(1R,4aR,4bS,7S,10aR)-7-ethenyl-1,4a,7-trimethyl-1,2,3,4,4a,4b,5,6,7,8,10,10a-dodecahydrophenanthrene-1-carboxylic acid

• ChemBase ID: 127910
• Molecular Formular: C20H30O2
• Molecular Mass: 302.451
• Monoisotopic Mass: 302.2245802
• SMILES: [C@H]12[C@](C)(C(=O)O)CCC[C@]1(C)[C@@H]1C(=CC2)C[C@](C=C)(C)CC1
• Canonical SMILES: C=C[C@@]1(C)CC[C@H]2C(=CC[C@@H]3[C@]2(C)CCC[C@@]3(C)C(=O)O)C1
• InChI: InChI=1S/C20H30O2/c1-5-18(2)12-9-15-14(13-18)7-8-16-19(15,3)10-6-11-20(16,4)17(21)22/h5,7,15-16H,1,6,8-13H2,2-4H3,(H,21,22)/t15-,16+,18-,19+,20+/m0/s1
• InChIKey: MXYATHGRPJZBNA-KRFUXDQASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,4aR,4bS,7S,10aR)-7-ethenyl-1,4a,7-trimethyl-1,2,3,4,4a,4b,5,6,7,8,10,10a-dodecahydrophenanthrene-1-carboxylic acid
• IUPAC Traditional name: isopimaric acid
• Synonyms: sandaracopimaric acid; Isopimaric acid; Isopimaric Acid; (1R,4aR,4bS,7S,10aR)-7-Ethenyl-1,2,3,4,4a,4b,5,6,7,8,10,10a-dodecahydro-1,4a,7-trimethyl-1-phenanthrenecarboxylic Acid; (-)-13β-Methyl-13-vinylpodocarp-7-en-15-oic Acid; (+)-Isopimaric Acid; 7,15-Isopimaradien-18-oic Acid; Δ7,15-Isopimaric Acid

Database IDs

• CAS Number: 5835-26-7
• MDL Number: MFCD04113116
• PubChem SID: 162222227; 24724518
• PubChem CID: 442048
• CHEMBL: 512164
• Wikipedia Title: Isopimaric_acid

CALCULATED PROPERTIES

• Acid pKa: 4.804501
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 4.29256
• LogD (pH = 7.4): 2.5184128
• Log P: 5.0671844
• Molar Refractivity: 90.3348 cm^3
• Polarizability: 35.413227 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: ~26 mg/mL
• Apperance: Powder; white solid

Safety Information

• German water hazard class: 3
• GHS Pictograms: GHS09
• GHS Signal Word: Warning
• GHS Hazard statements: H400
• GHS Precautionary statements: P273
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (GC); 96.0
• Empirical Formula (Hill Notation): C20H30O2

DETAILS

Sigma Aldrich - I6783

Biochem/physiol Actions
Potent opener of large conductance calcium activated K+ (BK) channels.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. I6783.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - I821940

A potent novel activators of large-conductance Ca2+-activated K+ channel.

REFERENCES

• Imaizumei, Y. et al.: Mol. Pharmacol., 62, 836 (2002)
• Chang, S. et al.: AM. J. Physiol., 298, F1416 (2002)