ChemFOnt: Showing chemical card for Allysine (CFc000000976)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:30 UTC

Chemfont ID

CFc000000976

Molecule Identification

Common Name

Allysine

Definition

Allysine (CAS: 1962-83-0), also known as 2-amino-6-oxohexanoic acid or 6-oxonorleucine, 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). Outside of the human body, allysine has been detected, but not quantified in, several different foods, such as winged beans, wasabi, common verbena, arrowhead, and oats. This could make allysine a potential biomarker for the consumption of these foods. Allysine is a derivative of lysine used in the production of elastin and collagen. It is produced by the actions of the enzyme lysyl oxidase in the extracellular matrix and is essential in the crosslink formation that stabilizes collagen and elastin.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Amino-5-formylvaleric acid	ChEBI
2-Aminoadipate 6-semialdehyde	ChEBI
6-Oxonorleucine	ChEBI
alpha-Aminoadipic acid delta-semialdehyde	ChEBI
alpha-Aminoadipic delta-semialdehyde	ChEBI
HCO-[CH2]3-CH(NH2)-COOH	ChEBI
2-Amino-5-formylvalerate	Generator
2-Aminoadipic acid 6-semialdehyde	Generator
a-Aminoadipate delta-semialdehyde	Generator
a-Aminoadipic acid delta-semialdehyde	Generator
alpha-Aminoadipate delta-semialdehyde	Generator
Α-aminoadipate δ-semialdehyde	Generator
Α-aminoadipic acid δ-semialdehyde	Generator
a-Aminoadipic delta-semialdehyde	Generator
Α-aminoadipic δ-semialdehyde	Generator
a-Aminoadipate δ-semialdehyde	Generator, HMDB
a-Aminoadipic acid δ-semialdehyde	Generator, HMDB
a-Aminoadipic δ-semialdehyde	Generator, HMDB
(2S)-2-amino-6-Oxohexanoate	HMDB
(2S)-2-amino-6-Oxohexanoic acid	HMDB
2-amino-Hexanedioate	HMDB
2-amino-Hexanedioic acid	HMDB
2-amino-Hexanedioic acid semialdhyde	HMDB
2-Aminoadipate semialdehyde	HMDB
2-Aminoadipate-6-semialdehyde	HMDB
5-Formyl-norvaline	HMDB
6-oxo-L-Norleucine	HMDB
6-oxo-Norleucine	HMDB
alpha-Aminoadipic semialdehyde	HMDB
L-2-Aminoadipate 6-semialdehyde	HMDB
L-6-Oxonorleucine	HMDB
L-Allysine	HMDB
2-Aminoadipic semialdehyde	MeSH, HMDB
alpha-AASA	MeSH, HMDB
alpha-Aminoadipate semialdehyde	MeSH, HMDB

Chemical Formula

C₆H₁₁NO₃

Average Molecular Weight

145.1564

Monoisotopic Molecular Weight

145.073893223

IUPAC Name

2-amino-6-oxohexanoic acid

Traditional Name

allysine

CAS Registry Number

6665-12-9

SMILES

NC(CCCC=O)C(O)=O

InChI Identifier

InChI=1S/C6H11NO3/c7-5(6(9)10)3-1-2-4-8/h4-5H,1-3,7H2,(H,9,10)

InChI Key

GFXYTQPNNXGICT-UHFFFAOYSA-N

Chemical Taxonomy

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

non-proteinogenic alpha-amino acid (CHEBI:17027 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 17068770)

Excreta

Biofluid or Excreta

Urine (PMID: 17068770)

Cellular substructure

Cytoplasm (HMDB: HMDB0001263)
Membrane (HMDB: HMDB0001263)

Organelle

Mitochondrion (HMDB: HMDB0001263)

Source

Exogenous

Exogenous (HMDB: HMDB0001263)

Food

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Endogenous

Endogenous (HMDB: HMDB0001263)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Lysine Degradation (HMDB: HMDB0001263)
Lysine Metabolism (PathBank: SMP0002337)

Disease pathway

Pyridoxine Dependency with Seizures (HMDB: HMDB0001263)
Glutaric Aciduria Type I (PathBank: SMP0120704)
Hyperlysinemia I, Familial (PathBank: SMP0120811)
Hyperlysinemia II or Saccharopinuria (PathBank: SMP0120812)
2-Aminoadipic 2-Oxoadipic Aciduria (PathBank: SMP0120870)
Saccharopinuria/Hyperlysinemia II (PathBank: SMP0120746)

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	49.4 g/L	ALOGPS
logP	-2.2	ALOGPS
logP	-2.9	ChemAxon
logS	-0.47	ALOGPS
pKa (Strongest Acidic)	2.25	ChemAxon
pKa (Strongest Basic)	9.33	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	80.39 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	34.96 m³·mol⁻¹	ChemAxon
Polarizability	14.59 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

External Links

HMDB ID

HMDB0303320

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022519

KNApSAcK ID

C00051877

Chemspider ID

202

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

17027

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Allysine (CFc000000976)

MOL for CFc000000976 (Allysine)

3D MOL for CFc000000976 (Allysine)

3D SDF for CFc000000976 (Allysine)

3D-SDF for CFc000000976 (Allysine)

PDB for CFc000000976 (Allysine)

3D PDB for CFc000000976 (Allysine)

SMILES for CFc000000976 (Allysine)

INCHI for CFc000000976 (Allysine)

Structure for CFc000000976 (Allysine)

3D Structure for CFc000000976 (Allysine)