Identification

Name
L-Lysine
Accession Number
DB00123
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 acts as a site for hydrogen binding and 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.

Type
Small Molecule
Groups
Approved, Nutraceutical
Structure
Thumb
Weight
Average: 146.1876
Monoisotopic: 146.105527702
Chemical Formula
C6H14N2O2
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

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.

Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More
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 AvailableHumans
UCationic amino acid transporter 4Not AvailableHumans
UCationic amino acid transporter 3Not AvailableHumans
ULow affinity cationic amino acid transporter 2Not AvailableHumans
ULysine--tRNA ligaseNot AvailableHumans
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
Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Biotin MetabolismMetabolic
2-Aminoadipic 2-Oxoadipic AciduriaDisease
Lysine DegradationMetabolic
Hyperlysinemia II or SaccharopinuriaDisease
Multiple Carboxylase Deficiency, Neonatal or Early Onset FormDisease
Pyridoxine Dependency with SeizuresDisease
Biotinidase DeficiencyDisease
Glutaric Aciduria Type IDisease
Saccharopinuria/Hyperlysinemia IIDisease
Carnitine SynthesisMetabolic
Hyperlysinemia I, FamilialDisease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
No interactions found.

Products

Product Ingredients
IngredientUNIICASInChI Key
L-Lysine acetateTTL6G7LIWZ57282-49-2RRNJROHIFSLGRA-JEDNCBNOSA-N
L-Lysine hydrochlorideJNJ23Q2COM657-27-2BVHLGVCQOALMSV-JEDNCBNOSA-N
L-Lysine monohydrateF7625B974U39665-12-8HZRUTVAFDWTKGD-JEDNCBNOSA-N
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
2.5% Travasol Amino Acid Injection With Electrolytes In 10% DextroseL-Lysine (145 mg) + Alanine (520 mg) + Arginine (290 mg) + Dextrose, unspecified form (10 g) + Dipotassium phosphate (130.5 mg) + Glycine (260 mg) + Histidine (120 mg) + Isoleucine (150 mg) + Leucine (182.5 mg) + Magnesium chloride (25.5 mg) + Methionine (100 mg) + Phenylalanine (140 mg) + Proline (170 mg) + Serine (125 mg) + Sodium acetate (170 mg) + Sodium chloride (29.3 mg) + Threonine (105 mg) + Tryptophan (45 mg) + Tyrosine (10 mg) + Valine (145 mg)SolutionIntravenousBaxter Corporation Clintec Nutrition Division1996-12-312015-08-05Canada flag
2.5% Travasol Amino Acid Injection With Electrolytes In 10% Dextrose ClinimixL-Lysine hydrochloride (145 mg) + Alanine (520 mg) + Arginine (260 mg) + Dextrose, unspecified form (10 g) + Dipotassium phosphate (130.5 mg) + Glycine (520 mg) + Histidine (110 mg) + Isoleucine (120 mg) + L-Leucine hydrochloride (155 mg) + Magnesium chloride (25.5 mg) + Methionine (145 mg) + Phenylalanine hydrochloride (155 mg) + Proline (105 mg) + Sodium acetate (170 mg) + Sodium chloride (29.3 mg) + Threonine (105 mg) + Tryptophan (45 mg) + Tyrosine (10 mg) + Valine (115 mg)SolutionIntravenousBaxter Corporation Clintec Nutrition Division1993-12-312015-08-05Canada flag
2.5% Travasol Amino Acid Injection Without Electrolytes In 10% Dextrose QuickmixL-Lysine hydrochloride (195 mg) + Alanine (520 mg) + Arginine (260 mg) + Dextrose, unspecified form (10 g) + Glycine (520 mg) + Histidine (110 mg) + Isoleucine (120 mg) + L-Leucine hydrochloride (155 mg) + Methionine (195 mg) + Phenylalanine hydrochloride (155 mg) + Proline (105 mg) + Threonine (105 mg) + Tryptophan (45 mg) + Tyrosine (10 mg) + Valine (115 mg)SolutionIntravenousBaxter Corporation Clintec Nutrition Division1995-12-312007-08-02Canada flag
