Record Information
Version1.0
Created at2020-04-17 18:40:33 UTC
Updated at2020-11-18 16:38:47 UTC
CannabisDB IDCDB004824
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameOxalacetic acid
DescriptionOxalacetic acid, also known as oxaloacetate or 2-oxosuccinate, 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. Oxalacetic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Oxalacetic acid exists in all living species, ranging from bacteria to humans. Within humans, oxalacetic acid participates in a number of enzymatic reactions. In particular, oxalacetic acid can be biosynthesized from D-aspartic acid through the action of the enzyme D-aspartate oxidase. In addition, oxalacetic acid can be biosynthesized from D-aspartic acid through the action of the enzyme D-aspartate oxidase. In humans, oxalacetic acid is involved in the metabolic disorder called the canavan disease pathway. Outside of the human body, Oxalacetic acid has been detected, but not quantified in, several different foods, such as chinese mustards, lowbush blueberries, brassicas, maitakes, and kombus. This could make oxalacetic acid a potential biomarker for the consumption of these foods. An oxodicarboxylic acid that is succinic acid bearing a single oxo group. Oxalacetic acid is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
Synonyms
ValueSource
2-Oxobutanedioic acidChEBI
2-Oxosuccinic acidChEBI
3-Carboxy-3-oxopropanoic acidChEBI
Keto-succinic acidChEBI
Ketosuccinic acidChEBI
OAAChEBI
Oxobutanedioic acidChEBI
Oxosuccinic acidChEBI
Oxaloacetic acidKegg
Keto-oxaloacetateKegg
2-OxobutanedioateGenerator
2-OxosuccinateGenerator
3-Carboxy-3-oxopropanoateGenerator
Keto-succinateGenerator
KetosuccinateGenerator
OxobutanedioateGenerator
OxosuccinateGenerator
OxaloacetateGenerator
Keto-oxaloacetic acidGenerator
OxalacetateGenerator
2-KetosuccinateHMDB
2-Ketosuccinic acidHMDB
a-KetosuccinateHMDB
a-Ketosuccinic acidHMDB
alpha-KetosuccinateHMDB
alpha-Ketosuccinic acidHMDB
OxaloethanoateHMDB
Oxaloethanoic acidHMDB
Acid, oxaloaceticHMDB
Acid, oxalaceticHMDB
2 Ketosuccinic acidHMDB
2 oxo Butanedioic acidHMDB
2-oxo-Butanedioic acidHMDB
Chemical FormulaC4H4O5
Average Molecular Weight132.07
Monoisotopic Molecular Weight132.0059
IUPAC Name2-oxobutanedioic acid
Traditional Nameoxalacetate
CAS Registry Number328-42-7
SMILES
OC(=O)CC(=O)C(O)=O
InChI Identifier
InChI=1S/C4H4O5/c5-2(4(8)9)1-3(6)7/h1H2,(H,6,7)(H,8,9)
InChI KeyKHPXUQMNIQBQEV-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
  • Beta-keto acid
  • Short-chain keto acid
  • Alpha-keto acid
  • Beta-hydroxy ketone
  • Dicarboxylic acid or derivatives
  • 1,3-dicarbonyl compound
  • Alpha-hydroxy ketone
  • Ketone
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carbonyl group
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point161 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility134 mg/mLNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.68ALOGPS
logP-0.042ChemAxon
logS-0.36ALOGPS
pKa (Strongest Acidic)2.41ChemAxon
pKa (Strongest Basic)-9.9ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area91.67 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity24.33 m³·mol⁻¹ChemAxon
Polarizability10.06 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-f371299a07d43c23ff1dSpectrum
GC-MSOxalacetic acid, non-derivatized, GC-MS Spectrumsplash10-00dr-4900000000-9d943d40beaca3c602a1Spectrum
GC-MSOxalacetic acid, 1 MEOX; 2 TMS, GC-MS Spectrumsplash10-007a-9210000000-020f60717e2ea79d1ccdSpectrum
GC-MSOxalacetic acid, 1 MEOX; 2 TMS, GC-MS Spectrumsplash10-000b-9540000000-a53f674cc98960834f88Spectrum
GC-MSOxalacetic acid, 1 MEOX; 3 TMS, GC-MS Spectrumsplash10-001a-8940000000-40b790e06141d7180938Spectrum
GC-MSOxalacetic acid, non-derivatized, GC-MS Spectrumsplash10-007a-9210000000-020f60717e2ea79d1ccdSpectrum
GC-MSOxalacetic acid, non-derivatized, GC-MS Spectrumsplash10-000b-9540000000-a53f674cc98960834f88Spectrum
GC-MSOxalacetic acid, non-derivatized, GC-MS Spectrumsplash10-001a-8940000000-40b790e06141d7180938Spectrum
GC-MSOxalacetic acid, non-derivatized, GC-MS Spectrumsplash10-0002-4930000000-7e995327b0b9c1af0914Spectrum
Predicted GC-MSOxalacetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000f-9100000000-6718417e7196063f9544Spectrum
