Showing Compound Card for Acetoacetic acid (CDB004793)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (10) Show 13 proteinsXML
Record Information
Version1.0
Created at2020-04-17 18:37:21 UTC
Updated at2020-12-07 19:10:57 UTC
CannabisDB IDCDB004793
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameAcetoacetic acid
DescriptionAcetoacetic acid, also known as 3-oxobutanoic acid or 3-oxobutyrate, belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms. Acetoacetic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Acetoacetic acid exists in all living species, ranging from bacteria to humans. Acetoacetic acid is a potentially toxic compound. A 3-oxo monocarboxylic acid that is butyric acid bearing a 3-oxo substituent. Acetoacetic acid, with regard to humans, has been found to be associated with several diseases such as late-onset preeclampsia, crohn's disease, and schizophrenia; acetoacetic acid has also been linked to several inborn metabolic disorders including 2-ketoglutarate dehydrogenase complex deficiency and glucose transporter type 1 deficiency syndrome. Acetoacetic acid is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
3-Ketobutanoic acidChEBI
3-Ketobutyric acidChEBI
3-Oxobutanoic acidChEBI
3-Oxobutyric acidChEBI
beta-Ketobutyric acidChEBI
3-KetobutanoateGenerator
3-KetobutyrateGenerator
3-OxobutanoateGenerator
3-OxobutyrateGenerator
b-KetobutyrateGenerator
b-Ketobutyric acidGenerator
beta-KetobutyrateGenerator
Β-ketobutyrateGenerator
Β-ketobutyric acidGenerator
AcetoacetateGenerator
Acetoacetic acid, calcium saltMeSH
Acetoacetic acid, lithium saltMeSH
Acetoacetic acid, sodium saltMeSH
OxobutyrateMeSH
Sodium acetoacetateMeSH
3-oxo-ButanoateHMDB
3-oxo-Butanoic acidHMDB
DiacetateHMDB
Diacetic acidHMDB
Chemical FormulaC4H6O3
Average Molecular Weight102.09
Monoisotopic Molecular Weight102.0317
IUPAC Name3-oxobutanoic acid
Traditional Nameacetoacetic acid
CAS Registry Number541-50-4
SMILES
CC(=O)CC(O)=O
InChI Identifier
InChI=1S/C4H6O3/c1-3(5)2-4(6)7/h2H2,1H3,(H,6,7)
InChI KeyWDJHALXBUFZDSR-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassShort-chain keto acids and derivatives
Direct ParentShort-chain keto acids and derivatives
Alternative Parents
Substituents
  • Short-chain keto acid
  • Beta-keto acid
  • 1,3-dicarbonyl compound
  • Beta-hydroxy ketone
  • Ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point36.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000 mg/mL at 20 °CNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.47ALOGPS
logP-0.0015ChemAxon
logS0.37ALOGPS
pKa (Strongest Acidic)4.02ChemAxon
pKa (Strongest Basic)-7.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity22.54 m³·mol⁻¹ChemAxon
Polarizability9.18 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSAcetoacetic acid, non-derivatized, GC-MS Spectrumsplash10-00kk-3940000000-008eb78d2ba3cfa053b4Spectrum
GC-MSAcetoacetic acid, 1 MEOX; 1 TMS, GC-MS Spectrumsplash10-000i-9500000000-c3940e591f8aef9d6aacSpectrum
GC-MSAcetoacetic acid, 1 MEOX; 1 TMS, GC-MS Spectrumsplash10-000i-9800000000-67a95675672c3f5447a7Spectrum
GC-MSAcetoacetic acid, 2 TMS, GC-MS Spectrumsplash10-001i-4950000000-1778836b3908a79b814fSpectrum
GC-MSAcetoacetic acid, 2 TMS, GC-MS Spectrumsplash10-001i-4950000000-4039bb48c98ec17b5c0cSpectrum
GC-MSAcetoacetic acid, non-derivatized, GC-MS Spectrumsplash10-00kk-3940000000-008eb78d2ba3cfa053b4Spectrum
GC-MSAcetoacetic acid, non-derivatized, GC-MS Spectrumsplash10-000i-9500000000-c3940e591f8aef9d6aacSpectrum
GC-MSAcetoacetic acid, non-derivatized, GC-MS Spectrumsplash10-000i-9800000000-67a95675672c3f5447a7Spectrum
GC-MSAcetoacetic acid, non-derivatized, GC-MS Spectrumsplash10-001i-4950000000-1778836b3908a79b814fSpectrum
GC-MSAcetoacetic acid, non-derivatized, GC-MS Spectrumsplash10-001i-4950000000-4039bb48c98ec17b5c0cSpectrum
