Common NameAcetyl-coa
DescriptionThe main function of coenzyme A is to carry acyl groups (such as the acetyl group) or thioesters. Acetyl-CoA is an important molecule itself. It is the precursor to HMG CoA, which is a vital component in cholesterol and ketone synthesis. (wikipedia). acetyl CoA participates in the biosynthesis of fatty acids and sterols, in the oxidation of fatty acids and in the metabolism of many amino acids. It also acts as a biological acetylating agent.
Structure
Molecular FormulaC23H38N7O17P3S
Average Mass809.57100
Monoisotopic Mass809.12577
IUPAC Name{[(2R,3S,4R,5R)-2-({[({[(3R)-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]oxy}phosphonic acid
Traditional Name[(2r,3s,4r,5r)-2-[({[(3r)-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]oxyphosphonic acid
CAS Registry Number72-89-9
SMILESCC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(=O)([O-])OP(=O)([O-])OC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1OP(=O)([O-])[O-]
InChI IdentifierInChI=1S/C23H38N7O17P3S/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)/t13-,16-,17-,18+,22-/m1/s1
InChI KeyZSLZBFCDCINBPY-ZSJPKINUSA-N
CHEBI IDCHEBI:57288
HMDB IDHMDB0001206
Pathways
NameSMPDB/PathBank
Valine, leucine and isoleucine degradation
Propanoate metabolism
Lysine degradation
Pyruvate metabolism
beta-Alanine metabolism
Biosynthesis of unsaturated fatty acids
Glycine, serine and threonine metabolism
Tryptophan metabolism
Steroid Biosynthesis
Caffeine Metabolism
Oxidation of Branched Chain Fatty Acids
Amino Sugar Metabolism
Fatty acid Metabolism
Fatty Acid Elongation In Mitochondria
Citric Acid Cycle
Ketone Body Metabolism
Glutamate Metabolism
Butyrate Metabolism
Retinol Metabolism
Ibandronate Action Pathway
Simvastatin Action Pathway
Pravastatin Action Pathway
Rosuvastatin Action Pathway
Alendronate Action Pathway
Lovastatin Action Pathway
Zoledronate Action Pathway
Cerivastatin Action Pathway
Risedronate Action Pathway
Pamidronate Action Pathway
Fluvastatin Action Pathway
Atorvastatin Action Pathway
2-Hydroxyglutric Aciduria (D And L Form)
2-Methyl-3-Hydroxybutryl CoA Dehydrogenase Deficiency
3-Hydroxy-3-Methylglutaryl-CoA Lyase Deficiency
3-Methylglutaconic Aciduria Type I
3-Methylglutaconic Aciduria Type III
3-Methylglutaconic Aciduria Type IV
Beta-Ketothiolase Deficiency
Dihydropyrimidine Dehydrogenase Deficiency (DHPD)
Ethylmalonic Encephalopathy
Glutaric Aciduria Type I
Glutaric Aciduria Type I
Leigh Syndrome
Malonic Aciduria
Maple Syrup Urine Disease
Methylmalonic Aciduria
Methylmalonic Aciduria Due to Cobalamin-Related Disorders
Hypercholesterolemia
Pyruvate Dehydrogenase Complex Deficiency
Sialuria or French Type Sialuria
Non Ketotic Hyperglycinemia
Short Chain Acyl CoA Dehydrogenase Deficiency (SCAD Deficiency)
Propionic Acidemia
3-Methylcrotonyl Coa Carboxylase Deficiency Type I
Isovaleric Aciduria
Saccharopinuria/Hyperlysinemia II
Salla Disease/Infantile Sialic Acid Storage Disease
Dimethylglycine Dehydrogenase Deficiency
4-Hydroxybutyric Aciduria/Succinic Semialdehyde Dehydrogenase Deficiency
Sarcosinemia
Lysosomal Acid Lipase Deficiency (Wolman Disease)
Pyruvate Decarboxylase E1 Component Deficiency (PDHE1 Deficiency)
Vitamin A Deficiency
