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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (6) Show 6 proteins XML

enzymes (6) Show 6 proteins

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-09-14 15:20:03 UTC

HMDB ID

HMDB0001263

Secondary Accession Numbers

HMDB0059595
HMDB01263
HMDB59595

Metabolite Identification

Common Name

Allysine

Description

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 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-AMINO-6-oxo-hexanoIC ACID	ChEBI
6-oxo-L-Norleucine	ChEBI
Allysine	ChEBI
L-2-Aminoadipate 6-semialdehyde	ChEBI
L-6-Oxonorleucine	ChEBI
2-Aminoadipate 6-semialdehyde	Kegg
L-Allysine	Kegg
2-AMINO-6-oxo-hexanoate	Generator
L-2-Aminoadipic acid 6-semialdehyde	Generator
2-Aminoadipic acid 6-semialdehyde	Generator
(S)-2-Amino-6-oxohexanoic acid	Generator
2-Aminoadipate semialdehyde	HMDB
alpha-AASA	HMDB
alpha-Aminoadipate semialdehyde	HMDB
2-Aminoadipic semialdehyde	HMDB
2-Amino-5-formylvaleric acid	HMDB
2-Amino-6-oxohexanoate	HMDB
6-Oxonorleucine	HMDB
L-Homoglutamic semialdehyde	HMDB
alpha-Aminoadipic acid delta-semialdehyde	HMDB
alpha-Aminoadipic delta-semialdehyde	HMDB
α-Aminoadipic acid δ-semialdehyde	HMDB
α-Aminoadipic δ-semialdehyde	HMDB

Chemical Formula

C₆H₁₁NO₃

Average Molecular Weight

145.1564

Monoisotopic Molecular Weight

145.073893223

IUPAC Name

(2S)-2-amino-6-oxohexanoic acid

Traditional Name

2-amino-6-oxo-hexanoic acid

CAS Registry Number

6665-12-9

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 Key

GFXYTQPNNXGICT-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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

L-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 Framework

Aliphatic acyclic compounds

External Descriptors

non-proteinogenic L-alpha-amino acid (CHEBI:17917 )
allysine (CHEBI:17917 )
aminoadipate semialdehyde (CHEBI:17917 )

Ontology

Disposition

Biological location

Excreta

Urine

Cellular substructure

Macromolecular complex

Blood

Cytoplasm

Ingestion

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Lysine degradation

Physical Properties

State

Solid

Experimental Molecular 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

Experimental Spectral Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	49.4 g/L	ALOGPS
logP	10^(-2.2) g/L	ALOGPS
logP	10^(-2.9) g/L	ChemAxon
logS	10^(-0.47) g/L	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	14.58 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

Predicted Spectral Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	132.251	31661259
DarkChem	[M-H]-	129.572	31661259
AllCCS	[M+H]+	133.601	32859911
AllCCS	[M-H]-	129.104	32859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Allysine,1TMS,#1	C[Si](C)(C)OC(=O)[C@@H](N)CCCC=O	1395.3	Semi standard non polar	https://arxiv.org/abs/1905.12712
Allysine,1TMS,#2	C[Si](C)(C)OC=CCC[C@H](N)C(=O)O	1561.0	Semi standard non polar	https://arxiv.org/abs/1905.12712
Allysine,1TMS,#3	C[Si](C)(C)N[C@@H](CCCC=O)C(=O)O	1476.5	Semi standard non polar	https://arxiv.org/abs/1905.12712
Allysine,1TBDMS,#1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CCCC=O	1618.3	Semi standard non polar	https://arxiv.org/abs/1905.12712
Allysine,1TBDMS,#2	CC(C)(C)[Si](C)(C)OC=CCC[C@H](N)C(=O)O	1808.3	Semi standard non polar	https://arxiv.org/abs/1905.12712
Allysine,1TBDMS,#3	CC(C)(C)[Si](C)(C)N[C@@H](CCCC=O)C(=O)O	1723.1	Semi standard non polar	https://arxiv.org/abs/1905.12712

