ID: ALA509075

Max Phase: Preclinical

Molecular Formula: C31H28F5N3O5

Molecular Weight: 617.57

Molecule Type: Small molecule

Representations

Canonical SMILES:  COc1cccc(-c2cn(Cc3c(F)cccc3C(F)(F)F)c(=O)n(C[C@H](NCCCC(=O)O)c3ccccc3)c2=O)c1F

Standard InChI:  InChI=1S/C31H28F5N3O5/c1-44-26-13-5-10-20(28(26)33)21-16-38(17-22-23(31(34,35)36)11-6-12-24(22)32)30(43)39(29(21)42)18-25(19-8-3-2-4-9-19)37-15-7-14-27(40)41/h2-6,8-13,16,25,37H,7,14-15,17-18H2,1H3,(H,40,41)/t25-/m0/s1

Standard InChI Key:  FWSQRSDDLDNXGE-VWLOTQADSA-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: 617.57

Molecular Weight (Monoisotopic): 617.1949

AlogP: 5.23

#Rotatable Bonds: 12

Polar Surface Area: 102.56

Molecular Species: ZWITTERION

HBA: 7

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.86

CX Basic pKa: 9.04

CX LogP: 2.94

CX LogD: 2.93

Aromatic Rings: 4

Heavy Atoms: 44

QED Weighted: 0.17

Np Likeness Score: -0.83

References

1. Chen C, Chen Y, Pontillo J, Guo Z, Huang CQ, Wu D, Madan A, Chen T, Wen J, Xie Q, Tucci FC, Rowbottom M, Zhu YF, Wade W, Saunders J, Bozigian H, Struthers RS..  (2008)  Potent and orally bioavailable zwitterion GnRH antagonists with low CYP3A4 inhibitory activity.,  18  (11): [PMID:18442910] [10.1016/j.bmcl.2008.04.036]

2. Regan CF, Guo Z, Chen Y, Huang CQ, Chen M, Jiang W, Rueter JK, Coon T, Chen C, Saunders J, Brown MS, Betz SF, Struthers RS, Yang C, Wen J, Madan A, Zhu YF..  (2008)  Zwitterionic uracil derivatives as potent GnRH receptor antagonists with improved pharmaceutical properties.,  18  (16): [PMID:18667310] [10.1016/j.bmcl.2008.07.059]

3. Chen C, Wu D, Guo Z, Xie Q, Reinhart GJ, Madan A, Wen J, Chen T, Huang CQ, Chen M, Chen Y, Tucci FC, Rowbottom M, Pontillo J, Zhu YF, Wade W, Saunders J, Bozigian H, Struthers RS..  (2008)  Discovery of sodium R-(+)-4-{2-[5-(2-fluoro-3-methoxyphenyl)-3-(2-fluoro-6-[trifluoromethyl]benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl]-1-phenylethylamino}butyrate (elagolix), a potent and orally available nonpeptide antagonist of the human gonadotropin-releasing hormone receptor.,  51  (23): [PMID:19006286] [10.1021/jm8006454]

Source

Source(1):

• Scientific Literature