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

• ChemBase ID: 132343
• Molecular Formular: C23H37N7NaO17P3S
• Molecular Mass: 831.552633
• Monoisotopic Mass: 831.10771793
• SMILES: CC(=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.[Na+]
• Canonical SMILES: O=C(NCCSC(=O)C)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.[Na+]
• InChI: InChI=1S/C23H38N7O17P3S.Na/c1-12(31)51-7-6-25-14(32)4-5-26-21(35)18(34)23(2,3)9-44-50(41,42)47-49(39,40)43-8-13-17(46-48(36,37)38)16(33)22(45-13)30-11-29-15-19(24)27-10-28-20(15)30;/h10-11,13,16-18,22,33-34H,4-9H2,1-3H3,(H,25,32)(H,26,35)(H,39,40)(H,41,42)(H2,24,27,28)(H2,36,37,38);/q;+1/p-1/t13-,16-,17-,18?,22-;/m1./s1
• InChIKey: HNLIOWFIXSPFEC-WLYMNMRISA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (2R,3S,4R,5R)-2-[({[({3-[(2-{[2-(acetylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-5-(6-amino-9H-purin-9-yl)-4-hydroxyoxolan-3-yl hydrogen phosphate
• IUPAC Traditional name: sodium (2R,3S,4R,5R)-2-{[({3-[(2-{[2-(acetylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-5-(6-aminopurin-9-yl)-4-hydroxyoxolan-3-yl hydrogen phosphate
• Synonyms: Acetyl CoA; Acetyl-S- CoA; Acetyl coenzyme A sodium salt; Acetyl coenzyme A 钠盐

Database IDs

• CAS Number: 102029-73-2
• MDL Number: MFCD00078858
• PubChem SID: 162226620; 24890621
• PubChem CID: 71308544

CALCULATED PROPERTIES

• Acid pKa: 0.8207477
• H Acceptors: 17
• H Donor: 8
• LogD (pH = 5.5): -10.527379
• LogD (pH = 7.4): -12.143686
• Log P: -5.9247446
• Molar Refractivity: 171.0863 cm^3
• Polarizability: 68.61595 Å^3
• Polar Surface Area: 366.46 Å^2
• Rotatable Bonds: 20
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: soluble100 mg/mL
• Apperance: powder

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... CHAT(1103), HAT1(8520), KAT2A(2648), KAT2B(8850), KAT5(10524)mouse ... HAT1(107435), KAT2A(14534), KAT2B(18519), KAT5(81601)rat ... HAT1(296501), KAT2A(303539), KAT2B(301164), KAT5(192218)

Product Information

• Purity: ≥93% (HPLC)
• Quality Level: PREMIUM

DETAILS

Sigma Aldrich - A2056

Frequently Asked Questions
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Application
An essential cofactor in enzymatic acetyl transfer reactions.
Acetyl-CoA is an essential cofactor and carrier of acyl groups in enzymatic acetyl transfer reactions. It is formed either by the oxidative decarboxylation of pyruvate in mitochondria, by the oxidation of long-chain fatty acids, or by the oxidative degradation of certain amino acids. Acetyl-CoA is the starting compound for the citric acid cycle (Kreb′s cycle). It is also a key precursor in lipid biosynthesis, and the source of all fatty acid carbons. Acetyl-CoA positively regulates the activity pyruvate carboxylase. It is a precursor of the neurotransmitter acetylcholine. Histone acetylases (HAT) use Acetyl-CoA as the donor for the acetyl group use in the post-translational acetylation reactions of histone and non-histone proteins.
Other Notes
For more more technical information and a complete list of Coenzyme A deriviatives visit the Acyl Transfer Reagents Resource.
Preparation Note
Prepared enzymatically
Biochem/physiol Actions
Acetyl-CoA is an essential cofactor and carrier of acyl groups in enzymatic acetyl transfer reactions. It is formed either by the oxidative decarboxylation of pyruvate in mitochondria, by the oxidation of long-chain fatty acids, or by the oxidative degradation of certain amino acids. Acetyl-CoA is the starting compound for the citric acid cycle (Kreb′s cycle). It is also a key precursor in lipid biosynthesis, and the source of all fatty acid carbons. Acetyl-CoA positively regulates the activity pyruvate carboxylase. It is a precursor of the neurotransmitter acetylcholine. Histone acetylases (HAT) use Acetyl-CoA as the donor for the acetyl group use in the post-translational acetylation reactions of histone and non-histone proteins.