lanthionine ketimine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

lanthionine ketimine: structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

lanthionine ketimine : A member of the class of 1,4-thiazines that is 3,6-dihydro-2H-1,4-thiazine substituted by carboxy groups at positions 3 and 5. It is a natural but non-proteogenic amino acid found in human urine and brain. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID Source	ID
PubMed CID	134340
CHEBI ID	89479
SCHEMBL ID	13438654
MeSH ID	M0108739

Synonyms (10)

Synonym
yf5l3mw7rm ,
unii-yf5l3mw7rm
lanthionine ketimine
2h-1,4-thiazine-3,5-dicarboxylic acid, 3,6-dihydro-
83711-67-5
3,6-dihydro-2h-1,4-thiazine-3,5-dicarboxylic acid
SCHEMBL13438654
CHEBI:89479
Q6487610
DTXSID801003724

Research Excerpts

Overview

Lanthionine ketimine (LK) is a natural sulfur amino acid metabolite with potent neurotrophic activity. It binds to collapsin response mediator protein-2 (CRMP2), an abundant brain protein that interacts with multiple partners to regulate microtubule dynamics, neurite growth and retraction.

Excerpt	Reference	Relevance
"Lanthionine ketimine (LK) is a natural sulfur amino acid metabolite with potent neurotrophic activity. "	( Lanthionine ketimine ethyl ester partially rescues neurodevelopmental defects in unc-33 (DPYSL2/CRMP2) mutants. Baxter, T; Benda, E; Hardin, T; Hensley, K; Holgado, AM; Hubbard, C; O'Brien, S; St John, E, 2013)	3.28
"Lanthionine ketimine (LK) is a natural sulfur amino acid metabolite which binds to collapsin response mediator protein-2 (CRMP2), an abundant brain protein that interacts with multiple partners to regulate microtubule dynamics, neurite growth and retraction, axonal transport, and neurotransmitter release. "	( Lanthionine ketimine ester provides benefit in a mouse model of multiple sclerosis. Dupree, JL; Feinstein, DL; Hensley, K; Pelligrino, D; Polak, PE, 2015)	3.3
"Lanthionine ketimine (LK) is a natural brain sulfur amino acid metabolite with demonstrated anti-neuroinflammatory and neurotrophic activities."	( Lanthionine ketimine ester promotes locomotor recovery after spinal cord injury by reducing neuroinflammation and promoting axon growth. Hensley, K; Kotaka, K; Nagai, J; Ohshima, T, 2017)	2.62

Treatment

Excerpt	Reference	Relevance
"Lanthionine ketimine ester treatment substantially diminished cognitive decline and brain amyloid-β (Aβ) peptide deposition and phospho-Tau accumulation in 3 × Tg-AD mice and also reduced the density of Iba1-positive microglia."	( A derivative of the brain metabolite lanthionine ketimine improves cognition and diminishes pathology in the 3 × Tg-AD mouse model of Alzheimer disease. Eslami, P; Gabbita, SP; Harris-White, ME; Hensley, K; Hristov, A; Johnson, MF; Venkova, K, 2013)	1.38

Bioavailability

Excerpt	Reference	Relevance
" An ultrahigh-pressure liquid chromatography/tandem mass spectrometry (UHPLC/MS/MS) assay was developed to evaluate bioavailability by measuring these compounds in mouse serum, whole blood and brain tissue."	( Analysis of lanthionine ketimine ethyl ester in mouse serum, whole blood and tissues using ultrahigh-pressure liquid chromatography/tandem mass spectrometry. Feinstein, DL; Hensley, K; Kowal, KE; Muchiri, RN; van Breemen, RB, 2018)	0.86
" This method is suitable for bioavailability and pharmacokinetic studies."	( Analysis of lanthionine ketimine ethyl ester in mouse serum, whole blood and tissues using ultrahigh-pressure liquid chromatography/tandem mass spectrometry. Feinstein, DL; Hensley, K; Kowal, KE; Muchiri, RN; van Breemen, RB, 2018)	0.86

[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (3)

Role	Description
human urinary metabolite	Any metabolite (endogenous or exogenous) found in human urine samples.
anti-inflammatory agent	Any compound that has anti-inflammatory effects.
neuroprotective agent	Any compound that can be used for the treatment of neurodegenerative disorders.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (3)

Class	Description
1,4-thiazine
dicarboxylic acid	Any carboxylic acid containing two carboxy groups.
sulfur-containing amino acid
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Research

Studies (27)

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	6 (22.22)	18.7374
1990's	5 (18.52)	18.2507
2000's	0 (0.00)	29.6817
2010's	13 (48.15)	24.3611
2020's	3 (11.11)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 24.90

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

Metric	This Compound (vs All)
Research Demand Index	24.90 (24.57)
Research Supply Index	3.40 (2.92)
Research Growth Index	5.94 (4.65)
Search Engine Demand Index	17.79 (26.88)
Search Engine Supply Index	2.00 (0.95)

This Compound (24.90)

All Compounds (24.57)

Study Types

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	1 (3.45%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	28 (96.55%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
ammonium hydroxide azane : Saturated acyclic nitrogen hydrides having the general formula NnHn+2.	1.97	1	azane; gas molecular entity; mononuclear parent hydride	EC 3.5.1.4 (amidase) inhibitor; metabolite; mouse metabolite; neurotoxin; NMR chemical shift reference compound; nucleophilic reagent; refrigerant
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine 1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine: A dopaminergic neurotoxic compound which produces irreversible clinical, chemical, and pathological alterations that mimic those found in Parkinson disease.. 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine : A tetrahydropyridine that is 1,2,3,6-tetrahydropyridine substituted by a methyl group at position 1 and a phenyl group at position 4.	2.25	1	methylpyridines; phenylpyridine; tetrahydropyridine	neurotoxin
tyrosine Tyrosine: A non-essential amino acid. In animals it is synthesized from PHENYLALANINE. It is also the precursor of EPINEPHRINE; THYROID HORMONES; and melanin.. tyrosine : An alpha-amino acid that is phenylalanine bearing a hydroxy substituent at position 4 on the phenyl ring.	1.99	1	amino acid zwitterion; erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid; proteinogenic amino acid; tyrosine	EC 1.3.1.43 (arogenate dehydrogenase) inhibitor; fundamental metabolite; micronutrient; nutraceutical
tert-butylhydroperoxide tert-Butylhydroperoxide: A direct-acting oxidative stress-inducing agent used to examine the effects of oxidant stress on Ca(2+)-dependent signal transduction in vascular endothelial cells. It is also used as a catalyst in polymerization reactions and to introduce peroxy groups into organic molecules.. tert-butyl hydroperoxide : An alkyl hydroperoxide in which the alkyl group is tert-butyl. It is widely used in a variety of oxidation processes.	2.07	1	alkyl hydroperoxide	antibacterial agent; oxidising agent
phenylisothiocyanate phenylisothiocyanate: structure. phenyl isothiocyanate : An isothiocyanate having a phenyl group attached to the nitrogen; used for amino acid sequencing in the Edman degradation.	2.37	2	isothiocyanate	allergen; reagent
3-((3-cholamidopropyl)dimethylammonium)-1-propanesulfonate 3-((3-cholamidopropyl)dimethylammonium)-1-propanesulfonate: a surfactant; structure given in first source	1.99	1	1,1-diunsubstituted alkanesulfonate
cystathionine ketimine cystathionine ketimine: structure given in first source. cystathionine ketimine : A 1-thia-4-azacyclohepta-3-ene-3,5-dicarboxylic acid that has R-configuration. It is cyclic sulfur-containing imino acid detected in bovine brain extracts.	7.89	4	1-thia-4-azacyclohepta-3-ene-3,5-dicarboxylic acid; sulfur-containing amino acid	human urinary metabolite; mammalian metabolite; rat metabolite; reactive oxygen species generator