2.5%travasol Amino Acid InJ.W.eleC.W.25%dexL-Lysine (145 mg) + Alanine (520 mg) + Arginine (290 mg) + Dextrose, unspecified form (25 g) + Dipotassium phosphate (130.5 mg) + Glycine (260 mg) + Histidine (120 mg) + Isoleucine (150 mg) + Leucine (182.5 mg) + Magnesium chloride (25.5 mg) + Methionine (100 mg) + Phenylalanine (140 mg) + Proline (170 mg) + Serine (125 mg) + Sodium acetate (170 mg) + Sodium chloride (29.3 mg) + Threonine (105 mg) + Tryptophan (45 mg) + Tyrosine (10 mg) + Valine (145 mg)LiquidIntravenousClintec Nutrition Company1996-07-301998-08-13Canada flag
2.75% Travas. Amino Acid InJ.W.elecw.25%dexL-Lysine (159.5 mg) + Alanine (570 mg) + Arginine (316 mg) + Dextrose, unspecified form (25 g) + Dipotassium phosphate (261 mg) + Glycine (283 mg) + Histidine (132 mg) + Isoleucine (165 mg) + Leucine (201 mg) + Magnesium chloride (51 mg) + Methionine (110 mg) + Phenylalanine (154 mg) + Proline (187 mg) + Serine (137.5 mg) + Sodium acetate (215.5 mg) + Sodium chloride (112 mg) + Threonine (115.5 mg) + Tryptophan (49.5 mg) + Tyrosine (11 mg) + Valine (159.5 mg)LiquidIntravenousClintec Nutrition Company1996-07-301998-08-13Canada flag
2.75% Travasol Amino Acid Injection With Electrolytes In 25% Dextrose QuickmixL-Lysine hydrochloride (159 mg) + Alanine (570 mg) + Arginine (285 mg) + Dextrose, unspecified form (25 g) + Dipotassium phosphate (261 mg) + Glycine (570 mg) + Histidine (120.5 mg) + Isoleucine (131.5 mg) + L-Leucine hydrochloride (170 mg) + Magnesium chloride (51 mg) + Methionine (159 mg) + Phenylalanine hydrochloride (170 mg) + Proline (115 mg) + Sodium acetate (215.5 mg) + Sodium chloride (112 mg) + Threonine (115 mg) + Tryptophan (49.5 mg) + Tyrosine (11 mg) + Valine (126 mg)SolutionIntravenousBaxter Corporation Clintec Nutrition Division1996-02-022007-08-02Canada flag
2.75% Travasol Amino Acid Injection With Electrolytes In 5% Dextrose QuickmixL-Lysine hydrochloride (159 mg) + Alanine (570 mg) + Arginine (285 mg) + Dextrose, unspecified form (5 g) + Dipotassium phosphate (215.5 mg) + Glycine (570 mg) + Histidine (120.5 mg) + Isoleucine (131.5 mg) + L-Leucine hydrochloride (170 mg) + Magnesium chloride (51 mg) + Methionine (159 mg) + Phenylalanine hydrochloride (170 mg) + Proline (115 mg) + Sodium acetate (256 mg) + Sodium chloride (112 mg) + Threonine (115 mg) + Tryptophan (49.5 mg) + Tyrosine (11 mg) + Valine (126 mg)SolutionIntravenousBaxter Corporation Clintec Nutrition Division1993-12-312007-08-02Canada flag
2.75%travasol Amino Acid InJ.W.eleC.W.5%dex.L-Lysine (159.5 mg) + Alanine (570 mg) + Arginine (316 mg) + Dextrose, unspecified form (5 g) + Dipotassium phosphate (261 mg) + Glycine (283 mg) + Histidine (132 mg) + Isoleucine (165 mg) + Leucine (201 mg) + Magnesium chloride (51 mg) + Methionine (110 mg) + Phenylalanine (154 mg) + Proline (187 mg) + Serine (137.5 mg) + Sodium acetate (215 mg) + Sodium chloride (112 mg) + Threonine (115.5 mg) + Tryptophan (49.5 mg) + Tyrosine (11 mg) + Valine (159.5 mg)LiquidIntravenousClintec Nutrition Company1996-12-311999-08-10Canada flag
20% ProsolL-Lysine (1.35 g) + Alanine (2.76 g) + Arginine (1.96 g) + Aspartic acid (0.6 g) + D-Methionine (0.76 g) + Glutamic acid (1.02 g) + Glycine (2.06 g) + Histidine (1.18 g) + Isoleucine (1.08 g) + Leucine (1.08 g) + Methionine (0.76 g) + Phenylalanine (1 g) + Proline (1.34 g) + Serine (1.02 g) + Threonine (0.98 g) + Tryptophan (0.32 g) + Tyrosine (0.05 g) + Valine (1.44 g)LiquidIntravenousBaxter Laboratories1996-10-09Not applicableCanada flag
