Bovine Metabolome Database: Showing metabocard for D-Lysine (BMDB0003405)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:04:19 UTC

Update Date

2020-05-11 20:30:53 UTC

BMDB ID

BMDB0003405

Secondary Accession Numbers

BMDB03405

Metabolite Identification

Common Name

D-Lysine

Description

L-Lysine, also known as (S)-lysine or L-lysin, belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. L-Lysine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. L-Lysine exists in all living species, ranging from bacteria to humans. In cattle, L-lysine is involved in the metabolic pathway called the biotin metabolism pathway. L-Lysine is a potentially toxic compound. L-Lysine has been found to be associated with several diseases known as citrullinemia type ii, neonatal-onset, autism, and leukemia; also l-lysine has been linked to several inborn metabolic disorders including histidinemia and fumarase deficiency.

Structure

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

Synonyms

Value	Source
(R)-2,6-Diaminohexanoic acid	ChEBI
D-2,6-Diaminohexanoic acid	ChEBI
D-Lysin	ChEBI
DLY	ChEBI
(R)-2,6-Diaminohexanoate	Generator
D-2,6-Diaminohexanoate	Generator

Chemical Formula

C₆H₁₄N₂O₂

Average Molecular Weight

146.19

Monoisotopic Molecular Weight

146.105527699

IUPAC Name

(2R)-2,6-diaminohexanoic acid

Traditional Name

D-lysine

CAS Registry Number

56-87-1

SMILES

NCCCC[C@@H](N)C(O)=O

InChI Identifier

InChI=1S/C6H14N2O2/c7-4-2-1-3-5(8)6(9)10/h5H,1-4,7-8H2,(H,9,10)/t5-/m1/s1

InChI Key

KDXKERNSBIXSRK-RXMQYKEDSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as d-alpha-amino acids. These are alpha amino acids which have the D-configuration of the alpha-carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

D-alpha-amino acids

Alternative Parents

Substituents

D-alpha-amino acid
Medium-chain fatty acid
Amino fatty acid
Fatty acid
Fatty acyl
Amino acid
Monocarboxylic acid or derivatives
Carboxylic acid
Organic oxide
Organopnictogen compound
Organic oxygen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Carbonyl group
Organic nitrogen compound
Amine
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

lysine (CHEBI:16855 )
D-alpha-amino acid (CHEBI:16855 )
Other amino acids (C00739 )

Ontology

Status

Expected 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	-3.8	ALOGPS
logP	-3.2	ChemAxon
logS	-0.14	ALOGPS
pKa (Strongest Acidic)	2.74	ChemAxon
pKa (Strongest Basic)	10.29	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	89.34 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	37.81 m³·mol⁻¹	ChemAxon
Polarizability	15.91 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