Cannabis Compound Database: Showing Compound Card for Oxalacetic acid (CDB004824)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (14) Show 20 proteins XML

Record Information

Version

1.0

Created at

2020-04-17 18:40:33 UTC

Updated at

2020-11-18 16:38:47 UTC

CannabisDB ID

CDB004824

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Oxalacetic acid

Description

Oxalacetic 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

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
2-Oxobutanedioic acid	ChEBI
2-Oxosuccinic acid	ChEBI
3-Carboxy-3-oxopropanoic acid	ChEBI
Keto-succinic acid	ChEBI
Ketosuccinic acid	ChEBI
OAA	ChEBI
Oxobutanedioic acid	ChEBI
Oxosuccinic acid	ChEBI
Oxaloacetic acid	Kegg
Keto-oxaloacetate	Kegg
2-Oxobutanedioate	Generator
2-Oxosuccinate	Generator
3-Carboxy-3-oxopropanoate	Generator
Keto-succinate	Generator
Ketosuccinate	Generator
Oxobutanedioate	Generator
Oxosuccinate	Generator
Oxaloacetate	Generator
Keto-oxaloacetic acid	Generator
Oxalacetate	Generator
2-Ketosuccinate	HMDB
2-Ketosuccinic acid	HMDB
a-Ketosuccinate	HMDB
a-Ketosuccinic acid	HMDB
alpha-Ketosuccinate	HMDB
alpha-Ketosuccinic acid	HMDB
Oxaloethanoate	HMDB
Oxaloethanoic acid	HMDB
Acid, oxaloacetic	HMDB
Acid, oxalacetic	HMDB
2 Ketosuccinic acid	HMDB
2 oxo Butanedioic acid	HMDB
2-oxo-Butanedioic acid	HMDB

Chemical Formula

C₄H₄O₅

Average Molecular Weight

132.07

Monoisotopic Molecular Weight

132.0059

IUPAC Name

2-oxobutanedioic acid

Traditional Name

oxalacetate

CAS Registry Number

328-42-7

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 Key

KHPXUQMNIQBQEV-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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Keto acids and derivatives

Sub Class

Short-chain keto acids and derivatives

Direct Parent

Short-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 Framework

Aliphatic acyclic compounds

External Descriptors

C4-dicarboxylic acid (CHEBI:30744 )
oxo dicarboxylic acid (CHEBI:30744 )
Dicarboxylic acids (LMFA01170120 )

Ontology

Physiological effect

Health effect:

Health condition:

Anoxia

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant:

Animal

Biological location:

Organ and components:

Liver

Biofluid and excreta:

Subcellular:

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	161 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	134 mg/mL	Not Available
logP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-0.68	ALOGPS
logP	-0.042	ChemAxon
logS	-0.36	ALOGPS
pKa (Strongest Acidic)	2.41	ChemAxon
pKa (Strongest Basic)	-9.9	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	91.67 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	24.33 m³·mol⁻¹	ChemAxon
Polarizability	10.06 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0006-9000000000-f371299a07d43c23ff1d	2015-03-01	View Spectrum
GC-MS	Oxalacetic acid, non-derivatized, GC-MS Spectrum	splash10-00dr-4900000000-9d943d40beaca3c602a1	Spectrum
GC-MS	Oxalacetic acid, 1 MEOX; 2 TMS, GC-MS Spectrum	splash10-007a-9210000000-020f60717e2ea79d1ccd	Spectrum
GC-MS	Oxalacetic acid, 1 MEOX; 2 TMS, GC-MS Spectrum	splash10-000b-9540000000-a53f674cc98960834f88	Spectrum
GC-MS	Oxalacetic acid, 1 MEOX; 3 TMS, GC-MS Spectrum	splash10-001a-8940000000-40b790e06141d7180938	Spectrum
GC-MS	Oxalacetic acid, non-derivatized, GC-MS Spectrum	splash10-007a-9210000000-020f60717e2ea79d1ccd	Spectrum
GC-MS	Oxalacetic acid, non-derivatized, GC-MS Spectrum	splash10-000b-9540000000-a53f674cc98960834f88	Spectrum
GC-MS	Oxalacetic acid, non-derivatized, GC-MS Spectrum	splash10-001a-8940000000-40b790e06141d7180938	Spectrum
GC-MS	Oxalacetic acid, non-derivatized, GC-MS Spectrum	splash10-0002-4930000000-7e995327b0b9c1af0914	Spectrum
Predicted GC-MS	Oxalacetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-000f-9100000000-6718417e7196063f9544	Spectrum
Predicted GC-MS	Oxalacetic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00ds-9520000000-5a082ec8843f6fbc3b15	Spectrum
Predicted GC-MS	Oxalacetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Oxalacetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Oxalacetic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Oxalacetic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Oxalacetic acid, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Oxalacetic acid, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Oxalacetic acid, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Oxalacetic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Oxalacetic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Oxalacetic acid, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Oxalacetic acid, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Oxalacetic acid, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Oxalacetic acid, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-000i-9000000000-0be675f3aa3e973393b7	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-000f-9000000000-4fba97fcd7b0f2215f75	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0006-9000000000-9b1f4171aee6283a3cbd	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - , negative	splash10-014i-0900000000-7c598fd9c78acb94dacd	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 3V, positive	splash10-014i-4900000000-e7803730ae7986a1b9fb	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 4V, positive	splash10-014r-5900000000-8e478338a7c0e65e62ba	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 5V, positive	splash10-014r-7900000000-f681763317e1ae86e691	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 7V, positive	splash10-00kr-9600000000-aa8adf9a96041dddbbdd	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 10V, positive	splash10-000i-9200000000-e62c47ca2bc492900178	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 15V, positive	splash10-000i-9000000000-5485ddd84a64ea0ca0b9	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 17V, positive	splash10-000i-9000000000-79521cb04a2b23e39c1e	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 20V, positive	splash10-000m-9000000000-601c8d2ec63f8b01a61e	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 23V, positive	splash10-000e-9000000000-13d369c58d8930958d92	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 25V, positive	splash10-0005-9000000000-df8387ef907fb71342eb	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 27V, positive	splash10-0005-9000000000-908644b5d7041346f582	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 30V, positive	splash10-0005-9000000000-ecca787a800164d0296f	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 33V, positive	splash10-0005-9000000000-180a7c51b1f93cb8fff2	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 35V, positive	splash10-0005-9000000000-709c49f609f5a711a288	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 40V, positive	splash10-0005-9000000000-aa103ab9beb03bd6eb22	2020-07-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-3900000000-6f4e965a3f513bf8db13	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-9600000000-8ae7abf60057088e14db	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01bc-9100000000-5724c215c46a4f568140	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0019-8900000000-829898d0849b1fbf1c28	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9100000000-5a5ff8fb7cb52eebf0c8	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-657d1384d478ddc33b6d	2015-04-25	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Sodium phosphate (pH 7.4) in 90% H₂O /10% D₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum
2D NMR	[¹H, ¹³C] NMR Spectrum (2D, 800 MHz, experimental)	Spectrum

