5Z-(9S,11R,15R)-13-Oxa-17-(3-trifluoromethyl)phenyl-9,11,15-trihydroxy-18,19,20-trinor-5-prostadienoic acid

ID: ALA521964

Chembl Id: CHEMBL521964

PubChem CID: 44564468

Max Phase: Preclinical

Molecular Formula: C23H31F3O6

Molecular Weight: 460.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)CCC/C=C\C[C@@H]1[C@@H](OC[C@H](O)CCc2cccc(C(F)(F)F)c2)[C@H](O)C[C@@H]1O

Standard InChI:  InChI=1S/C23H31F3O6/c24-23(25,26)16-7-5-6-15(12-16)10-11-17(27)14-32-22-18(19(28)13-20(22)29)8-3-1-2-4-9-21(30)31/h1,3,5-7,12,17-20,22,27-29H,2,4,8-11,13-14H2,(H,30,31)/b3-1-/t17-,18+,19+,20-,22-/m1/s1

Standard InChI Key:  XLSNJVCYRKKOFS-AGDVZXGHSA-N

Alternative Forms

1. Parent:

   

   ALA521964

   (Z)-7-[(1S,2R,3R,5S)-3,5-dihydroxy-2-[(2R)-2-hydroxy-4-[3-(trifluoromethyl)phenyl]butoxy]cyclopentyl]hept-5-enoic acid

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: 460.49

Molecular Weight (Monoisotopic): 460.2073

AlogP: 3.33

#Rotatable Bonds: 12

Polar Surface Area: 107.22

Molecular Species: ACID

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.22

CX Basic pKa: ┄

CX LogP: 3.04

CX LogD: 0.03

Aromatic Rings: 1

Heavy Atoms: 32

QED Weighted: 0.28

Np Likeness Score: 0.89

References

1. Feng Z, Hellberg MR, Sharif NA, McLaughlin MA, Williams GW, Scott D, Wallace T..  (2009)  Discovery of 13-oxa prostaglandin analogs as antiglaucoma agents: synthesis and biological activity.,  17  (2): [PMID:19101156] [10.1016/j.bmc.2008.11.070]

Source

Source(1):

• Scientific Literature