4.25% Amino Acid Injection Without Electrolytes In 20% Dextrose QuickmixL-Lysine hydrochloride (246 mg) + Alanine (880 mg) + Arginine (440 mg) + Dextrose, unspecified form (20 g) + Glycine (880 mg) + Histidine (186 mg) + Isoleucine (203 mg) + L-Leucine hydrochloride (263 mg) + Methionine (246 mg) + Phenylalanine hydrochloride (263 mg) + Proline (178 mg) + Threonine (178 mg) + Tryptophan (76 mg) + Tyrosine (17 mg) + Valine (195 mg)SolutionIntravenousBaxter Corporation Clintec Nutrition Division1995-12-312007-08-02Canada flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
ClinimixL-Lysine (2.00 g/1L) + Alanine (5.70 g/1L) + Arginine (3.17 g/1L) + Calcium chloride dihydrate (0.33 g/1L) + D-glucose monohydrate (100.00 g/1L) + Dipotassium phosphate (2.61 g/1L) + Glycine (2.84 g/1L) + Histidine (1.32 g/1L) + Isoleucine (1.65 g/1L) + Leucine (2.01 g/1L) + Magnesium chloride hexahydrate (0.51 g/1L) + Methionine (1.10 g/1L) + Phenylalanine (1.54 g/1L) + Proline (1.87 g/1L) + Serine (1.38 g/1L) + Sodium acetate trihydrate (2.16 g/1L) + Sodium chloride (1.12 g/1L) + Threonine (1.16 g/1L) + Tryptophan (0.50 g/1L) + Tyrosine (0.11 g/1L) + Valine (1.60 g/1L)SolutionIntravenousBaxter Healthcare Corporation2017-10-252019-11-30US flag
ClinimixL-Lysine (4.93 g/2L) + Alanine (17.60 g/2L) + Arginine (9.78 g/2L) + Calcium chloride dihydrate (0.66 g/2L) + D-glucose monohydrate (300.00 g/2L) + Dipotassium phosphate (5.22 g/2L) + Glycine (8.76 g/2L) + Histidine (4.08 g/2L) + Isoleucine (5.10 g/2L) + Leucine (6.20 g/2L) + Magnesium chloride hexahydrate (1.02 g/2L) + Methionine (3.40 g/2L) + Phenylalanine (4.76 g/2L) + Proline (5.78 g/2L) + Serine (4.25 g/2L) + Sodium acetate trihydrate (5.94 g/2L) + Sodium chloride (1.54 g/2L) + Threonine (3.57 g/2L) + Tryptophan (1.53 g/2L) + Tyrosine (0.34 g/2L) + Valine (4.93 g/2L)SolutionIntravenousBaxter Healthcare Corporation2017-10-252019-11-30US flag
ClinimixL-Lysine (2.00 g/1L) + Alanine (5.70 g/1L) + Arginine (3.17 g/1L) + Calcium chloride dihydrate (0.33 g/1L) + D-glucose monohydrate (75.00 g/1L) + Dipotassium phosphate (2.61 g/1L) + Glycine (2.84 g/1L) + Histidine (1.32 g/1L) + Isoleucine (1.65 g/1L) + Leucine (2.01 g/1L) + Magnesium chloride hexahydrate (0.51 g/1L) + Methionine (1.10 g/1L) + Phenylalanine (1.54 g/1L) + Proline (1.87 g/1L) + Serine (1.38 g/1L) + Sodium acetate trihydrate (2.16 g/1L) + Sodium chloride (1.12 g/1L) + Threonine (1.16 g/1L) + Tryptophan (0.50 g/1L) + Tyrosine (0.11 g/1L) + Valine (1.60 g/1L)SolutionIntravenousBaxter Healthcare Corporation2017-10-252019-11-30US flag
Effervescent Potassium ChlorideL-Lysine hydrochloride (1.5 g/1) + Potassium bicarbonate (0.7 g/1) + Potassium chloride (1.25 g/1)Tablet, effervescentOralQualitest2006-01-062021-07-31US flag
PrimeneL-Lysine (2.75 g/250mL) + Alanine (2 g/250mL) + Arginine (2.1 g/250mL) + Aspartic acid (1.5 g/250mL) + Cysteine (0.47 g/250mL) + Glutamic acid (2.5 g/250mL) + Glycine (1 g/250mL) + Histidine (0.95 g/250mL) + Isoleucine (1.675 g/250mL) + Leucine (2.5 g/250mL) + Methionine (0.6 g/250mL) + Ornithine hydrochloride (0.8 g/250mL) + Phenylalanine (1.05 g/250mL) + Proline (0.75 g/250mL) + Serine (1 g/250mL) + Taurine (0.15 g/250mL) + Threonine (0.9 g/250mL) + Tryptophan (0.5 g/250mL) + Tyrosine (0.11 g/250mL) + Valine (1.9 g/250mL)Injection, solutionIntravenousBaxter Healthcare Corporation2017-11-222019-05-31US flag
SynthaminL-Lysine (5.80 g/1000mL) + Alanine (20.70 g/1000mL) + Arginine (11.50 g/1000mL) + Glycine (10.30 g/1000mL) + Histidine (4.80 g/1000mL) + Isoleucine (6 g/1000mL) + Leucine (7.30 g/1000mL) + Methionine (4 g/1000mL) + Phenylalanine (5.60 g/1000mL) + Proline (6.80 g/1000mL) + Serine (5 g/1000mL) + Threonine (4.20 g/1000mL) + Tryptophan (1.80 g/1000mL) + Tyrosine (400 mg/1000mL) + Valine (5.80 g/1000mL)Injection, solutionIntravenousBaxter Healthcare Corporation2017-11-032020-06-30US flag

