(5S,6S)-5,6-Diacetoxy-7-[(1R,2S)-4-chloro-2-hydroxy-2-((Z)-oct-2-enyl)-5-oxo-cyclopent-3-enyl]-heptanoic acid methyl ester

ID: ALA304706

PubChem CID: 5283258

Max Phase: Preclinical

Molecular Formula: C25H37ClO8

Molecular Weight: 501.02

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C25H37ClO8/c1-5-6-7-8-9-10-14-25(31)16-20(26)24(30)19(25)15-22(34-18(3)28)21(33-17(2)27)12-11-13-23(29)32-4/h9-10,16,19,21-22,31H,5-8,11-15H2,1-4H3/b10-9-/t19-,21-,22-,25+/m0/s1

Standard InChI Key:  UQSBPTWIGBVTJJ-WRXYSHGISA-N

Molfile:  

     RDKit          2D

 34 34  0  0  1  0  0  0  0  0999 V2000
    3.8417   -0.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7625   -0.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5875   -0.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5042   -0.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1750    0.4458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6292    0.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2917   -0.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2917   -1.0917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0750    0.9250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0000   -1.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8125    1.2958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0292    0.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1667    1.2708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8792   -0.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9917   -2.3375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    8.9292    0.7708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7250    0.2125    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.7292   -2.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2167   -2.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1667   -1.5417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0667   -1.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5750   -0.5042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1500   -0.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4542    0.0208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7167   -0.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5042    0.8458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7167   -1.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0375   -2.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3125   -0.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5167   -3.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8250   -4.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3417   -3.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6417   -3.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  1  1  0
  4  5  1  0
  5  1  1  0
  1  6  1  6
  7  6  1  0
  7  8  1  1
 12  9  1  1
 10  8  1  0
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 13  5  2  0
 14 24  1  0
 15 10  2  0
 16 11  2  0
 17 14  2  0
 18  4  1  0
 19 22  1  0
 20 19  2  0
  3 21  1  6
  3 22  1  1
 23 14  1  0
 24 25  1  0
 25 26  1  0
 26 12  1  0
 27 11  1  0
 28 10  1  0
 29 20  1  0
 30 23  1  0
 31 29  1  0
 32 33  1  0
 33 31  1  0
 34 32  1  0
  2  4  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA304706

   Punaglandin 6

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: 501.02

Molecular Weight (Monoisotopic): 500.2177

AlogP: 4.16

#Rotatable Bonds: 15

Polar Surface Area: 116.20

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.79

CX Basic pKa: ┄

CX LogP: 3.92

CX LogD: 3.92

Aromatic Rings: ┄

Heavy Atoms: 34

QED Weighted: 0.15

Np Likeness Score: 1.54

References

1. Verbitski SM, Mullally JE, Fitzpatrick FA, Ireland CM..  (2004)  Punaglandins, chlorinated prostaglandins, function as potent Michael receptors to inhibit ubiquitin isopeptidase activity.,  47  (8): [PMID:15056003] [10.1021/jm030448l]

Source

Source(1):

• Scientific Literature