Predicted GC-MSAcetoacetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9000000000-9f6c0d100736f4d183c9Spectrum
Predicted GC-MSAcetoacetic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0100-9600000000-470bf0676151478bca3eSpectrum
Predicted GC-MSAcetoacetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAcetoacetic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAcetoacetic acid, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAcetoacetic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAcetoacetic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAcetoacetic acid, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-000i-9200000000-9b4ab7b6a41632cb125b2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-0udi-6900000000-cfab9d4cdb56acafe8cc2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-0pb9-9800000000-108aa5ef93455fb1ba282012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-000i-9100000000-869e2338bbadb32272d42017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 7V, negativesplash10-0a4i-9000000000-3f979a5a82ec557199d22020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-000f-9000000000-2b35e5493fb76f714c222021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-05fr-9000000000-d2734268ae2c1230e50f2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-00di-9000000000-0d73b25163774c0d1eb12021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f79-9400000000-081c4a1a05f5581a5ffb2016-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000l-9100000000-960a06fd90db43d3e0f62016-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-bd091454ccc8f532b42e2016-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zfr-9700000000-b01f47bb6cd4f10439832016-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9100000000-d2649829e8a79045e73b2016-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-1486ce68d51ba83ed4992016-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0pb9-9400000000-2f187d15e3b22b7629d92021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9100000000-1e5e193606848f9d64b42021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-73a6b61cfeb4b8ae96122021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9000000000-de86214ccec455e1860b2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-42af30a03d7e2d4c22fc2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-6aa1f4078505fa3b09712021-09-25View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 125 MHz, H2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Hydroxymethylglutaryl-CoA lyase, mitochondrialHMGCL1p36.1-p35P35914 details
Aldehyde dehydrogenase, mitochondrialALDH212q24.2P05091 details
D-beta-hydroxybutyrate dehydrogenase, mitochondrialBDH13q29Q02338 details
Succinyl-CoA:3-ketoacid coenzyme A transferase 1, mitochondrialOXCT15p13.1P55809 details
FumarylacetoacetaseFAH15q25.1P16930 details
Succinyl-CoA:3-ketoacid coenzyme A transferase 2, mitochondrialOXCT21p34Q9BYC2 details
Hydroxyacid-oxoacid transhydrogenase, mitochondrialADHFE18q13.1Q8IWW8 details
Acetoacetyl-CoA synthetaseAACS12q24.31Q86V21 details
3-hydroxymethyl-3-methylglutaryl-CoA lyase, cytoplasmicHMGCLL16p12.1Q8TB92 details
3-hydroxybutyrate dehydrogenase type 2BDH24q24Q9BUT1 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
FumarylacetoacetaseFAH15q25.1P16930 details
Hydroxyacid-oxoacid transhydrogenase, mitochondrialADHFE18q13.1Q8IWW8 details
3-hydroxymethyl-3-methylglutaryl-CoA lyase, cytoplasmicHMGCLL16p12.1Q8TB92 details
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0000060
DrugBank IDDB01762
Phenol Explorer Compound IDNot Available
FoodDB IDFDB112157
KNApSAcK IDC00007458
Chemspider ID94
KEGG Compound IDC00164
BioCyc ID3-KETOBUTYRATE
BiGG IDNot Available
Wikipedia LinkAcetoacetic_acid
METLIN IDNot Available
PubChem Compound96
PDB IDNot Available
ChEBI ID15344
References
General ReferencesNot Available

Only showing the first 10 proteins. There are 13 proteins in total.

Show All

Enzymes

Enzyme Details
1. Hydroxymethylglutaryl-CoA lyase, mitochondrial
General function:
Involved in catalytic activity
Specific function:
Key enzyme in ketogenesis (ketone body formation). Terminal step in leucine catabolism.
Gene Name:
HMGCL
Uniprot ID:
P35914
Molecular weight:
34359.84
Enzyme Details
2. Aldehyde dehydrogenase, mitochondrial
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
ALDH2
Uniprot ID:
P05091
Molecular weight:
56380.93
Enzyme Details
3. D-beta-hydroxybutyrate dehydrogenase, mitochondrial
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
BDH1
Uniprot ID:
Q02338
Molecular weight:
38156.77
Enzyme Details
4. Succinyl-CoA:3-ketoacid coenzyme A transferase 1, mitochondrial
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
Enzyme Details
5. Fumarylacetoacetase
General function:
Involved in fumarylacetoacetase activity
Specific function:
Not Available
Gene Name:
FAH
Uniprot ID:
P16930
Molecular weight:
46373.97
Enzyme Details
6. Succinyl-CoA:3-ketoacid coenzyme A transferase 2, mitochondrial
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 (By similarity).
Gene Name:
OXCT2
Uniprot ID:
Q9BYC2
Molecular weight:
56139.41
Enzyme Details
7. Hydroxyacid-oxoacid transhydrogenase, mitochondrial
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the cofactor-independent reversible oxidation of gamma-hydroxybutyrate (GHB) to succinic semialdehyde (SSA) coupled to reduction of 2-ketoglutarate (2-KG) to D-2-hydroxyglutarate (D-2-HG). D,L-3-hydroxyisobutyrate and L-3-hydroxybutyrate (L-3-OHB) are also substrates for HOT with 10-fold lower activities.
Gene Name:
ADHFE1
Uniprot ID:
Q8IWW8
Molecular weight:
50307.42
Enzyme Details
8. Acetoacetyl-CoA synthetase
General function:
Involved in acetoacetate-CoA ligase activity
Specific function:
Activates acetoacetate to acetoacetyl-CoA. May be involved in utilizing ketone body for the fatty acid-synthesis during adipose tissue development (By similarity).
Gene Name:
AACS
Uniprot ID:
Q86V21
Molecular weight:
75143.645
Enzyme Details
9. 3-hydroxymethyl-3-methylglutaryl-CoA lyase, cytoplasmic
General function:
Involved in catalytic activity
Specific function:
Non-mitochondrial 3-hydroxymethyl-3-methylglutaryl-CoA lyase that catalyzes a cation-dependent cleavage of (S)-3-hydroxy-3-methylglutaryl-CoA into acetyl-CoA and acetoacetate, a key step in ketogenesis, the products of which support energy production in nonhepatic animal tissues.
Gene Name:
HMGCLL1
Uniprot ID:
Q8TB92
Molecular weight:
36327.465
Enzyme Details
10. 3-hydroxybutyrate dehydrogenase type 2
General function:
Involved in oxidoreductase activity
Specific function:
Dehydrogenase that mediates the formation of 2,5-dihydroxybenzoic acid (2,5-DHBA), a siderophore that shares structural similarities with bacterial enterobactin and associates with LCN2, thereby playing a key role in iron homeostasis and transport. Also acts as a 3-hydroxybutyrate dehydrogenase (By similarity).
Gene Name:
BDH2
Uniprot ID:
Q9BUT1
Molecular weight:
26723.57

Only showing the first 10 proteins. There are 13 proteins in total.

Show All