trilithium(1+) ion (3R)-3-[(2-{[2-(acetylsulfanyl)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: 133708
• Molecular Formular: C23H35Li3N7O17P3S
• Molecular Mass: 827.369983
• Monoisotopic Mass: 827.15031224
• SMILES: [Li+].[Li+].[Li+].CC(=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: O=C(NCCSC(=O)C)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+]
• InChI: InChI=1S/C23H38N7O17P3S.3Li/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;3*+1/p-3/t13-,16-,17-,18+,22-;;;/m1.../s1
• InChIKey: FTRFBNATWBKIQU-JHJDYNLLSA-K

NAMES AND DATABASE IDS

Names

• IUPAC name: trilithium(1+) ion (3R)-3-[(2-{[2-(acetylsulfanyl)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 (3R)-3-[(2-{[2-(acetylsulfanyl)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: Acetyl-CoA; Acetyl coenzyme A lithium salt; Acetyl-S-CoA Li3; 乙酰辅酶 A 三锂盐; 乙酰辅酶 A 三锂盐

Database IDs

• CAS Number: 32140-51-5
• MDL Number: MFCD00167406
• PubChem SID: 24890633; 162227985
• PubChem CID: 16218870

CALCULATED PROPERTIES

• Acid pKa: 0.8207477
• H Acceptors: 17
• H Donor: 6
• LogD (pH = 5.5): -10.527379
• LogD (pH = 7.4): -12.143686
• Log P: -5.9247446
• Molar Refractivity: 168.8429 cm^3
• Polarizability: 68.37998 Å^3
• Polar Surface Area: 372.12 Å^2
• Rotatable Bonds: 20
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36/37
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• 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); ≥93.0% (HPLC)
• Quality Level: PREMIUM
• Empirical Formula (Hill Notation): C23H38N7O17P3S · xLi+

DETAILS

Sigma Aldrich - A2181

Application
An essential cofactor in enzymatic acetyl transfer reactions.
Biochem/physiol Actions
在酶催化乙酰基转移反应中，乙酰辅酶 A 是必要的辅因子和酰基载体。它可以通过线粒体中丙酮酸的氧化脱羧反应，或者长链脂肪酸的氧化反应，或者某些氨基酸的氧化降解反应而形成。它是脂质生物合成的重要前体以及所有脂肪酸的碳源。它是丙酮酸羧化酶的正调节物。它是神经递质乙酰胆碱的前体。
Other Notes
For more more technical information and a complete list of Coenzyme A deriviatives visit the Acyl Transfer Reagents Resource.
Preparation Note
酶法制备
Reconstitution
Acetyl CoA is soluble in deionized water at 100 mg/mL. Acetyl CoA is stable in neutral and moderately acidic solutions but will hydrolyze in alkaline and strongly acidic solutions. Aqueous solutions stored in single-use aliquots are stable for up to two weeks at -20°C and up to 6 months at -80°C.
Physical properties
This moisture-sensitive powder should be stored desiccated at -20°C.

Sigma Aldrich - 01031

Application
An essential cofactor in enzymatic acetyl transfer reactions.
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.
Other Notes
For more more technical information and a complete list of Coenzyme A deriviatives visit the Acyl Transfer Reagents Resource.