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

ID: ALA291597

PubChem CID: 5283244

Max Phase: Preclinical

Molecular Formula: C27H39ClO10

Molecular Weight: 559.05

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C27H39ClO10/c1-6-7-8-9-10-11-15-27(34)16-20(28)24(33)23(27)26(38-19(4)31)25(37-18(3)30)21(36-17(2)29)13-12-14-22(32)35-5/h10-11,16,21,23,25-26,34H,6-9,12-15H2,1-5H3/b11-10-/t21-,23+,25+,26+,27+/m0/s1

Standard InChI Key:  JJPYFSVYYQRFTK-BWCUSQEASA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA291597

   Punaglandin 2

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: 559.05

Molecular Weight (Monoisotopic): 558.2232

AlogP: 3.70

#Rotatable Bonds: 16

Polar Surface Area: 142.50

Molecular Species: NEUTRAL

HBA: 10

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.70

CX Basic pKa: ┄

CX LogP: 3.44

CX LogD: 3.44

Aromatic Rings: ┄

Heavy Atoms: 38

QED Weighted: 0.13

Np Likeness Score: 1.66

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