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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-06-15 17:04:52 UTC
HMDB IDHMDB0001263
Secondary Accession Numbers
  • HMDB0059595
  • HMDB01263
  • HMDB59595
Metabolite Identification
Common NameAllysine
DescriptionAllysine (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
Data?1590604871
Synonyms
ValueSource
2-AMINO-6-oxo-hexanoIC ACIDChEBI
6-oxo-L-NorleucineChEBI
AllysineChEBI
L-2-Aminoadipate 6-semialdehydeChEBI
L-6-OxonorleucineChEBI
2-Aminoadipate 6-semialdehydeKegg
L-AllysineKegg
2-AMINO-6-oxo-hexanoateGenerator
L-2-Aminoadipic acid 6-semialdehydeGenerator
2-Aminoadipic acid 6-semialdehydeGenerator
(S)-2-Amino-6-oxohexanoic acidGenerator
2-Aminoadipate semialdehydeHMDB
alpha-AASAHMDB
alpha-Aminoadipate semialdehydeHMDB
2-Aminoadipic semialdehydeHMDB
2-Amino-5-formylvaleric acidHMDB
2-Amino-6-oxohexanoateHMDB
6-OxonorleucineHMDB
L-Homoglutamic semialdehydeHMDB
alpha-Aminoadipic acid delta-semialdehydeHMDB
alpha-Aminoadipic delta-semialdehydeHMDB
α-Aminoadipic acid δ-semialdehydeHMDB
α-Aminoadipic δ-semialdehydeHMDB
Chemical FormulaC6H11NO3
Average Molecular Weight145.1564
Monoisotopic Molecular Weight145.073893223
IUPAC Name(2S)-2-amino-6-oxohexanoic acid
Traditional Name2-amino-6-oxo-hexanoic acid
CAS Registry Number6665-12-9
SMILES
N[C@@H](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)/t5-/m0/s1
InChI KeyGFXYTQPNNXGICT-YFKPBYRVSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative Parents
Substituents
  • L-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
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Primary aliphatic amine
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Amine
  • Organic nitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility49.4 g/LALOGPS
logP-2.9ChemAxon
pKa (Strongest Acidic)2.25ChemAxon
pKa (Strongest Basic)9.33ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area80.39 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity34.96 m³·mol⁻¹ChemAxon
Polarizability14.58 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-9100000000-e7c5c166681ba0316b25Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0udi-7900000000-a87d074458b671b94f65Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ufs-2900000000-cc3c3ade4cefc6b57880Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ue9-9700000000-1f5f0f3378ed80283ec8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0abc-9000000000-dd87ab890dceec9e01cbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-5623b839bf292d641b92Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-4900000000-7473bdea5b2f626515f1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-12c42805d877e4f712b6Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified<0.2 uMInfant (0-1 year old)Not SpecifiedNormal details
UrineDetected and Quantified<1 umol/mmol creatinineInfant (0-1 year old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified1.6-28 umol/mmol creatinineInfant (0-1 year old)Not SpecifiedPyridoxine dependency with seizures (PDE) details
Associated Disorders and Diseases
Disease References
Pyridoxine-dependent epilepsy
  1. Plecko B, Paul K, Paschke E, Stoeckler-Ipsiroglu S, Struys E, Jakobs C, Hartmann H, Luecke T, di Capua M, Korenke C, Hikel C, Reutershahn E, Freilinger M, Baumeister F, Bosch F, Erwa W: Biochemical and molecular characterization of 18 patients with pyridoxine-dependent epilepsy and mutations of the antiquitin (ALDH7A1) gene. Hum Mutat. 2007 Jan;28(1):19-26. [PubMed:17068770 ]
Associated OMIM IDs
  • 266100 (Pyridoxine-dependent epilepsy)
DrugBank IDDB02571
Phenol Explorer Compound IDNot Available
FooDB IDFDB010644
KNApSAcK IDNot Available
Chemspider ID141126
KEGG Compound IDC04076
BioCyc IDALLYSINE
BiGG IDNot Available
Wikipedia LinkAllysine
METLIN IDNot Available
PubChem Compound160603
PDB IDNot Available
ChEBI ID17917
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
NADPH-dependent reductase with broad substrate specificity. Catalyzes the reduction of a wide variety of carbonyl compounds including quinones, prostaglandins, menadione, plus various xenobiotics. Catalyzes the reduction of the antitumor anthracyclines doxorubicin and daunorubicin to the cardiotoxic compounds doxorubicinol and daunorubicinol. Can convert prostaglandin E2 to prostaglandin F2-alpha. Can bind glutathione, which explains its higher affinity for glutathione-conjugated substrates. Catalyzes the reduction of S-nitrosoglutathione.
Gene Name:
CBR1
Uniprot ID:
P16152
Molecular weight:
30374.73
Reactions
Allysine → 2-amino-6-hydroxyhexanoic aciddetails
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
AOX1
Uniprot ID:
Q06278
Molecular weight:
147916.735
Reactions
Allysine → Aminoadipic aciddetails
General function:
Involved in oxidoreductase activity
Specific function:
Multifunctional enzyme mediating important protective effects. Metabolizes betaine aldehyde to betaine, an important cellular osmolyte and methyl donor. Protects cells from oxidative stress by metabolizing a number of lipid peroxidation-derived aldehydes. Involved in lysine catabolism.
Gene Name:
ALDH7A1
Uniprot ID:
P49419
Molecular weight:
58486.74
Reactions
Allysine + NAD(P)(+) + Water → Aminoadipic acid + NAD(P)Hdetails
Allysine + NAD + Water → Aminoadipic acid + NADH + Hydrogen Iondetails
Allysine + NADP + Water → Aminoadipic acid + NADPH + Hydrogen Iondetails
alpha-Aminoadipoyl-S-acyl enzyme + NADPH + Hydrogen Ion → Allysine + Holo-Lys2 + NADPdetails
General function:
Involved in oxidoreductase activity
Specific function:
Bifunctional enzyme that catalyzes the first two steps in lysine degradation. The N-terminal and the C-terminal contain lysine-ketoglutarate reductase and saccharopine dehydrogenase activity, respectively.
Gene Name:
AASS
Uniprot ID:
Q9UDR5
Molecular weight:
102130.895
Reactions
N(6)-(L-1,3-dicarboxypropyl)-L-lysine + NAD + Water → L-Glutamic acid + Allysine + NADHdetails
Saccharopine + NAD + Water → L-Glutamic acid + Allysine + NADH + Hydrogen Iondetails
General function:
Involved in acyl carrier activity
Specific function:
Acyl-CoA synthases catalyze the initial reaction in fatty acid metabolism, by forming a thioester with CoA
Gene Name:
AASDH
Uniprot ID:
Q4L235
Molecular weight:
122596.1
General function:
Involved in transaminase activity
Specific function:
Catalyzes the pyridoxal-phosphate-dependent breakdown of 5-phosphohydroxy-L-lysine, converting it to ammonia, inorganic phosphate and 2-aminoadipate semialdehyde.
Gene Name:
AGXT2L2
Uniprot ID:
Q8IUZ5
Molecular weight:
49710.245
Reactions
5-phosphonooxy-L-lysine + Water → Allysine + Ammonia + Phosphatedetails