L-Lysine

Identification

Name
L-Lysine
Accession Number
DB00123  (NUTR00037, DB11101)
Type
Small Molecule
Groups
Approved, Nutraceutical
Description

L-Lysine (abbreviated as Lys or K) is an α-amino acid with the chemical formula HO2CCH(NH2)(CH2)4NH2. This amino acid is an essential amino acid, which means that humans cannot synthesize it. Its codons are AAA and AAG. L-Lysine is a base, as are arginine and histidine. The ε-amino group often participates in hydrogen bonding and as a general base in catalysis. Common posttranslational modifications include methylation of the ε-amino group, giving methyl-, dimethyl-, and trimethyllysine. The latter occurs in calmodulin. Other posttranslational modifications include acetylation. Collagen contains hydroxylysine which is derived from lysine by lysyl hydroxylase. O-Glycosylation of lysine residues in the endoplasmic reticulum or Golgi apparatus is used to mark certain proteins for secretion from the cell.

Structure
Thumb
Synonyms
  • (S)-2,6-diaminohexanoic acid
  • (S)-lysine
  • (S)-α,ε-diaminocaproic acid
  • 6-ammonio-L-norleucine
  • L-2,6-Diaminocaproic acid
  • L-lys
  • L-Lysin
  • LYS
  • Lysina
  • Lysine
  • Lysine acid
  • Lysinum
External IDs
Not Available
Product Ingredients
IngredientUNIICASInChI Key
L-Lysine acetateTTL6G7LIWZ 57282-49-2RRNJROHIFSLGRA-JEDNCBNOSA-N
L-Lysine hydrochlorideJNJ23Q2COM 657-27-2BVHLGVCQOALMSV-JEDNCBNOSA-N
Approved Prescription Products
Not Available
Approved Generic Prescription Products
Not Available
Approved Over the Counter Products
Not Available
Unapproved/Other Products
Not Available
International/Other Brands
Not Available
Brand mixtures
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
2.5% Travasol Amino Acid Injection With Electrolytes In 10% DextroseSolutionIntravenousBaxter Corporation Clintec Nutrition Division1996-12-312015-08-05Canada
2.5% Travasol Amino Acid Injection With Electrolytes In 10% Dextrose ClinimixSolutionIntravenousBaxter Corporation Clintec Nutrition Division1993-12-312015-08-05Canada
2.5% Travasol Amino Acid Injection Without Electrolytes In 10% Dextrose QuickmixSolutionIntravenousBaxter Corporation Clintec Nutrition Division1995-12-312007-08-02Canada
2.5%travasol Amino Acid InJ.W.eleC.W.25%dexLiquidIntravenousClintec Nutrition Company1996-07-301998-08-13Canada
2.75% Travas. Amino Acid InJ.W.elecw.25%dexLiquidIntravenousClintec Nutrition Company1996-07-301998-08-13Canada
2.75% Travasol Amino Acid Injection With Electrolytes In 25% Dextrose QuickmixSolutionIntravenousBaxter Corporation Clintec Nutrition Division1996-02-022007-08-02Canada
2.75% Travasol Amino Acid Injection With Electrolytes In 5% Dextrose QuickmixSolutionIntravenousBaxter Corporation Clintec Nutrition Division1993-12-312007-08-02Canada
2.75%travasol Amino Acid InJ.W.eleC.W.5%dex.LiquidIntravenousClintec Nutrition Company1996-12-311999-08-10Canada
4.25% Amino Acid Injection Without Electrolytes In 20% Dextrose QuickmixSolutionIntravenousBaxter Corporation Clintec Nutrition Division1995-12-312007-08-02Canada
4.25% Travasol Amino Acid Injection With Electrolytes In 10% DextroseSolutionIntravenousBaxter Corporation Clintec Nutrition Division1996-12-312015-08-05Canada
4.25% Travasol Amino Acid Injection With Electrolytes In 20% DextroseSolutionIntravenousBaxter Corporation Clintec Nutrition Division1996-12-312007-08-02Canada
4.25% Travasol Amino Acid Injection With Electrolytes In 20% Dextrose QuickmixSolutionIntravenousBaxter Corporation Clintec Nutrition Division1995-12-312007-08-02Canada
