sodium 3-{[(3aR,4R,5R,6aS)-4-[(3S)-3-cyclohexyl-3-hydroxyprop-1-en-1-yl]-5-hydroxy-hexahydro-2H-cyclopenta[b]furan-2-ylidene]methyl}benzoate

• ChemBase ID: 153769
• Molecular Formular: C24H29NaO5
• Molecular Mass: 420.47383
• Monoisotopic Mass: 420.19126831
• SMILES: c1cc(cc(c1)C(=O)[O-])/C=C\1/C[C@H]2[C@@H](O1)C[C@H]([C@@H]2C=C[C@H](C1CCCCC1)O)O.[Na+]
• Canonical SMILES: O[C@@H]1C[C@H]2[C@@H]([C@H]1C=C[C@H](C1CCCCC1)O)C/C(=C/c1cccc(c1)C(=O)[O-])/O2.[Na+]
• InChI: InChI=1S/C24H30O5.Na/c25-21(16-6-2-1-3-7-16)10-9-19-20-13-18(29-23(20)14-22(19)26)12-15-5-4-8-17(11-15)24(27)28;/h4-5,8-12,16,19-23,25-26H,1-3,6-7,13-14H2,(H,27,28);/q;+1/p-1/t19-,20-,21-,22-,23+;/m1./s1
• InChIKey: KPQVOJYDUCZQEQ-RCTOXBDISA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium 3-{[(3aR,4R,5R,6aS)-4-[(3S)-3-cyclohexyl-3-hydroxyprop-1-en-1-yl]-5-hydroxy-hexahydro-2H-cyclopenta[b]furan-2-ylidene]methyl}benzoate
• IUPAC Traditional name: sodium 3-{[(3aR,4R,5R,6aS)-4-[(3S)-3-cyclohexyl-3-hydroxyprop-1-en-1-yl]-5-hydroxy-hexahydrocyclopenta[b]furan-2-ylidene]methyl}benzoate
• Synonyms: Rheocyclan; Sodium 3-[(Z)-[(3aR,4R,5R,6aS)-4-[(1E,3S)-3-cyclohexyl-3-hydroxy-1-propenyl]hexahydro-5-hydroxy-2H-cyclopenta[b]furan-2-ylidene]methyl]benzoate; Taprostene sodium salt

Database IDs

• CAS Number: 87440-45-7
• MDL Number: MFCD05664743
• PubChem SID: 162247908; 24724631
• PubChem CID: 71311726

CALCULATED PROPERTIES

• Acid pKa: 4.0042586
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 1.6721783
• LogD (pH = 7.4): 0.020950532
• Log P: 3.1775742
• Molar Refractivity: 124.3962 cm^3
• Polarizability: 43.20927 Å^3
• Polar Surface Area: 89.82 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble26 mg/mL
• Apperance: off-white
• Melting Point: 173-182.5 °C(lit.)

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22
• Safety Statements: 36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H332
• GHS Precautionary statements: P280
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C24H29NaO5

DETAILS

Sigma Aldrich - T4949

Biochem/physiol Actions
Highly selective IP1 prostanoid receptor agonist.