Hyperinsulinism-Hyperammonemia Syndrome
GABA-Transaminase Deficiency
Methylmalonate Semialdehyde Dehydrogenase Deficiency
Homocarnosinosis
Desmosterolosis
CHILD Syndrome
Chondrodysplasia Punctata II, X Linked Dominant (CDPX2)
Smith-Lemli-Opitz Syndrome (SLOS)
Tay-Sachs Disease
Disulfiram Action Pathway
Ethanol Degradation
Phytanic Acid Peroxisomal Oxidation
Refsum Disease
Fatty Acid Biosynthesis
Transfer of Acetyl Groups into Mitochondria
Mitochondrial Beta-Oxidation of Short Chain Saturated Fatty Acids
Mitochondrial Beta-Oxidation of Medium Chain Saturated Fatty Acids
Mitochondrial Beta-Oxidation of Long Chain Saturated Fatty Acids
Dimethylglycine Dehydrogenase Deficiency
Hyperglycinemia, non-ketotic
Ureidopropionase Deficiency
Carnosinuria, carnosinemia
Malonyl-coa decarboxylase deficiency
Cholesteryl ester storage disease
Hyper-IgD syndrome
Mevalonic aciduria
Wolman disease
Adrenoleukodystrophy, X-linked
Carnitine-acylcarnitine translocase deficiency
3-hydroxyisobutyric acid dehydrogenase deficiency
3-hydroxyisobutyric aciduria
Isobutyryl-coa dehydrogenase deficiency
Isovaleric acidemia
Hyperlysinemia I, Familial
Hyperlysinemia II or Saccharopinuria
G(M2)-Gangliosidosis: Variant B, Tay-sachs disease
Carnitine palmitoyl transferase deficiency (I)
Long chain acyl-CoA dehydrogenase deficiency (LCAD)
Very-long-chain acyl coa dehydrogenase deficiency (VLCAD)
Carnitine palmitoyl transferase deficiency (II)
Medium chain acyl-coa dehydrogenase deficiency (MCAD)
Long-chain-3-hydroxyacyl-coa dehydrogenase deficiency (LCHAD)
Trifunctional protein deficiency
Congenital lactic acidosis
Fumarase deficiency
Mitochondrial complex II deficiency
2-ketoglutarate dehydrogenase complex deficiency
Pyruvate dehydrogenase deficiency (E3)
Pyruvate dehydrogenase deficiency (E2)
Primary hyperoxaluria II, PH2
Pyruvate kinase deficiency
Succinic semialdehyde dehydrogenase deficiency
Short-chain 3-hydroxyacyl-CoA dehydrogenase deficiency (SCHAD)
Succinyl CoA: 3-ketoacid CoA transferase deficiency
Pyridoxine dependency with seizures
Warburg Effect
2-aminoadipic 2-oxoadipic aciduria
3-Phosphoglycerate dehydrogenase deficiency
Acylcarnitine 3-Hydroxydecanoylcarnitine
Acylcarnitine (7Z,9Z,12Z,15Z,18Z,21Z)-tetracosa-7,9,12,15,18,21-hexaenoylcarnitine
Acylcarnitine Pentacosanoylcarnitine
Acylcarnitine Hexacosanoylcarnitine
Acylcarnitine (17Z)-Hexacos-17-enoylcarnitine
Acylcarnitine (13Z,16Z)-Hexacosa-13,16-dienoylcarnitine
Acylcarnitine Heptacosanoylcarnitine
Acylcarnitine Octacosanoylcarnitine
Acylcarnitine Nonacosanoylcarnitine
Acylcarnitine (2S,3R)-3-Hydroxy-2-methylbutanoylcarnitine
The oncogenic action of 2-hydroxyglutarate
The Oncogenic Action of Succinate
The Oncogenic Action of Fumarate
Glutaminolysis and Cancer
The oncogenic action of L-2-hydroxyglutarate in Hydroxygluaricaciduria
The oncogenic action of D-2-hydroxyglutarate in Hydroxygluaricaciduria
StateSolid
Water Solubility4.30e+00 g/l
logP-0.58
logS-2.27
pKa (Strongest Acidic)0.83
pKa (Strongest Basic)4.95
Hydrogen Acceptor Count17
Hydrogen Donor Count9
Polar Surface Area363.63 Ų
Rotatable Bond Count20
Physiological Charge-4
Formal Charge0
Refractivity172.21 m³·mol⁻¹
Polarizability71.40

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