4.25% Travasol Amino Acid Injection With Electrolytes In 25% DextroseSolutionIntravenousBaxter Corporation Clintec Nutrition Division1996-12-312015-08-05Canada
4.25% Travasol Amino Acid Injection With Electrolytes In 5% Dextrose QuickmixSolutionIntravenousBaxter Corporation Clintec Nutrition Division1995-12-312007-08-02Canada
4.25% Travasol Amino Acid Injection Without Electrlytes In 10% DextroseSolutionIntravenousBaxter Corporation Clintec Nutrition Division1996-12-312015-08-05Canada
4.25% Travasol Amino Acid Injection Without Electrolytes In 20% DextroseSolutionIntravenousBaxter Corporation Clintec Nutrition Division1996-12-312007-08-02Canada
4.25% Travasol Amino Acid Injection Without Electrolytes In 25% DextroseSolutionIntravenousBaxter Corporation Clintec Nutrition Division1996-12-312015-08-05Canada
4.25% Travasol Amino Acid Without Electrolytes In 5% Dextrose QuickmixSolutionIntravenousBaxter Corporation Clintec Nutrition Division1995-12-312007-08-02Canada
4.25%trav. Amino Acid InJ.W.O.elect.5%dext.LiquidIntravenousClintec Nutrition Company1996-12-311999-08-10Canada
4.25%travasol Amino Acid InJ.W.elecw.5%dex.LiquidIntravenousClintec Nutrition Company1996-12-311999-08-10Canada
5% Travasol Amino Acid Injection With Electrolytes In 20% DextroseSolutionIntravenousBaxter Corporation Clintec Nutrition Division1996-12-312015-08-05Canada
5% Travasol Amino Acid Injection Without Electrolytes In 20% DextroseSolutionIntravenousBaxter Corporation Clintec Nutrition Division1996-12-312015-08-05Canada
5% Travasol Amino Acid Injection Without Electrolytes In 25% DextroseSolutionIntravenousBaxter Corporation Clintec Nutrition Division1996-12-312007-08-02Canada
AminosynInjection, solutionIntravenousHospira, Inc.2012-03-06Not applicableUs
Aminosyn 10%SolutionIntravenousHospira, Inc.1979-12-31Not applicableCanada
Aminosyn 10% W ElectrolytesLiquidIntravenousAbbott1984-12-311999-08-09Canada
Aminosyn 3.5% MLiquidIntravenousAbbott1980-12-311999-08-09Canada
Aminosyn 5%SolutionIntravenousHospira, Inc.1977-12-312016-07-29Canada
Aminosyn 7%SolutionIntravenousHospira, Inc.1979-12-312016-07-29Canada
Aminosyn 8.5%SolutionIntravenousHospira, Inc.1984-12-312016-07-29Canada
Aminosyn 8.5% Injection With ElectrolytesSolutionIntravenousHospira, Inc.1984-12-312012-08-03Canada
Aminosyn IIInjection, solutionIntravenousHospira, Inc.1986-04-032017-05-18Us
Aminosyn II 10%SolutionIntravenousHospira, Inc.1987-12-31Not applicableCanada
Aminosyn II 10% With ElectrolytesSolutionIntravenousHospira, Inc.1991-12-312016-07-29Canada
Aminosyn II 15%SolutionIntravenousHospira, Inc.1995-12-31Not applicableCanada
Aminosyn II 5% InjLiquidIntravenousAbbott1988-12-311999-08-09Canada
Aminosyn II 7% InjectionSolutionIntravenousHospira, Inc.1987-12-312016-07-29Canada
Aminosyn II 7% M In 10% Dextrose(dual Chamber)SolutionIntravenousHospira, Inc.1987-12-312012-08-03Canada
Aminosyn II 7% With 10% DextroseSolutionIntravenousHospira, Inc.1988-12-312012-08-03Canada
Aminosyn II 7% With 50% DextroseSolutionIntravenousHospira, Inc.1988-12-312012-08-03Canada
Aminosyn II 8.5% InjectionSolutionIntravenousHospira, Inc.1987-12-312016-07-29Canada
Aminosyn II 8.5% M In 20% Dextrose (dual Chamber)SolutionIntravenousHospira, Inc.1987-12-312012-08-03Canada
Aminosyn II 8.5% With 50% DextroseSolutionIntravenousHospira, Inc.1988-12-312012-08-03Canada
Aminosyn II In Dextrose InjectionSolutionIntravenousHospira, Inc.1987-12-312012-08-03Canada
Aminosyn II with ElectrolytesInjection, solutionIntravenousHospira, Inc.1986-04-03Not applicableUs
Aminosyn RFInjection, solutionIntravenousHospira, Inc.2011-02-18Not applicableUs