Pathways

Name	SMPDB/Pathwhiz	KEGG
Alanine Metabolism
Malate-Aspartate Shuttle		Not Available
Citric Acid Cycle
Gluconeogenesis
Aspartate Metabolism

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
ATP-citrate synthase	ACLY	17q21.2	P53396	details
Pyruvate carboxylase, mitochondrial	PC	11q13.4-q13.5	P11498	details
Citrate synthase, mitochondrial	CS	12q13.2	O75390	details
D-aspartate oxidase	DDO	6q21	Q99489	details
Aspartate aminotransferase, cytoplasmic	GOT1	10q24.1-q25.1	P17174	details
Aspartate aminotransferase, mitochondrial	GOT2	16q21	P00505	details
Malate dehydrogenase, mitochondrial	MDH2	7cen-q22	P40926	details
Malate dehydrogenase, cytoplasmic	MDH1	2p13.3	P40925	details
Phosphoenolpyruvate carboxykinase [GTP], mitochondrial	PCK2	14q11.2	Q16822	details
Phosphoenolpyruvate carboxykinase, cytosolic [GTP]	PCK1	20q13.31	P35558	details
L-amino-acid oxidase	IL4I1	19q13.3-q13.4	Q96RQ9	details
Putative L-aspartate dehydrogenase	ASPDH	19q13.33	A6ND91	details
Putative aspartate aminotransferase, cytoplasmic 2	GOT1L1	8p11.23	Q8NHS2	details
Omega-amidase NIT2	NIT2	3q12.2	Q9NQR4	details

Transporters

Not Available

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
ATP-citrate synthase	ACLY	17q21.2	P53396	details
Pyruvate carboxylase, mitochondrial	PC	11q13.4-q13.5	P11498	details
NADP-dependent malic enzyme	ME1	6q12	P48163	details
NADP-dependent malic enzyme, mitochondrial	ME3	11cen-q22.3	Q16798	details
NAD-dependent malic enzyme, mitochondrial	ME2	18q21	P23368	details
Phosphoenolpyruvate carboxykinase [GTP], mitochondrial	PCK2	14q11.2	Q16822	details

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0000223

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

30744

References

General References

Not Available

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

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Enzymes

Enzyme Details

1. ATP-citrate synthase

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

Enzyme Details

2. Pyruvate carboxylase, mitochondrial

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

Enzyme Details

3. Citrate synthase, mitochondrial

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

Enzyme Details

4. D-aspartate oxidase

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

Enzyme Details

5. Aspartate aminotransferase, cytoplasmic

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

Enzyme Details

6. Aspartate aminotransferase, mitochondrial

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

Enzyme Details

7. Malate dehydrogenase, mitochondrial

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

Enzyme Details

8. Malate dehydrogenase, cytoplasmic

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

Enzyme Details

9. Phosphoenolpyruvate carboxykinase [GTP], mitochondrial

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

Enzyme Details

10. Phosphoenolpyruvate carboxykinase, cytosolic [GTP]

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.

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Showing Compound Card for Oxalacetic acid (CDB004824)

Structure for CDB004824 (Oxalacetic acid)

Enzymes