disodium (2Z)-2-(2H3)methyl-3-tetradecylbut-2-enedioate

• ChemBase ID: 163887
• Molecular Formular: C19H32Na2O4
• Molecular Mass: 370.43452
• Monoisotopic Mass: 370.20959807
• SMILES: C(=C(\CCCCCCCCCCCCCC)/C(=O)[O-])(/C(=O)[O-])\C.[Na+].[Na+]
• Canonical SMILES: CCCCCCCCCCCCCC/C(=C(/C(=O)[O-])\C)/C(=O)[O-].[Na+].[Na+]
• InChI: InChI=1S/C19H34O4.2Na/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-17(19(22)23)16(2)18(20)21;;/h3-15H2,1-2H3,(H,20,21)(H,22,23);;/q;2*+1/p-2/b17-16-
• InChIKey: FIKFWCKPWWTJBB-LSSNYKSTSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: disodium (2Z)-2-(^2H₃)methyl-3-tetradecylbut-2-enedioate
• IUPAC Traditional name: disodium (2Z)-2-(^2H₃)methyl-3-tetradecylbut-2-enedioate
• Synonyms: (2Z)-2-(Methyl-d3)-3-tetradecyl-2-butenedioic Acid Disodium Salt; Chaetomellic Acid A-d3 Disodium Salt

Database IDs

• PubChem SID: 162258022
• PubChem CID: 71314592

CALCULATED PROPERTIES

• Acid pKa: 2.9883614
• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 3.977376
• LogD (pH = 7.4): 1.8274739
• Log P: 6.529579
• Molar Refractivity: 114.8084 cm^3
• Polarizability: 36.282993 Å^3
• Polar Surface Area: 80.26 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - C291817

Labelled Chaetomellic Acid A (C291815). It is an alkyl dicarboxylic acid isolated from the fermentation of Chaetomella acutiseta. Chaetomellic acid A 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 A 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)