ContaminantDB: 2-Oxobutanedioic acid

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-22 03:33:01 UTC

Update Date

2016-11-09 01:15:24 UTC

Accession Number

CHEM016469

Identification

Common Name

2-Oxobutanedioic acid

Class

Small Molecule

Description

Oxalacetic acid, also known as ketosuccinic acid or oxaloacetate, belongs to short-chain keto acids and derivatives class of compounds. Those are keto acids with an alkyl chain the contains less than 6 carbon atoms. Thus, oxalacetic acid is considered to be a fatty acid lipid molecule. Oxalacetic acid is soluble (in water) and a moderately acidic compound (based on its pKa). Oxalacetic acid can be synthesized from succinic acid. Oxalacetic acid can also be synthesized into oxaloacetic acid 4-methyl ester. Oxalacetic acid can be found in a number of food items such as daikon radish, sacred lotus, cucurbita (gourd), and tarragon, which makes oxalacetic acid a potential biomarker for the consumption of these food products. Oxalacetic acid can be found primarily in cellular cytoplasm, cerebrospinal fluid (CSF), and urine, as well as in human liver tissue. Oxalacetic acid exists in all living species, ranging from bacteria to humans. In humans, oxalacetic acid is involved in several metabolic pathways, some of which include the oncogenic action of succinate, the oncogenic action of 2-hydroxyglutarate, glycogenosis, type IB, and the oncogenic action of fumarate. Oxalacetic acid is also involved in several metabolic disorders, some of which include the oncogenic action of l-2-hydroxyglutarate in hydroxygluaricaciduria, transfer of acetyl groups into mitochondria, argininemia, and 2-ketoglutarate dehydrogenase complex deficiency. Moreover, oxalacetic acid is found to be associated with anoxia.

Contaminant Sources

FooDB Chemicals
HMDB Contaminants - Urine
ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical 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 Mass

132.072 g/mol

Monoisotopic Mass

132.006 g/mol

CAS Registry Number

328-42-7

IUPAC Name

2-oxobutanedioic acid

Traditional Name

oxalacetate

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 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	57.1 g/L	ALOGPS
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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-00dr-4900000000-9d943d40beaca3c602a1	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)	splash10-007a-9210000000-020f60717e2ea79d1ccd	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)	splash10-000b-9540000000-a53f674cc98960834f88	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 3 TMS)	splash10-001a-8940000000-40b790e06141d7180938	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-007a-9210000000-020f60717e2ea79d1ccd	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-000b-9540000000-a53f674cc98960834f88	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-001a-8940000000-40b790e06141d7180938	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-4930000000-7e995327b0b9c1af0914	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-000f-9100000000-6718417e7196063f9544	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00ds-9520000000-5a082ec8843f6fbc3b15	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-000i-9000000000-0be675f3aa3e973393b7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-000f-9000000000-4fba97fcd7b0f2215f75	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0006-9000000000-9b1f4171aee6283a3cbd	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-014i-0900000000-7c598fd9c78acb94dacd	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 3V, positive	splash10-014i-4900000000-e7803730ae7986a1b9fb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 4V, positive	splash10-014r-5900000000-8e478338a7c0e65e62ba	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 5V, positive	splash10-014r-7900000000-f681763317e1ae86e691	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 7V, positive	splash10-00kr-9600000000-aa8adf9a96041dddbbdd	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 10V, positive	splash10-000i-9200000000-e62c47ca2bc492900178	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 15V, positive	splash10-000i-9000000000-5485ddd84a64ea0ca0b9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 17V, positive	splash10-000i-9000000000-79521cb04a2b23e39c1e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 20V, positive	splash10-000m-9000000000-601c8d2ec63f8b01a61e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 23V, positive	splash10-000e-9000000000-13d369c58d8930958d92	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 25V, positive	splash10-0005-9000000000-df8387ef907fb71342eb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 27V, positive	splash10-0005-9000000000-908644b5d7041346f582	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 30V, positive	splash10-0005-9000000000-ecca787a800164d0296f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 33V, positive	splash10-0005-9000000000-180a7c51b1f93cb8fff2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 35V, positive	splash10-0005-9000000000-709c49f609f5a711a288	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 40V, positive	splash10-0005-9000000000-aa103ab9beb03bd6eb22	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-3900000000-6f4e965a3f513bf8db13	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-9600000000-8ae7abf60057088e14db	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01bc-9100000000-5724c215c46a4f568140	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0019-8900000000-829898d0849b1fbf1c28	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9100000000-5a5ff8fb7cb52eebf0c8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-657d1384d478ddc33b6d	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0006-9000000000-f371299a07d43c23ff1d	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum