(5S,8R,9S,10S,13S,14S,17S)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,17-diol

ID: ALA4644154

PubChem CID: 445071

Max Phase: Preclinical

Molecular Formula: C19H32O2

Molecular Weight: 292.46

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C[C@]12CCC(O)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O)CC[C@@H]12

Standard InChI:  InChI=1S/C19H32O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-17,20-21H,3-11H2,1-2H3/t12-,13?,14-,15-,16-,17-,18-,19-/m0/s1

Standard InChI Key:  CBMYJHIOYJEBSB-DYSINSMMSA-N

Molfile:  

 
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    3.5268   -5.4740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2399   -5.0634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9530   -5.4740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9530   -6.2994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2399   -6.7142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5268   -6.2994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8091   -6.7143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6704   -6.7142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3835   -6.2995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3835   -5.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6704   -5.0635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6704   -4.2381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3836   -3.8274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0968   -4.2382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0968   -5.0635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8810   -5.3155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3661   -4.6531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8812   -3.9820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0948   -3.1882    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0968   -5.8893    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0968   -3.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6704   -5.8892    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3835   -4.6526    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9530   -7.1252    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9530   -4.6525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
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  4  5  1  0
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 18 17  1  0
 14 18  1  0
 18 19  1  1
 15 20  1  6
 14 21  1  1
 11 22  1  6
 10 23  1  1
  4 24  1  6
  3 25  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4644154

   (5S,8R,9S,10S,13S,14S,17S)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,17-diol

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 292.46

Molecular Weight (Monoisotopic): 292.2402

AlogP: 3.75

#Rotatable Bonds: ┄

Polar Surface Area: 40.46

Molecular Species: NEUTRAL

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.20

CX LogD: 3.20

Aromatic Rings: ┄

Heavy Atoms: 21

QED Weighted: 0.71

Np Likeness Score: 2.37

References

1. Boutin S, Roy J, Maltais R, Poirier D..  (2020)  Formation of 5α-dihydrotestosterone from 5α-androstane-3α,17β-diol in prostate cancer LAPC-4 cells - Identifying inhibitors of non-classical pathways producing the most potent androgen.,  30  (2): [PMID:31753699] [10.1016/j.bmcl.2019.126783]

Source

Source(1):

• Scientific Literature