Showing Compound Methylsuccinic acid (FDB022704)

Record Information

Version

1.0

Creation date

2011-09-21 00:18:13 UTC

Update date

2015-10-09 22:30:52 UTC

Primary ID

FDB022704

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Methylsuccinic acid

Description

Methylsuccinic acid is a normal metabolite found in human fluids. Increased urinary levels of Methylsuccinic acid (together with ethylmalonic acid) are the main biochemical measurable features in ethylmalonic encephalopathy (OMIM 602473 ), a rare metabolic disorder with an autosomal recessive mode of inheritance that is clinically characterized by neuromotor delay, hyperlactic acidemia, recurrent petechiae, orthostatic acrocyanosis, and chronic diarrhea. (PMID 12382164) T he underlying biochemical defect involves isoleucine catabolism. (PMID 9667231) It has been found decreases in the urine of animals under D-serine-induced nephrotoxicity (D-Serine causes selective necrosis of the proximal straight tubules in the rat kidney). (PMID 15596249) [HMDB]

CAS Number

498-21-5

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Methylsuccinate	Generator
2-Methylbutanedioic acid	HMDB
Methylsuccinic acid, (+-)-isomer	HMDB
(S)-2-Hydroxy-2-methylsuccinate	HMDB
(S)-2-Hydroxy-2-methylsuccinic acid	HMDB
(S)-Citramalate	HMDB
(S)-Citramalic acid	HMDB
2-Methylbutanedioate	HMDB
2-Methylsuccinate	HMDB
2-Methylsuccinic acid	HMDB
Methyl succinate	HMDB
Methyl succinic acid	HMDB
Methylbutanedioate	HMDB
Methylbutanedioic acid	HMDB
MEZ	HMDB
Pyrotartarate	HMDB
Pyrotartaric acid	HMDB
Methyl Succinic acid	hmdb

Predicted Properties

Property	Value	Source
Water Solubility	103 g/L	ALOGPS
logP	0.13	ALOGPS
logP	0.14	ChemAxon
logS	-0.11	ALOGPS
pKa (Strongest Acidic)	3.99	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	3	ChemAxon
Refractivity	28.11 m³·mol⁻¹	ChemAxon
Polarizability	11.91 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

C5H8O4

IUPAC name

2-methylbutanedioic acid

InChI Identifier

InChI=1S/C5H8O4/c1-3(5(8)9)2-4(6)7/h3H,2H2,1H3,(H,6,7)(H,8,9)

InChI Key

WXUAQHNMJWJLTG-UHFFFAOYSA-N

Isomeric SMILES

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

Average Molecular Weight

132.1146

Monoisotopic Molecular Weight

132.042258744

Classification

Description

Belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Methyl-branched fatty acids

Alternative Parents

Substituents

Methyl-branched fatty acid
Dicarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Dicarboxylic acids (LMFA01170119 )

Ontology

Ingestion

Source:

Biological:

Animal

Biological location:

Subcellular:

Biofluid and excreta:

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Role

Biological role:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0077-9000000000-1bd08b69cec7f9966cb2	2014-09-20	View Spectrum
GC-MS	Methylsuccinic acid, non-derivatized, GC-MS Spectrum	splash10-0002-0910000000-b99795b0e5069d573c2d	Spectrum
GC-MS	Methylsuccinic acid, non-derivatized, GC-MS Spectrum	splash10-0002-0920000000-c96774045667ea1804df	Spectrum
GC-MS	Methylsuccinic acid, non-derivatized, GC-MS Spectrum	splash10-0002-0910000000-b99795b0e5069d573c2d	Spectrum
Predicted GC-MS	Methylsuccinic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-007c-9100000000-bb48993db83be2104b10	Spectrum
Predicted GC-MS	Methylsuccinic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00du-9320000000-5f34c9f97642781028e4	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-014i-3900000000-4afd6f9cd1309a7a392b	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00kr-9600000000-e212a368f465b41cc1fa	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0l0i-9200000000-c712b36382fde51f3ae5	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-000i-9400000000-f709b1c905420a006038	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negative	splash10-0019-9400000000-40a1055d8102e323a077	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-000i-9400000000-f709b1c905420a006038	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0019-9400000000-40a1055d8102e323a077	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-5900000000-e50cb8068b9ea6aa88c8	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014r-9100000000-86a85f9d829697c248dd	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-687b61805462d04b5ded	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001r-5900000000-4fd3ea5da8eb91f1951d	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0019-9500000000-ec3019482baef20b293d	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kf-9000000000-23ddfbfc967e6df1168e	2017-09-01	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 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
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

External Links

ChemSpider ID

9922

ChEMBL ID

Not Available

KEGG Compound ID

C08645

Pubchem Compound ID

10349

Pubchem Substance ID

Not Available

ChEBI ID

29003

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB01844

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

Showing Compound Methylsuccinic acid (FDB022704)

Structure for FDB022704 (Methylsuccinic acid)