Rac-17alpha-Etynyl-17beta-hydroxy-13beta,16beta-propanogon-4-en-3-one

ID: ALA3250931

PubChem CID: 90674764

Max Phase: Preclinical

Molecular Formula: C22H28O2

Molecular Weight: 324.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C#C[C@]1(O)[C@H]2CCC[C@@]13CC[C@H]1[C@@H](CCC4=CC(=O)CC[C@@H]41)[C@@H]3C2

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

Standard InChI Key:  CIMNBVZRHJNKLI-CJRUCWEJSA-N

Molfile:  

     RDKit          2D

 29 33  0  0  0  0  0  0  0  0999 V2000
   28.3448   -0.9999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.5699   -1.7749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3703   -1.9863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2033   -3.2416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2033   -4.0665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9153   -4.4748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9153   -2.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6273   -3.2416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6238   -4.0665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3326   -4.4797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0494   -4.0726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3396   -2.8298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0529   -3.2525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0699   -1.5972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3449   -2.0030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7833   -2.0198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7698   -2.8463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5517   -3.1146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0484   -2.4537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6300   -2.2416    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   26.9158   -3.7578    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   24.4750   -2.3273    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   26.8621   -3.8420    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   22.4895   -4.4800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.9949   -1.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2574   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8068   -0.9885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2211   -2.2193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1477   -2.0192    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  6
 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
  5 24  2  0
 16 25  1  0
 19 26  1  0
 25 27  1  0
 26 27  1  0
  3 28  3  0
 19 29  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA3250931

   (1S,4S,5R,13R,14S,16S,20R)-20-ethynyl-20-hydroxypentacyclo[14.3.1.01,14.04,13.05,10]icos-9-en-8-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: 3.56

CX LogD: 3.56

Aromatic Rings: ┄

Heavy Atoms: 24

QED Weighted: 0.69

Np Likeness Score: 2.20

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