{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-[({[({3-[(2-{[2-(heptadecanoylsulfanyl)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: 134264
• Molecular Formular: C38H68N7O17P3S
• Molecular Mass: 1019.969503
• Monoisotopic Mass: 1019.36052464
• SMILES: CCCCCCCCCCCCCCCCC(=O)SCCNC(=O)CCNC(=O)C(C(C)(C)COP(=O)(O)OP(=O)(O)OC[C@@H]1[C@H]([C@H]([C@@H](O1)n1cnc2c1ncnc2N)O)OP(=O)(O)O)O
• Canonical SMILES: CCCCCCCCCCCCCCCCC(=O)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
• InChI: InChI=1S/C38H68N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-29(47)66-22-21-40-28(46)19-20-41-36(50)33(49)38(2,3)24-59-65(56,57)62-64(54,55)58-23-27-32(61-63(51,52)53)31(48)37(60-27)45-26-44-30-34(39)42-25-43-35(30)45/h25-27,31-33,37,48-49H,4-24H2,1-3H3,(H,40,46)(H,41,50)(H,54,55)(H,56,57)(H2,39,42,43)(H2,51,52,53)/t27-,31-,32-,33?,37-/m1/s1
• InChIKey: DRABUZIHHACUPI-UVICFMDKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-[({[({3-[(2-{[2-(heptadecanoylsulfanyl)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: [(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-2-{[({3-[(2-{[2-(heptadecanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-4-hydroxyoxolan-3-yl]oxyphosphonic acid
• Synonyms: n-Heptadecanoyl coenzyme A lithium salt

Database IDs

• CAS Number: 3546-17-6
• MDL Number: MFCD00079338
• PubChem SID: 24895454; 162228541
• PubChem CID: 71308784

CALCULATED PROPERTIES

• Acid pKa: 0.8207477
• H Acceptors: 17
• H Donor: 9
• LogD (pH = 5.5): -3.602882
• LogD (pH = 7.4): -5.219189
• Log P: 0.99975276
• Molar Refractivity: 241.2489 cm^3
• Polarizability: 95.88711 Å^3
• Polar Surface Area: 363.63 Å^2
• Rotatable Bonds: 35
• 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%

DETAILS

Sigma Aldrich - H1385

Biochem/physiol Actions
Coenzyme A functions as an acyl group carrier, acetyl-CoA. Heptadecanoyl Coenzyme A (C17-CoA), a long-chain (C-17) saturated fatty acyl-CoA, is used as an intermediate in lipid metabolism. It is a substrate of acyl-CoA dehydrogenase (EC 1.3.99.3) within the mitochondria and of carnitine O-palmitoyltransferase (EC 2.3.1.21) within the cytoplasm. Heptadecanoyl Coenzyme A is an inhibitor of general acyl-coenzyme A dehydrogenase (EC 1.3.99.3).
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. H1385.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.