Record Information
Version1.0
Created at2020-04-17 19:13:28 UTC
Updated at2020-12-07 19:11:39 UTC
CannabisDB IDCDB005141
Secondary Accession NumbersNot Available
Cannabis Compound Identification
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. A 3-oxoacyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of acetoacetic acid. 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 expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
Synonyms
ValueSource
3-Acetoacetyl-CoAChEBI
Acetoacetyl coenzyme AChEBI
S-Acetoacetyl-CoAChEBI
S-Acetoacetyl-coenzym aChEBI
S-Acetoacetyl-coenzyme AChEBI
Acetoacetyl CoAMeSH
Chemical FormulaC25H40N7O18P3S
Average Molecular Weight851.61
Monoisotopic Molecular Weight851.1363
IUPAC Name{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-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 Nameacetoacetyl-coa
CAS Registry Number1420-36-6
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]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N
InChI Identifier
InChI=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
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aminopiperidines. Aminopiperidines are compounds containing a piperidine that carries an amino group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPiperidines
Sub ClassAminopiperidines
Direct ParentAminopiperidines
Alternative Parents
Substituents
  • 4-aminopiperidine
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Secondary amine
  • Secondary aliphatic amine
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.24ALOGPS
logP-5.7ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)0.82ChemAxon
pKa (Strongest Basic)4.01ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area380.7 ŲChemAxon
Rotatable Bond Count22ChemAxon
Refractivity182.1 m³·mol⁻¹ChemAxon
Polarizability76.33 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - n/a 59V, negativesplash10-000i-0004009000-9559fa356f1bae03b7caSpectrum
MS/MSLC-MS/MS Spectrum - n/a 59V, negativesplash10-0a4i-0269300000-d5574d3fd84812c0057dSpectrum
MS/MSLC-MS/MS Spectrum - n/a 59V, negativesplash10-05n1-0009600000-a29b94fc4d454c655babSpectrum
MS/MSLC-MS/MS Spectrum - n/a 59V, negativesplash10-000i-0001209000-21979fdba010c3871c5aSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 42V, negativesplash10-0udi-0000000090-aa1f97ad009df4ad9439Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 57V, negativesplash10-0udi-0000100490-97b56edeb43a5d82ba85Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 71V, negativesplash10-014i-0000910830-9d7a9bb5d2817f98fbf1Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 93V, negativesplash10-0ar9-0101901000-ee3c1d5ebb3142f3c5afSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 115V, negativesplash10-0a6r-5524900000-2d745cfa452462059e2cSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 136V, negativesplash10-056r-9513200000-037d88669e973d0dff1cSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 158V, negativesplash10-004i-9400000000-fca9f3020e4e007e8164Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 187V, negativesplash10-004i-9300000000-13ad94b2682d99b6234dSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 216V, negativesplash10-004i-9200000000-32dfa0b8d343e2eb7b7bSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 260V, negativesplash10-004i-9100000000-6461ef6280ce0db781b2Spectrum
MS/MSLC-MS/MS Spectrum - n/a 59V, negativesplash10-014i-0000000900-727bb0c3c925e7bbeba4Spectrum
MS/MSLC-MS/MS Spectrum - n/a 59V, negativesplash10-00di-0190000000-0e093fb5398057b2093dSpectrum
MS/MSLC-MS/MS Spectrum - n/a 59V, negativesplash10-0a4i-0900000000-b4c90f8c858e783159b8Spectrum
MS/MSLC-MS/MS Spectrum - n/a 59V, negativesplash10-0udl-0018900000-91aaf6888a10aac16f57Spectrum
MS/MSLC-MS/MS Spectrum - n/a 59V, negativesplash10-00xr-0092000000-2dd3c44dfb7a39ee9a59Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1912000130-163ca7231778bddd9739Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0913000000-4f4f26abcf9b0d9f285eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-2911000000-cc9acdeb298fa6ebbdb7Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-9730140350-cefdc8a0886f8e9e2b86Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-5910110010-51e3282fd98f872b9ff5Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-6900100000-4a6e405bfbd488ea01d4Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Acetyl-CoA acetyltransferase, cytosolicACAT26q25.3Q9BWD1 details
3-ketoacyl-CoA thiolase, mitochondrialACAA218q21.1P42765 details
Acetyl-CoA acetyltransferase, mitochondrialACAT111q22.3P24752 details
Hydroxymethylglutaryl-CoA synthase, mitochondrialHMGCS21p13-p12P54868 details
3-ketoacyl-CoA thiolase, peroxisomalACAA13p22.2P09110 details
Trifunctional enzyme subunit beta, mitochondrialHADHB2p23P55084 details
Hydroxymethylglutaryl-CoA synthase, cytoplasmicHMGCS15p14-p13Q01581 details
3-hydroxyacyl-CoA dehydrogenase type-2HSD17B10Xp11.2Q99714 details
Hydroxyacyl-coenzyme A dehydrogenase, mitochondrialHADH4q22-q26Q16836 details
Succinyl-CoA:3-ketoacid coenzyme A transferase 1, mitochondrialOXCT15p13.1P55809 details
Succinyl-CoA:3-ketoacid coenzyme A transferase 2, mitochondrialOXCT21p34Q9BYC2 details
Acetoacetyl-CoA synthetaseAACS12q24.31Q86V21 details
Estradiol 17-beta-dehydrogenase 12HSD17B1211p11.2Q53GQ0 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Acetyl-CoA acetyltransferase, mitochondrialACAT111q22.3P24752 details
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0001484
DrugBank IDDB03059
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022648
KNApSAcK IDC00007269
Chemspider ID83198
KEGG Compound IDC00332
BioCyc IDACETOACETYL-COA
BiGG IDNot Available
Wikipedia LinkAcetoacetyl-CoA
METLIN IDNot Available
PubChem Compound92153
PDB IDNot Available
ChEBI ID15345
References
General ReferencesNot Available

