3,5-dihydroxy-3-(2H3)methylpentanoic acid; N-cyclohexylcyclohexanamine

• ChemBase ID: 174606
• Molecular Formular: C18H35NO4
• Molecular Mass: 329.4748
• Monoisotopic Mass: 329.25660861
• SMILES: OCCC(CC(=O)O)(O)C.C1(NC2CCCCC2)CCCCC1
• Canonical SMILES: C1CCC(CC1)NC1CCCCC1.OCCC(CC(=O)O)(O)C
• InChI: InChI=1S/C12H23N.C6H12O4/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12;1-6(10,2-3-7)4-5(8)9/h11-13H,1-10H2;7,10H,2-4H2,1H3,(H,8,9)
• InChIKey: DCKUKHIZWLYMEF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3,5-dihydroxy-3-(^2H₃)methylpentanoic acid; N-cyclohexylcyclohexanamine
• IUPAC Traditional name: 3,5-dihydroxy-3-(^2H₃)methylpentanoic acid; dicha
• Synonyms: 3,5-Dihydroxy-3-(methyl-d3) Pentanoic Acid Dicyclohexylamine Salt; Hiochic Acid-d3 Dicyclohexylamine Salt; 3,5-Dihydroxy-3-(methyl-d3)valeric Acid Dicyclohexylamine Salt; 2,4-Dideoxy-3-C-(methyl-d3)pentonic Acid Dicyclohexylamine Salt; Mevalonic Acid-d3 Dicyclohexylamine Salt; (RS)-Mevalonic Acid-d3 Dicyclohexylamine Salt; D,L-Mevalonic Acid-d3 Dicyclohexylamine Salt

Database IDs

• PubChem SID: 164230516
• PubChem CID: 71750724

CALCULATED PROPERTIES

• Acid pKa: 4.384681
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -2.2391148
• LogD (pH = 7.4): -3.993144
• Log P: -1.0933796
• Molar Refractivity: 34.5114 cm^3
• Polarizability: 13.665351 Å^3
• Polar Surface Area: 77.76 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: White Solid
• Melting Point: 137-140°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - M339022

Labelled Mevalonic Acid. Precursor in the biosynthesis of cholesterol. Occurs in equilibrium with the δ-lactone.

REFERENCES

• Chen, Z., et al.: Biochem. Biophys. Res. Commun., 333, 664 (1990)
• Heintze, A., et al.: Plant Physiol., 93, 1121 (1990)
• Dubey, V., et al.: J. Biosci., 28, 637 (1990)
• Hemmerlin, A., et al.: J. Biol. Chem., 278, 26666 (1990)