{[5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy(3-hydroxy-2,2-dimethyl-3-{[2-({2-[(2-phenylacetyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid lithium

• ChemBase ID: 133424
• Molecular Formular: C29H42LiN7O17P3S
• Molecular Mass: 892.607763
• Monoisotopic Mass: 892.17307836
• SMILES: [Li].CC(C)(COP(=O)(O)OP(=O)(O)OCC1C(C(C(O1)n1cnc2c1ncnc2N)O)OP(=O)(O)O)C(C(=O)NCCC(=O)NCCSC(=O)Cc1ccccc1)O
• Canonical SMILES: O=C(NCCSC(=O)Cc1ccccc1)CCNC(=O)C(C(COP(=O)(OP(=O)(OCC1OC(C(C1OP(=O)(O)O)O)n1cnc2c1ncnc2N)O)O)(C)C)O.[Li]
• InChI: InChI=1S/C29H42N7O17P3S.Li/c1-29(2,24(40)27(41)32-9-8-19(37)31-10-11-57-20(38)12-17-6-4-3-5-7-17)14-50-56(47,48)53-55(45,46)49-13-18-23(52-54(42,43)44)22(39)28(51-18)36-16-35-21-25(30)33-15-34-26(21)36;/h3-7,15-16,18,22-24,28,39-40H,8-14H2,1-2H3,(H,31,37)(H,32,41)(H,45,46)(H,47,48)(H2,30,33,34)(H2,42,43,44)
• InChIKey: PQZFFEIEACTQRR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy(3-hydroxy-2,2-dimethyl-3-{[2-({2-[(2-phenylacetyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid lithium
• IUPAC Traditional name: [5-(6-aminopurin-9-yl)-4-hydroxy-2-[({hydroxy[hydroxy(3-hydroxy-2,2-dimethyl-3-{[2-({2-[(2-phenylacetyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid lithium
• Synonyms: Phenylacetyl coenzyme A lithium salt

Database IDs

• CAS Number: 108321-26-2
• MDL Number: MFCD00079225
• PubChem SID: 162227701; 24898281
• PubChem CID: 6419738

CALCULATED PROPERTIES

• Acid pKa: 0.8207477
• H Acceptors: 17
• H Donor: 9
• LogD (pH = 5.5): -8.693039
• LogD (pH = 7.4): -10.309346
• Log P: -4.0904045
• Molar Refractivity: 196.9299 cm^3
• Polarizability: 78.101746 Å^3
• Polar Surface Area: 363.63 Å^2
• Rotatable Bonds: 22
• 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: ~95%

DETAILS

Sigma Aldrich - P2153

Application
Coenzyme A functions as an acyl group carrier, acetyl-CoA. Phenylacetyl coenzyme A (Phenylacetyl-CoA) is used to study the mechanism of action of the TetR family transcriptional repressor PaaR. Phenylacetyl-CoA is used to study the phenylacetyl-CoA monooxygenase complex found in bacteria such as E. coli.