Showing Compound oxaloacetate (FDB031075)

Record Information

Version

1.0

Creation date

2015-05-07 20:57:37 UTC

Update date

2019-11-26 03:22:07 UTC

Primary ID

FDB031075

Secondary Accession Numbers

FDB001479

Chemical Information

FooDB Name

oxaloacetate

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.

CAS Number

328-42-7

Structure

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

Synonyms

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Synonym	Source
2 Ketosuccinic acid	HMDB
2 oxo Butanedioic acid	HMDB
2-Ketosuccinate	HMDB
2-Ketosuccinic acid	HMDB
2-oxo-Butanedioic acid	HMDB
2-Oxobutanedioate	Generator
2-Oxobutanedioic acid	ChEBI
2-Oxosuccinate	Generator
2-Oxosuccinic acid	ChEBI
3-Carboxy-3-oxopropanoate	Generator

Showing 1 to 10 of 33 entries

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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C4H4O5

IUPAC name

2-oxobutanedioic acid

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

Isomeric SMILES

OC(=O)CC(=O)C(O)=O

Average Molecular Weight

132.0716

Monoisotopic Molecular Weight

132.005873238

Classification

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

Subcellular:

Biofluid and excreta:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

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

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Showing Compound oxaloacetate (FDB031075)

Structure for FDB031075 (oxaloacetate)