Methyl(2S)-2-[(3R,8R,9S,10S,13S,14S)-10,13-dimethyl-2',17-dioxohexadecahydro-3'H-spiro[cyclopenta[a]phenanthrene-3,5'-[1,3]oxazolidin]-3'-yl]-3-phenyl propanoate

ID: ALA3605187

PubChem CID: 90085993

Max Phase: Preclinical

Molecular Formula: C31H41NO5

Molecular Weight: 507.67

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)[C@H](Cc1ccccc1)N1C[C@]2(CC[C@@]3(C)[C@@H](CC[C@@H]4[C@@H]3CC[C@]3(C)C(=O)CC[C@@H]43)C2)OC1=O

Standard InChI:  InChI=1S/C31H41NO5/c1-29-15-16-31(18-21(29)9-10-22-23-11-12-26(33)30(23,2)14-13-24(22)29)19-32(28(35)37-31)25(27(34)36-3)17-20-7-5-4-6-8-20/h4-8,21-25H,9-19H2,1-3H3/t21-,22-,23-,24-,25-,29-,30-,31+/m0/s1

Standard InChI Key:  HEHFUHPBYAMEAS-SKUNGOIASA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA3605187

   methyl (2S)-2-[(5R,5'S,8'R,9'S,10'S,13'S,14'S)-10',13'-dimethyl-2,17'-dioxospiro[1,3-oxazolidine-5,3'-2,4,5,6,7,8,9,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthrene]-3-yl]-3-phenylpropanoate

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: 507.67

Molecular Weight (Monoisotopic): 507.2985

AlogP: 5.57

#Rotatable Bonds: 4

Polar Surface Area: 72.91

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.92

CX LogD: 5.92

Aromatic Rings: 1

Heavy Atoms: 37

QED Weighted: 0.50

Np Likeness Score: 1.26

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