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

• ChemBase ID: 131224
• Molecular Formular: C21H36N7O16P3
• Molecular Mass: 735.469123
• Monoisotopic Mass: 735.143138
• SMILES: CCNC(=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: CCNC(=O)CCNC(=O)C(C(COP(=O)(OP(=O)(OCC1OC(C(C1OP(=O)(O)O)O)n1cnc2c1ncnc2N)O)O)(C)C)O
• InChI: InChI=1S/C21H36N7O16P3/c1-4-23-12(29)5-6-24-19(32)16(31)21(2,3)8-41-47(38,39)44-46(36,37)40-7-11-15(43-45(33,34)35)14(30)20(42-11)28-10-27-13-17(22)25-9-26-18(13)28/h9-11,14-16,20,30-31H,4-8H2,1-3H3,(H,23,29)(H,24,32)(H,36,37)(H,38,39)(H2,22,25,26)(H2,33,34,35)
• InChIKey: ILWZMFJBPIYQKW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[5-(6-amino-9H-purin-9-yl)-2-{[({[(3-{[2-(ethylcarbamoyl)ethyl]carbamoyl}-3-hydroxy-2,2-dimethylpropoxy)(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl)oxy]methyl}-4-hydroxyoxolan-3-yl]oxy}phosphonic acid
• IUPAC Traditional name: desulfo-coa
• Synonyms: Dethiocoenzyme A; Desulfocoenzyme A lithium salt

Database IDs

• CAS Number: 5863-40-1
• MDL Number: MFCD00063449
• PubChem SID: 162225502
• PubChem CID: 3002

CALCULATED PROPERTIES

• Acid pKa: 0.8207477
• H Acceptors: 16
• H Donor: 9
• LogD (pH = 5.5): -10.416538
• LogD (pH = 7.4): -12.0328455
• Log P: -5.813904
• Molar Refractivity: 155.0139 cm^3
• Polarizability: 61.86386 Å^3
• Polar Surface Area: 346.56 Å^2
• Rotatable Bonds: 17
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Storage Temperature: -20°C

Product Information

• Impurities: <1% CoA

DETAILS

Sigma Aldrich - D2776

Application
Useful in affinity chromatography and as an inhibitor of CoA-requiring enzymes in metabolic studies.