Aminosyn RF InjectionSolutionIntravenousHospira, Inc.1986-12-312016-07-29Canada
Aminosyn Sulfite FreeInjection, solutionIntravenousHospira, Inc.2011-10-27Not applicableUs
Aminosyn-PFInjection, solutionIntravenousHospira, Inc.1985-09-06Not applicableUs
Aminosyn-PF 10%SolutionIntravenousHospira, Inc.1990-12-312016-07-29Canada
Aminosyn-PF 7%SolutionIntravenousHospira, Inc.1990-12-312016-07-29Canada
ClinimixInjectionIntravenousBaxter Laboratories1997-09-29Not applicableUs
Clinimix 2.5% Travasol Aa Without Electrolytes In 10% Dextrose InjecSolutionIntravenousBaxter Corporation Clintec Nutrition Division1996-12-312007-08-02Canada
Clinimix EInjectionIntravenousBaxter Laboratories1997-03-26Not applicableUs
ClinisolInjection, solutionIntravenousBaxter Laboratories1996-08-30Not applicableUs
Effervescent Potassium ChlorideTablet, effervescentOralQualitest2006-01-06Not applicableUs
FreAmine HBCInjection, solutionIntravenousB. Braun Medical Inc.1971-09-24Not applicableUs
FreAmine IIIInjection, solutionIntravenousB. Braun Medical Inc.1971-09-24Not applicableUs
HepatAmineInjection, solutionIntravenousB. Braun Medical Inc.1982-08-03Not applicableUs
NephrAmineInjection, solutionIntravenousB. Braun Medical Inc.1978-02-24Not applicableUs
NovamineInjection, solution, concentrateIntravenousHospira, Inc.2011-11-22Not applicableUs
Olimel 3.3% EEmulsionIntravenousBaxter LaboratoriesNot applicableNot applicableCanada
Olimel 4.4%EmulsionIntravenousBaxter Laboratories2011-09-29Not applicableCanada
Olimel 4.4% EEmulsionIntravenousBaxter Laboratories2011-02-26Not applicableCanada
Olimel 5.7%EmulsionIntravenousBaxter Laboratories2011-03-01Not applicableCanada
Olimel 5.7% EEmulsionIntravenousBaxter Laboratories2011-01-19Not applicableCanada
Periolimel 2.5% EEmulsionIntravenousBaxter Laboratories2011-02-28Not applicableCanada
PlenamineSolutionIntravenousB. Braun Medical Inc.2015-01-30Not applicableUs
Premasol - sulfite-free (Amino Acid)Injection, solutionIntravenousBaxter Laboratories2003-06-19Not applicableUs
Primene 10%LiquidIntravenousBaxter Laboratories1997-11-14Not applicableCanada
Primene 10%-liq IVLiquidIntravenousClintec Nutrition Company1995-12-311998-08-13Canada
ProSolInjection, solutionIntravenousBaxter Laboratories1998-08-26Not applicableUs
Quick Mix 2.5% Travasol Aa With Electrolytes With 25% Dextrose InjecLiquidIntravenousBaxter Corporation Clintec Nutrition Division1993-12-312000-07-20Canada
Renamin (amino Acids) InjectionSolutionIntravenousBaxter Laboratories1996-02-022011-05-10Canada
TravasolInjectionIntravenousBaxter Laboratories1984-08-23Not applicableUs
Travasol Amino Acid Inj 5.5%SolutionIntravenousBaxter Laboratories1981-12-312007-08-02Canada
Travasol Amino Acid Inj 8.5%SolutionIntravenousBaxter Laboratories1980-12-312008-03-26Canada
Travasol ESolutionIntravenousBaxter Laboratories1974-12-31Not applicableCanada
Travasol Inj Without Electrolytes 5.5%SolutionIntravenousBaxter Laboratories1978-12-312007-08-02Canada
TrophAmineSolutionIntravenousB. Braun Medical Inc.1984-07-20Not applicableUs
Vamin 18 Electrolyte-freeSolutionIntravenousFresenius Kabi Ab1996-12-302006-07-17Canada
Vamin NSolutionIntravenousFresenius Kabi Ab1995-12-312006-07-17Canada
Categories
UNII
K3Z4F929H6
CAS number
56-87-1
Weight
Average: 146.1876
Monoisotopic: 146.105527702
Chemical Formula
C6H14N2O2
InChI Key
KDXKERNSBIXSRK-YFKPBYRVSA-N
InChI
InChI=1S/C6H14N2O2/c7-4-2-1-3-5(8)6(9)10/h5H,1-4,7-8H2,(H,9,10)/t5-/m0/s1
IUPAC Name
(2S)-2,6-diaminohexanoic acid
SMILES
NCCCC[[email protected]](N)C(O)=O