Predicted GC-MSOxalacetic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00ds-9520000000-5a082ec8843f6fbc3b15Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-000i-9000000000-0be675f3aa3e973393b7Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-000f-9000000000-4fba97fcd7b0f2215f75Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0006-9000000000-9b1f4171aee6283a3cbdSpectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-014i-0900000000-7c598fd9c78acb94dacdSpectrum
MS/MSLC-MS/MS Spectrum - QTOF 3V, positivesplash10-014i-4900000000-e7803730ae7986a1b9fbSpectrum
MS/MSLC-MS/MS Spectrum - QTOF 4V, positivesplash10-014r-5900000000-8e478338a7c0e65e62baSpectrum
MS/MSLC-MS/MS Spectrum - QTOF 5V, positivesplash10-014r-7900000000-f681763317e1ae86e691Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 7V, positivesplash10-00kr-9600000000-aa8adf9a96041dddbbddSpectrum
MS/MSLC-MS/MS Spectrum - QTOF 10V, positivesplash10-000i-9200000000-e62c47ca2bc492900178Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 15V, positivesplash10-000i-9000000000-5485ddd84a64ea0ca0b9Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 17V, positivesplash10-000i-9000000000-79521cb04a2b23e39c1eSpectrum
MS/MSLC-MS/MS Spectrum - QTOF 20V, positivesplash10-000m-9000000000-601c8d2ec63f8b01a61eSpectrum
MS/MSLC-MS/MS Spectrum - QTOF 23V, positivesplash10-000e-9000000000-13d369c58d8930958d92Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 25V, positivesplash10-0005-9000000000-df8387ef907fb71342ebSpectrum
MS/MSLC-MS/MS Spectrum - QTOF 27V, positivesplash10-0005-9000000000-908644b5d7041346f582Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 30V, positivesplash10-0005-9000000000-ecca787a800164d0296fSpectrum
MS/MSLC-MS/MS Spectrum - QTOF 33V, positivesplash10-0005-9000000000-180a7c51b1f93cb8fff2Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 35V, positivesplash10-0005-9000000000-709c49f609f5a711a288Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 40V, positivesplash10-0005-9000000000-aa103ab9beb03bd6eb22Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-3900000000-6f4e965a3f513bf8db13Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-9600000000-8ae7abf60057088e14dbSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01bc-9100000000-5724c215c46a4f568140Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0019-8900000000-829898d0849b1fbf1c28Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9100000000-5a5ff8fb7cb52eebf0c8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-657d1384d478ddc33b6dSpectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
ATP-citrate synthaseACLY17q21.2P53396 details
Pyruvate carboxylase, mitochondrialPC11q13.4-q13.5P11498 details
Citrate synthase, mitochondrialCS12q13.2O75390 details
D-aspartate oxidaseDDO6q21Q99489 details
Aspartate aminotransferase, cytoplasmicGOT110q24.1-q25.1P17174 details
Aspartate aminotransferase, mitochondrialGOT216q21P00505 details
Malate dehydrogenase, mitochondrialMDH27cen-q22P40926 details
Malate dehydrogenase, cytoplasmicMDH12p13.3P40925 details
Phosphoenolpyruvate carboxykinase [GTP], mitochondrialPCK214q11.2Q16822 details
Phosphoenolpyruvate carboxykinase, cytosolic [GTP]PCK120q13.31P35558 details
L-amino-acid oxidaseIL4I119q13.3-q13.4Q96RQ9 details
Putative L-aspartate dehydrogenaseASPDH19q13.33A6ND91 details
Putative aspartate aminotransferase, cytoplasmic 2GOT1L18p11.23Q8NHS2 details
Omega-amidase NIT2NIT23q12.2Q9NQR4 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
ATP-citrate synthaseACLY17q21.2P53396 details
Pyruvate carboxylase, mitochondrialPC11q13.4-q13.5P11498 details
NADP-dependent malic enzymeME16q12P48163 details
NADP-dependent malic enzyme, mitochondrialME311cen-q22.3Q16798 details
NAD-dependent malic enzyme, mitochondrialME218q21P23368 details
Phosphoenolpyruvate carboxykinase [GTP], mitochondrialPCK214q11.2Q16822 details
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0000223
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB031075
KNApSAcK IDC00001197
Chemspider ID945
KEGG Compound IDC00036
BioCyc IDOXALACETIC_ACID
BiGG ID33604
Wikipedia LinkOxaloacetic_acid
METLIN ID123
PubChem Compound970
PDB IDNot Available
ChEBI ID30744
References
General ReferencesNot Available

Only showing the first 10 proteins. There are 20 proteins in total.

