Livestock Metabolome Database: Showing metabocard for Tiglylglycine (LMDB00291)

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

Record Information

Version

1.0

Creation Date

2016-07-13 19:46:36 UTC

Update Date

2016-07-20 20:59:36 UTC

Lmdb

LMDB00291

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Tiglylglycine

Description

Tiglylglycine 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. Tiglylglycine is an intermediate product of the catabolism of isoleucine. An elevated level of tiglylglycine is identified in urine of patients with beta-ketothiolase deficiency or with disorders of propionate metabolism (PMID 7923765 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
N-Tiglylglycine	ChEBI
(e)-N-(2-Methyl-1-oxo-2-butenyl)-glycine	HMDB
N-((e)-2-Methyl-but-2-enoyl)-glycine	HMDB
N-Tigloylglycine	HMDB

Chemical Formula

C₇H₁₁NO₃

Average Molecular Weight

157.1671

Monoisotopic Molecular Weight

157.073893223

IUPAC Name

2-[(2E)-2-methylbut-2-enamido]acetic acid

Traditional Name

[(2E)-2-methylbut-2-enamido]acetic acid

CAS Registry Number

35842-45-6

SMILES

C\C=C(/C)C(=O)NCC(O)=O

InChI Identifier

InChI=1S/C7H11NO3/c1-3-5(2)7(11)8-4-6(9)10/h3H,4H2,1-2H3,(H,8,11)(H,9,10)/b5-3+

InChI Key

WRUSVQOKJIDBLP-HWKANZROSA-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
N-acyl-amine
Secondary carboxylic acid amide
Carboxamide group
Monocarboxylic acid or derivatives
Carboxylic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

N-acylglycine (CHEBI:73018 )

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	0.33	ALOGPS
logP	0.21	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	4.09	ChemAxon
pKa (Strongest Basic)	-0.49	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	3	ChemAxon
Refractivity	40.13 m³·mol⁻¹	ChemAxon
Polarizability	15.97 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
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9200000000-092824f74c108907a49e	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00e9-9100000000-5d3935f85eccdefefb59	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 (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 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_1_2) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-004i-9000000000-4f7bd3c47a6d77fcc178	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-004i-9000000000-7ee9df3c83b8760c7e09	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-03fr-9000000000-da47f9a5f3d8fdcaf90a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-001i-9000000000-6fdd0ba2be939d0a161a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0a4i-1900000000-2cd6e4c6ab2eeb847328	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0a4i-1900000000-2cd6e4c6ab2eeb847328	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-001i-9000000000-6fdd0ba2be939d0a161a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9000000000-6640ab0bba7f488fb1b7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-001i-9000000000-52faded097646da69ec7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0bt9-2900000000-605b7b7b40a77223a8f9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-86f6f96695e2d9fe9a9a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-ddf9655db6a774124c69	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-03di-7900000000-ecab07cf409aa411046f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a59-5900000000-7e583345ae99d6656bad	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a59-9300000000-25bd55529a83deba5ea2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-c359dba2d89f41f03224	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-3376764fa5c9bcdde347	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-2900000000-4dde97028084b16db2bd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ab9-9000000000-7185fafe7ab0f33f5c5d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-5900000000-4d9d366aa5db2c493277	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9000000000-69e0efbc2e71d768a57c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4r-9000000000-fe61e613b1d7fd7c77e5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-052r-0900000000-c31bc851b562c2b42930	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-05fu-9300000000-2ec83a972a0157664b35	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-372794b6f97a5c4c1481	Spectrum
1D NMR	1H 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	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	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	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
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Serum
Urine

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Serum	Detected but not Quantified	Not Applicable	Not Available	Ovine	21142080	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Ovine	21142080	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Ovine	21142080	details

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0000959

FooDB ID

FDB022337

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

4246

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

4945715

ChEBI ID

73018

PubChem Compound ID

6441567

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Bennett MJ, Powell S, Swartling DJ, Gibson KM: Tiglylglycine excreted in urine in disorders of isoleucine metabolism and the respiratory chain measured by stable isotope dilution GC-MS. Clin Chem. 1994 Oct;40(10):1879-83. [7923765 ]

Showing metabocard for Tiglylglycine (LMDB00291)

Structure for LMDB00291 (Tiglylglycine)