disodium (2Z)-2-[(7Z)-hexadec-7-en-1-yl]-3-methylbut-2-enedioate

• ChemBase ID: 164024
• Molecular Formular: C21H34Na2O4
• Molecular Mass: 396.4718
• Monoisotopic Mass: 396.22524813
• SMILES: C(=C(\CCCCCC/C=C\CCCCCCCC)/C(=O)[O-])(\C)/C(=O)[O-].[Na+].[Na+]
• Canonical SMILES: CCCCCCCC/C=C\CCCCCC/C(=C(/C(=O)[O-])\C)/C(=O)[O-].[Na+].[Na+]
• InChI: InChI=1S/C21H36O4.2Na/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-19(21(24)25)18(2)20(22)23;;/h10-11H,3-9,12-17H2,1-2H3,(H,22,23)(H,24,25);;/q;2*+1/p-2/b11-10-,19-18-
• InChIKey: FJQLDNIZWYJEEX-MPGFSKLGSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: disodium (2Z)-2-[(7Z)-hexadec-7-en-1-yl]-3-methylbut-2-enedioate
• IUPAC Traditional name: disodium (2Z)-2-[(7Z)-hexadec-7-en-1-yl]-3-methylbut-2-enedioate
• Synonyms: (2Z)-2-(7Z)-7-Hexadecen-1-yl-3-methyl-2-butenedioic Acid Disodium Salt; (Z,Z)-2-(7-Hexadecenyl)-3-methyl-2-butenedioic Acid Disodium Salt; (2Z)-2-(7Z)-7-Hexadecenyl-3-methyl-2-butenedioic Acid Disodium Salt; Chaetomellic Acid B Disodium Salt

Database IDs

• PubChem SID: 162258159
• PubChem CID: 71314658

CALCULATED PROPERTIES

• Acid pKa: 3.0370898
• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 4.552983
• LogD (pH = 7.4): 2.3827543
• Log P: 7.056795
• Molar Refractivity: 125.127 cm^3
• Polarizability: 39.723324 Å^3
• Polar Surface Area: 80.26 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - C291830

Chaetomellic acid B is an alkyl dicarboxylic acid isolated from the fermentation of Chaetomella acutiseta. Chaetomellic acid B has been shown to be a potent, highly specific inhibitor of RAS farnesyl protein transferase (FPTase). The association between RAS proteins and cancer has made Chaetomellic acid B a potential chemotherapeutic agent.

REFERENCES

• Gibbs, J.B., et al.: J. Biol. Chem., 268, 7618 (1993)
• Tamanoi, F., et al.: Trends Biochem. Sci., 18, 349 (1993)