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

ID: ALA65090

PubChem CID: 5283248

Max Phase: Preclinical

Molecular Formula: C25H35ClO8

Molecular Weight: 499.00

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Punaglandin 4 | punaglandin 4|methyl 5S,6S-diacetoxy-9-oxo-10-chloro-12R-hydroxy-7E,10E,14Z-prostatrienoate-cyclo[8,12R]|CHEMBL65090|CHEBI:169859|LMFA03120033|methyl (5S,6S,7E)-5,6-diacetyloxy-7-[(2R)-4-chloro-2-hydroxy-2-[(Z)-oct-2-enyl]-5-oxocyclopent-3-en-1-ylidene]heptanoate

Canonical SMILES:  CCCCC/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/C25H35ClO8/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/h9-10,15-16,21-22,31H,5-8,11-14H2,1-4H3/b10-9-,19-15-/t21-,22-,25+/m0/s1

Standard InChI Key:  HMDYASDJIREJJW-ORSYJHFOSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA65090

   PUNAGLANDIN 4

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: 499.00

Molecular Weight (Monoisotopic): 498.2020

AlogP: 4.08

#Rotatable Bonds: 14

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: 3.93

CX LogD: 3.93

Aromatic Rings: ┄

Heavy Atoms: 34

QED Weighted: 0.13

Np Likeness Score: 2.12

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]

2. Baker BJ, Scheuer PJ..  (1994)  The punaglandins: 10-chloroprostanoids from the octocoral Telesto riisei.,  57  (10): [PMID:7857405] [10.1021/np50112a003]

Source

Source(1):

• Scientific Literature