UNOPROSTONE ISOPROPYL

ID: ALA1200661

Cas Number: 120373-24-2

PubChem CID: 5282175

Product Number: U341844, Order Now?

Max Phase: Approved

First Approval: 2000

Molecular Formula: C25H44O5

Molecular Weight: 424.62

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Isopropyl unoprostone | Unoprostone isopropyl | UF-021 | isopropyl unoprostone|unoprostone isopropyl|Unoprostone isopropyl ester|Rescula|120373-24-2|UF-021|UF 021|UNII-5M161S5O5P|CHEBI:31731|5M161S5O5P|Rescula (proposed trade name)|DTXSID5049071|isopropyl (5Z,9alpha,11alpha)-9,11-dihydroxy-15-oxo-20a,20b-dihomoprost-5-en-1-oate|isopropyl (Z)-7-((1R,2R,3R,5S)-3,5-dihydroxy-2-(3-oxodecyl)cyclopentyl)hept-5-enoate|propan-2-yl (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-(3-oxodecyl)cyclopentyl]hept-5-enoatShow More⌵

Trade Names(1): Rescula

Canonical SMILES:  CCCCCCCC(=O)CC[C@@H]1[C@@H](C/C=C\CCCC(=O)OC(C)C)[C@@H](O)C[C@H]1O

Standard InChI:  InChI=1S/C25H44O5/c1-4-5-6-7-10-13-20(26)16-17-22-21(23(27)18-24(22)28)14-11-8-9-12-15-25(29)30-19(2)3/h8,11,19,21-24,27-28H,4-7,9-10,12-18H2,1-3H3/b11-8-/t21-,22-,23+,24-/m1/s1

Standard InChI Key:  XXUPXHKCPIKWLR-JHUOEJJVSA-N

Molfile:  

     RDKit          2D

 30 30  0  0  0  0  0  0  0  0999 V2000
    0.1250   -2.6708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9625   -2.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1292   -1.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5458   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5458   -1.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7375   -3.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5167   -1.9458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5208   -2.6542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1250   -1.5875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9625   -3.7292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3542   -1.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -1.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9625   -3.0208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3500   -2.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7667   -3.5625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7625   -1.0667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7417   -1.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7417   -1.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9000   -1.5958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6750   -1.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5750   -2.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2875   -1.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1833   -3.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0000   -4.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3542   -1.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7458   -2.6458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3958   -3.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1750   -3.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7750   -4.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6208   -3.7833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  1  0
  3  1  1  0
  4  1  1  0
  5  3  1  0
  1  6  1  1
  7 19  1  0
  8  7  2  0
  9  7  1  0
 10 13  2  0
 11 17  1  0
 12 11  2  0
 13 14  1  0
 14  6  1  0
  4 15  1  6
  5 16  1  6
  3 17  1  6
 18  9  1  0
 19 22  1  0
 20 12  1  0
 21 13  1  0
 22 20  1  0
 23 21  1  0
 24 27  1  0
 25 18  1  0
 26 18  1  0
 27 29  1  0
 28 23  1  0
 29 28  1  0
 30 24  1  0
  2  5  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1200661

   Unoprostone isopropyl ester

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: Yes

First In Class: No

Black Box: No

Chirality: Yes

Availability: Yes

Prodrug: Yes

Calculated Properties

Molecular Weight: 424.62

Molecular Weight (Monoisotopic): 424.3189

AlogP: 5.12

#Rotatable Bonds: 16

Polar Surface Area: 83.83

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.83

CX LogD: 4.83

Aromatic Rings: ┄

Heavy Atoms: 30

QED Weighted: 0.20

Np Likeness Score: 1.24

References

1. Unpublished dataset, 

2. Gao B, Huber RD, Wenzel A, Vavricka SR, Ismair MG, Remé C, Meier PJ..  (2005)  Localization of organic anion transporting polypeptides in the rat and human ciliary body epithelium.,  80  (1): [PMID:15652527] [10.1016/j.exer.2004.08.013]

3. PubChem BioAssay data set, 

4. Unpublished dataset, 

5. Sutherland JJ, Yonchev D, Fekete A, Urban L..  (2023)  A preclinical secondary pharmacology resource illuminates target-adverse drug reaction associations of marketed drugs.,  14  (1): [PMID:37468498] [10.1038/s41467-023-40064-9]

Source

Source(5):

• Scientific Literature
• PubChem BioAssays
• Clinical Candidates
• FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book)
• TP-search Transporter Database