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

ID: ALA3250928

PubChem CID: 22803981

Max Phase: Preclinical

Molecular Formula: C21H28O2

Molecular Weight: 312.45

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@@]21C

Standard InChI:  InChI=1S/C21H28O2/c1-4-21(23)10-9-18-17-7-5-14-11-15(22)6-8-16(14)19(17)13(2)12-20(18,21)3/h1,11,13,16-19,23H,5-10,12H2,2-3H3/t13-,16-,17-,18-,19+,20-,21-/m0/s1

Standard InChI Key:  KRAXPOBQAXPJOO-BLNWYVPNSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   11.4276   -4.0650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2161   -4.8614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0116   -4.6464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9874   -5.0896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6922   -5.5385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2668   -7.1552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6867   -5.5136    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6949   -6.3371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9749   -6.7407    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2777   -4.6721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4070   -6.7574    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4289   -5.1065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9821   -5.9164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7119   -4.6858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1970   -6.2026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5589   -7.5614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8474   -7.1552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4154   -5.9331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9750   -7.5664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4237   -4.2783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2629   -5.5052    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8474   -6.3303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5589   -5.9115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2703   -6.3303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6913   -7.1571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8034   -4.4316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1372   -7.5675    0.0000 O   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
M  END

Alternative Forms

1. Parent:

   

   ALA3250928

   (8R,9S,10R,11S,13S,14S,17R)-17-ethynyl-17-hydroxy-11,13-dimethyl-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: 312.45

Molecular Weight (Monoisotopic): 312.2089

AlogP: 3.74

#Rotatable Bonds: ┄

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: 3.50

CX LogD: 3.50

Aromatic Rings: ┄

Heavy Atoms: 23

QED Weighted: 0.69

Np Likeness Score: 2.10

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