Pharmacology

Indication

Supplemental L-lysine has putative anti-herpes simplex virus activity. There is preliminary research suggesting that it may have some anti-osteoporotic activity.

Structured Indications
Not Available
Pharmacodynamics

Insures the adequate absorption of calcium; helps form collagen ( which makes up bone cartilage & connective tissues); aids in the production of antibodies, hormones & enzymes. Recent studies have shown that Lysine may be effective against herpes by improving the balance of nutrients that reduce viral growth. A deficiency may result in tiredness, inability to concentrate, irritability, bloodshot eyes, retarded growth, hair loss, anemia & reproductive problems.

Mechanism of action

Proteins of the herpes simplex virus are rich in L-arginine, and tissue culture studies indicate an enhancing effect on viral replication when the amino acid ratio of L-arginine to L-lysine is high in the tissue culture media. When the ratio of L-lysine to L-arginine is high, viral replication and the cytopathogenicity of herpes simplex virus have been found to be inhibited. L-lysine may facilitate the absorption of calcium from the small intestine.

TargetActionsOrganism
UHigh affinity cationic amino acid transporter 1Not AvailableHuman
UCationic amino acid transporter 4Not AvailableHuman
UCationic amino acid transporter 3Not AvailableHuman
ULow affinity cationic amino acid transporter 2Not AvailableHuman
ULysine--tRNA ligaseNot AvailableHuman
Absorption

Absorbed from the lumen of the small intestine into the enterocytes by an active transport process

Volume of distribution
Not Available
Protein binding
Not Available
Metabolism

Hepatic

Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Hyperlysinemia I, FamilialDisease
Lysine DegradationMetabolic
2-aminoadipic 2-oxoadipic aciduriaDisease
Saccharopinuria/Hyperlysinemia IIDisease
Multiple carboxylase deficiency, neonatal or early onset formDisease
Biotin MetabolismMetabolic
Biotinidase DeficiencyDisease
Glutaric Aciduria Type IDisease
Carnitine SynthesisMetabolic
Hyperlysinemia II or SaccharopinuriaDisease
Pyridoxine dependency with seizuresDisease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference

Joseph Michael Stevens, Thomas P. Binder, "Process for making granular L-lysine." U.S. Patent US5990350, issued 0000.

