Basic information
- Standard SMILES
CC(=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- InChIKey
OJFDKHTZOUZBOS-CITAKDKDSA-N- Molecular formula
- C25H40N7O18P3S
- Average molar mass
- 851.6 g/mol
- Monoisotopic mass
- 851.13633833
Overview
Acetoacetyl-CoA is a 3-oxoacyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of acetoacetic acid. It has a role as a mouse metabolite and an Escherichia coli metabolite. It is functionally related to an acetoacetic acid and a butyryl-CoA. It is a conjugate acid of an acetoacetyl-CoA(4-).
Names & identifiers
- Preferred name
- acetoacetyl-CoA
- IUPAC
- S-[2-[3-[[(2R)-4-[[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-2-hydroxy-3,3-dimethylbutanoyl]amino]propanoylamino]ethyl] 3-oxobutanethioate
- English name
- S-acetoacetylcoenzyme A
- Molecular formula
- C25H40N7O18P3S
- Molecular weight
- 851.61
Names & synonyms
acetoacetyl-CoA1420-36-6Acetoacetyl coenzyme AAcetoacetyl coa3-acetoacetyl-CoAS-Acetoacetyl-CoAS-acetoacetyl-coenzyme ACHEBI:15345S-[2-[3-[[(2R)-4-[[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-2-hydroxy-3,3-dimethylbutanoyl]amino]propanoylamino]ethyl] 3-oxobutanethioateS-(2-(3-(((2R)-4-((((2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl)methoxy-hydroxyphosphoryl)oxy-hydroxyphosphoryl)oxy-2-hydroxy-3,3-dimethylbutanoyl)amino)propanoylamino)ethyl) 3-oxobutanethioateRefChem:552369(((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
Show more names
Acetoacetyl coenzymeA[A1625]Coenzyme A S-(3-oxobutanoate)Coenzyme A Impurity 2 （S-Acetoacetate Coenzyme A)(Acetoacetyl-CoA)5'-O-[[[(5,9-Diaza-3-hydroxy-2,2-dimethyl-4,8,13,15-tetraoxo-12-thiahexadecan)-1-yl]phosphono]phosphono]adenosine-3'-phosphoric acid[5-(6-aminopurin-9-yl)-4-hydroxy-2-[[hydroxy-[hydroxy-[3-hydroxy-2,2-dimethyl-3-[2-[2-(3-oxobutanoylsulfanyl)ethylcarbamoyl]ethylcarbamoyl]propoxy]-phosphoryl]oxy-phosphoryl]oxymethyl]oxolan-3-yl]oxyphosphonic acid
215-815-9S-Acetoacetylcoenzyme Aacetoacetyl-coenzyme aAcetoacetylcoenzyme ACoenzyme A, S-acetoacetateS-(2-(3-((2R)-4-(((((((2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)tetrahydrofuran-2-yl)methoxy)(hydroxy)phosphoryl)oxy)(hydroxy)phosphoryl)oxy)-2-hydroxy-3,3-dimethylbutanamido)propanamido)ethyl) 3-oxobutanethioateacetoacetyl-S-CoAS-Acetoacetate Coenzyme A
Database identifiers
- CAS
1420-36-6- PubChem CID
- 92153
- DTXSID
DTXSID30931292- ChEBI
CHEBI:15345- EC Number
- 215-815-9
- Nikkaji
- J670.888I
Properties
Computed structural properties
- XLogP
- -5.8
- Topological polar surface area
- 406 Ų
- Hydrogen bond donors
- 9
- Hydrogen bond acceptors
- 23
- Rotatable bonds
- 22
- Heavy atoms
- 54
- Formal charge
- 0
- Complexity
- 1,490
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
LipidsFatty Acyls [FA] -> Fatty esters [FA07] -> Fatty acyl CoAs [FA0705]
Physical DescriptionSolid
Collision Cross Section247.8 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
Physicochemical properties
- Density
- 1.87 · 1.87±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C
- solubility
- Methanol (Slightly, Heated, Sonicated), Water
- pka
- 1.16 · 1.16±0.50(Predicted)
- form
- Solid
- color
- White to Off-White
- biological source
- synthetic (Organic)
- Water Solubility
- 2 O: · H2O: soluble~-50g/L
- InChIKey
- OJFDKHTZOUZBOS-CITAKDKDSA-N
- SMILES
- [Na+].[Na+].[Na+].CC(=O)CC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP([O-])(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP([O-])([O-])=O)n2cnc3c(N)ncnc23
- UNSPSC Code
- 41106305 · 41106305
- NACRES
- 51 · NA.51
- PPE
- 95 · Eyeshields, Gloves, type N95 (US)
- WGK Germany
- 3 · 3
- Storage Class
- 11 · 11 - Combustible Solids
Safety & regulation
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Pharmacology
Tissue LocationsFibroblasts
Cellular LocationsExtracellular
Metabolite Pathways2-aminoadipic 2-oxoadipic aciduria
Applications
UsesAcetoacetyl coenzyme A (Acetoacetyl-CoA) may be used as a substrate for a number of enzymes including; acetoacetyl-CoA thiolase (EC 2.3.1) which produces acetyl-CoA in reverse condensation reaction and (3-Hydroxy-3-methylglutaryl coenzyme A (CoA) synthase (HMGCS)) which produces 3-hydroxy-3-methylglutaryl (HMG)-CoA in the mevalonate pathway leading to terpenoid biosynthesis. Acetoacetyl-CoA is also a precursor of poly-beta-hydroxybutyrate polymers in microorganisms.
Suppliers3 total
北京天净沙基因科技有限公司19852949191 19852949191 · [email protected]
凯试（上海）科技有限公司021-50135380 · [email protected]
上海智溯科生物科技有限公司021-58056897 15399714481 · [email protected]
Additional notes
DefinitionChEBI: A 3-oxoacyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of acetoacetic acid.
Related reactions
5 records
Linked notes
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