillus sp.: isolation, structure elucidation, and synthesis.,  74  (5): [PMID:21539394] [10.1021/np200033y]

Source

Source(1):

• Scientific Literature