Showing Compound Methylmalonic acid (FDB021905)

Record Information

Version

1.0

Creation date

2011-09-21 00:04:56 UTC

Update date

2019-11-26 03:21:00 UTC

Primary ID

FDB021905

Secondary Accession Numbers

Not Available

Chemical Information

FooDB 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. 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 the diseases such as methylmalonic aciduria mitochondrial encephelopathy leigh-like; methylmalonic acid has also been linked to several inborn metabolic disorders including transcobalamin II deficiency, cobalamin malabsorption, fumarase deficiency, and propionic acidemia.

CAS Number

516-05-2

Structure

MOL SDF PDB SMILES InChI

Synonyms

Show entries

Search:

Synonym	Source
1,1-Ethanedicarboxylate	Generator
1,1-Ethanedicarboxylic acid	ChEBI
2-Methylmalonate	Generator
2-Methylmalonic acid	ChEBI
a-Methylmalonate	Generator
a-Methylmalonic acid	Generator
Acid, methylmalonic	HMDB
alpha-Methylmalonate	Generator
alpha-Methylmalonic acid	ChEBI
Isosuccinate	Generator

Showing 1 to 10 of 27 entries

Predicted Properties

Property	Value	Source
Water Solubility	149 g/L	ALOGPS
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	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C4H6O4

IUPAC name

2-methylpropanedioic acid

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

Isomeric SMILES

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

Average Molecular Weight

118.088

Monoisotopic Molecular Weight

118.02660868

Classification

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

Endogenous

Biological location:

Organ and components:

Subcellular:

Cytoplasm

Biofluid and excreta:

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Indirect biological role:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Show entries

Search:

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)	splash10-05di-9000000000-8d09b408489f7b1743b5	2014-09-20	View Spectrum
GC-MS	Methylmalonic acid, 2 TMS, GC-MS Spectrum	splash10-0002-1910000000-cf95dd8a481761a28664	Spectrum
GC-MS	Methylmalonic acid, 2 TMS, GC-MS Spectrum	splash10-006t-8900000000-4d8795e7e4300cc7ceff	Spectrum
GC-MS	Methylmalonic acid, 2 TMS, GC-MS Spectrum	splash10-00lr-5940000000-56b86ada220d335ce30a	Spectrum
GC-MS	Methylmalonic acid, 3 TMS, GC-MS Spectrum	splash10-001i-9301000000-54e5247d046de566ac1e	Spectrum
GC-MS	Methylmalonic acid, non-derivatized, GC-MS Spectrum	splash10-004i-9000000000-b9ee59dddf90dfc7c461	Spectrum
GC-MS	Methylmalonic acid, non-derivatized, GC-MS Spectrum	splash10-0002-1910000000-cf95dd8a481761a28664	Spectrum
GC-MS	Methylmalonic acid, non-derivatized, GC-MS Spectrum	splash10-006t-8900000000-4d8795e7e4300cc7ceff	Spectrum
GC-MS	Methylmalonic acid, non-derivatized, GC-MS Spectrum	splash10-001i-9301000000-54e5247d046de566ac1e	Spectrum
GC-MS	Methylmalonic acid, non-derivatized, GC-MS Spectrum	splash10-00lr-5940000000-56b86ada220d335ce30a	Spectrum
GC-MS	Methylmalonic acid, non-derivatized, GC-MS Spectrum	splash10-0002-0900000000-684a11ce99cccbd9194a	Spectrum
Predicted GC-MS	Methylmalonic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0g4i-9400000000-baa4ea6d613ebb8bffc7	Spectrum
Predicted GC-MS	Methylmalonic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00dr-9310000000-a99f1bb4adbde62446d9	Spectrum
Predicted GC-MS	Methylmalonic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Methylmalonic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Methylmalonic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Methylmalonic acid, TBDMS_2_1, 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)	splash10-00di-9000000000-1578bea9a6b8b12e2f9b	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-05fr-9000000000-0e443f81ee9c6c9b1fa5	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0ab9-9100000000-d23d6a0a35141ed9a950	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-01b9-6900000000-6d969044a89f00e1b46f	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-00di-9000000000-0f655174050263224e67	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0ab9-9000000000-26a654fb133b28a816a0	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0a4i-9000000000-7afd566e443d5fa38887	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0a4i-9000000000-5c4795e954d5c3e9b74e	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-01b9-6900000000-6d969044a89f00e1b46f	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-9000000000-0f655174050263224e67	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0ab9-9000000000-26a654fb133b28a816a0	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-9000000000-7afd566e443d5fa38887	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-9000000000-5c4795e954d5c3e9b74e	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-175b62a78de8d2295d7c	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-00dm-9100000000-2118d1ea1507076c595c	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0007-9000000000-5ead13e9a754843f3de4	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-00di-9000000000-04818c3d6cdaf0e910eb	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-ea4a508808f00639e8c2	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0002-9100000000-e8e132c8d454aa8a0490	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-5900000000-9b75ec910fa494f0ad6a	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05di-9200000000-87a71ae13cf70d990bb1	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-9000000000-e7ae04912b5ee745a992	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-4900000000-0714f0bc5c29e5d61ac4	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9100000000-ecfebddbd3d8f7224994	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05fr-9000000000-506ee5ec2100e13e09ce	2016-09-12	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 22.53 MHz, DMSO-d6, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum