ChemFOnt: Showing chemical card for 2-Keto-6-aminocaproate (CFc000007706)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:54:09 UTC

Chemfont ID

CFc000007706

Molecule Identification

Common Name

2-Keto-6-aminocaproate

Definition

2-Keto-6-aminocaproate is an intermediate in lysine degradation and can be formed from L-lysine. L-Lysine is an essential amino-acid that is a necessary building block for all protein in the body. L-Lysine plays a major role in calcium absorption; building muscle protein; recovering from surgery or sports injuries; and the body's production of hormones, enzymes, and antibodies. L-Lysine can be converted to 2-keto-6-aminocaproate via the enzyme L-lysine alpha-oxidase. 2-Keto-6-aminocaproate can spontaneously decarboxylate to 5-aminovalerate in the presence of the reaction product, hydrogen peroxide. It can also be spontaneously converted in solution to its cyclic form delta-piperideine-2-carboxylate. This has been demonstrated in vitro in the presence of catalase, which splits hydrogen peroxide.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-oxo-6-Aminocaproate	ChEBI
6-Amino-2-oxohexanoate	ChEBI
2-oxo-6-Aminocaproic acid	Generator
6-Amino-2-oxohexanoic acid	Generator
2-Keto-6-aminocaproic acid	Generator
2-keto-6-amino-Caproate	HMDB
2-keto-6-amino-Caproic acid	HMDB
2-oxo-6-Aminohexanoate	HMDB
2-oxo-6-Aminohexanoic acid	HMDB
alpha-keto-epsilon-Aminocaproate	HMDB
alpha-keto-epsilon-Aminocaproic acid	HMDB
alpha-keto-epsilon-Aminohexanoate	HMDB
alpha-keto-epsilon-Aminohexanoic acid	HMDB
alpha-Ketolysine	HMDB

Chemical Formula

C₆H₁₁NO₃

Average Molecular Weight

145.1564

Monoisotopic Molecular Weight

145.073893223

IUPAC Name

6-amino-2-oxohexanoic acid

Traditional Name

6-amino-2-oxohexanoic acid

CAS Registry Number

None

SMILES

NCCCCC(=O)C(O)=O

InChI Identifier

InChI=1S/C6H11NO3/c7-4-2-1-3-5(8)6(9)10/h1-4,7H2,(H,9,10)

InChI Key

GWENQMVPLJAMAE-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as medium-chain keto acids and derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Keto acids and derivatives

Sub Class

Medium-chain keto acids and derivatives

Direct Parent

Medium-chain keto acids and derivatives

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

2-oxo monocarboxylic acid (CHEBI:17534 )
epsilon-amino acid (CHEBI:17534 )

Functional Ontology

Not Available

Endogenous (HMDB: HMDB0012151)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	17.1 g/L	ALOGPS
logP	-2.3	ALOGPS
logP	-2.2	ChemAxon
logS	-0.93	ALOGPS
pKa (Strongest Acidic)	3.24	ChemAxon
pKa (Strongest Basic)	10.01	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	35.4 m³·mol⁻¹	ChemAxon
Polarizability	14.62 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