US5990350
General References
  1. Griffith RS, Norins AL, Kagan C: A multicentered study of lysine therapy in Herpes simplex infection. Dermatologica. 1978;156(5):257-67. [PubMed:640102 ]
External Links
Human Metabolome Database
HMDB00182
KEGG Drug
D02304
KEGG Compound
C00047
ChemSpider
5747
BindingDB
217367
ChEBI
18019
ChEMBL
CHEMBL8085
PharmGKB
PA450280
HET
LYS
PDRhealth
PDRhealth Drug Page
Wikipedia
L-Lysine
ATC Codes
B05XB03 — Lysine
AHFS Codes
Not Available
PDB Entries
FDA label
Not Available
MSDS
Download (73.3 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingSupportive CareProtein Feeding in Post-traumatic Injury Patients1
1CompletedBasic ScienceHealthy Volunteers / Pre-Diabetic1
2Active Not RecruitingTreatmentCarcinoid Tumors / Medulloblastomas / Neuroblastomas / Neuroendocrine Tumors1
2WithdrawnTreatmentMedulloblastomas / Meningiomas / Neuroblastomas / Neuroendrocrine Tumors1
3CompletedTreatmentCritical Illness1
3CompletedTreatmentInfant, Low Birth Weight / Infant, Small for Gestational Age / Infants, Premature / Newborn Infants / Sepsis1
Not AvailableActive Not RecruitingTreatmentMenopause1
Not AvailableCompletedBasic ScienceHealthy Volunteers1
Not AvailableCompletedTreatmentSchizophrenic Disorders1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Dosage forms
FormRouteStrength
Injection, solutionIntravenous
Tablet, effervescentOral
Injection, solution, concentrateIntravenous
EmulsionIntravenous
SolutionIntravenous
LiquidIntravenous
InjectionIntravenous
Prices
Unit descriptionCostUnit
Neoprofen 20 mg/2 ml vial304.5USD ml
Cayston 75 mg inhal solution63.24USD ml
L-lysine ointment0.16USD g
Lysine hcl powder0.16USD g
Ra l-lysine 1000 mg tablet0.08USD tablet
L-lysine hcl 500 mg tablet0.07USD tablet
L-lysine 1000 mg tablet0.04USD tablet
L-lysine 500 mg tablet0.04USD tablet
CVS Pharmacy l-lysine 500 mg tablet0.03USD tablet
Lysine 500 mg tablet0.02USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)224.5 dec °CPhysProp
water solubility1E+006 mg/L (at 20 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP-3.05HANSCH,C ET AL. (1995)
pKa3.12 (at 0 °C)KORTUM,G ET AL (1961)
Predicted Properties
PropertyValueSource
Water Solubility105.0 mg/mLALOGPS
logP-3.8ALOGPS
logP-3.2ChemAxon
logS-0.14ALOGPS
pKa (Strongest Acidic)2.74ChemAxon
pKa (Strongest Basic)10.29ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area89.34 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity37.81 m3·mol-1ChemAxon
Polarizability15.84 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Download (9.31 KB)
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)GC-MSsplash10-00di-3910000000-98c565675de67aa87900
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-0ab9-1910000000-87ef8534f592041f50f2
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)GC-MSsplash10-0a4i-1921000000-84f7815b0f650fa17444
GC-MS Spectrum - GC-MS (3 TMS)GC-MSsplash10-001i-9600000000-823408dba509cb204acf
GC-MS Spectrum - GC-MS (3 TMS)GC-MSsplash10-00di-3910000000-4f5578af5e7d8b6c49f7
GC-MS Spectrum - GC-MS (4 TMS)GC-MSsplash10-0adi-1921000000-4e56d95e623e792f9e6b
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-00di-0921000000-eeb49e57bc1a75193058
GC-MS Spectrum - EI-BGC-MSsplash10-0ab9-0921000000-ebb902be0f3754225b2f
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00di-3910000000-98c565675de67aa87900
