Showing Metabocard for acetoacetyl-CoA (BASm0002555)

Common NameAcetoacetyl-coa
DescriptionAcetoacetyl-CoA belongs to the class of organic compounds known as aminopiperidines. Aminopiperidines are compounds containing a piperidine that carries an amino group. Acetoacetyl-CoA is a strong basic compound (based on its pKa). In humans, acetoacetyl-CoA is involved in the metabolic disorder called the short-chain 3-hydroxyacyl-CoA dehydrogenase deficiency (HADH) pathway. Acetoacetyl-CoA is an intermediate in the metabolism of butanoate. It is a substrate for succinyl-CoA:3-ketoacid-coenzyme A transferase, hydroxymethylglutaryl-CoA synthase, short-chain 3-hydroxyacyl-CoA dehydrogenase, peroxisomal bifunctional enzyme, acetyl-CoA acetyltransferase, and 3-ketoacyl-CoA thiolase.
Structure
Molecular FormulaC25H40N7O18P3S
Average Mass851.60700
Monoisotopic Mass851.13634
IUPAC Name{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy(3-hydroxy-2,2-dimethyl-3-{[2-({2-[(3-oxobutanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
Traditional Name[(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-4-hydroxy-2-[({hydroxy[hydroxy(3-hydroxy-2,2-dimethyl-3-{[2-({2-[(3-oxobutanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid
CAS Registry Number1420-36-6
SMILESCC(=O)CC(=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/C25H40N7O18P3S/c1-13(33)8-16(35)54-7-6-27-15(34)4-5-28-23(38)20(37)25(2,3)10-47-53(44,45)50-52(42,43)46-9-14-19(49-51(39,40)41)18(36)24(48-14)32-12-31-17-21(26)29-11-30-22(17)32/h11-12,14,18-20,24,36-37H,4-10H2,1-3H3,(H,27,34)(H,28,38)(H,42,43)(H,44,45)(H2,26,29,30)(H2,39,40,41)/t14-,18-,19-,20+,24-/m1/s1
InChI KeyOJFDKHTZOUZBOS-CITAKDKDSA-N
CHEBI IDCHEBI:57286
HMDB IDHMDB0001484
Pathways
NameSMPDB/PathBank
Valine, leucine and isoleucine degradation
Propanoate metabolism
Lysine degradation
Pyruvate metabolism
Steroid Biosynthesis
Fatty acid Metabolism
Ketone Body Metabolism
Butyrate 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-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
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
Short Chain Acyl CoA Dehydrogenase Deficiency (SCAD Deficiency)
Propionic Acidemia
3-Methylcrotonyl Coa Carboxylase Deficiency Type I
Isovaleric Aciduria
Saccharopinuria/Hyperlysinemia II
Lysosomal Acid Lipase Deficiency (Wolman Disease)
Pyruvate Decarboxylase E1 Component Deficiency (PDHE1 Deficiency)
Methylmalonate Semialdehyde Dehydrogenase Deficiency
Desmosterolosis
CHILD Syndrome
Chondrodysplasia Punctata II, X Linked Dominant (CDPX2)
Smith-Lemli-Opitz Syndrome (SLOS)
Mitochondrial Beta-Oxidation of Short Chain Saturated Fatty Acids
Malonyl-coa decarboxylase deficiency
Cholesteryl ester storage disease
Hyper-IgD syndrome
Mevalonic aciduria
Wolman disease
3-hydroxyisobutyric acid dehydrogenase deficiency
3-hydroxyisobutyric aciduria
Isobutyryl-coa dehydrogenase deficiency
Isovaleric acidemia
Hyperlysinemia I, Familial
Hyperlysinemia II or Saccharopinuria
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)
Trifunctional protein deficiency
Primary hyperoxaluria II, PH2
Pyruvate kinase deficiency
Short-chain 3-hydroxyacyl-CoA dehydrogenase deficiency (SCHAD)
Succinyl CoA: 3-ketoacid CoA transferase deficiency
Pyridoxine dependency with seizures
2-aminoadipic 2-oxoadipic aciduria
StateSolid
Water Solubility3.83e+00 g/l
logP-0.37
logS-2.35
pKa (Strongest Acidic)0.83
pKa (Strongest Basic)4.95
Hydrogen Acceptor Count18
Hydrogen Donor Count9
Polar Surface Area380.7 Ų
Rotatable Bond Count22
Physiological Charge-4
Formal Charge0
Refractivity182.10 m³·mol⁻¹
Polarizability75.05

We require the use of cookies for essential features like storing your previously submitted BASys2 queries. Rejecting the usage of cookies will result in certain features being disabled. By clicking ACCEPT or continuing to use the website you are agreeing to our use of cookies.

ACCEPT