AFCDB: (±)-Leucine (FDB000899)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:45 UTC

Update date

2019-11-26 02:55:36 UTC

Primary ID

FDB000899

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

(±)-Leucine

Description

(±)-Leucine, also known as DL-leucine or hleu, belongs to the class of organic compounds known as leucine and derivatives. Leucine and derivatives are compounds containing leucine or a derivative thereof resulting from reaction of leucine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Thus, (±)-leucine is considered to be a fatty acid lipid molecule (±)-Leucine is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (±)-Leucine is found, on average, in the highest concentration within a few different foods, such as red bell peppers, green zucchinis, and italian sweet red peppers and in a lower concentration in green bell peppers. This could make (±)-leucine a potential biomarker for the consumption of these foods.

CAS Number

328-39-2

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	69.8 g/L	ALOGPS
logP	-1.8	ALOGPS
logP	-1.6	ChemAxon
logS	-0.27	ALOGPS
pKa (Strongest Acidic)	2.79	ChemAxon
pKa (Strongest Basic)	9.52	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	63.32 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	34.17 m³·mol⁻¹	ChemAxon
Polarizability	14.33 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

C6H13NO2

IUPAC name

2-amino-4-methylpentanoic acid

InChI Identifier

InChI=1S/C6H13NO2/c1-4(2)3-5(7)6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9)

InChI Key

ROHFNLRQFUQHCH-UHFFFAOYSA-N

Isomeric SMILES

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

Average Molecular Weight

131.1729

Monoisotopic Molecular Weight

131.094628665

Classification

Description

Belongs to the class of organic compounds known as leucine and derivatives. Leucine and derivatives are compounds containing leucine or a derivative thereof resulting from reaction of leucine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Leucine and derivatives

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

alpha-amino acid (CHEBI:25017 )
branched-chain amino acid (CHEBI:25017 )
Amino fatty acids (LMFA01100048 )
a D-amino acid (CPD-12150 )

Ontology

No ontology term

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 54.94%; H 9.99%; N 10.68%; O 24.39%	DFC
Melting Point	Mp 293-295° (sealed tube)	DFC
Boiling Point	Not Available
Experimental Water Solubility	11.8 mg/mL at 25 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP	Not Available
Experimental pKa	pKa2 9.74 (25°)	DFC
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)	splash10-000l-9000000000-bf752e458f13eed8d7a2	2014-09-20	View Spectrum
GC-MS	(±)-Leucine, 1 TMS, GC-MS Spectrum	splash10-000i-9200000000-e6d3b36c12a4aec4abd2	Spectrum
GC-MS	(±)-Leucine, 2 TMS, GC-MS Spectrum	splash10-0a4i-1900000000-03b3ec429e0aedc946f6	Spectrum
GC-MS	(±)-Leucine, non-derivatized, GC-MS Spectrum	splash10-0a4i-0900000000-f79f4d95d2df43505233	Spectrum
Predicted GC-MS	(±)-Leucine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-9000000000-9e1901c72ddf2bca4bd8	Spectrum
Predicted GC-MS	(±)-Leucine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-000i-9100000000-991398731b9d8305622c	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - , negative	splash10-001i-0900000000-df557ff1e5f2eb62cf86	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-000i-9100000000-5c9c34467c6dfc48536c	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-000i-9000000000-f34b46cb8fb87529bdf4	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0006-9000000000-b3dd318079998826e948	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , positive	splash10-000i-9000000000-18fba445b980b0e31f7e	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-000i-9000000000-eada8640560aac9a5800	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-000i-9000000000-74bdf2f3d46a846bbebd	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-001i-4900000000-c727d81624633c25a855	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-000i-9210000000-dad2c30020b4d935371f	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-000i-9000000000-1d904829702e07958a70	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-000i-9000000000-d73af3689d7870fc55cc	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-000i-9020000000-baee1e363027b359a5bf	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-000i-9100000000-d0d93ac13dda78e787fb	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-000i-9010000000-6102833218f4329e1e82	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-001i-3900000000-065a2b56e0115c2fa6ec	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-000i-9000000000-11c00b9c192007f304c8	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0019-9700000000-9ca0528cb0f5d4c4e482	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-9100000000-688e4e815455b96d48d3	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-9a4bc07778f76172e1ec	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-1900000000-d15c14abb456ab271111	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01q9-7900000000-afc0316154ddc47ccade	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05fr-9000000000-b32e913349f93775ffb8	2015-05-27	View Spectrum

NMR

Type	Description		View
1D NMR	¹³C NMR Spectrum (1D, 22.5 MHz, D₂O, experimental)		Spectrum

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

857

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

BCS72-F:BMC06-E

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

Leucine

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

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).

(±)-Leucine (FDB000899)

Structure for FDB000899 ((±)-Leucine)