Bovine Metabolome Database: Showing metabocard for N-Butyrylglycine (BMDB0000808)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:36:53 UTC

Update Date

2020-05-05 18:37:24 UTC

BMDB ID

BMDB0000808

Secondary Accession Numbers

BMDB00808

Metabolite Identification

Common Name

N-Butyrylglycine

Description

N-Butyrylglycine, also known as 2-butanamidoacetate or N-butanoylglycine, 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. N-Butyrylglycine is an extremely weak basic (essentially neutral) compound (based on its pKa). N-Butyrylglycine is a potentially toxic compound. N-Butyrylglycine, with regard to humans, has been found to be associated with the diseases such as colorectal cancer; N-butyrylglycine has also been linked to several inborn metabolic disorders including ethylmalonic encephalopathy, short chain acyl-coa dehydrogenase deficiency, and propionic acidemia.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Butanamidoacetic acid	ChEBI
2-Butyramidoacetic acid	ChEBI
Butanamidoacetic acid	ChEBI
Butyramidoacetic acid	ChEBI
N-(1-Oxobutyl)glycine	ChEBI
N-Butyryl-glycine	ChEBI
2-Butanamidoacetate	Generator
2-Butyramidoacetate	Generator
Butanamidoacetate	Generator
Butyramidoacetate	Generator
N-Butanoylglycine	HMDB
Butyrylglycine	HMDB
N-Butyrylglycine	ChEBI

Chemical Formula

C₆H₁₁NO₃

Average Molecular Weight

145.1564

Monoisotopic Molecular Weight

145.073893223

IUPAC Name

2-butanamidoacetic acid

Traditional Name

butyrylglycine

CAS Registry Number

20208-73-5

SMILES

CCCC(=O)NCC(O)=O

InChI Identifier

InChI=1S/C6H11NO3/c1-2-3-5(8)7-4-6(9)10/h2-4H2,1H3,(H,7,8)(H,9,10)

InChI Key

WPSSBBPLVMTKRN-UHFFFAOYSA-N

Chemical Taxonomy

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

Not Available

Ontology

Status

Detected but not Quantified

Origin

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cytoplasm

Physical Properties

State

Solid

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	0.03	ALOGPS
logP	-0.18	ChemAxon
logS	-0.92	ALOGPS
pKa (Strongest Acidic)	4.06	ChemAxon
pKa (Strongest Basic)	-1.9	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	34.68 m³·mol⁻¹	ChemAxon
Polarizability	14.64 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
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dl-9100000000-9d6efb3c85f5b734b957	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9100000000-4ce0b184f69d62f09945	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00b9-9000000000-7adf49075b14108e9349	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0006-9000000000-576cac3520e069cb3320	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0006-9000000000-589800c2ea24ecb7aebf	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9000000000-b3e19fb89ab7f8339f2e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-00di-9200000000-b60655767fe4a769d266	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9000000000-f47f0bb4cb0efbf144fa	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-00di-9000000000-95316273955129cf7e6b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9000000000-302b2ee38de565a37b1c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-00di-9200000000-2189f5ead5cd1348492e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0007-9000000000-67ae386d2d6c2621c353	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-00b9-9000000000-71dc9b997be4266692de	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0006-9000000000-a613b064539c5ea98c20	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 0V, Positive	splash10-004i-9200000000-718939a915913fcec1e8	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-c131993ed337f3b0feea	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-58824233a2ab6bd149d4	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-00b9-9000000000-89d3b4c8bf2d57d6c879	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9000000000-b14c7d503bd32ff268c6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-002b-6900000000-e59b7f02c0f7ab1a8783	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-056r-9200000000-11ba905b90d514e98295	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-054o-9000000000-3cb204e64741c19ece1d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0900000000-07244fdd0645eec30736	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-006x-6900000000-575a19c7ca83334fdfb6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05fu-9000000000-0ad3481b5038bd801906	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-9500000000-d854cf8e092f96476049	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-addf5ac376eea5fcd4fc	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Liver

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31867104	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0000808

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022256

KNApSAcK ID

Not Available

Chemspider ID

79766

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5772

PubChem Compound

88412

PDB ID

Not Available

ChEBI ID

89963

References

Synthesis Reference

Bondi, S.; Eissler, F. Lipoproteins and the Fatty Degeneration of Cells. Biochemische Zeitschrift (1910), 23 499-513.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for N-Butyrylglycine (BMDB0000808)

Structure for BMDB0000808 (N-Butyrylglycine)