Enzymes

General function:
Involved in ATP citrate synthase activity
Specific function:
ATP citrate-lyase is the primary enzyme responsible for the synthesis of cytosolic acetyl-CoA in many tissues. Has a central role in de novo lipid synthesis. In nervous tissue it may be involved in the biosynthesis of acetylcholine.
Gene Name:
ACLY
Uniprot ID:
P53396
Molecular weight:
120838.27
General function:
Involved in catalytic activity
Specific function:
Pyruvate carboxylase catalyzes a 2-step reaction, involving the ATP-dependent carboxylation of the covalently attached biotin in the first step and the transfer of the carboxyl group to pyruvate in the second. Catalyzes in a tissue specific manner, the initial reactions of glucose (liver, kidney) and lipid (adipose tissue, liver, brain) synthesis from pyruvate.
Gene Name:
PC
Uniprot ID:
P11498
Molecular weight:
129632.565
General function:
Involved in transferase activity, transferring acyl groups, acyl groups converted into alkyl on transfer
Specific function:
Not Available
Gene Name:
CS
Uniprot ID:
O75390
Molecular weight:
51712.025
General function:
Involved in D-amino-acid oxidase activity
Specific function:
Selectively catalyzes the oxidative deamination of D-aspartate and its N-methylated derivative, N-methyl D-aspartate.
Gene Name:
DDO
Uniprot ID:
Q99489
Molecular weight:
40992.53
General function:
Involved in transferase activity, transferring nitrogenous groups
Specific function:
Plays a key role in amino acid metabolism (By similarity).
Gene Name:
GOT1
Uniprot ID:
P17174
Molecular weight:
46247.14
General function:
Involved in transferase activity, transferring nitrogenous groups
Specific function:
Catalyzes the irreversible transamination of the L-tryptophan metabolite L-kynurenine to form kynurenic acid (KA). Plays a key role in amino acid metabolism. Important for metabolite exchange between mitochondria and cytosol. Facilitates cellular uptake of long-chain free fatty acids.
Gene Name:
GOT2
Uniprot ID:
P00505
Molecular weight:
47517.285
General function:
Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:
Not Available
Gene Name:
MDH2
Uniprot ID:
P40926
Molecular weight:
35502.935
General function:
Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:
Not Available
Gene Name:
MDH1
Uniprot ID:
P40925
Molecular weight:
38627.255
General function:
Involved in phosphoenolpyruvate carboxykinase activity
Specific function:
Catalyzes the conversion of oxaloacetate (OAA) to phosphoenolpyruvate (PEP), the rate-limiting step in the metabolic pathway that produces glucose from lactate and other precursors derived from the citric acid cycle (By similarity).
Gene Name:
PCK2
Uniprot ID:
Q16822
Molecular weight:
47563.34
General function:
Involved in phosphoenolpyruvate carboxykinase activity
Specific function:
Catalyzes the conversion of oxaloacetate (OAA) to phosphoenolpyruvate (PEP), the rate-limiting step in the metabolic pathway that produces glucose from lactate and other precursors derived from the citric acid cycle.
Gene Name:
PCK1
Uniprot ID:
P35558
Molecular weight:
69193.975

Only showing the first 10 proteins. There are 20 proteins in total.