N-butyl-6-((6R,8R,9S,13S,14S,17S)-3,17-dihydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-6-ylthio)-N-methylhexanamide

ID: ALA373383

Chembl Id: CHEMBL373383

PubChem CID: 44422488

Max Phase: Preclinical

Molecular Formula: C29H45NO3S

Molecular Weight: 487.75

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCN(C)C(=O)CCCCCS[C@@H]1C[C@@H]2[C@H](CC[C@]3(C)[C@@H](O)CC[C@@H]23)c2ccc(O)cc21

Standard InChI:  InChI=1S/C29H45NO3S/c1-4-5-16-30(3)28(33)9-7-6-8-17-34-26-19-23-22(21-11-10-20(31)18-24(21)26)14-15-29(2)25(23)12-13-27(29)32/h10-11,18,22-23,25-27,31-32H,4-9,12-17,19H2,1-3H3/t22-,23-,25+,26-,27+,29+/m1/s1

Standard InChI Key:  VGNKNUFQBPNMSA-DJJDEFPASA-N

Alternative Forms

1. Parent:

   

   ALA373383

   N-butyl-6-((6R,8R,9S,13S,14S,17S)-3,17-dihydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-6-ylthio)-N-methylhexanamide

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: 487.75

Molecular Weight (Monoisotopic): 487.3120

AlogP: 6.66

#Rotatable Bonds: 10

Polar Surface Area: 60.77

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.67

CX Basic pKa: ┄

CX LogP: 5.80

CX LogD: 5.80

Aromatic Rings: 1

Heavy Atoms: 34

QED Weighted: 0.36

Np Likeness Score: 0.80

References

1. Cadot C, Laplante Y, Kamal F, Luu-The V, Poirier D..  (2007)  C6-(N,N-butyl-methyl-heptanamide) derivatives of estrone and estradiol as inhibitors of type 1 17beta-hydroxysteroid dehydrogenase: Chemical synthesis and biological evaluation.,  15  (2): [PMID:17110114] [10.1016/j.bmc.2006.10.055]

2. Schuster D, Nashev LG, Kirchmair J, Laggner C, Wolber G, Langer T, Odermatt A..  (2008)  Discovery of nonsteroidal 17beta-hydroxysteroid dehydrogenase 1 inhibitors by pharmacophore-based screening of virtual compound libraries.,  51  (14): [PMID:18533708] [10.1021/jm800054h]

Source

Source(1):

• Scientific Literature