Human Metabolome Database: Showing metabocard for D-Lysine (HMDB0003405)

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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

3.6

Creation Date

2006-08-12 20:14:46 UTC

Update Date

2017-08-16 04:08:54 UTC

HMDB ID

HMDB0003405

Secondary Accession Numbers

HMDB03405

Metabolite Identification

Common Name

D-Lysine

Description

D-Lysine is an essential amino acid. It is often added to animal feed.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
(S)-2,6-Diaminohexanoic acid	ChEBI
(S)-alpha,epsilon-Diaminocaproic acid	ChEBI
(S)-Lysine	ChEBI
6-ammonio-L-Norleucine	ChEBI
K	ChEBI
L-2,6-Diaminocaproic acid	ChEBI
L-Lysin	ChEBI
Lys	ChEBI
Lysina	ChEBI
Lysine	ChEBI
Lysine acid	ChEBI
Lysinum	ChEBI
(S)-2,6-Diaminohexanoate	Generator
(S)-a,epsilon-Diaminocaproate	Generator
(S)-a,epsilon-Diaminocaproic acid	Generator
(S)-alpha,epsilon-Diaminocaproate	Generator
(S)-α,epsilon-diaminocaproate	Generator
(S)-α,epsilon-diaminocaproic acid	Generator
L-2,6-Diaminocaproate	Generator
(+)-S-Lysine	HMDB
(S)-2,6-diamino-Hexanoate	HMDB
(S)-2,6-diamino-Hexanoic acid	HMDB
(S)-a,e-Diaminocaproate	HMDB
(S)-a,e-Diaminocaproic acid	HMDB
2,6-Diaminohexanoate	HMDB
2,6-Diaminohexanoic acid	HMDB
6-amino-Aminutrin	HMDB
6-amino-L-Norleucine	HMDB
a-Lysine	HMDB
alpha-Lysine	HMDB
Aminutrin	HMDB
H-Lys-OH	HMDB
L-(+)-Lysine	HMDB
L-2,6-Diainohexanoate	HMDB
L-2,6-Diainohexanoic acid	HMDB
L-Lys	HMDB
Acetate, lysine	MeSH
Enisyl	MeSH
Lysine hydrochloride	MeSH
L Lysine	MeSH
Lysine acetate	MeSH

Chemical Formula

C₆H₁₄N₂O₂

Average Molecular Weight

146.1876

Monoisotopic Molecular Weight

146.105527702

IUPAC Name

(2S)-2,6-diaminohexanoic acid

Traditional Name

L-lysine

CAS Registry Number

923-27-3

SMILES

NCCCC[C@H](N)C(O)=O

InChI Identifier

InChI=1S/C6H14N2O2/c7-4-2-1-3-5(8)6(9)10/h5H,1-4,7-8H2,(H,9,10)/t5-/m0/s1

InChI Key

KDXKERNSBIXSRK-YFKPBYRVSA-N

Chemical Taxonomy

Description

This compound 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 acid
Fatty acyl
Amino acid
Monocarboxylic acid or derivatives
Carboxylic acid
Organic oxide
Organopnictogen compound
Organic oxygen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Carbonyl group
Organic nitrogen compound
Amine
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

lysine (CHEBI:18019 )
aspartate family amino acid (CHEBI:18019 )
proteinogenic amino acid (CHEBI:18019 )
L-alpha-amino acid (CHEBI:18019 )
Common amino acids (C00047 )

Ontology

Status

Detected but not Quantified

Origin

Endogenous

Biofunction

Protein synthesis, amino acid biosynthesis

Application

Not Available

Cellular locations

Cytoplasm (predicted from logP)

