trilithium(1+) ion (3R)-3-[(2-{[2-(but-2-enoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropyl ({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3-(hydrogen phosphonatooxy)-4-hydroxyoxolan-2-yl]methyl phosphonato}oxy)phosphonate

• ChemBase ID: 156041
• Molecular Formular: C25H37Li3N7O17P3S
• Molecular Mass: 853.407263
• Monoisotopic Mass: 853.1659623
• SMILES: [Li+].[Li+].[Li+].C/C=C/C(=O)SCCNC(=O)CCNC(=O)[C@@H](C(C)(C)COP(=O)([O-])OP(=O)([O-])OC[C@@H]1[C@H]([C@H]([C@@H](O1)n1cnc2c1ncnc2N)O)OP(=O)(O)[O-])O
• Canonical SMILES: C/C=C/C(=O)SCCNC(=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+]
• InChI: InChI=1S/C25H40N7O17P3S.3Li/c1-4-5-16(34)53-9-8-27-15(33)6-7-28-23(37)20(36)25(2,3)11-46-52(43,44)49-51(41,42)45-10-14-19(48-50(38,39)40)18(35)24(47-14)32-13-31-17-21(26)29-12-30-22(17)32;;;/h4-5,12-14,18-20,24,35-36H,6-11H2,1-3H3,(H,27,33)(H,28,37)(H,41,42)(H,43,44)(H2,26,29,30)(H2,38,39,40);;;/q;3*+1/p-3/t14-,18-,19-,20+,24-;;;/m1.../s1
• InChIKey: LUYQFKSDLNQLEG-WSRMJXCZSA-K

NAMES AND DATABASE IDS

Names

• IUPAC name: trilithium(1+) ion (3R)-3-[(2-{[2-(but-2-enoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropyl ({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3-(hydrogen phosphonatooxy)-4-hydroxyoxolan-2-yl]methyl phosphonato}oxy)phosphonate
• IUPAC Traditional name: trilithium(1+) ion (3R)-3-[(2-{[2-(but-2-enoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropyl {[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3-(hydrogen phosphonatooxy)-4-hydroxyoxolan-2-yl]methyl phosphonato}oxyphosphonate
• Synonyms: trans-2-Butenoyl coenzyme A trilithium salt; Crotonoyl coenzyme A trilithium salt

Database IDs

• MDL Number: MFCD00151226
• PubChem SID: 24856925; 162250179
• PubChem CID: 16211811

CALCULATED PROPERTIES

• Acid pKa: 0.8207477
• H Acceptors: 17
• H Donor: 6
• LogD (pH = 5.5): -9.151117
• LogD (pH = 7.4): -10.767425
• Log P: -4.548483
• Molar Refractivity: 179.1641 cm^3
• Polarizability: 71.72874 Å^3
• Polar Surface Area: 372.12 Å^2
• Rotatable Bonds: 21
• 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: ≤10% water
• Empirical Formula (Hill Notation): C25H37Li3N7O17P3S

DETAILS

Sigma Aldrich - 28007

Other Notes
Oxidation-reduction of general acyl-CoA dehydrogenase by the butyryl-CoA/crotonyl-CoA couple1; Purification of rat liver microsomal trans-2-enoyl-CoA reductase2
Application
Crotonoyl coenzyme A (Crotonoyl -CoA) may be used as a substrate of enzymes such as Plasmodium falciparum enoyl-ACP reductase and other enoyl-CoA reductases. Crotonoyl -CoA may be used as a substrate analogue for kinetic studies on β-hydroxyacyl-acyl carrier protein (ACP) dehydratase (FabZ).