tetralithium(1+) ion (3R)-3-{[2-({2-[(2-carboxyacetyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-3-hydroxy-2,2-dimethylpropyl ({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonatooxy)oxolan-2-yl]methyl phosphonato}oxy)phosphonate

• ChemBase ID: 155975
• Molecular Formular: C24H34Li4N7O19P3S
• Molecular Mass: 877.312543
• Monoisotopic Mass: 877.14832099
• SMILES: [Li+].[Li+].[Li+].[Li+].CC(C)(COP(=O)([O-])OP(=O)([O-])OC[C@@H]1[C@H]([C@H]([C@@H](O1)n1cnc2c1ncnc2N)O)OP(=O)([O-])[O-])[C@H](C(=O)NCCC(=O)NCCSC(=O)CC(=O)O)O
• Canonical SMILES: O=C(NCCSC(=O)CC(=O)O)CCNC(=O)[C@@H](C(COP(=O)(OP(=O)(OC[C@H]1O[C@H]([C@@H]([C@@H]1OP(=O)([O-])[O-])O)n1cnc2c1ncnc2N)[O-])[O-])(C)C)O.[Li+].[Li+].[Li+].[Li+]
• InChI: InChI=1S/C24H38N7O19P3S.4Li/c1-24(2,19(37)22(38)27-4-3-13(32)26-5-6-54-15(35)7-14(33)34)9-47-53(44,45)50-52(42,43)46-8-12-18(49-51(39,40)41)17(36)23(48-12)31-11-30-16-20(25)28-10-29-21(16)31;;;;/h10-12,17-19,23,36-37H,3-9H2,1-2H3,(H,26,32)(H,27,38)(H,33,34)(H,42,43)(H,44,45)(H2,25,28,29)(H2,39,40,41);;;;/q;4*+1/p-4/t12-,17-,18-,19+,23-;;;;/m1..../s1
• InChIKey: DQLXXYMNINXQSV-QTRRCMKVSA-J

NAMES AND DATABASE IDS

Names

• IUPAC name: tetralithium(1+) ion (3R)-3-{[2-({2-[(2-carboxyacetyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-3-hydroxy-2,2-dimethylpropyl ({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonatooxy)oxolan-2-yl]methyl phosphonato}oxy)phosphonate
• IUPAC Traditional name: tetralithium(1+) ion (3R)-3-{[2-({2-[(2-carboxyacetyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-3-hydroxy-2,2-dimethylpropyl {[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonatooxy)oxolan-2-yl]methyl phosphonato}oxyphosphonate
• Synonyms: Malonyl-CoA tetralithium salt; Malonyl coenzyme A tetralithium salt

Database IDs

• CAS Number: 116928-84-8
• PubChem SID: 24882603; 162250113
• PubChem CID: 16217662

CALCULATED PROPERTIES

• Acid pKa: 0.8202491
• H Acceptors: 19
• H Donor: 6
• LogD (pH = 5.5): -12.335554
• LogD (pH = 7.4): -15.512446
• Log P: -6.0328665
• Molar Refractivity: 174.0653 cm^3
• Polarizability: 70.80719 Å^3
• Polar Surface Area: 412.25 Å^2
• Rotatable Bonds: 22
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: soluble50 mg/mL, clear, colorless

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥90% (HPLC)
• Impurities: ≤12% water
• Empirical Formula (Hill Notation): C24H34Li4N7O19P3S

DETAILS

Sigma Aldrich - 63410

Biochem/physiol Actions
Malonyl Coenzyme A is a Coenzyme A derivative that is utilized in fatty acid and polyketide synthesis and in the transport of α-ketoglutarate across the mitochondrial membrane. Malonyl CoA is formed by the Acetyl CoA Carboxylase-mediated carboxylation of acetyl CoA.
Other Notes
Malonyl-CoA in glucose-stimulated insulin secretion from clonal pancreatic β-cells1