ID: ALA1813731

Max Phase: Preclinical

Molecular Formula: C33H47F3N2O4S

Molecular Weight: 624.81

Molecule Type: Small molecule

Representations

Canonical SMILES:  C[C@@H]1CN(S(=O)(=O)c2ccccc2C(F)(F)F)[C@@H](C)CN1C[C@@]1(O)CC[C@@]2(C)[C@@H](CC[C@@H]3[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]32)C1

Standard InChI:  InChI=1S/C33H47F3N2O4S/c1-21-19-38(43(41,42)28-8-6-5-7-27(28)33(34,35)36)22(2)18-37(21)20-32(40)16-15-30(3)23(17-32)9-10-24-25-11-12-29(39)31(25,4)14-13-26(24)30/h5-8,21-26,40H,9-20H2,1-4H3/t21-,22+,23+,24+,25+,26+,30+,31+,32-/m1/s1

Standard InChI Key:  IYHGEKFCMCXIEF-AIQQMPNKSA-N

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

Properties

Molecular Weight: 624.81

Molecular Weight (Monoisotopic): 624.3209

AlogP: 6.13

#Rotatable Bonds: 4

Polar Surface Area: 77.92

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa:

CX Basic pKa: 7.37

CX LogP: 6.10

CX LogD: 5.82

Aromatic Rings: 1

Heavy Atoms: 43

QED Weighted: 0.44

Np Likeness Score: 0.54

References

1. Maltais R, Fournier MA, Poirier D..  (2011)  Development of 3-substituted-androsterone derivatives as potent inhibitors of 17β-hydroxysteroid dehydrogenase type 3.,  19  (15): [PMID:21741247] [10.1016/j.bmc.2011.06.003]

2. 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]

3. Kenmogne LC, Maltais R, Poirier D..  (2016)  Synthesis of a dansyl-labeled inhibitor of 17β-hydroxysteroid dehydrogenase type 3 for optical imaging.,  26  (9): [PMID:27025340] [10.1016/j.bmcl.2016.03.069]

4. Cortés-Benítez F, Roy J, Maltais R, Poirier D..  (2017)  Impact of androstane A- and D-ring inversion on 17β-hydroxysteroid dehydrogenase type 3 inhibitory activity, androgenic effect and metabolic stability.,  25  (7): [PMID:28254377] [10.1016/j.bmc.2017.02.008]

Source

Source(1):

• Scientific Literature