Rac-17alpha-Etynyl-17beta-hydroxy-11beta,13beta-propanogon-4-en-3-one

ID: ALA3250930

PubChem CID: 90674763

Max Phase: Preclinical

Molecular Formula: C22H28O2

Molecular Weight: 324.46

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]3CCC[C@]21C3

Standard InChI:  InChI=1S/C22H28O2/c1-2-22(24)11-9-19-18-7-5-14-12-16(23)6-8-17(14)20(18)15-4-3-10-21(19,22)13-15/h1,12,15,17-20,24H,3-11,13H2/t15-,17-,18-,19-,20+,21-,22-/m0/s1

Standard InChI Key:  JININHMTTQSUHC-CDSHGXNMSA-N

Molfile:  

     RDKit          2D

 29 33  0  0  0  0  0  0  0  0999 V2000
   19.4621   -0.9417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.4663   -1.7666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1787   -1.3506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0997   -3.2332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0997   -4.0582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8118   -4.4666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8118   -2.8166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5237   -3.2332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5202   -4.0582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2289   -4.4714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9457   -4.0643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2360   -2.8216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9493   -3.2441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9663   -1.5889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2414   -1.9946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6796   -2.0116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6662   -2.8381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4481   -3.1062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9449   -2.4455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5163   -2.4082    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.9413   -2.4166    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.2288   -3.6457    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.6579   -3.6624    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.6746   -1.1833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3859   -4.4717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.8869   -0.9361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2371   -1.1666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9497   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4413   -1.7750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  3  2  1  0
  4  5  1  0
  4  7  1  0
  5  6  1  0
  6  9  2  0
  8  7  1  0
  8  9  1  0
  8 12  1  0
  9 10  1  0
 10 11  1  0
 11 13  1  0
 12 13  1  0
 12 15  1  0
 13 17  1  0
 16 14  1  0
 14 15  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19  2  1  0
  2 16  1  0
  8 20  1  1
 13 21  1  1
 12 22  1  6
 17 23  1  6
 16 24  1  1
  5 25  2  0
  3 26  3  0
 15 27  1  0
 27 28  1  0
 24 28  1  0
 15 29  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA3250930

   (1S,2R,5S,6R,14R,15S,16S)-2-ethynyl-2-hydroxypentacyclo[14.3.1.01,5.06,15.09,14]icos-9-en-11-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: 324.46

Molecular Weight (Monoisotopic): 324.2089

AlogP: 3.88

#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: 3.49

CX LogD: 3.49

Aromatic Rings: ┄

Heavy Atoms: 24

QED Weighted: 0.69

Np Likeness Score: 2.28

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