trilithium(1+) ion hydrate (3R)-3-[(2-{[2-(hexanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropyl ({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3-(hydrogen phosphonatooxy)-4-hydroxyoxolan-2-yl]methyl phosphonato}oxy)phosphonate

• ChemBase ID: 132398
• Molecular Formular: C27H45Li3N7O18P3S
• Molecular Mass: 901.491583
• Monoisotopic Mass: 901.22347718
• SMILES: [Li+].[Li+].[Li+].CCCCCC(=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.O
• Canonical SMILES: CCCCCC(=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+].[Li+].[Li+].O
• InChI: InChI=1S/C27H46N7O17P3S.3Li.H2O/c1-4-5-6-7-18(36)55-11-10-29-17(35)8-9-30-25(39)22(38)27(2,3)13-48-54(45,46)51-53(43,44)47-12-16-21(50-52(40,41)42)20(37)26(49-16)34-15-33-19-23(28)31-14-32-24(19)34;;;;/h14-16,20-22,26,37-38H,4-13H2,1-3H3,(H,29,35)(H,30,39)(H,43,44)(H,45,46)(H2,28,31,32)(H2,40,41,42);;;;1H2/q;3*+1;/p-3/t16-,20-,21-,22+,26-;;;;/m1..../s1
• InChIKey: YMMJFYLVSRICJX-ZTADYLHKSA-K

NAMES AND DATABASE IDS

Names

• IUPAC name: trilithium(1+) ion hydrate (3R)-3-[(2-{[2-(hexanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropyl ({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3-(hydrogen phosphonatooxy)-4-hydroxyoxolan-2-yl]methyl phosphonato}oxy)phosphonate
• IUPAC Traditional name: trilithium(1+) ion hydrate (3R)-3-[(2-{[2-(hexanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropyl {[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3-(hydrogen phosphonatooxy)-4-hydroxyoxolan-2-yl]methyl phosphonato}oxyphosphonate
• Synonyms: Caproyl Coenzyme A trilithium salt; Hexanoyl coenzyme A trilithium salt hydrate

Database IDs

• CAS Number: 103476-19-3(anhydrous)
• PubChem SID: 162226675; 24895496
• PubChem CID: 71308558

CALCULATED PROPERTIES

• Acid pKa: 0.8207477
• H Acceptors: 17
• H Donor: 6
• LogD (pH = 5.5): -8.493137
• LogD (pH = 7.4): -10.109445
• Log P: -3.8905027
• Molar Refractivity: 187.2728 cm^3
• Polarizability: 75.59438 Å^3
• Polar Surface Area: 372.12 Å^2
• Rotatable Bonds: 24
• 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: ≥85%

DETAILS

Sigma Aldrich - H2012

Biochem/physiol Actions
Coenzyme A functions as an acyl group carrier, acetyl-CoA. Hexanoyl CoA is involved in fatty acid oxidation, lipid biosynthesis, and ceramide formation. Ghrelin O-acyltransferase (GOAT) has a preference for n-hexanoyl-CoA over n-octanoyl-CoA as an acyl donor. Hexanoyl CoA is also used as a starter unit for polyketide biosynthesis.