ID: ALA2298601

Max Phase: Preclinical

Molecular Formula: C24H40N2O2

Molecular Weight: 388.60

Molecule Type: Small molecule

Representations

Canonical SMILES:  CCN(CC)C(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4N(C)C(=O)CC[C@]4(C)[C@H]3CC[C@]12C

Standard InChI:  InChI=1S/C24H40N2O2/c1-6-26(7-2)22(28)19-10-9-17-16-8-11-20-24(4,15-13-21(27)25(20)5)18(16)12-14-23(17,19)3/h16-20H,6-15H2,1-5H3/t16-,17-,18-,19+,20+,23-,24+/m0/s1

Standard InChI Key:  GNWBLLYJQXKPIP-ZOGIJGBBSA-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: 388.60

Molecular Weight (Monoisotopic): 388.3090

AlogP: 4.33

#Rotatable Bonds: 3

Polar Surface Area: 40.62

Molecular Species: NEUTRAL

HBA: 2

HBD: 0

#RO5 Violations: 0

HBA (Lipinski): 4

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 0.52

CX LogP: 3.18

CX LogD: 3.18

Aromatic Rings: 0

Heavy Atoms: 28

QED Weighted: 0.72

Np Likeness Score: 0.90

References

1. Li X, Singh SM, Labrie F..  (1995)  Synthesis and in vitro activity of 17 beta-(N-alkyl/arylformamido)- and 17 beta-[(N-alkyl/aryl)alkyl/arylamido]-4-methyl-4-aza-3-oxo-5 alpha-androstan-3-ones as inhibitors of human 5 alpha-reductases and antagonists of the androgen receptor.,  38  (7): [PMID:7707319] [10.1021/jm00007a013]

2. Kenny B, Ballard S, Blagg J, Fox D..  (1997)  Pharmacological options in the treatment of benign prostatic hyperplasia.,  40  (9): [PMID:9135028] [10.1021/jm960697s]

3. Rasmusson GH, Reynolds GF, Utne T, Jobson RB, Primka RL, Berman C, Brooks JR..  (1984)  Azasteroids as inhibitors of rat prostatic 5 alpha-reductase.,  27  (12): [PMID:6502599] [10.1021/jm00378a028]

4. Rasmusson GH, Reynolds GF, Steinberg NG, Walton E, Patel GF, Liang T, Cascieri MA, Cheung AH, Brooks JR, Berman C..  (1986)  Azasteroids: structure-activity relationships for inhibition of 5 alpha-reductase and of androgen receptor binding.,  29  (11): [PMID:3783591] [10.1021/jm00161a028]

5. Frye SV, Haffner CD, Maloney PR, Mook RA, Dorsey GF, Hiner RN, Cribbs CM, Wheeler TN, Ray JA, Andrews RC..  (1994)  6-Azasteroids: structure-activity relationships for inhibition of type 1 and 2 human 5 alpha-reductase and human adrenal 3 beta-hydroxy-delta 5-steroid dehydrogenase/3-keto-delta 5-steroid isomerase.,  37  (15): [PMID:8057283] [10.1021/jm00041a014]

6. Abell AD, Brandt M, Levy MA, Holt DA.  (1996)  A comparison of steroidal and non-steroidal inhibitors of human steroid 5-reductase: New tricyclic aryl acid inhibitors of the type-1 isozyme,  6  (4): [10.1016/0960-894X(96)00054-6]

7. Weintraub PM, Blohm TR, Laughlin M..  (1985)  Preparation of 20-(hydroxymethyl)-4-methyl-4-aza-2-oxa-5 alpha-pregnan-3-one as an inhibitor of testosterone 5 alpha-reductase.,  28  (6): [PMID:4009607] [10.1021/jm00383a026]

8. McDonald IA, Nyce PL, Muench DM, Gates CA, Blohm TR, Laughlin ME, Weintruab PM.  (1994)  Inhibition of steroid 5-reductase by inverted, competitive inhibitors,  4  (6): [10.1016/S0960-894X(01)80861-1]

9. Kumar R, Malla P, Verma A, Kumar M.  (2013)  Design of potent human steroid 5-reductase inhibitors: 3D-QSAR CoMFA, CoMSIA and docking studies,  22  (10): [10.1007/s00044-012-0456-5]

Source

Source(1):

• Scientific Literature