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

• ChemBase ID: 155417
• Molecular Formular: C37H64N7O17P3S
• Molecular Mass: 1003.927043
• Monoisotopic Mass: 1003.32922451
• SMILES: CCCCCC/C=C/CCCCCCCC(=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: CCCCCC/C=C/CCCCCCCC(=O)SCCNC(=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/C37H64N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-28(46)65-21-20-39-27(45)18-19-40-35(49)32(48)37(2,3)23-58-64(55,56)61-63(53,54)57-22-26-31(60-62(50,51)52)30(47)36(59-26)44-25-43-29-33(38)41-24-42-34(29)44/h9-10,24-26,30-32,36,47-48H,4-8,11-23H2,1-3H3,(H,39,45)(H,40,49)(H,53,54)(H,55,56)(H2,38,41,42)(H2,50,51,52)
• InChIKey: QBYOCCWNZAOZTL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[5-(6-amino-9H-purin-9-yl)-2-[({[({3-[(2-{[2-(hexadec-9-enoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-4-hydroxyoxolan-3-yl]oxy}phosphonic acid
• IUPAC Traditional name: [5-(6-aminopurin-9-yl)-2-{[({3-[(2-{[2-(hexadec-9-enoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-4-hydroxyoxolan-3-yl]oxyphosphonic acid
• Synonyms: cis-9-Hexadecenoyl Coenzyme A; Palmitoleoyl coenzyme A lithium salt

Database IDs

• CAS Number: 18198-76-0
• MDL Number: MFCD00079261
• PubChem SID: 24898796; 162249555
• PubChem CID: 6115728

CALCULATED PROPERTIES

• Acid pKa: 0.8207477
• H Acceptors: 17
• H Donor: 9
• LogD (pH = 5.5): -4.4093723
• LogD (pH = 7.4): -6.0256796
• Log P: 0.19326241
• Molar Refractivity: 237.7645 cm^3
• Polarizability: 93.81715 Å^3
• Polar Surface Area: 363.63 Å^2
• Rotatable Bonds: 33
• 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%
• Empirical Formula (Hill Notation): C37H64N7O17P3S

DETAILS

Sigma Aldrich - P6775

Application
Coenzyme A functions as an acyl group carrier, acetyl-CoA. Palmitoleoyl coenzyme A (Palmitoleoyl-CoA) may be used in comparative long chain fatty acyl-CoA studies such as the effects of long-chain acyl-coenzyme A esters on cardiac K(ATP) channels and lipotoxic footprinting.