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0ab9-1910000000-87ef8534f592041f50f2
GC-MS Spectrum - GC-EI-QQGC-MSsplash10-0fdk-3923000000-15b84c2649c1b0455de1
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0a4i-1921000000-84f7815b0f650fa17444
GC-MS Spectrum - GC-MSGC-MSsplash10-001i-9600000000-823408dba509cb204acf
GC-MS Spectrum - GC-MSGC-MSsplash10-00di-3910000000-4f5578af5e7d8b6c49f7
GC-MS Spectrum - GC-MSGC-MSsplash10-0adi-1921000000-4e56d95e623e792f9e6b
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0abi-1900000000-9ad174122e4d6e003eb8
LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-003r-8900000000-470a0beb4f338ed89bca
LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-001i-9000000000-74e9193d9d33c2509bfa
LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-0a59-9000000000-822c4e78250fffa56e39
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-0002-0900000000-04f9a62a77fb5a37ca22
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-001i-9000000000-035035ecfa084671479b
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-001i-0900000000-5bb15839f86f4fca0d0b
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-001i-0900000000-6c8ef03aa83eb1cab35b
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-01ot-0910000000-c182a7dcdbc260666978
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-0a4j-0900000000-6c5f378cef2f14204e15
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-001i-0900000000-41e1a6499097748934b0
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-03di-0390000000-7270a0b85b9e3f9f6373
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-0002-0900000000-a997e809874357908880
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-0002-2900000000-f64110414f82c93e1fe8
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-014m-9200000000-33a38e6370811c5ddc82
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, NegativeLC-MS/MSsplash10-0006-9000000000-3a8b0b6e62f5c66d3720
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, NegativeLC-MS/MSsplash10-0006-9000000000-d5167570d11d77fd541e
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, PositiveLC-MS/MSsplash10-0002-0900000000-a46231bd529176101129
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, PositiveLC-MS/MSsplash10-001i-9200000000-f8b9f01b2a9886c51df9
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, PositiveLC-MS/MSsplash10-001i-9000000000-ace0361476d939043e98
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, PositiveLC-MS/MSsplash10-001i-9000000000-5b06b6e9dcf9faf8e89c
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, PositiveLC-MS/MSsplash10-053r-9000000000-2894ef6d7f72ea71688e
LC-MS/MS Spectrum - CE-ESI-TOF (CE-system connected to 6210 Time-of-Flight MS, Agilent) , PositiveLC-MS/MSsplash10-0002-0900000000-290902f43cf851e8ef5e
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-001i-9300000000-f81193f6b50235ec8147
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-001i-9300000000-8931d2193adab166d5e4
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-0002-0900000000-b4825cc64fcb830c6967
1H NMR Spectrum1D NMRNot applicable
13C NMR Spectrum1D NMRNot applicable
1H NMR Spectrum1D NMRNot applicable
[1H,1H] 2D NMR Spectrum2D NMRNot applicable
[1H,13C] 2D NMR Spectrum2D NMRNot applicable

