(5S,6S)-5-Acetoxy-6-[(R)-4-chloro-2-hydroxy-2-((Z)-oct-2-enyl)-5-oxo-cyclopent-3-en-(Z)-ylidenemethyl]-7-oxo-octanoic acid methyl ester

ID: ALA293403

PubChem CID: 44305606

Max Phase: Preclinical

Molecular Formula: C25H35ClO7

Molecular Weight: 483.00

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C25H35ClO7/c1-5-6-7-8-9-10-14-25(31)16-21(26)24(30)20(25)15-19(17(2)27)22(33-18(3)28)12-11-13-23(29)32-4/h9-10,15-16,19,22,31H,5-8,11-14H2,1-4H3/b10-9-,20-15+/t19-,22+,25-/m1/s1

Standard InChI Key:  AOJGKPUHSISGHQ-HYBNKAMISA-N

Molfile:  

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    8.3042    0.6208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6542    1.8958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8542    2.3208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6792   -3.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4667    0.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1667   -3.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.2917   -4.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  5  6  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA293403

   methyl (5S,6S)-5-acetyloxy-6-[(Z)-[(2R)-4-chloro-2-hydroxy-2-[(Z)-oct-2-enyl]-5-oxocyclopent-3-en-1-ylidene]methyl]-7-oxooctanoate

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: 483.00

Molecular Weight (Monoisotopic): 482.2071

AlogP: 4.36

#Rotatable Bonds: 14

Polar Surface Area: 106.97

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.30

CX Basic pKa: ┄

CX LogP: 4.11

CX LogD: 4.11

Aromatic Rings: ┄

Heavy Atoms: 33

QED Weighted: 0.17

Np Likeness Score: 1.92

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