13beta-(3'-chloropropyl)-17alpha-Etynyl-17beta-hydroxygon-4-en-3-one

ID: ALA3250933

PubChem CID: 90674766

Max Phase: Preclinical

Molecular Formula: C22H29ClO2

Molecular Weight: 360.93

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]3CC[C@@]21CCCCl

Standard InChI:  InChI=1S/C22H29ClO2/c1-2-22(25)12-9-20-19-6-4-15-14-16(24)5-7-17(15)18(19)8-11-21(20,22)10-3-13-23/h1,14,17-20,25H,3-13H2/t17-,18+,19+,20-,21-,22-/m0/s1

Standard InChI Key:  LPYDODHXSJLTMK-ZCPXKWAGSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   11.2797   -6.9007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2838   -7.7179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9895   -7.3057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9585   -9.1707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9585   -9.9879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6638  -10.3924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6638   -8.7580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3691   -9.1707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3656   -9.9879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0677  -10.3972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7777   -9.9939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0746   -8.7628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7812   -9.1815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7981   -7.5419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0799   -7.9438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5046   -7.9605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4913   -8.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2659   -9.0449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7579   -8.3904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3618   -8.3535    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7733   -8.3618    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0675   -9.5793    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4832   -9.5958    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4997   -7.1401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2514  -10.3975    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6910   -6.8953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7895   -6.7358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7846   -5.9186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0744   -5.5143    0.0000 Cl  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
 24 27  1  0
 27 28  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3250933

   (8R,9S,10R,13R,14S,17R)-13-(3-chloropropyl)-17-ethynyl-17-hydroxy-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: 360.93

Molecular Weight (Monoisotopic): 360.1856

AlogP: 4.49

#Rotatable Bonds: 3

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: 4.02

CX LogD: 4.02

Aromatic Rings: ┄

Heavy Atoms: 25

QED Weighted: 0.59

Np Likeness Score: 1.82

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