thialysine ketimine thialysine ketimine: structure given in first source	3.06	5	1,4-thiazine; thiomorpholinemonocarboxylic acid
n-formylmethionine leucyl-phenylalanine N-Formylmethionine Leucyl-Phenylalanine: A formylated tripeptide originally isolated from bacterial filtrates that is positively chemotactic to polymorphonuclear leucocytes, and causes them to release lysosomal enzymes and become metabolically activated.. N-formyl-L-methionyl-L-leucyl-L-phenylalanine : A tripeptide composed of L-Met, L-Leu and L-Phe in a linear sequence with a formyl group at the amino terminus. It acts as a potent inducer of leucocyte chemotaxis and macrophage activator as well as a ligand for the FPR receptor.	1.99	1	tripeptide
myelin basic protein Myelin Basic Protein: An abundant cytosolic protein that plays a critical role in the structure of multilamellar myelin. Myelin basic protein binds to the cytosolic sides of myelin cell membranes and causes a tight adhesion between opposing cell membranes.	2.05	1
genistein [no description available]	1.99	1	7-hydroxyisoflavones	antineoplastic agent; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; geroprotector; human urinary metabolite; phytoestrogen; plant metabolite; tyrosine kinase inhibitor
sirolimus Sirolimus: A macrolide compound obtained from Streptomyces hygroscopicus that acts by selectively blocking the transcriptional activation of cytokines thereby inhibiting cytokine production. It is bioactive only when bound to IMMUNOPHILINS. Sirolimus is a potent immunosuppressant and possesses both antifungal and antineoplastic properties.. sirolimus : A macrolide lactam isolated from Streptomyces hygroscopicus consisting of a 29-membered ring containing 4 trans double bonds, three of which are conjugated. It is an antibiotic, immunosupressive and antineoplastic agent.	2.11	1	antibiotic antifungal drug; cyclic acetal; cyclic ketone; ether; macrolide lactam; organic heterotricyclic compound; secondary alcohol	antibacterial drug; anticoronaviral agent; antineoplastic agent; bacterial metabolite; geroprotector; immunosuppressive agent; mTOR inhibitor
sulfur Sulfur: An element that is a member of the chalcogen family. It has an atomic symbol S, atomic number 16, and atomic weight [32.059; 32.076]. It is found in the amino acids cysteine and methionine.	1.96	1	chalcogen; nonmetal atom	macronutrient
bafilomycin a1 bafilomycin A1: from Streptomyces griseus; structure given in first source. bafilomycin A1 : The most used of the bafilomycins, a family of toxic macrolide antibiotics derived from Streptomyces griseus.	2.17	1	cyclic hemiketal; macrolide antibiotic; oxanes	apoptosis inducer; autophagy inhibitor; bacterial metabolite; EC 3.6.3.10 (H(+)/K(+)-exchanging ATPase) inhibitor; EC 3.6.3.14 (H(+)-transporting two-sector ATPase) inhibitor; ferroptosis inhibitor; fungicide; potassium ionophore; toxin
1,4-thiomorpholine-3,5-dicarboxylic acid 1,4-thiomorpholine-3,5-dicarboxylic acid: cyclic imino acid from bovine brain; structure given in first source	6.97	1	dicarboxylic acid; sulfur-containing carboxylic acid; thiomorpholines
cystathionine Cystathionine: Sulfur-containing amino acid formed as an intermediate in the conversion of METHIONINE to CYSTEINE.. cystathionine : A modified amino acid generated by enzymic means from homocysteine and serine.	2.89	4	cysteine derivative
alpha-synuclein alpha-Synuclein: A synuclein that is a major component of LEWY BODIES and plays a role in SYNUCLEINOPATHIES, neurodegeneration and neuroprotection.	2.41	1
okadaic acid Okadaic Acid: A specific inhibitor of phosphoserine/threonine protein phosphatase 1 and 2a. It is also a potent tumor promoter. It is produced by DINOFLAGELLATES and causes diarrhetic SHELLFISH POISONING.. okadaic acid : A polycyclic ether that is produced by several species of dinoflagellates, and is known to accumulate in both marine sponges and shellfish. A polyketide, polyether derivative of a C38 fatty acid, it is one of the primary causes of diarrhetic shellfish poisoning (DSP). It is a potent inhibitor of specific protein phosphatases and is known to have a variety of negative effects on cells.	7.17	1	ketal

