(Z)-7-((1R,2R,3R)-3-hydroxy-2-((S,E)-3-hydroxy-5-phenylpent-1-en-1-yl)-5-oxocyclopentyl)-N-(2-hydroxyethyl)hept-5-enamide

ID: ALA3398545

PubChem CID: 118727545

Max Phase: Preclinical

Molecular Formula: C25H35NO5

Molecular Weight: 429.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(CCC/C=C\C[C@H]1C(=O)C[C@@H](O)[C@@H]1/C=C/[C@@H](O)CCc1ccccc1)NCCO

Standard InChI:  InChI=1S/C25H35NO5/c27-17-16-26-25(31)11-7-2-1-6-10-21-22(24(30)18-23(21)29)15-14-20(28)13-12-19-8-4-3-5-9-19/h1,3-6,8-9,14-15,20-22,24,27-28,30H,2,7,10-13,16-18H2,(H,26,31)/b6-1-,15-14+/t20-,21+,22+,24+/m0/s1

Standard InChI Key:  UNRIGVDTQLYALV-JFZJXZSWSA-N

Molfile:  

     RDKit          2D

 31 32  0  0  0  0  0  0  0  0999 V2000
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    5.1873   -7.5117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.9293   -9.8007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4293   -9.7955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6313  -10.7740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8197   -7.9039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8330   -7.9858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1894   -6.0109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8912   -5.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1234   -6.4341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5478   -5.9613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6701   -6.9578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0945   -6.4850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2168   -7.4814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6412   -7.0086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7635   -8.0051    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.8829   -5.8332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1879   -7.5323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3102   -8.5288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4491   -8.1508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8933   -3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5951   -3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9336   -3.1588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    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  1
  1  8  1  1
  2  9  1  6
  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
 20 21  1  0
 10 22  1  0
 22 23  1  0
 22 24  1  6
 23 25  1  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3398545

   ---

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: 429.56

Molecular Weight (Monoisotopic): 429.2515

AlogP: 2.33

#Rotatable Bonds: 13

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: 2.20

CX LogD: 2.20

Aromatic Rings: 1

Heavy Atoms: 31

QED Weighted: 0.28

Np Likeness Score: 1.19

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