(2E)-7-[(1R,2R,3R)-3-hydroxy-2-[(1E,3S,5R)-3-hydroxy-5-(2H3)methylnon-1-en-1-yl]-5-oxocyclopentyl]hept-2-enoic acid

• ChemBase ID: 172302
• Molecular Formular: C22H36O5
• Molecular Mass: 380.51824
• Monoisotopic Mass: 380.25627425
• SMILES: [C@H]1([C@H]([C@@H](CC1=O)O)/C=C/[C@H](C[C@@H](CCCC)C)O)CCCC/C=C/C(=O)O
• Canonical SMILES: CCCC[C@H](C[C@@H](/C=C/[C@H]1[C@H](O)CC(=O)[C@@H]1CCCC/C=C/C(=O)O)O)C
• InChI: InChI=1S/C22H36O5/c1-3-4-9-16(2)14-17(23)12-13-19-18(20(24)15-21(19)25)10-7-5-6-8-11-22(26)27/h8,11-13,16-19,21,23,25H,3-7,9-10,14-15H2,1-2H3,(H,26,27)/b11-8+,13-12+/t16-,17-,18-,19-,21-/m1/s1
• InChIKey: OJZYRQPMEIEQFC-PKBPMWMXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E)-7-[(1R,2R,3R)-3-hydroxy-2-[(1E,3S,5R)-3-hydroxy-5-(^2H₃)methylnon-1-en-1-yl]-5-oxocyclopentyl]hept-2-enoic acid
• IUPAC Traditional name: (2E)-7-[(1R,2R,3R)-3-hydroxy-2-[(1E,3S,5R)-3-hydroxy-5-(^2H₃)methylnon-1-en-1-yl]-5-oxocyclopentyl]hept-2-enoic acid
• Synonyms: (2E,11α,13E,15S,17S)-11,15-Dihydroxy-17-(methyl-d3),20-methyl-9-oxoprosta-2,13-dien-1-oic Acid; 17S-(Methyl-d3),20-methyl-trans-2-PGE1; ONO 1206-d3; OP 1206-d3; Opalmon-d3; Prorenal-d3; Limaprost-d3

Database IDs

• PubChem SID: 164228212
• PubChem CID: 71749787

CALCULATED PROPERTIES

• Acid pKa: 4.4431877
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 3.2247262
• LogD (pH = 7.4): 1.4622635
• Log P: 4.316603
• Molar Refractivity: 108.5614 cm^3
• Polarizability: 41.864788 Å^3
• Polar Surface Area: 94.83 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White Solid
• Melting Point: 96-98°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - L461502

Labelled Limaprost (L461500). Limaprost is an analog of Prostaglandin E1 with structural modifications intended to give it a prolonged half-life and greater potency. Limaprost is used as an antianginal.

REFERENCES

• Tsuboi, T., et al.: Arch. Int. Pharmacodyn., 247, 89 (1980)
• Adaikan, P.G., et al.: Prostaglandins Med., 6, 449 (1980)
• Kottegoda, S.R., et al.: Prostaglandins Leukotrienes Med., 8, 343 (1980)
• Ishizaki, T., et al.: Chest, 85, 382 (1980)