(5S,6S)-5,6-Diacetoxy-7-[(R)-4-chloro-2-hydroxy-2-((2Z,5E)-octa-2,5-dienyl)-5-oxo-cyclopent-3-en-(E)-ylidene]-heptanoic acid methyl ester

ID: ALA61953

PubChem CID: 44305602

Max Phase: Preclinical

Molecular Formula: C25H33ClO8

Molecular Weight: 496.98

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC/C=C/C/C=C\C[C@@]1(O)C=C(Cl)C(=O)/C1=C/[C@H](OC(C)=O)[C@H](CCCC(=O)OC)OC(C)=O

Standard InChI:  InChI=1S/C25H33ClO8/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/h6-7,9-10,15-16,21-22,31H,5,8,11-14H2,1-4H3/b7-6+,10-9-,19-15-/t21-,22-,25+/m0/s1

Standard InChI Key:  DWJPUNIYVACWRP-NXBRMUBPSA-N

Molfile:  

     RDKit          2D

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    6.2125    1.6708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.5500   -0.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8542    0.3958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1167    0.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9042    1.2208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1167   -0.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.7125    0.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0417   -3.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 34 32  1  0
  5  6  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA61953

   methyl (5S,6S,7E)-5,6-diacetyloxy-7-[(2R)-4-chloro-2-hydroxy-2-[(2Z,5E)-octa-2,5-dienyl]-5-oxocyclopent-3-en-1-ylidene]heptanoate

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: 496.98

Molecular Weight (Monoisotopic): 496.1864

AlogP: 3.86

#Rotatable Bonds: 13

Polar Surface Area: 116.20

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.41

CX Basic pKa: ┄

CX LogP: 3.57

CX LogD: 3.57

Aromatic Rings: ┄

Heavy Atoms: 34

QED Weighted: 0.18

Np Likeness Score: 2.15

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