Categories

ATC Codes
V03AF11 — Arginine and lysineB05XB03 — Lysine
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Aliphatic acyclic compound / Amine / Amino acid / Amino fatty acid / Carbonyl group / Carboxylic acid / Fatty acid / Fatty acyl / Hydrocarbon derivative / L-alpha-amino acid
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)

Chemical Identifiers

UNII
K3Z4F929H6
CAS number
56-87-1
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

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]
Human Metabolome Database
HMDB0003405
KEGG Drug
D02304
KEGG Compound
C00047
PubChem Compound
5962
PubChem Substance
46504770
ChemSpider
5747
BindingDB
217367
RxNav
6536
ChEBI
18019
ChEMBL
CHEMBL8085
ZINC
ZINC000001532522
PharmGKB
PA450280
PDBe Ligand
LYS
PDRhealth
PDRhealth Drug Page
Wikipedia
Lysine
MSDS
Download (73.3 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingTreatmentIllness, Critical / Starvation1
4Not Yet RecruitingOtherGastroenteropancreatic Neuroendocrine Tumors1
4TerminatedSupportive CareCancer-related Malnutrition1
4TerminatedSupportive CareIllness, Critical1
4TerminatedSupportive CareParenteral Nutrition (No Primary Condition Studied)1
4WithdrawnSupportive CareMalnutrition1
3CompletedTreatmentGeneral Surgery / Parenteral Feeding1
3CompletedTreatmentGeneral Surgery / Parenteral Nutrition1
3CompletedTreatmentIllness, Critical1
3CompletedTreatmentInfant, Low Birth Weight / Infant, Small for Gestational Age / Infants, Premature / Newborn Infants / Sepsis1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Basic Organics
  • CVS Pharmacy
  • Gilead Sciences Inc.
  • Longs Drug Store
  • Lundbeck Inc.
  • Marlex Pharmaceuticals
  • Medisca Inc.
  • Rite Aid Corp.
  • Rugby Laboratories
  • Walgreen Co.
Dosage Forms
FormRouteStrength
LiquidIntravenous
SolutionIntravenous0.25 g/mL
TabletOral45 mg
Injection, solutionIntravenous2.5 g/500mL
SolutionIntravenous2.453 g
Solution, concentrateIntravenous5 g
SolutionIntravenous10.4 g/L
Injection, solutionIntravenous
SolutionIntravenous5 g
SolutionIntravenous4.15 g
SolutionIntravenous1.566 g
Granule, for solutionOral216.2 mg/2.5g
SolutionIntraperitoneal951 mg/L
Tablet, coatedOral2 mg
Syrup2 mg/5mL
Tablet, effervescentOral
SolutionIntravenous0.69 %
SolutionIntravenous0.59 %
SolutionIntravenous1.03 g
Injection, emulsionIntravenous
InjectionIntravenous110 g
InjectionIntravenous165 g
InjectionIntravenous220 g
InjectionIntravenous275 g
InjectionIntravenous107 g
InjectionIntravenous143 g
InjectionIntravenous178 g
Injection, solutionIntravenous25 G
Injection, solutionIntravenous600 mg/200mL
Solution16 g/L
Injection, solution, concentrateIntravenous
EmulsionIntravenous1.83 g
InjectionIntravenous1.03 g
Injection, emulsionIntravenous1.6 g/100mL
Injection, emulsion; injection, solutionIntravenous3.2 g/100mL
EmulsionIntravenous20 mg
EmulsionIntravenous16 g
LiquidHemodialysis
SolutionIntraperitoneal510 mg/l
Injection, emulsionIntravenous1.6 g
InjectionIntravenous2.27 g/l
InjectionIntravenous4.12 g/l
EmulsionIntravenous4 g
SolutionIntravenous7.14 g
SolutionIntravenous9.52 g
SolutionIntravenous11.9 g
EmulsionIntravenous6.41 g
EmulsionIntravenous9.61 g
EmulsionIntravenous12.82 g
SolutionIntravenous8.24 g
SolutionIntravenous12.36 g
SolutionIntravenous16.48 g
EmulsionIntravenous
EmulsionIntravenous3 g
Injection, solutionIntravenous0.69 %
Injection, solutionIntravenous0.59 %