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
Water Solubility	105.0 mg/mL	ALOGPS
logP	-3.8	ALOGPS
logP	-3.2	ChemAxon
logS	-0.14	ALOGPS
pKa (Strongest Acidic)	2.74	ChemAxon
pKa (Strongest Basic)	10.29	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	89.34 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	37.81 m³·mol^-1	ChemAxon
Polarizability	15.84 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)	splash10-00di-3910000000-98c565675de67aa87900	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)	splash10-0ab9-1910000000-87ef8534f592041f50f2	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)	splash10-0a4i-1921000000-84f7815b0f650fa17444	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-001i-9600000000-823408dba509cb204acf	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-00di-3910000000-4f5578af5e7d8b6c49f7	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (4 TMS)	splash10-0adi-1921000000-4e56d95e623e792f9e6b	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS	Not Available
GC-MS	GC-MS Spectrum - EI-B	splash10-00di-0921000000-eeb49e57bc1a75193058	View in MoNA
GC-MS	GC-MS Spectrum - EI-B	splash10-0ab9-0921000000-ebb902be0f3754225b2f	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-QQ	splash10-0fdk-3923000000-15b84c2649c1b0455de1	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-003r-8900000000-470a0beb4f338ed89bca	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-001i-9000000000-74e9193d9d33c2509bfa	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0a59-9000000000-822c4e78250fffa56e39	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0002-0900000000-04f9a62a77fb5a37ca22	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-9000000000-035035ecfa084671479b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0900000000-5bb15839f86f4fca0d0b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0900000000-6c8ef03aa83eb1cab35b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-01ot-0910000000-c182a7dcdbc260666978	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0a4j-0900000000-6c5f378cef2f14204e15	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0900000000-41e1a6499097748934b0	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-03di-0390000000-7270a0b85b9e3f9f6373	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0002-0900000000-a997e809874357908880	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0002-2900000000-f64110414f82c93e1fe8	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-014m-9200000000-33a38e6370811c5ddc82	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0006-9000000000-3a8b0b6e62f5c66d3720	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0006-9000000000-d5167570d11d77fd541e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-0002-0900000000-a46231bd529176101129	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-001i-9200000000-f8b9f01b2a9886c51df9	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-001i-9000000000-ace0361476d939043e98	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-001i-9000000000-5b06b6e9dcf9faf8e89c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-053r-9000000000-2894ef6d7f72ea71688e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - CE-ESI-TOF (CE-system connected to 6210 Time-of-Flight MS, Agilent) , Positive	splash10-0002-0900000000-290902f43cf851e8ef5e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-001i-9300000000-f81193f6b50235ec8147	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-001i-9300000000-8931d2193adab166d5e4	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0002-0900000000-b4825cc64fcb830c6967	View in MoNA
1D NMR	1H NMR Spectrum	Not Available
1D NMR	13C NMR Spectrum	Not Available
1D NMR	1H NMR Spectrum	Not Available
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available

Biological Properties

Cellular Locations

Cytoplasm (predicted from logP)

Biofluid Locations

Feces

Tissue Location

Neuron

Pathways

Not Available

Normal Concentrations

Biofluid	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified		Infant (0-1 year old)	Both	Normal	22411374	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

DrugBank Metabolite ID

Not Available

Phenol Explorer Compound ID

Not Available

Phenol Explorer Metabolite ID

Not Available

FoodDB ID

FDB023163

KNApSAcK ID

Not Available

Chemspider ID

51793

KEGG Compound ID

C00739

BioCyc ID

CPD-219

BiGG ID

Not Available

Wikipedia Link

Not Available

NuGOwiki Link

METLIN ID

PubChem Compound

PDB ID

ChEBI ID

References

Synthesis Reference

Furui, Masakatsu; Takahashi, Eiji; Seko, Hiroyasu. Process for preparing D-lysine. Eur. Pat. Appl. (1996), 7 pp.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Wakisaka K, Arano Y, Uezono T, Akizawa H, Ono M, Kawai K, Ohomomo Y, Nakayama M, Saji H: A novel radioiodination reagent for protein radiopharmaceuticals with L-lysine as a plasma-stable metabolizable linkage to liberate m-iodohippuric acid after lysosomal proteolysis. J Med Chem. 1997 Aug 1;40(16):2643-52. [PubMed:9258371 ]
Darling PB, Bross R, Wykes LJ, Ball RO, Pencharz PB: Isotopic enrichment of amino acids in urine following oral infusions of L-[1-(13)C]phenylalanine and L-[1-(13)C]lysine in humans: confounding effect of D-[13C]amino acids. Metabolism. 1999 Jun;48(6):732-7. [PubMed:10381147 ]
Bross R, Ball RO, Pencharz PB: Development of a minimally invasive protocol for the determination of phenylalanine and lysine kinetics in humans during the fed state. J Nutr. 1998 Nov;128(11):1913-9. [PubMed:9808642 ]
Hayman MW, Smith KH, Cameron NR, Przyborski SA: Growth of human stem cell-derived neurons on solid three-dimensional polymers. J Biochem Biophys Methods. 2005 Mar 31;62(3):231-40. Epub 2004 Dec 30. [PubMed:15733583 ]

Showing metabocard for D-Lysine (HMDB0003405)

Structure for HMDB0003405 (D-Lysine)