Showing Compound 2-Methylbutyrylglycine (FDB021963)

Record Information

Version

1.0

Creation date

2011-09-21 00:05:57 UTC

Update date

2015-10-09 22:33:40 UTC

Primary ID

FDB021963

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

2-Methylbutyrylglycine

Description

2-Methylbutyrylglycine is an acyl glycine. Acyl glycines are normally minor metabolites of fatty acids. However, the excretion of certain acyl glycines is increased in several inborn errors of metabolism. In certain cases the measurement of these metabolites in body fluids can be used to diagnose disorders associated with mitochondrial fatty acid beta-oxidation. Acyl glycines are produced through the action of glycine N-acyltransferase (EC 2.3.1.13) which is an enzyme that catalyzes the chemical reaction: acyl-CoA + glycine < -- > CoA + N-acylglycine. The isolated excretion of 2-methylbutyrylglycine (2-MBG) is the hallmark of short/branched-chain acyl-CoA dehydrogenase deficiency (PubMedID 15615815). A number of previously unrecognized abnormal metabolites have been identified and quantitated in the urine of patients with propionyl-CoA carboxylase deficiency. These include the isoleucine metabolites, 2-methyl-3-hydroxybutyric acid and 2-methylacetoacetic acid. Additionally, 3-hydroxyvaleric acid and 3-oxovaleric acid were found, which may be products of the condensation of propionyl-CoA with acetyl-CoA catalyzed by 3-oxoacyl-CoA thiolases. Following a load of isoleucine, 2-methylbutyrylglycine was identified. This metabolite has not previously been observed in man. (PMID: 630060) [HMDB]

CAS Number

52320-67-9

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
alpha-Methylbutyrylglycine	ChEBI
a-Methylbutyrylglycine	Generator
Α-methylbutyrylglycine	Generator
(2-Methyl-butyrylamino)-acetate	HMDB
(2-Methyl-butyrylamino)-acetic acid	HMDB
2-MBG	HMDB
2-Methylbutyryl glycine	HMDB
N-(2-Methylbutyryl)glycine	HMDB
N-Sec-valerylglycine	HMDB
2-Methylbutyrylglycine	ChEBI
(2-methyl-butyrylamino)-acetate	hmdb
(2-methyl-butyrylamino)-acetic acid	hmdb
N-sec-Valerylglycine	hmdb

Predicted Properties

Property	Value	Source
Water Solubility	9 g/L	ALOGPS
logP	0.41	ALOGPS
logP	0.36	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	4.17	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.4 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	39.25 m³·mol⁻¹	ChemAxon
Polarizability	16.55 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

C7H13NO3

IUPAC name

2-(2-methylbutanamido)acetic acid

InChI Identifier

InChI=1S/C7H13NO3/c1-3-5(2)7(11)8-4-6(9)10/h5H,3-4H2,1-2H3,(H,8,11)(H,9,10)

InChI Key

HOACIBQKYRHBOW-UHFFFAOYSA-N

Isomeric SMILES

CCC(C)C(=O)NCC(O)=O

Average Molecular Weight

159.183

Monoisotopic Molecular Weight

159.089543287

Classification

Description

Belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-alpha amino acids

Alternative Parents

Substituents

N-acyl-alpha-amino acid
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carbonyl group
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

N-acylglycine (CHEBI:86366 )

Ontology

Physiological effect

Health effect:

Health condition:

Metabolism and nutrition disorders:

Glutaric aciduria type 2

Disposition

Source:

Endogenous

Biological location:

Biofluid and excreta:

Urine

Subcellular:

Cytoplasm

Process

Naturally occurring process:

Biological process:

Biochemical pathway:

Ethylmalonic encephalopathy

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
Predicted GC-MS	2-Methylbutyrylglycine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0a4r-9200000000-037c365f69a94a2795e3	Spectrum
Predicted GC-MS	2-Methylbutyrylglycine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-9100000000-e433d3dc8126ab0a8a11	Spectrum
Predicted GC-MS	2-Methylbutyrylglycine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2-Methylbutyrylglycine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2-Methylbutyrylglycine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2-Methylbutyrylglycine, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2-Methylbutyrylglycine, TBDMS_1_2, 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, Positive (Annotated)	splash10-0a70-9000000000-677b36115959d21d1f09	Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0a4i-9000000000-8acb9e6da8ae025a1f8d	Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0a4l-9000000000-e9d59f38263024d831c0	Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9000000000-5b8594d1ae20d3cefd30	Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9100000000-5616d01ed9501db46e06	Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-dc3a1247ae093f314b43	Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-9000000000-3dfb1ee5e780367552f0	Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-05fr-8900000000-1ee8e7b73ae88fd1ef8f	Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9000000000-d2b9a5139d838d79d4cc	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03dr-5900000000-0b42996566d3baf8c66b	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-06ri-9400000000-711387fe57829069d6f3	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-6fc57261ee60bbc3af11	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-1fa66530dedcfabf00e7	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-2900000000-975416bc76e2d0f660c1	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ab9-9000000000-d1bb15a1be690ed64b19	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0bt9-9400000000-c1ffbc1b6124d8ccd7f3	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9000000000-d49a18704d3772cb3e92	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-5f02bb141e31e9a67e6a	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-1900000000-7a07dd16a49c33b82c5c	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-05fu-9600000000-2a213e61a98edbd8d71a	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05fu-9000000000-8a65567da0b6dd8bfb83	Spectrum

NMR

Type	Description	View
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Spectrum

External Links

ChemSpider ID

168243

ChEMBL ID

CHEMBL314835

KEGG Compound ID

Not Available

Pubchem Compound ID

193872

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB00339

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

Name	Gene Name	UniProt ID
Glycine N-acyltransferase	GLYAT	Q6IB77
Glycine N-acyltransferase-like protein 1	GLYATL1	Q969I3
Glycine N-acyltransferase-like protein 2	GLYATL2	Q8WU03
Glycine N-acyltransferase-like protein 3	GLYATL3	Q5SZD4