Injection, solutionIntravenous0.9 %
Injection, solutionIntravenous0.56 %
Injection, solutionIntravenous0.49 %
Injection, solutionIntravenous0.76 %
Syrup5 mg/5mL
Syrup5 mg/100mL
SolutionIntravenous
Solution3.2 g/100mL
Solution1.6 g/100mL
InjectionIntravenous0.67 g/100ml
SolutionParenteral3 g/100ml
EmulsionParenteral50 g
Syrup100 iu/5mL
Injection, solutionIntravenous0.76 g/100mL
InjectionIntravenous
SolutionIntravenous434 mg
SolutionIntravenous594 mg
SolutionIntravenous12 g/L
SolutionIntravenous16 g/L
SolutionIntravenous5.1 g/16g N
Syrup20 mg/5mL
CapsuleOral
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
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-003r-8900000000-470a0beb4f338ed89bca
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-001i-9000000000-74e9193d9d33c2509bfa
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
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
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0002-0900000000-a997e809874357908880
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0002-2900000000-c4ff775e954fa48b2c19
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-014m-9200000000-33a38e6370811c5ddc82
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0006-9000000000-3a8b0b6e62f5c66d3720
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0006-9000000000-d5167570d11d77fd541e
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0002-0900000000-b4825cc64fcb830c6967
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0002-0900000000-a46231bd529176101129
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-001i-9200000000-f8b9f01b2a9886c51df9
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-001i-9000000000-ace0361476d939043e98
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-001i-9000000000-5b06b6e9dcf9faf8e89c
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-053r-9000000000-2894ef6d7f72ea71688e
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-001i-9300000000-6fee0965bd2d3966d3ce
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-001i-9000000000-035035ecfa084671479b
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-001i-0900000000-5bb15839f86f4fca0d0b
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-001i-0900000000-6c8ef03aa83eb1cab35b
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-001i-0900000000-41e1a6499097748934b0
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-001i-9300000000-f81193f6b50235ec8147
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-001i-9300000000-8931d2193adab166d5e4
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

Targets

Kind
Protein
Organism
Humans
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
Humans
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
Humans
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
Humans
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
Humans
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
Humans
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
Humans
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 August 21, 2020 13:37

Logo pink
Are you a
new drug developer?
Contact us to learn more about our customized products and solutions.
Logo pink
Stay in the know!
As part of our commitment to providing the most up-to-date drug information, we will be releasing #DrugBankUpdates with our newly added curated drug pages.
#DrugBankUpdates