Record Information
Version1.0
Created at2020-04-17 19:12:39 UTC
Updated at2020-11-18 16:39:25 UTC
CannabisDB IDCDB005133
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name(S)-2-amino-6-oxohexanoate
Description(S)-2-amino-6-oxohexanoate, also known as allysine or L-2-aminoadipate 6-semialdehyde, 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 (S)-2-amino-6-oxohexanoate is a very strong basic compound (based on its pKa) (S)-2-amino-6-oxohexanoate exists in all living species, ranging from bacteria to humans. Outside of the human body, (S)-2-amino-6-oxohexanoate has been detected, but not quantified in, several different foods, such as winged beans, wasabis, common verbena, arrowhead, and oats. This could make (S)-2-amino-6-oxohexanoate a potential biomarker for the consumption of these foods. An optically active form of (S)-2-amino-6-oxohexanoate having L-configuration. (S)-2-amino-6-oxohexanoate is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
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 Weight145.16
Monoisotopic Molecular Weight145.0739
IUPAC Name(2S)-2-amino-6-oxohexanoic acid
Traditional Name2-amino-6-oxo-hexanoic acid
CAS Registry Number34897-38-6
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:

Role

Industrial application:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2.2ALOGPS
logP-2.9ChemAxon
logS-0.47ALOGPS
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS(S)-2-amino-6-oxohexanoate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-9100000000-e7c5c166681ba0316b25Spectrum
Predicted GC-MS(S)-2-amino-6-oxohexanoate, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0udi-7900000000-a87d074458b671b94f65Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ufs-2900000000-cc3c3ade4cefc6b57880Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ue9-9700000000-1f5f0f3378ed80283ec8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0abc-9000000000-dd87ab890dceec9e01cbSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-5623b839bf292d641b92Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-4900000000-7473bdea5b2f626515f1Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-12c42805d877e4f712b6Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Carbonyl reductase [NADPH] 1CBR121q22.13P16152 details
Aldehyde oxidaseAOX12q33Q06278 details
Alpha-aminoadipic semialdehyde dehydrogenaseALDH7A15q31P49419 details
Alpha-aminoadipic semialdehyde synthase, mitochondrialAASS7q31.3Q9UDR5 details
Acyl-CoA synthetase family member 4AASDH4q12Q4L235 details
5-phosphohydroxy-L-lysine phospho-lyaseAGXT2L25q35.3Q8IUZ5 details
Transporters
Protein NameGene NameLocusUniprot IDDetails
Acyl-CoA synthetase family member 4AASDH4q12Q4L235 details
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Aldehyde oxidaseAOX12q33Q06278 details
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0001263
DrugBank IDDB02571
Phenol Explorer Compound IDNot Available
FoodDB 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
References
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
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
AOX1
Uniprot ID:
Q06278
Molecular weight:
147916.735
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
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
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

Transporters

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