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Allysine GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-9100000000-e7c5c166681ba0316b25	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Allysine GC-MS (1 TMS) - 70eV, Positive	splash10-0udi-7900000000-a87d074458b671b94f65	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Allysine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allysine 10V, Positive-QTOF	splash10-0ufs-2900000000-cc3c3ade4cefc6b57880	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allysine 20V, Positive-QTOF	splash10-0ue9-9700000000-1f5f0f3378ed80283ec8	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allysine 40V, Positive-QTOF	splash10-0abc-9000000000-dd87ab890dceec9e01cb	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allysine 10V, Negative-QTOF	splash10-0006-0900000000-5623b839bf292d641b92	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allysine 20V, Negative-QTOF	splash10-0006-4900000000-7473bdea5b2f626515f1	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allysine 40V, Negative-QTOF	splash10-0006-9000000000-12c42805d877e4f712b6	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allysine 10V, Positive-QTOF	splash10-0ue9-6900000000-d34f08b905440e7d7964	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allysine 20V, Positive-QTOF	splash10-001i-9000000000-684e25a1d77f85cbfa55	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allysine 40V, Positive-QTOF	splash10-0a4r-9000000000-96069f1c2588457b97ce	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allysine 10V, Negative-QTOF	splash10-004l-0900000000-06ca102489283c43f7e6	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allysine 20V, Negative-QTOF	splash10-054o-2900000000-46f0e454239e803a8554	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allysine 40V, Negative-QTOF	splash10-0006-9000000000-3fc953bdebc8fddb25d1	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Mitochondria

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Lysine degradation	Not Available
Glutaric Aciduria Type I		Not Available
Saccharopinuria/Hyperlysinemia II		Not Available
Hyperlysinemia I, Familial		Not Available
Hyperlysinemia II or Saccharopinuria		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	<0.2 uM	Infant (0-1 year old)	Not Specified	Normal	17068770	details
Urine	Detected and Quantified	<1 umol/mmol creatinine	Infant (0-1 year old)	Not Specified	Normal	17068770	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected and Quantified	1.6-28 umol/mmol creatinine	Infant (0-1 year old)	Not Specified	Pyridoxine dependency with seizures (PDE)	17068770	details

Associated Disorders and Diseases

Disease References

Pyridoxine-dependent epilepsy
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)

External Links

DrugBank ID

DB02571

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB010644

KNApSAcK ID

Not Available

Chemspider ID

141126

KEGG Compound ID

C04076

BioCyc ID

ALLYSINE

BiGG ID

Not Available

Wikipedia Link

Allysine

METLIN ID

Not Available

PubChem Compound

160603

PDB ID

Not Available

ChEBI ID

17917

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Carbonyl reductase [NADPH] 1

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 acid	details

Enzyme Details

2. Aldehyde oxidase

General function:: Involved in oxidoreductase activity
Specific function:: Not Available
Gene Name:: AOX1
Uniprot ID:: Q06278
Molecular weight:: 147916.735

Reactions

Allysine → Aminoadipic acid	details

Enzyme Details

3. Alpha-aminoadipic semialdehyde dehydrogenase

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)H	details
Allysine + NAD + Water → Aminoadipic acid + NADH + Hydrogen Ion	details
Allysine + NADP + Water → Aminoadipic acid + NADPH + Hydrogen Ion	details
alpha-Aminoadipoyl-S-acyl enzyme + NADPH + Hydrogen Ion → Allysine + Holo-Lys2 + NADP	details

Enzyme Details

4. Alpha-aminoadipic semialdehyde synthase, mitochondrial

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 + NADH	details
Saccharopine + NAD + Water → L-Glutamic acid + Allysine + NADH + Hydrogen Ion	details

Enzyme Details

5. Acyl-CoA synthetase family member 4

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

Enzyme Details

6. 5-phosphohydroxy-L-lysine phospho-lyase

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 + Phosphate	details

Showing metabocard for Allysine (HMDB0001263)

MOL for HMDB0001263 (Allysine)

3D MOL for HMDB0001263 (Allysine)

3D SDF for HMDB0001263 (Allysine)

3D-SDF for HMDB0001263 (Allysine)

PDB for HMDB0001263 (Allysine)

3D PDB for HMDB0001263 (Allysine)

SMILES for HMDB0001263 (Allysine)

INCHI for HMDB0001263 (Allysine)

Structure for HMDB0001263 (Allysine)

3D Structure for HMDB0001263 (Allysine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

Reactions

Reactions

Reactions

Reactions