Only showing the first 10 proteins. There are 14 proteins in total.

Enzymes

General function:
Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:
Not Available
Gene Name:
ACAT2
Uniprot ID:
Q9BWD1
Molecular weight:
41350.5
General function:
Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:
Abolishes BNIP3-mediated apoptosis and mitochondrial damage.
Gene Name:
ACAA2
Uniprot ID:
P42765
Molecular weight:
41923.82
General function:
Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:
Plays a major role in ketone body metabolism.
Gene Name:
ACAT1
Uniprot ID:
P24752
Molecular weight:
45199.2
General function:
Involved in hydroxymethylglutaryl-CoA synthase activity
Specific function:
This enzyme condenses acetyl-CoA with acetoacetyl-CoA to form HMG-CoA, which is the substrate for HMG-CoA reductase.
Gene Name:
HMGCS2
Uniprot ID:
P54868
Molecular weight:
52481.065
General function:
Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:
Not Available
Gene Name:
ACAA1
Uniprot ID:
P09110
Molecular weight:
34664.46
General function:
Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:
Not Available
Gene Name:
HADHB
Uniprot ID:
P55084
Molecular weight:
51293.955
General function:
Involved in hydroxymethylglutaryl-CoA synthase activity
Specific function:
This enzyme condenses acetyl-CoA with acetoacetyl-CoA to form HMG-CoA, which is the substrate for HMG-CoA reductase.
Gene Name:
HMGCS1
Uniprot ID:
Q01581
Molecular weight:
57293.105
General function:
Involved in oxidoreductase activity
Specific function:
Functions in mitochondrial tRNA maturation. Part of mitochondrial ribonuclease P, an enzyme composed of MRPP1/TRMT10C, MRPP2/HSD17B10 and MRPP3/KIAA0391, which cleaves tRNA molecules in their 5'-ends. By interacting with intracellular amyloid-beta, it may contribute to the neuronal dysfunction associated with Alzheimer disease (AD).
Gene Name:
HSD17B10
Uniprot ID:
Q99714
Molecular weight:
25983.695
General function:
Involved in 3-hydroxyacyl-CoA dehydrogenase activity
Specific function:
Plays an essential role in the mitochondrial beta-oxidation of short chain fatty acids. Exerts it highest activity toward 3-hydroxybutyryl-CoA.
Gene Name:
HADH
Uniprot ID:
Q16836
Molecular weight:
36035.11
General function:
Involved in CoA-transferase activity
Specific function:
Key enzyme for ketone body catabolism. Transfers the CoA moiety from succinate to acetoacetate. Formation of the enzyme-CoA intermediate proceeds via an unstable anhydride species formed between the carboxylate groups of the enzyme and substrate.
Gene Name:
OXCT1
Uniprot ID:
P55809
Molecular weight:
56157.175

Only showing the first 10 proteins. There are 14 proteins in total.