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

ID: ALA3250932

PubChem CID: 90674765

Max Phase: Preclinical

Molecular Formula: C22H30O3

Molecular Weight: 342.48

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@@]21CCCO

Standard InChI:  InChI=1S/C22H30O3/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/h1,14,17-20,23,25H,3-13H2/t17-,18+,19+,20-,21-,22-/m0/s1

Standard InChI Key:  NNUPASPCKWGLHG-ZCPXKWAGSA-N

Molfile:  

     RDKit          2D

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    4.9609   -9.3275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6666   -8.9154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6356  -10.7803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6356  -11.5975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3409  -12.0020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3409  -10.3676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0462  -10.7803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0427  -11.5975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7447  -12.0068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4548  -11.6035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.4583  -10.7911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4751   -9.1515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7570   -9.5534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1817   -9.5701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1684  -10.3888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9429  -10.6545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4350  -10.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0389   -9.9631    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4504   -9.9714    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7446  -11.1889    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1602  -11.2054    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1768   -8.7497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0771  -12.0071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3681   -8.5049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4666   -8.3454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4616   -7.5282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7515   -7.1239    0.0000 O   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:

   

   ALA3250932

   (8R,9S,10R,13R,14S,17R)-17-ethynyl-17-hydroxy-13-(3-hydroxypropyl)-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: 342.48

Molecular Weight (Monoisotopic): 342.2195

AlogP: 3.25

#Rotatable Bonds: 3

Polar Surface Area: 57.53

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.67

CX LogD: 2.67

Aromatic Rings: ┄

Heavy Atoms: 25

QED Weighted: 0.77

Np Likeness Score: 2.07

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