ID: ALA120432

Max Phase: Preclinical

Molecular Formula: C28H28ClN5O3

Molecular Weight: 518.02

Molecule Type: Small molecule

Representations

Canonical SMILES:  Cc1cc(-c2c(OCC[C@@H]3CCN3)c3cc(C(=O)Nc4ccncn4)c(Cl)cc3[nH]c2=O)cc(C)c1C

Standard InChI:  InChI=1S/C28H28ClN5O3/c1-15-10-18(11-16(2)17(15)3)25-26(37-9-6-19-4-8-31-19)21-12-20(22(29)13-23(21)33-28(25)36)27(35)34-24-5-7-30-14-32-24/h5,7,10-14,19,31H,4,6,8-9H2,1-3H3,(H,33,36)(H,30,32,34,35)/t19-/m0/s1

Standard InChI Key:  XESORVDKNANWAB-IBGZPJMESA-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: 518.02

Molecular Weight (Monoisotopic): 517.1881

AlogP: 4.95

#Rotatable Bonds: 7

Polar Surface Area: 109.00

Molecular Species: BASE

HBA: 6

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.84

CX Basic pKa: 10.59

CX LogP: 3.96

CX LogD: 1.24

Aromatic Rings: 4

Heavy Atoms: 37

QED Weighted: 0.32

Np Likeness Score: -0.80

References

1. Guo Z, Chen Y, Wu D, Zhu YF, Struthers RS, Saunders J, Xie Q, Chen C..  (2003)  Synthesis and structure-activity relationships of thieno[2,3-d]pyrimidine-2,4-dione derivatives as potent GnRH receptor antagonists.,  13  (20): [PMID:14505682] [10.1016/s0960-894x(03)00746-7]

2. DeVita RJ, Walsh TF, Young JR, Jiang J, Ujjainwalla F, Toupence RB, Parikh M, Huang SX, Fair JA, Goulet MT, Wyvratt MJ, Lo JL, Ren N, Yudkovitz JB, Yang YT, Cheng K, Cui J, Mount G, Rohrer SP, Schaeffer JM, Rhodes L, Drisko JE, McGowan E, MacIntyre DE, Vincent S, Carlin JR, Cameron J, Smith RG..  (2001)  A potent, nonpeptidyl 1H-quinolone antagonist for the gonadotropin-releasing hormone receptor.,  44  (6): [PMID:11300873] [10.1021/jm000275p]

3. Tucci FC, Zhu YF, Struthers RS, Guo Z, Gross TD, Rowbottom MW, Acevedo O, Gao Y, Saunders J, Xie Q, Reinhart GJ, Liu XJ, Ling N, Bonneville AK, Chen T, Bozigian H, Chen C..  (2005)  3-[(2R)-Amino-2-phenylethyl]-1-(2,6-difluorobenzyl)-5-(2-fluoro-3-methoxyphenyl)- 6-methylpyrimidin-2,4-dione (NBI 42902) as a potent and orally active antagonist of the human gonadotropin-releasing hormone receptor. Design, synthesis, and in vitro and in vivo characterization.,  48  (4): [PMID:15715483] [10.1021/jm049218c]

4. DeVita RJ, Parikh M, Jiang J, Fair JA, Young JR, Walsh TF, Goulet MT, Lo JL, Ren N, Yudkovitz JB, Cui J, Yang YT, Cheng K, Rohrer SP, Wyvratt MJ..  (2004)  Identification of neutral 4-O-alkyl quinolone nonpeptide GnRH receptor antagonists.,  14  (22): [PMID:15482932] [10.1016/j.bmcl.2004.08.056]

5. Betz SF, Zhu YF, Chen C, Struthers RS..  (2008)  Non-peptide gonadotropin-releasing hormone receptor antagonists.,  51  (12): [PMID:18419112] [10.1021/jm701249f]

Source

Source(1):

• Scientific Literature