5-[(2E,3aS,4R,5R,6aS)-5-hydroxy-4-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-octahydropentalen-2-ylidene]pentanoic acid

• ChemBase ID: 133140
• Molecular Formular: C21H34O4
• Molecular Mass: 350.49226
• Monoisotopic Mass: 350.24570957
• SMILES: CCCCC[C@@H](/C=C/[C@H]1[C@@H](C[C@H]2[C@@H]1C/C(=C/CCCC(=O)O)/C2)O)O
• Canonical SMILES: CCCCC[C@@H](/C=C/[C@H]1[C@H](O)C[C@H]2[C@@H]1C/C(=C/CCCC(=O)O)/C2)O
• InChI: InChI=1S/C21H34O4/c1-2-3-4-8-17(22)10-11-18-19-13-15(7-5-6-9-21(24)25)12-16(19)14-20(18)23/h7,10-11,16-20,22-23H,2-6,8-9,12-14H2,1H3,(H,24,25)/b11-10+,15-7+/t16-,17-,18+,19-,20+/m0/s1
• InChIKey: XZFRIPGNUQRGPI-WBQKLGIQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-[(2E,3aS,4R,5R,6aS)-5-hydroxy-4-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-octahydropentalen-2-ylidene]pentanoic acid
• IUPAC Traditional name: 5-[(2E,3aS,4R,5R,6aS)-5-hydroxy-4-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-hexahydro-1H-pentalen-2-ylidene]pentanoic acid
• Synonyms: 6a-Carba-prostaglandin I2; Carbocyclic PGI2; Carbacyclin

Database IDs

• CAS Number: 69552-46-1
• MDL Number: MFCD00210824
• PubChem SID: 24892602; 162227417
• PubChem CID: 6436393

CALCULATED PROPERTIES

• Acid pKa: 4.6648154
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 2.721147
• LogD (pH = 7.4): 0.9433939
• Log P: 3.6146991
• Molar Refractivity: 101.3492 cm^3
• Polarizability: 39.21552 Å^3
• Polar Surface Area: 77.76 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22
• Safety Statements: 22-36
• 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: -20°C

Pharmacology Properties

• Gene Information: human ... PPARA(5465), PPARD(5467), PPARG(5468)

Product Information

• Purity: ≥90% (HPLC)

DETAILS

Sigma Aldrich - C3305

Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. C3305.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.