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

• ChemBase ID: 132399
• Molecular Formular: C31H56N7O18P3S
• Molecular Mass: 939.798723
• Monoisotopic Mass: 939.26153888
• SMILES: CCCCCCCCCC(=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: CCCCCCCCCC(=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.O
• InChI: InChI=1S/C31H54N7O17P3S.H2O/c1-4-5-6-7-8-9-10-11-22(40)59-15-14-33-21(39)12-13-34-29(43)26(42)31(2,3)17-52-58(49,50)55-57(47,48)51-16-20-25(54-56(44,45)46)24(41)30(53-20)38-19-37-23-27(32)35-18-36-28(23)38;/h18-20,24-26,30,41-42H,4-17H2,1-3H3,(H,33,39)(H,34,43)(H,47,48)(H,49,50)(H2,32,35,36)(H2,44,45,46);1H2/t20-,24-,25-,26+,30-;/m1./s1
• InChIKey: IRILGPHKFKSRQN-ASEPKIFHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-({[({[(3R)-3-[(2-{[2-(decanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}methyl)-4-hydroxyoxolan-3-yl]oxy}phosphonic acid hydrate
• IUPAC Traditional name: decanoyl-coa hydrate
• Synonyms: Decanoyl coenzyme A monohydrate

Database IDs

• CAS Number: 1264-57-9
• MDL Number: MFCD00166975
• PubChem SID: 24893934; 162226676
• PubChem CID: 57347490

CALCULATED PROPERTIES

• Acid pKa: 0.8207477
• H Acceptors: 17
• H Donor: 9
• LogD (pH = 5.5): -6.7148623
• LogD (pH = 7.4): -8.33117
• Log P: -2.112228
• Molar Refractivity: 209.0419 cm^3
• Polarizability: 83.181816 Å^3
• Polar Surface Area: 363.63 Å^2
• Rotatable Bonds: 28
• 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 - D5269

Application
Decanoyl coenzyme A (Decanoyl CoA) is coupled with S-adenosylmethionine (SAM) by Vibrio cholera CqsA enzyme to produce a potent quorum-sensing molecule, 3-aminotridec-2-en-4-one (Ea-CAI-1.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. D5269.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.