17-beta-Hydroxy-7(8->11alpha)abeo-19-nor-10-iso-17alpha-pregn-4-en-20-yn-3-one

ID: ALA3276478

PubChem CID: 90679519

Max Phase: Preclinical

Molecular Formula: C20H26O2

Molecular Weight: 298.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C#C[C@]1(O)CC[C@H]2C[C@@H]3[C@@H](CCC4=CC(=O)CC[C@H]43)C[C@@]21C

Standard InChI:  InChI=1S/C20H26O2/c1-3-20(22)9-8-15-11-18-14(12-19(15,20)2)5-4-13-10-16(21)6-7-17(13)18/h1,10,14-15,17-18,22H,4-9,11-12H2,2H3/t14-,15-,17+,18+,19-,20-/m0/s1

Standard InChI Key:  FQGICGMVLPPTNE-AFMPOKAISA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
    9.7197  -10.0992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3677  -11.5811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3665  -12.4056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0789  -12.8171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7929  -12.4052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0771  -11.1697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7930  -11.5803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7864   -9.9325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0707  -10.3467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5024  -10.3430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4989  -11.1703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2096  -11.5846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2167   -9.9301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9319  -10.3490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9262  -11.1754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7103  -11.4363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2008  -10.7712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4951   -9.5174    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9277   -9.5257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6542  -12.8162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4910  -11.9922    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9194  -11.9964    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9793   -9.3191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5098   -9.8828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3028   -9.6656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7930  -10.7553    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  7  1  0
  6  2  2  0
  6  7  1  0
  6  9  1  0
  7 11  1  0
 10  8  1  0
  8  9  1  0
 10 11  1  0
 10 13  1  0
 11 12  1  0
 12 15  1  0
 14 13  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17  1  1  0
  1 14  1  0
 10 18  1  6
 14 19  1  1
  3 20  2  0
 11 21  1  6
 15 22  1  6
  1 23  1  1
  1 24  1  0
 24 25  3  0
  7 26  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA3276478

   (6aS,7aS,8R,10aS,11aR,11bS)-8-ethynyl-8-hydroxy-7a-methyl-1,2,5,6,6a,7,9,10,10a,11,11a,11b-dodecahydrocyclopenta[b]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: 298.43

Molecular Weight (Monoisotopic): 298.1933

AlogP: 3.49

#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: 3.22

CX LogD: 3.22

Aromatic Rings: ┄

Heavy Atoms: 22

QED Weighted: 0.70

Np Likeness Score: 2.10

References

1. Wani MC, Rector DH, White DH, Pitt CG, Kimmel GL..  (1977)  Synthesis, antifertility activity, and protein binding affinity of 7(8 leads to 11 alpha)abeo steroids.,  20  (4): [PMID:850240] [10.1021/jm00214a017]

Source

Source(1):

• Scientific Literature