Condition	Relationship Strength	Studies
a-Synucleinopathies [description not available]	2.41	1
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	3.4	6
Idiopathic Parkinson Disease [description not available]	2.25	1
Parkinson Disease A progressive, degenerative neurologic disease characterized by a TREMOR that is maximal at rest, retropulsion (i.e. a tendency to fall backwards), rigidity, stooped posture, slowness of voluntary movements, and a masklike facial expression. Pathologic features include loss of melanin containing neurons in the substantia nigra and other pigmented nuclei of the brainstem. LEWY BODIES are present in the substantia nigra and locus coeruleus but may also be found in a related condition (LEWY BODY DISEASE, DIFFUSE) characterized by dementia in combination with varying degrees of parkinsonism. (Adams et al., Principles of Neurology, 6th ed, p1059, pp1067-75)	2.25	1
Acute Confusional Senile Dementia [description not available]	2.52	2
Alzheimer Disease A degenerative disease of the BRAIN characterized by the insidious onset of DEMENTIA. Impairment of MEMORY, judgment, attention span, and problem solving skills are followed by severe APRAXIAS and a global loss of cognitive abilities. The condition primarily occurs after age 60, and is marked pathologically by severe cortical atrophy and the triad of SENILE PLAQUES; NEUROFIBRILLARY TANGLES; and NEUROPIL THREADS. (From Adams et al., Principles of Neurology, 6th ed, pp1049-57)	7.52	2
Pregnancy The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.	2.21	1
Brain Disorders [description not available]	2.08	1
Child Development Deviations [description not available]	2.08	1
Brain Diseases Pathologic conditions affecting the BRAIN, which is composed of the intracranial components of the CENTRAL NERVOUS SYSTEM. This includes (but is not limited to) the CEREBRAL CORTEX; intracranial white matter; BASAL GANGLIA; THALAMUS; HYPOTHALAMUS; BRAIN STEM; and CEREBELLUM.	2.08	1
Developmental Disabilities Disorders in which there is a delay in development based on that expected for a given age level or stage of development. These impairments or disabilities originate before age 18, may be expected to continue indefinitely, and constitute a substantial impairment. Biological and nonbiological factors are involved in these disorders. (From American Psychiatric Glossary, 6th ed)	2.08	1
Allergic Encephalomyelitis [description not available]	2.11	1
Nerve Degeneration Loss of functional activity and trophic degeneration of nerve axons and their terminal arborizations following the destruction of their cells of origin or interruption of their continuity with these cells. The pathology is characteristic of neurodegenerative diseases. Often the process of nerve degeneration is studied in research on neuroanatomical localization and correlation of the neurophysiology of neural pathways.	2.11	1
Axonal Injury, Diffuse [description not available]	2.13	1
Innate Inflammatory Response [description not available]	2.15	1
Injuries, Spinal Cord [description not available]	2.15	1
Inflammation A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.	7.15	1
Spinal Cord Injuries Penetrating and non-penetrating injuries to the spinal cord resulting from traumatic external forces (e.g., WOUNDS, GUNSHOT; WHIPLASH INJURIES; etc.).	2.15	1
Cerebral Infarction, Middle Cerebral Artery [description not available]	2.07	1
Brain Damage, Chronic A condition characterized by long-standing brain dysfunction or damage, usually of three months duration or longer. Potential etiologies include BRAIN INFARCTION; certain NEURODEGENERATIVE DISORDERS; CRANIOCEREBRAL TRAUMA; ANOXIA, BRAIN; ENCEPHALITIS; certain NEUROTOXICITY SYNDROMES; metabolic disorders (see BRAIN DISEASES, METABOLIC); and other conditions.	2.07	1
Infarction, Middle Cerebral Artery NECROSIS occurring in the MIDDLE CEREBRAL ARTERY distribution system which brings blood to the entire lateral aspects of each CEREBRAL HEMISPHERE. Clinical signs include impaired cognition; APHASIA; AGRAPHIA; weak and numbness in the face and arms, contralaterally or bilaterally depending on the infarction.	2.07	1

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