5Z-(9S,11R,15S)-13-Oxa-16-phenoxy-propoxy]-9,11,15-trihydroxy-17,18,19,20-tetranor-5-prostadienoic acid

ID: ALA491475

Chembl Id: CHEMBL491475

PubChem CID: 44564519

Max Phase: Preclinical

Molecular Formula: C21H30O7

Molecular Weight: 394.46

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)COc2ccccc2)[C@H](O)C[C@@H]1O

Standard InChI:  InChI=1S/C21H30O7/c22-15(13-27-16-8-4-3-5-9-16)14-28-21-17(18(23)12-19(21)24)10-6-1-2-7-11-20(25)26/h1,3-6,8-9,15,17-19,21-24H,2,7,10-14H2,(H,25,26)/b6-1-/t15-,17+,18+,19-,21-/m1/s1

Standard InChI Key:  HYMKBRFXEHNVOK-XKRIOCRBSA-N

Alternative Forms

1. Parent:

   

   ALA491475

   (Z)-7-[(1S,2R,3R,5S)-3,5-dihydroxy-2-[(2S)-2-hydroxy-3-phenoxypropoxy]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: 394.46

Molecular Weight (Monoisotopic): 394.1992

AlogP: 1.75

#Rotatable Bonds: 12

Polar Surface Area: 116.45

Molecular Species: ACID

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.22

CX Basic pKa: ┄

CX LogP: 1.35

CX LogD: -1.67

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.32

Np Likeness Score: 1.11

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