Milk Composition Database: Showing metabocard for Allysine (BMDB0001263)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:43:16 UTC

Update Date

2020-05-19 22:01:07 UTC

MCDB ID

BMDB0001263

Secondary Accession Numbers

BMDB01263

Metabolite Identification

Common Name

Allysine

Description

Allysine, also known as 6-oxonorleucine or alpha-aasa, 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). Allysine is possibly soluble (in water) and a very strong basic compound (based on its pKa). Allysine exists in all eukaryotes, ranging from yeast to humans. Allysine participates in a number of enzymatic reactions, within cattle. In particular, Allysine and L-glutamic acid can be biosynthesized from saccharopine through the action of the enzyme Alpha-aminoadipic semialdehyde synthase, mitochondrial. In addition, Allysine can be converted into aminoadipic acid; which is catalyzed by the enzyme Alpha-aminoadipic semialdehyde dehydrogenase. In cattle, allysine is involved in the metabolic pathway called the lysine degradation pathway. Allysine is a potentially toxic compound.

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

1962-83-0

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 )

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	-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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-9100000000-e7c5c166681ba0316b25	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00di-8910000000-8fb215d3dd09e5553352	2017-10-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0ufs-2900000000-cc3c3ade4cefc6b57880	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ue9-9700000000-1f5f0f3378ed80283ec8	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0abc-9000000000-dd87ab890dceec9e01cb	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0900000000-5623b839bf292d641b92	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-4900000000-7473bdea5b2f626515f1	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-12c42805d877e4f712b6	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0ue9-6900000000-d34f08b905440e7d7964	2021-10-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-9000000000-684e25a1d77f85cbfa55	2021-10-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4r-9000000000-96069f1c2588457b97ce	2021-10-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004l-0900000000-06ca102489283c43f7e6	2021-10-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-054o-2900000000-46f0e454239e803a8554	2021-10-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-3fc953bdebc8fddb25d1	2021-10-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	2022-08-21	View Spectrum

Concentrations

Status	Value		Reference	Details
Detected but not Quantified	Not Applicable		PMID: 29565828	details

External Links

HMDB ID

HMDB0303320

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735. [PubMed:29565828 ]

Showing metabocard for Allysine (BMDB0001263)

Structure for BMDB0001263 (Allysine)