(3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyltetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione

ID: ALA3605181

PubChem CID: 90085988

Max Phase: Preclinical

Molecular Formula: C22H33NO3

Molecular Weight: 359.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@]12CC[C@]3(CNCC(=O)O3)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12

Standard InChI:  InChI=1S/C22H33NO3/c1-20-9-10-22(13-23-12-19(25)26-22)11-14(20)3-4-15-16-5-6-18(24)21(16,2)8-7-17(15)20/h14-17,23H,3-13H2,1-2H3/t14-,15-,16-,17-,20-,21-,22+/m0/s1

Standard InChI Key:  AVHXQCXDMNNIEN-QDYOMNNKSA-N

Molfile:  

     RDKit          2D

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    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1406   -2.0490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1405    0.5490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.3477   -0.4439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2385   -1.2479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5947   -1.7216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8906   -1.6160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1405    1.4151    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3906   -1.6160    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1405    1.4151    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7327    1.4621    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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  5 30  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3605181

   (3R,5S,8R,9S,10S,13S,14S)-10,13-dimethylspiro[2,4,5,6,7,8,9,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthrene-3,6'-morpholine]-2',17-dione

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: 359.51

Molecular Weight (Monoisotopic): 359.2460

AlogP: 3.48

#Rotatable Bonds: ┄

Polar Surface Area: 55.40

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.56

CX LogP: 3.47

CX LogD: 3.46

Aromatic Rings: ┄

Heavy Atoms: 26

QED Weighted: 0.67

Np Likeness Score: 2.10

References

1. Djigoué GB, Kenmogne LC, Roy J, Maltais R, Poirier D..  (2015)  Design, chemical synthesis and biological evaluation of 3-spiromorpholinone/3-spirocarbamate androsterone derivatives as inhibitors of 17β-hydroxysteroid dehydrogenase type 3.,  23  (17): [PMID:26277760] [10.1016/j.bmc.2015.07.049]

Source

Source(1):

• Scientific Literature