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
Medium-chain fatty acids / Amino fatty acids / Amino acids / Monocarboxylic acids and derivatives / Carboxylic acids / Organopnictogen compounds / Organic oxides / Monoalkylamines / Hydrocarbon derivatives / Carbonyl compounds
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
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
lysine, aspartate family amino acid, proteinogenic amino acid, L-alpha-amino acid (CHEBI:18019 ) / Common amino acids (C00047 )

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
L-ornithine transmembrane transporter activity
Specific Function
High-affinity, low capacity permease involved in the transport of the cationic amino acids (arginine, lysine and ornithine) in non-hepatic tissues. May also function as an ecotropic retroviral leuk...
Gene Name
SLC7A1
Uniprot ID
P30825
Uniprot Name
High affinity cationic amino acid transporter 1
Molecular Weight
67637.62 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Fernandez J, Lopez AB, Wang C, Mishra R, Zhou L, Yaman I, Snider MD, Hatzoglou M: Transcriptional control of the arginine/lysine transporter, cat-1, by physiological stress. J Biol Chem. 2003 Dec 12;278(50):50000-9. Epub 2003 Sep 30. [PubMed:14523001 ]
  4. Lopez AB, Wang C, Huang CC, Yaman I, Li Y, Chakravarty K, Johnson PF, Chiang CM, Snider MD, Wek RC, Hatzoglou M: A feedback transcriptional mechanism controls the level of the arginine/lysine transporter cat-1 during amino acid starvation. Biochem J. 2007 Feb 15;402(1):163-73. [PubMed:17042743 ]
  5. Nicholson B, Sawamura T, Masaki T, MacLeod CL: Increased Cat3-mediated cationic amino acid transport functionally compensates in Cat1 knockout cell lines. J Biol Chem. 1998 Jun 12;273(24):14663-6. [PubMed:9614060 ]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
L-ornithine transmembrane transporter activity
Specific Function
Involved in the transport of the cationic amino acids (arginine, lysine and ornithine).
Gene Name
SLC7A4
Uniprot ID
O43246
Uniprot Name
Cationic amino acid transporter 4
Molecular Weight
68267.17 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Rotoli BM, Bussolati O, Sala R, Gazzola GC, Dall'Asta V: The transport of cationic amino acids in human airway cells: expression of system y+L activity and transepithelial delivery of NOS inhibitors. FASEB J. 2005 May;19(7):810-2. Epub 2005 Mar 3. [PubMed:15746185 ]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
L-ornithine transmembrane transporter activity
Specific Function
Mediates the uptake of the cationic amino acids arginine, lysine and ornithine in a sodium-independent manner.
Gene Name
SLC7A3
Uniprot ID
Q8WY07
Uniprot Name
Cationic amino acid transporter 3
Molecular Weight
67168.31 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Hosokawa H, Sawamura T, Kobayashi S, Ninomiya H, Miwa S, Masaki T: Cloning and characterization of a brain-specific cationic amino acid transporter. J Biol Chem. 1997 Mar 28;272(13):8717-22. [PubMed:9079705 ]
  4. Humphrey BD, Stephensen CB, Calvert CC, Klasing KC: Lysine deficiency and feed restriction independently alter cationic amino acid transporter expression in chickens (Gallus gallus domesticus). Comp Biochem Physiol A Mol Integr Physiol. 2006 Feb;143(2):218-27. Epub 2006 Jan 10. [PubMed:16406639 ]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Low-affinity l-arginine transmembrane transporter activity
Specific Function
Functions as permease involved in the transport of the cationic amino acids (arginine, lysine and ornithine); the affinity for its substrates differs between isoforms created by alternative splicin...
Gene Name
SLC7A2
Uniprot ID
P52569
Uniprot Name
Cationic amino acid transporter 2
Molecular Weight
