[({[5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy][3-hydroxy-2,2-dimethyl-3-({2-[(2-sulfanylethyl)carbamoyl]ethyl}carbamoyl)propoxy]phosphinic acid

• ChemBase ID: 133981
• Molecular Formular: C21H35N7O13P2S
• Molecular Mass: 687.554222
• Monoisotopic Mass: 687.14887848
• SMILES: CC(C)(COP(=O)(O)OP(=O)(O)OCC1C(C(C(O1)n1cnc2c1ncnc2N)O)O)C(C(=O)NCCC(=O)NCCS)O
• Canonical SMILES: SCCNC(=O)CCNC(=O)C(C(COP(=O)(OP(=O)(OCC1OC(C(C1O)O)n1cnc2c1ncnc2N)O)O)(C)C)O
• InChI: InChI=1S/C21H35N7O13P2S/c1-21(2,16(32)19(33)24-4-3-12(29)23-5-6-44)8-39-43(36,37)41-42(34,35)38-7-11-14(30)15(31)20(40-11)28-10-27-13-17(22)25-9-26-18(13)28/h9-11,14-16,20,30-32,44H,3-8H2,1-2H3,(H,23,29)(H,24,33)(H,34,35)(H,36,37)(H2,22,25,26)
• InChIKey: KDTSHFARGAKYJN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [({[5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy][3-hydroxy-2,2-dimethyl-3-({2-[(2-sulfanylethyl)carbamoyl]ethyl}carbamoyl)propoxy]phosphinic acid
• IUPAC Traditional name: dephospho coa
• Synonyms: 3′-Dephosphocoenzyme A

Database IDs

• CAS Number: 3633-59-8
• MDL Number: MFCD00057010
• PubChem SID: 162228258; 24893748
• PubChem CID: 642

CALCULATED PROPERTIES

• Acid pKa: 1.8640848
• H Acceptors: 14
• H Donor: 9
• LogD (pH = 5.5): -7.7243567
• LogD (pH = 7.4): -8.020404
• Log P: -6.1288533
• Molar Refractivity: 151.8673 cm^3
• Polarizability: 60.341892 Å^3
• Polar Surface Area: 300.03 Å^2
• Rotatable Bonds: 16
• 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)
• Impurities: ≤1% CoA

DETAILS

Sigma Aldrich - D3385

Application
Dephosphocoenzyme A is the direct precursor of coenzyme A. It is used for the synthesis of coenzyme A by bifunctional CoA Synthase (CoASy, 4′-phosphopantetheine adenylyltransferase/dephospho-CoA kinase) which performs the transfer of the γ-phosphate of ATP to dephosphocoenzyme A.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. D3385.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.