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

• ChemBase ID: 155599
• Molecular Formular: C22H36O5
• Molecular Mass: 380.51824
• Monoisotopic Mass: 380.25627425
• SMILES: CCCC[C@H](C)C[C@@H](C=C[C@H]1[C@@H](CC(=O)[C@@H]1CCCC/C=C/C(=O)O)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)/t16-,17+,18+,19+,21+/m0/s1
• InChIKey: OJZYRQPMEIEQFC-HMPZBHLVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E)-7-[(1R,2R,3R)-3-hydroxy-2-[(1E,3S,5S)-3-hydroxy-5-methylnon-1-en-1-yl]-5-oxocyclopentyl]hept-2-enoic acid; 7-[(1R,2R,3R)-3-hydroxy-2-[(3S,5S)-3-hydroxy-5-methylnon-1-en-1-yl]-5-oxocyclopentyl]hept-2-enoic acid
• IUPAC Traditional name: limaprost; 7-[(1R,2R,3R)-3-hydroxy-2-[(3S,5S)-3-hydroxy-5-methylnon-1-en-1-yl]-5-oxocyclopentyl]hept-2-enoic acid
• Synonyms: (2E)-7-[(1R,2R,3R)-3-Hydroxy-2-[(1E,3S,5S)-3-hydroxy-5-methyl-1-nonen-1-yl]-5-oxocyclopentyl]-2-heptenoic Acid; (2E,11α,13E,15S,17S)-11,15-Dihydroxy-17,20-dimethyl-9-oxo-prosta-2,13-dien-1-oic Acid; 17S,20-Dimethyl-trans-Δ2-PGE1; ONO 1206; OP 1206; Limaprost; 11α,15S-Dihydroxy-17S,20-dimethyl-9-oxo-prosta-2E,13E-dien-1-oic acid; 17α,20-dimethyl-δ2-PGE1; Limaprost

Database IDs

• CAS Number: 74397-12-9
• MDL Number: MFCD00868275
• PubChem SID: 162249737
• PubChem CID: 71312166

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: DMF: soluble; DMSO: soluble; ethanol: soluble
• Apperance: crystalline

Safety Information

• RTECS: UK8362500
• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2
• Risk Statements: 25
• Safety Statements: 36/37/39-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300
• GHS Precautionary statements: P264-P301 + P310
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 2
• Storage Temperature: -20°C

Product Information

• Purity: ≥99%
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C22H36O5

DETAILS

Sigma Aldrich - L6538

Other Notes
Potent analog of PGE1 with prolonged half-life.

Toronto Research Chemicals - 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)