71672.175 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Low BC, Grigor MR: Angiotensin II stimulates system y+ and cationic amino acid transporter gene expression in cultured vascular smooth muscle cells. J Biol Chem. 1995 Nov 17;270(46):27577-83. [PubMed:7499219 ]
  4. Rotoli BM, Bussolati O, Sala R, Gazzola GC, Dall'Asta V: The transport of cationic amino acids in human airway cells: expression of system y+L activity and transepithelial delivery of NOS inhibitors. FASEB J. 2005 May;19(7):810-2. Epub 2005 Mar 3. [PubMed:15746185 ]
  5. Schwartz D, Schwartz IF, Gnessin E, Wollman Y, Chernichovsky T, Blum M, Iaina A: Differential regulation of glomerular arginine transporters (CAT-1 and CAT-2) in lipopolysaccharide-treated rats. Am J Physiol Renal Physiol. 2003 Apr;284(4):F788-95. Epub 2002 Dec 10. [PubMed:12475743 ]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Trna binding
Specific Function
Catalyzes the specific attachment of an amino acid to its cognate tRNA in a 2 step reaction: the amino acid (AA) is first activated by ATP to form AA-AMP and then transferred to the acceptor end of...
Gene Name
KARS
Uniprot ID
Q15046
Uniprot Name
Lysine--tRNA ligase
Molecular Weight
68047.54 Da
References
  1. Wu XR, Kenzior A, Willmot D, Scanlon S, Chen Z, Topin A, He SH, Acevedo A, Folk WR: Altered expression of plant lysyl tRNA synthetase promotes tRNA misacylation and translational recoding of lysine. Plant J. 2007 May;50(4):627-36. Epub 2007 Apr 8. [PubMed:17425721 ]
  2. Chou TF, Wagner CR: Lysyl-tRNA synthetase-generated lysyl-adenylate is a substrate for histidine triad nucleotide binding proteins. J Biol Chem. 2007 Feb 16;282(7):4719-27. Epub 2006 Dec 8. [PubMed:17158446 ]
  3. Kamenski P, Kolesnikova O, Jubenot V, Entelis N, Krasheninnikov IA, Martin RP, Tarassov I: Evidence for an adaptation mechanism of mitochondrial translation via tRNA import from the cytosol. Mol Cell. 2007 Jun 8;26(5):625-37. [PubMed:17560369 ]
  4. Kwon I, Wang P, Tirrell DA: Design of a bacterial host for site-specific incorporation of p-bromophenylalanine into recombinant proteins. J Am Chem Soc. 2006 Sep 13;128(36):11778-83. [PubMed:16953616 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Transporter activity
Specific Function
Sodium-independent transporter that mediates the update of aromatic acid. Can function as a net efflux pathway for aromatic amino acids in the basosolateral epithelial cells (By similarity).
Gene Name
SLC16A10
Uniprot ID
Q8TF71
Uniprot Name
Monocarboxylate transporter 10
Molecular Weight
55492.07 Da
References
  1. Kim DK, Kanai Y, Chairoungdua A, Matsuo H, Cha SH, Endou H: Expression cloning of a Na+-independent aromatic amino acid transporter with structural similarity to H+/monocarboxylate transporters. J Biol Chem. 2001 May 18;276(20):17221-8. Epub 2001 Feb 20. [PubMed:11278508 ]
  2. Kim DK, Kanai Y, Matsuo H, Kim JY, Chairoungdua A, Kobayashi Y, Enomoto A, Cha SH, Goya T, Endou H: The human T-type amino acid transporter-1: characterization, gene organization, and chromosomal location. Genomics. 2002 Jan;79(1):95-103. [PubMed:11827462 ]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Symporter activity
Specific Function
Sodium-ion dependent, low affinity carnitine transporter. Probably transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without...
Gene Name
SLC22A4
Uniprot ID
Q9H015
Uniprot Name
Solute carrier family 22 member 4
Molecular Weight
62154.48 Da
References
  1. Yabuuchi H, Tamai I, Nezu J, Sakamoto K, Oku A, Shimane M, Sai Y, Tsuji A: Novel membrane transporter OCTN1 mediates multispecific, bidirectional, and pH-dependent transport of organic cations. J Pharmacol Exp Ther. 1999 May;289(2):768-73. [PubMed:10215651 ]
Drug created on June 13, 2005 07:24 / Updated on September 01, 2017 10:23