Rac-(11S,13S,17R)-13-ethyl-17-ethynyl-17-hydroxy-11-methyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3(2H)-one

ID: ALA3250929

PubChem CID: 90674762

Max Phase: Preclinical

Molecular Formula: C22H30O2

Molecular Weight: 326.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C#C[C@]1(O)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3[C@@H](C)C[C@@]21CC

Standard InChI:  InChI=1S/C22H30O2/c1-4-21-13-14(3)20-17-9-7-16(23)12-15(17)6-8-18(20)19(21)10-11-22(21,24)5-2/h2,12,14,17-20,24H,4,6-11,13H2,1,3H3/t14-,17-,18-,19-,20+,21-,22-/m0/s1

Standard InChI Key:  QQOBJLCATUUZQQ-HAAZFOEOSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   11.0600   -4.2854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8484   -5.0820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6440   -4.8669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6194   -5.3102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3245   -5.7591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8987   -7.3760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3188   -5.7342    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3270   -6.5578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6069   -6.9614    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9096   -4.8925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0392   -6.9782    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0610   -5.3270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6140   -6.1371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3440   -4.9064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8293   -6.4234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1907   -7.7823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4792   -7.3760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0475   -6.1537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6070   -7.7873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0559   -4.4987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8948   -5.7259    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4792   -6.5510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1907   -6.1321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9022   -6.5510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3234   -7.3780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4359   -4.6521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7688   -7.7884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3420   -4.0924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  2  3  1  0
 18 15  1  0
 15  5  1  0
 12 14  1  0
 25  8  1  0
  2 12  1  0
 19 25  1  0
 24 23  1  0
  5  2  1  0
 16  6  2  0
 12 20  1  1
  8 18  1  0
  6 19  1  0
  4 10  1  1
 24 21  1  1
 22 17  1  0
 24  6  1  0
 14  4  1  0
 22 23  1  0
 18 11  1  6
 17 16  1  0
 13  4  1  0
 24 13  1  0
 13  9  1  6
  8  7  1  1
 12 18  1  0
 13  8  1  0
  3 26  3  0
 17 27  2  0
 20 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3250929

   (8R,9S,10R,11S,13S,14S,17R)-13-ethyl-17-ethynyl-17-hydroxy-11-methyl-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one

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: 326.48

Molecular Weight (Monoisotopic): 326.2246

AlogP: 4.13

#Rotatable Bonds: 1

Polar Surface Area: 37.30

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.95

CX LogD: 3.95

Aromatic Rings: ┄

Heavy Atoms: 24

QED Weighted: 0.74

Np Likeness Score: 1.90

References

1. Pitt CG, Rector DH, Cook CE, Wani MC..  (1979)  Synthesis of 11 beta,13 beta- and 13 beta,16 beta-propano steroids: probes of hormonal activity.,  22  (8): [PMID:226703] [10.1021/jm00194a016]

Source

Source(1):

• Scientific Literature