Milk Composition Database: Showing metabocard for Oxalacetic acid (BMDB0000223)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:26:59 UTC

Update Date

2020-06-04 19:53:36 UTC

MCDB ID

BMDB0000223

Secondary Accession Numbers

BMDB00223

Metabolite 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 exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Oxalacetic acid exists in all living species, ranging from bacteria to humans.

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

132.0716

Monoisotopic Molecular Weight

132.005873238

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 )

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	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	Deposition Date	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	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)	splash10-007a-9210000000-020f60717e2ea79d1ccd	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)	splash10-000b-9540000000-a53f674cc98960834f88	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 3 TMS)	splash10-001a-8940000000-40b790e06141d7180938	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-007a-9210000000-020f60717e2ea79d1ccd	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-000b-9540000000-a53f674cc98960834f88	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-001a-8940000000-40b790e06141d7180938	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-4930000000-7e995327b0b9c1af0914	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-000f-9100000000-6718417e7196063f9544	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00ds-9520000000-5a082ec8843f6fbc3b15	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-000i-9000000000-0be675f3aa3e973393b7	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-000f-9000000000-4fba97fcd7b0f2215f75	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0006-9000000000-9b1f4171aee6283a3cbd	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-014i-0900000000-7c598fd9c78acb94dacd	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 3V, positive	splash10-014i-4900000000-e7803730ae7986a1b9fb	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 4V, positive	splash10-014r-5900000000-8e478338a7c0e65e62ba	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 5V, positive	splash10-014r-7900000000-f681763317e1ae86e691	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 7V, positive	splash10-00kr-9600000000-aa8adf9a96041dddbbdd	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 10V, positive	splash10-000i-9200000000-e62c47ca2bc492900178	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 15V, positive	splash10-000i-9000000000-5485ddd84a64ea0ca0b9	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 17V, positive	splash10-000i-9000000000-79521cb04a2b23e39c1e	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 20V, positive	splash10-000m-9000000000-601c8d2ec63f8b01a61e	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 23V, positive	splash10-000e-9000000000-13d369c58d8930958d92	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 25V, positive	splash10-0005-9000000000-df8387ef907fb71342eb	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 27V, positive	splash10-0005-9000000000-908644b5d7041346f582	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 30V, positive	splash10-0005-9000000000-ecca787a800164d0296f	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 33V, positive	splash10-0005-9000000000-180a7c51b1f93cb8fff2	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 35V, positive	splash10-0005-9000000000-709c49f609f5a711a288	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 40V, positive	splash10-0005-9000000000-aa103ab9beb03bd6eb22	2020-07-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-3900000000-6f4e965a3f513bf8db13	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-9600000000-8ae7abf60057088e14db	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01bc-9100000000-5724c215c46a4f568140	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0019-8900000000-829898d0849b1fbf1c28	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9100000000-5a5ff8fb7cb52eebf0c8	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-657d1384d478ddc33b6d	2015-04-25	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0006-9000000000-f371299a07d43c23ff1d	2015-03-01	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Sodium phosphate (pH 7.4) in 90% H₂O /10% D₂O, experimental)	Not Available	2019-09-11	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	2012-12-05	View Spectrum
2D NMR	[¹H, ¹³C] NMR Spectrum (2D, 800 MHz, experimental)	Not Available	2019-09-11	View Spectrum

Concentrations

Status	Value		Reference	Details
Detected and Quantified	7 - 24 uM		PMID: 22098372	details

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

Synthesis Reference

Heidelberger, Charles; Hurlbert, Robert B. The synthesis of oxalacetic acid-I-C14 and orotic acid-6-C14. Journal of the American Chemical Society (1950), 72 4704-6.

Material Safety Data Sheet (MSDS)

Not Available

General References

Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9. [PubMed:22098372 ]
Antunes-Fernandes EC, van Gastelen S, Dijkstra J, Hettinga KA, Vervoort J: Milk metabolome relates enteric methane emission to milk synthesis and energy metabolism pathways. J Dairy Sci. 2016 Aug;99(8):6251-6262. doi: 10.3168/jds.2015-10248. Epub 2016 May 26. [PubMed:27236769 ]

Showing metabocard for Oxalacetic acid (BMDB0000223)

Structure for BMDB0000223 (Oxalacetic acid)