lithium(1+) ion (2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-({[({[(3R)-3-[(2-{[2-(hexadecanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}methyl)-4-hydroxyoxolan-3-yl hydrogen phosphate

• ChemBase ID: 134156
• Molecular Formular: C37H65LiN7O17P3S
• Molecular Mass: 1011.875983
• Monoisotopic Mass: 1011.3530541
• SMILES: [Li+].CCCCCCCCCCCCCCCC(=O)SCCNC(=O)CCNC(=O)[C@@H](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: CCCCCCCCCCCCCCCC(=O)SCCNC(=O)CCNC(=O)[C@@H](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.[Li+]
• InChI: InChI=1S/C37H66N7O17P3S.Li/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;/h24-26,30-32,36,47-48H,4-23H2,1-3H3,(H,39,45)(H,40,49)(H,53,54)(H,55,56)(H2,38,41,42)(H2,50,51,52);/q;+1/p-1/t26-,30-,31-,32+,36-;/m1./s1
• InChIKey: BSAYABVAJQBKKB-NNGKVBCISA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: lithium(1+) ion (2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-({[({[(3R)-3-[(2-{[2-(hexadecanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}methyl)-4-hydroxyoxolan-3-yl hydrogen phosphate
• IUPAC Traditional name: lithium(1+) ion (2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-2-[({[(3R)-3-[(2-{[2-(hexadecanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy(hydroxy)phosphoryl]oxy(hydroxy)phosphoryl}oxy)methyl]-4-hydroxyoxolan-3-yl hydrogen phosphate
• Synonyms: n-Hexadecanoyl Coenzyme A; Hexadecanoyl coenzyme A; Palmitoyl coenzyme A lithium salt

Database IDs

• CAS Number: 188174-64-3
• MDL Number: MFCD01863103
• PubChem SID: 24899057; 162228433
• PubChem CID: 71308765

CALCULATED PROPERTIES

• Acid pKa: 0.8207477
• H Acceptors: 17
• H Donor: 8
• LogD (pH = 5.5): -4.0474505
• LogD (pH = 7.4): -5.663758
• Log P: 0.55518407
• Molar Refractivity: 235.5262 cm^3
• Polarizability: 93.95324 Å^3
• Polar Surface Area: 366.46 Å^2
• Rotatable Bonds: 34
• 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%; ≥90% (HPLC)
• Impurities: ≤6% water
• Empirical Formula (Hill Notation): C37H65N7O17P3S · xLi+

DETAILS

Sigma Aldrich - P9716

Biochem/physiol Actions
Long chain fatty acid (C16) covalently linked to Coenzyme A. Covalent attachment of palmitate is a common occurrence on a wide variety of viral and cellular proteins and plays a role in promoting membrane binding. Palmitoylation may also be a general mechanism for prolonging or potentiating G-protein signaling.