Livestock Metabolome Database: Showing metabocard for Methylmalonic acid (LMDB00092)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:42:11 UTC

Update Date

2016-07-20 20:56:25 UTC

Lmdb

LMDB00092

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Methylmalonic acid

Description

Methylmalonic acid, also known as 2-methylmalonate or methyl-propanedioate, belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. Methylmalonic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Methylmalonic acid exists in all living species, ranging from bacteria to humans. Within humans, methylmalonic acid participates in a number of enzymatic reactions. In particular, methylmalonic acid and hydrogen peroxide can be biosynthesized from (S)-methylmalonic acid semialdehyde; which is catalyzed by the enzyme aldehyde oxidase. In addition, methylmalonic acid can be biosynthesized from (S)-methylmalonic acid semialdehyde; which is mediated by the enzyme aldehyde dehydrogenase, mitochondrial. In humans, methylmalonic acid is involved in the metabolic disorder called the 2-methyl-3-hydroxybutyryl-coa dehydrogenase deficiency pathway. A dicarboxylic acid that is malonic acid in which one of the methylene hydrogens is substituted by a methyl group. Outside of the human body, Methylmalonic acid has been detected, but not quantified in, milk (cow). This could make methylmalonic acid a potential biomarker for the consumption of these foods. Methylmalonic acid is a potentially toxic compound. Methylmalonic acid, with regard to humans, has been found to be associated with several diseases such as cobalamin f disease (cblf) and methylmalonic aciduria, cblb type; methylmalonic acid has also been linked to several inborn metabolic disorders including cobalamin malabsorption, malonyl-coa decarboxylase deficiency, and propionic acidemia.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,1-Ethanedicarboxylic acid	ChEBI
2-Methylmalonic acid	ChEBI
alpha-Methylmalonic acid	ChEBI
Isosuccinic acid	ChEBI
1,1-Ethanedicarboxylate	Generator
2-Methylmalonate	Generator
a-Methylmalonate	Generator
a-Methylmalonic acid	Generator
alpha-Methylmalonate	Generator
Α-methylmalonate	Generator
Α-methylmalonic acid	Generator
Isosuccinate	Generator
Methylmalonate	Generator
Methyl-malonate	HMDB
Methyl-malonic acid	HMDB
Methyl-propanedioate	HMDB
Methyl-propanedioic acid	HMDB
Methylpropanedioate	HMDB
Methylpropanedioic acid	HMDB
Acid, methylmalonic	HMDB
Methylmalonic acid	KEGG

Chemical Formula

C₄H₆O₄

Average Molecular Weight

118.088

Monoisotopic Molecular Weight

118.02660868

IUPAC Name

2-methylpropanedioic acid

Traditional Name

methylmalonic acid

CAS Registry Number

516-05-2

SMILES

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

InChI Identifier

InChI=1S/C4H6O4/c1-2(3(5)6)4(7)8/h2H,1H3,(H,5,6)(H,7,8)

InChI Key

ZIYVHBGGAOATLY-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Dicarboxylic acids and derivatives

Direct Parent

Dicarboxylic acids and derivatives

Alternative Parents

Substituents

1,3-dicarbonyl compound
Dicarboxylic acid or derivatives
Carboxylic acid
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

C4-dicarboxylic acid (CHEBI:30860 )
Dicarboxylic acids (LMFA01170118 )

Ontology

Status

Detected but not Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	0.17	ALOGPS
logP	0.21	ChemAxon
logS	0.1	ALOGPS
pKa (Strongest Acidic)	2.48	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	23.56 m³·mol⁻¹	ChemAxon
Polarizability	10.06 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	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) (2 TMS)	splash10-0002-1910000000-cf95dd8a481761a28664	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-006t-8900000000-4d8795e7e4300cc7ceff	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-00lr-5940000000-56b86ada220d335ce30a	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-001i-9301000000-54e5247d046de566ac1e	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-9000000000-b9ee59dddf90dfc7c461	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-1910000000-cf95dd8a481761a28664	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-006t-8900000000-4d8795e7e4300cc7ceff	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-001i-9301000000-54e5247d046de566ac1e	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00lr-5940000000-56b86ada220d335ce30a	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0900000000-684a11ce99cccbd9194a	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0g4i-9400000000-baa4ea6d613ebb8bffc7	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00dr-9310000000-a99f1bb4adbde62446d9	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 (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-00di-9000000000-1578bea9a6b8b12e2f9b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-05fr-9000000000-0e443f81ee9c6c9b1fa5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0ab9-9100000000-d23d6a0a35141ed9a950	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-01b9-6900000000-6d969044a89f00e1b46f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-00di-9000000000-0f655174050263224e67	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0ab9-9000000000-26a654fb133b28a816a0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0a4i-9000000000-7afd566e443d5fa38887	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0a4i-9000000000-5c4795e954d5c3e9b74e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-01b9-6900000000-6d969044a89f00e1b46f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-9000000000-0f655174050263224e67	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0ab9-9000000000-26a654fb133b28a816a0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-9000000000-7afd566e443d5fa38887	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-9000000000-5c4795e954d5c3e9b74e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-175b62a78de8d2295d7c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-00dm-9100000000-2118d1ea1507076c595c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0007-9000000000-5ead13e9a754843f3de4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-00di-9000000000-04818c3d6cdaf0e910eb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-ea4a508808f00639e8c2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0002-9100000000-e8e132c8d454aa8a0490	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-5900000000-9b75ec910fa494f0ad6a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05di-9200000000-87a71ae13cf70d990bb1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-9000000000-e7ae04912b5ee745a992	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-4900000000-0714f0bc5c29e5d61ac4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9100000000-ecfebddbd3d8f7224994	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05fr-9000000000-506ee5ec2100e13e09ce	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-05di-9000000000-8d09b408489f7b1743b5	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	13C NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Plasma
Urine

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Bovine	24070026	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Porcine	21761043	details