(4S,5S,10R,13S,17S)-17-Hydroxy-10,13-dimethyl-3-oxo-hexadecahydro-20-oxa-cyclopropa[4,5]cyclopenta[a]phenanthrene-2-carboxylic acid methyl ester

ID: ALA3137910

Chembl Id: CHEMBL3137910

PubChem CID: 10316593

Max Phase: Preclinical

Molecular Formula: C21H30O5

Molecular Weight: 362.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)C1C[C@]2(C)[C@H]3CC[C@]4(C)[C@@H](O)CC[C@H]4[C@@H]3CC[C@]23O[C@@H]3C1=O

Standard InChI:  InChI=1S/C21H30O5/c1-19-8-7-14-11(13(19)4-5-15(19)22)6-9-21-17(26-21)16(23)12(18(24)25-3)10-20(14,21)2/h11-15,17,22H,4-10H2,1-3H3/t11-,12?,13-,14-,15-,17+,19-,20+,21+/m0/s1

Standard InChI Key:  HOAXCALWNZDPTE-NHNXKMDDSA-N

Alternative Forms

1. Parent:

   

   ALA3137910

   methyl (1S,2R,6S,8S,11S,12S,15S,16S)-15-hydroxy-2,16-dimethyl-5-oxo-7-oxapentacyclo[9.7.0.02,8.06,8.012,16]octadecane-4-carboxylate

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: 362.47

Molecular Weight (Monoisotopic): 362.2093

AlogP: 2.49

#Rotatable Bonds: 1

Polar Surface Area: 76.13

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.22

CX Basic pKa: ┄

CX LogP: 2.73

CX LogD: 2.73

Aromatic Rings: ┄

Heavy Atoms: 26

QED Weighted: 0.44

Np Likeness Score: 2.13

References

1. Michne WF, Schroeder JD, Bailey TR, Neumann HC, Cooke D, Young DC, Hughes JV, Kingsley SD, Ryan KA, Putz HS..  (1995)  Keto/enol epoxy steroids as HIV-1 Tat inhibitors: structure-activity relationships and pharmacophore localization.,  38  (17): [PMID:7650672] [10.1021/jm00017a003]

Source

Source(1):

• Scientific Literature