{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[3-hydroxy-2,2-dimethyl-3-({2-[(2-sulfanylethyl)carbamoyl]ethyl}carbamoyl)propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid trihydrate

• ChemBase ID: 156140
• Molecular Formular: C21H42N7O19P3S
• Molecular Mass: 821.579963
• Monoisotopic Mass: 821.14690305
• SMILES: 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(C(=O)NCCC(=O)NCCS)O.O.O.O
• Canonical SMILES: SCCNC(=O)CCNC(=O)C(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.O.O.O
• InChI: InChI=1S/C21H36N7O16P3S.3H2O/c1-21(2,16(31)19(32)24-4-3-12(29)23-5-6-48)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;;;/h9-11,14-16,20,30-31,48H,3-8H2,1-2H3,(H,23,29)(H,24,32)(H,36,37)(H,38,39)(H2,22,25,26)(H2,33,34,35);3*1H2/t11-,14-,15-,16?,20-;;;/m1.../s1
• InChIKey: JUPZQBBEINCFCX-HJKJOZROSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[3-hydroxy-2,2-dimethyl-3-({2-[(2-sulfanylethyl)carbamoyl]ethyl}carbamoyl)propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid trihydrate
• IUPAC Traditional name: coenzyme A trihydrate
• Synonyms: CoA; Coenzyme A trihydrate; 辅酶 A 三水合物

Database IDs

• CAS Number: 85-61-0
• EC Number: 201-619-0
• MDL Number: MFCD00150983
• Beilstein Number: 77809
• PubChem SID: 162250278
• PubChem CID: 45051781

CALCULATED PROPERTIES

• Acid pKa: 0.8207477
• H Acceptors: 16
• H Donor: 10
• LogD (pH = 5.5): -10.367997
• LogD (pH = 7.4): -11.985149
• Log P: -5.765352
• Molar Refractivity: 162.7402 cm^3
• Polarizability: 64.9052 Å^3
• Polar Surface Area: 346.56 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

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

Product Information

• Purity: ≥80% (enzymatic)
• Empirical Formula (Hill Notation): C21H36N7O16P3S · 3H2O

DETAILS

Sigma Aldrich - 27590

Other Notes
Review: Immobilized coenzymes and derivatives1