{[5-(6-amino-9H-purin-9-yl)-2-[({[({3-[(2-{[2-(but-2-enoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-4-hydroxyoxolan-3-yl]oxy}phosphonic acid lithium

• ChemBase ID: 155551
• Molecular Formular: C25H40LiN7O17P3S
• Molecular Mass: 842.549083
• Monoisotopic Mass: 842.1574283
• SMILES: [Li].C/C=C/C(=O)SCCNC(=O)CCNC(=O)C(C(C)(C)COP(=O)(O)OP(=O)(O)OCC1C(C(C(O1)n1cnc2c1ncnc2N)O)OP(=O)(O)O)O
• Canonical SMILES: C/C=C/C(=O)SCCNC(=O)CCNC(=O)C(C(COP(=O)(OP(=O)(OCC1OC(C(C1OP(=O)(O)O)O)n1cnc2c1ncnc2N)O)O)(C)C)O.[Li]
• InChI: InChI=1S/C25H40N7O17P3S.Li/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)
• InChIKey: VVVNZHYHSLNWDW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[5-(6-amino-9H-purin-9-yl)-2-[({[({3-[(2-{[2-(but-2-enoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-4-hydroxyoxolan-3-yl]oxy}phosphonic acid lithium
• IUPAC Traditional name: Crotonyl-CoA lithium
• Synonyms: 2-Butenoyl CoA lithium salt; Crotonoyl Co A lithium salt; Crotonoyl coenzyme A lithium salt; 2-Butenoyl coenzyme A lithium salt

Database IDs

• CAS Number: 102680-35-3
• MDL Number: MFCD00167413
• PubChem SID: 24892840; 162249689
• PubChem CID: 16219146

CALCULATED PROPERTIES

• Acid pKa: 0.8207477
• H Acceptors: 17
• H Donor: 9
• LogD (pH = 5.5): -9.151117
• LogD (pH = 7.4): -10.767425
• Log P: -4.548483
• Molar Refractivity: 182.5292 cm^3
• Polarizability: 72.08168 Å^3
• Polar Surface Area: 363.63 Å^2
• Rotatable Bonds: 21
• Lipinski's Rule of Five: false

PROPERTIES

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)
• Empirical Formula (Hill Notation): C25H40N7O17P3S

DETAILS

Sigma Aldrich - C6146

Application
Crotonoyl coenzyme A (2-Butenoyl coenzyme A) 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).
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. C6146.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. C6146.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.