(Z)-7-((1R,2R,3R)-3-hydroxy-2-((S,E)-3-hydroxyoct-1-enyl)-5-oxocyclopentyl)-N-(2-hydroxyethyl)hept-5-enamide

ID: ALA3398551

Cas Number: 194935-38-1

PubChem CID: 5283119

Product Number: P355679, Order Now?

Max Phase: Preclinical

Molecular Formula: C22H37NO5

Molecular Weight: 395.54

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C22H37NO5/c1-2-3-6-9-17(25)12-13-19-18(20(26)16-21(19)27)10-7-4-5-8-11-22(28)23-14-15-24/h4,7,12-13,17-19,21,24-25,27H,2-3,5-6,8-11,14-16H2,1H3,(H,23,28)/b7-4-,13-12+/t17-,18+,19+,21+/m0/s1

Standard InChI Key:  GKKWUSPPIQURFM-IGDGGSTLSA-N

Molfile:  

     RDKit          2D

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    1.2135    0.3943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.2760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2135    0.3943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7500   -1.0323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3548    0.7651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0031    2.7742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4553   -2.0031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6394    0.8543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7533   -0.1515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3039    3.5228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3070    5.0236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0093    5.7775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0124    7.2783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2853    8.0323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2822    9.5331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5799   10.2870    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2415   10.1306    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5768   11.7878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8745   12.5418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1816    0.3093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2955   -0.6965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4332    1.4827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7238   -0.2357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8377   -1.2416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8720   13.7418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2660   -0.7807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1567   -1.5850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  1  1  0
  4  6  2  0
  3  7  1  6
  1  8  1  6
  2  9  1  1
  9 10  2  0
  7 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 17 19  1  0
 19 20  1  0
 10 21  1  0
 21 22  1  0
 21 23  1  1
 22 24  1  0
 24 25  1  0
 20 26  1  0
 25 27  1  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3398551

   Prostaglandin E2 Ethanolamide

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: 395.54

Molecular Weight (Monoisotopic): 395.2672

AlogP: 2.27

#Rotatable Bonds: 14

Polar Surface Area: 106.86

Molecular Species: NEUTRAL

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 1.95

CX LogD: 1.95

Aromatic Rings: ┄

Heavy Atoms: 28

QED Weighted: 0.27

Np Likeness Score: 1.50

References

1. Finnegan DF, Shelnut EL, Nikas SP, Chiang N, Serhan CN, Makriyannis A..  (2015)  Novel tail and head group prostamide probes.,  25  (6): [PMID:25701254] [10.1016/j.bmcl.2015.01.064]

Source

Source(1):

• Scientific Literature