(1R,4S,5R,9S,10R,13S)-5,9,13-trimethyl-14-oxotetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylic acid

• ChemBase ID: 171978
• Molecular Formular: C20H30O3
• Molecular Mass: 318.4504
• Monoisotopic Mass: 318.21949482
• SMILES: C1C[C@@]([C@@H]2[C@@](C1)([C@H]1[C@]3(CC2)C[C@](CC1)(C(=O)C3)C)C)(C)C(=O)O
• Canonical SMILES: OC(=O)[C@]1(C)CCC[C@@]2([C@@H]1CC[C@]13[C@H]2CC[C@@](C3)(C(=O)C1)C)C
• InChI: InChI=1S/C20H30O3/c1-17-9-5-14-18(2)7-4-8-19(3,16(22)23)13(18)6-10-20(14,12-17)11-15(17)21/h13-14H,4-12H2,1-3H3,(H,22,23)/t13-,14-,17-,18+,19+,20-/m0/s1
• InChIKey: KFVUFODCZDRVSS-XGBBNYNSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,4S,5R,9S,10R,13S)-5,9,13-trimethyl-14-oxotetracyclo[11.2.1.0^1,^1^0.0^4,^9]hexadecane-5-carboxylic acid
• IUPAC Traditional name: (1R,4S,5R,9S,10R,13S)-5,9,13-trimethyl-14-oxotetracyclo[11.2.1.0^1,^1^0.0^4,^9]hexadecane-5-carboxylic acid
• Synonyms: (4α,8β,13β)-13-Methyl-16-oxo-17-norkauran-18-oic Acid; (2S,4aR,4bS,8R,8aS,10aR)-Dodecahydro-2,4b,8-trimethyl-12-oxo-1H-2,10a-ethanophenanthrene-8-carboxylic Acid; Isosteviol; (-)-Isosteviol; Ketoisostevic Acid; NSC 231875; Isosteviol

Database IDs

• CAS Number: 27975-19-5
• PubChem SID: 164227888
• PubChem CID: 99514

CALCULATED PROPERTIES

• Acid pKa: 4.650878
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 3.595514
• LogD (pH = 7.4): 1.81796
• Log P: 4.501221
• Molar Refractivity: 88.2058 cm^3
• Polarizability: 35.235 Å^3
• Polar Surface Area: 54.37 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Product Information

• Classification: Rare Genuine Natural Compounds

DETAILS

Toronto Research Chemicals - I902200

A tetracyclic diterpenoid with a beyerane core has drawn attention because it can exhibit antihypertensive activity, reduce blood glucose, suppress cancer cells.

REFERENCES

• Jeppesen, P., et al.: Metabolism, 52, 372 (2003)
• Chen, J., et al.: Am. J. Physiol. Endocrinol. Metab., 292, 1906 (2003)
• Jeppesen, P., et al.: Diabetologia, A0217 (2003)