AFCDB: Levoglutamide (FDB012164)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:01 UTC

Update date

2019-11-26 03:06:18 UTC

Primary ID

FDB012164

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Levoglutamide

Description

Levoglutamide, also known as glutamin or HGLN, belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Levoglutamide is a very strong basic compound (based on its pKa). Levoglutamide is a mild, cocoa, and custard tasting compound. Levoglutamide is found, on average, in the highest concentration within a few different foods, such as wheats, broccoli, and red beetroots and in a lower concentration in potato, green bell peppers, and japanese pumpkins. Levoglutamide has also been detected, but not quantified in, several different foods, such as cow milks, wild celeries, cow milks, common sages, and wild leeks. This could make levoglutamide a potential biomarker for the consumption of these foods.

CAS Number

56-85-9

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	3.44 g/L	ALOGPS
logP	-3.4	ALOGPS
logP	-5.8	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	-0.46	ChemAxon
pKa (Strongest Basic)	13.07	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	107.4 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	44.05 m³·mol⁻¹	ChemAxon
Polarizability	13.93 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

C5H10N2O3

IUPAC name

2-amino-4-(C-hydroxycarbonimidoyl)butanoic acid

InChI Identifier

InChI=1S/C5H10N2O3/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H2,7,8)(H,9,10)

InChI Key

ZDXPYRJPNDTMRX-UHFFFAOYSA-N

Isomeric SMILES

NC(CCC(O)=N)C(O)=O

Average Molecular Weight

146.1445

Monoisotopic Molecular Weight

146.069142196

Classification

Description

Belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids

Alternative Parents

Substituents

Alpha-amino acid
Fatty acid
Amino acid
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic nitrogen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Primary aliphatic amine
Organic oxide
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

alpha-amino acid (CHEBI:28300 )

Ontology

No ontology term

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 41.09%; H 6.90%; N 19.17%; O 32.84%	DFC
Melting Point	Mp 184-185° dec.	DFC
Boiling Point	Not Available
Experimental Water Solubility	41.3 mg/mL at 25 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP	-3.64	CHMELIK,J ET AL. (1991)
Experimental pKa	pKa2 9.01 (25°, 0.1M KNO3)	DFC
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]D +46.5 (5M HCl)	DFC
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Levoglutamide, 2 TMS, GC-MS Spectrum	splash10-0a4i-0900000000-f5c3e469b28e7ddd1ed2	Spectrum
GC-MS	Levoglutamide, 3 TMS, GC-MS Spectrum	splash10-0fb9-1942000000-b99e36f8a6678634505e	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0ugj-2900000000-31acb66301700f32a8bb	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0f89-9600000000-62ca6d658ffe48116192	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-fac990fe6ddad443984e	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-1900000000-639fa6841a11c86d9c0e	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004m-7900000000-df522f5e8b3404021329	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-0cf14bf810f9866ab61d	2015-05-27	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

18050

Phenol-Explorer ID

Not Available

DrugBank ID

DB00130

HMDB ID

HMDB00641

CRC / DFC (Dictionary of Food Compounds) ID

EAFUS ID

Dr. Duke ID

BIGG ID

KNApSAcK ID

HET ID

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1037431

SuperScent ID

Not Available

Wikipedia ID

L-Glutamine

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

Descriptor	ID	Definition	Reference
anti alcoholic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti depressant	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti sickling			DUKE
anti ulcer	49201	One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract.	DUKE
catabolic			DUKE

Enzymes

Name	Gene Name	UniProt ID
Glycine N-acyltransferase-like protein 1	GLYATL1	Q969I3
Asparagine synthetase [glutamine-hydrolyzing]	ASNS	P08243
Kynurenine--oxoglutarate transaminase 1	CCBL1	Q16773
Glutamine synthetase	GLUL	P15104
Glutaminase liver isoform, mitochondrial	GLS2	Q9UI32
Glutaminase kidney isoform, mitochondrial	GLS	O94925
CTP synthase 2	CTPS2	Q9NRF8
Glutamine--fructose-6-phosphate aminotransferase [isomerizing] 2	GFPT2	O94808
Glutamine--fructose-6-phosphate aminotransferase [isomerizing] 1	GFPT1	Q06210
Glutamine--tRNA ligase	QARS	P47897
Phosphoribosylformylglycinamidine synthase	PFAS	O15067
Glutamyl-tRNA(Gln) amidotransferase subunit B, mitochondrial	PET112	O75879
Glutamyl-tRNA(Gln) amidotransferase subunit A, mitochondrial	QRSL1	Q9H0R6

Pathways

Name	SMPDB Link	KEGG Link
Amino Sugar Metabolism	SMP00045	map00520
Ammonia Recycling	SMP00009	map00910
Glutamate Metabolism	SMP00072	map00250
Phenylacetate Metabolism	SMP00126	map00360
Purine Metabolism	SMP00050	map00230
Pyrimidine Metabolism	SMP00046	map00240
Transcription/Translation	SMP00019	Not Available
Urea Cycle	SMP00059	map00330

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
mild	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
milky	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
custard	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
cocoa	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
oily	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).

Levoglutamide (FDB012164)

Structure for FDB012164 (Levoglutamide)