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]-4-methylpentanoate

ID: ALA3605185

PubChem CID: 70811384

Max Phase: Preclinical

Molecular Formula: C28H43NO5

Molecular Weight: 473.65

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)[C@H](CC(C)C)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/C28H43NO5/c1-17(2)14-22(24(31)33-5)29-16-28(34-25(29)32)13-12-26(3)18(15-28)6-7-19-20-8-9-23(30)27(20,4)11-10-21(19)26/h17-22H,6-16H2,1-5H3/t18-,19-,20-,21-,22-,26-,27-,28+/m0/s1

Standard InChI Key:  MAZLGBCIZJGEGL-JXACFJRDSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA3605185

   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]-4-methylpentanoate

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: 473.65

Molecular Weight (Monoisotopic): 473.3141

AlogP: 5.38

#Rotatable Bonds: 4

Polar Surface Area: 72.91

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.52

CX LogD: 5.52

Aromatic Rings: ┄

Heavy Atoms: 34

QED Weighted: 0.51

Np Likeness Score: 1.43

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