Compounds > D-tyrosine
Page last updated: 2024-12-06

D-tyrosine

D-tyrosine is a non-proteinogenic amino acid, meaning it is not found in proteins. It is a stereoisomer of the more common L-tyrosine, differing only in the spatial arrangement of its atoms. D-tyrosine is produced synthetically and is not found naturally in significant amounts in food. While L-tyrosine is a precursor to the neurotransmitters dopamine, norepinephrine, and epinephrine, D-tyrosine is not. However, D-tyrosine has been studied for its potential effects on cognitive function, mood, and athletic performance. Some research suggests that D-tyrosine may improve mental performance under stress, but more research is needed to confirm these effects. D-tyrosine is also studied for its potential as a treatment for conditions such as depression and anxiety.'

Cross-References

ID SourceID
PubMed CID71098
CHEMBL ID1076637
CHEBI ID28479
SCHEMBL ID20787

Synonyms (52)

Synonym
d-tyrosin
(2r)-2-amino-3-(4-hydroxyphenyl)propanoic acid
DTY ,
d-tyr
CHEBI:28479 ,
dtyr
D-TYROSINE ,
C06420
(r)-3-(p-hydroxyphenyl)alanine
556-02-5
(r)-2-amino-3-(p-hydroxyphenyl)propionic acid
d-tyrosine, reagentplus(r), 99%
DB03839
NCGC00142608-01
NCGC00142608-02
T-9000
1168FFD2-192C-4DB4-9161-4BF71A6C98C9
h-d-tyr-oh
T1141
CHEMBL1076637 ,
A830718
(2r)-2-amino-3-(4-hydroxyphenyl)propanoic acid;d-tyrosine
einecs 209-112-6
wq5g9jq7gc ,
unii-wq5g9jq7gc
3-(4-hydroxyphenyl)-d-alanine
AKOS015854094
(d)-tyrosine
(r)-tyrosine
AM82303
SCHEMBL20787
J-300275
(r)-2-amino-3-(4-hydroxyphenyl)propanoic acid
d-(+)-tyrosine
tyrosine, d-
d-p-tyrosine
mfcd00063073
d-tyrosine, puriss., >=99.0% (nt)
AC-8668
d-tyrosine, vetec(tm) reagent grade, 99%
CS-D1377
(2r)-2-amino-3-(4-hydroxyphenyl)propanoic acid; (r)-tyrosine; d-p-tyrosine
d-4-hydroxyphenylalanine
Q27115118
AS-11715
Q16082044
M02937
DTXSID50883441
HY-Y0444
bdbm50463198
EN300-61693
Z969739284
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
Escherichia coli metaboliteAny bacterial metabolite produced during a metabolic reaction in Escherichia coli.
[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)

ClassDescription
D-alpha-amino acid zwitterionZwitterionic form of a D-alpha-amino acid having an anionic carboxy group and a protonated amino group.
tyrosineAn alpha-amino acid that is phenylalanine bearing a hydroxy substituent at position 4 on the phenyl ring.
D-alpha-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]

Protein Targets (10)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
regulator of G-protein signaling 4Homo sapiens (human)Potency0.07520.531815.435837.6858AID504845
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Carbonic anhydrase 1Homo sapiens (human)KA0.24000.02001.72197.4000AID1397319; AID691713; AID725228
Carbonic anhydrase 2Homo sapiens (human)KA0.06120.01101.42737.8000AID1397320; AID464319; AID691714; AID725229
Adenosine receptor A1Rattus norvegicus (Norway rat)KA0.08700.01101.32337.8000AID691714
Adenosine receptor A2aRattus norvegicus (Norway rat)KA0.08700.01101.32337.8000AID691714
Carbonic anhydraseSaccharomyces cerevisiae S288CKa84.00000.95005.12509.3000AID464321
Carbonic anhydrase-like protein, putativeTrypanosoma cruzi strain CL BrenerKA2.80000.14002.80507.5400AID1397322
Carbonic anhydrase Nakaseomyces glabratus CBS 138Ka7.10007.10008.30009.5000AID464322
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (45)

Processvia Protein(s)Taxonomy
one-carbon metabolic processCarbonic anhydrase 1Homo sapiens (human)
morphogenesis of an epitheliumCarbonic anhydrase 2Homo sapiens (human)
positive regulation of synaptic transmission, GABAergicCarbonic anhydrase 2Homo sapiens (human)
positive regulation of cellular pH reductionCarbonic anhydrase 2Homo sapiens (human)
angiotensin-activated signaling pathwayCarbonic anhydrase 2Homo sapiens (human)
regulation of monoatomic anion transportCarbonic anhydrase 2Homo sapiens (human)
secretionCarbonic anhydrase 2Homo sapiens (human)
regulation of intracellular pHCarbonic anhydrase 2Homo sapiens (human)
neuron cellular homeostasisCarbonic anhydrase 2Homo sapiens (human)
positive regulation of dipeptide transmembrane transportCarbonic anhydrase 2Homo sapiens (human)
regulation of chloride transportCarbonic anhydrase 2Homo sapiens (human)
carbon dioxide transportCarbonic anhydrase 2Homo sapiens (human)
one-carbon metabolic processCarbonic anhydrase 2Homo sapiens (human)
positive regulation of cytokine production involved in immune responseLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
negative regulation of gene expressionLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
positive regulation of type II interferon productionLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
positive regulation of interleukin-17 productionLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
positive regulation of interleukin-4 productionLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
negative regulation of autophagyLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
response to muscle activityLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
neutral amino acid transportLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
isoleucine transportLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
L-leucine transportLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
methionine transportLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
phenylalanine transportLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
proline transportLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
tryptophan transportLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
tyrosine transportLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
valine transportLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
alanine transportLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
cellular response to glucose starvationLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
xenobiotic transportLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
response to hyperoxiaLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
positive regulation of glial cell proliferationLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
thyroid hormone transportLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
cellular response to lipopolysaccharideLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
amino acid import across plasma membraneLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
liver regenerationLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
transport across blood-brain barrierLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
L-histidine transportLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
cellular response to L-arginineLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
L-leucine import across plasma membraneLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
L-tryptophan transmembrane transportLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
negative regulation of vascular associated smooth muscle cell apoptotic processLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
positive regulation of L-leucine import across plasma membraneLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
amino acid transmembrane transportLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (16)

Processvia Protein(s)Taxonomy
arylesterase activityCarbonic anhydrase 1Homo sapiens (human)
carbonate dehydratase activityCarbonic anhydrase 1Homo sapiens (human)
protein bindingCarbonic anhydrase 1Homo sapiens (human)
zinc ion bindingCarbonic anhydrase 1Homo sapiens (human)
hydro-lyase activityCarbonic anhydrase 1Homo sapiens (human)
cyanamide hydratase activityCarbonic anhydrase 1Homo sapiens (human)
arylesterase activityCarbonic anhydrase 2Homo sapiens (human)
carbonate dehydratase activityCarbonic anhydrase 2Homo sapiens (human)
protein bindingCarbonic anhydrase 2Homo sapiens (human)
zinc ion bindingCarbonic anhydrase 2Homo sapiens (human)
cyanamide hydratase activityCarbonic anhydrase 2Homo sapiens (human)
G protein-coupled adenosine receptor activityAdenosine receptor A2aRattus norvegicus (Norway rat)
protein bindingLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
amino acid transmembrane transporter activityLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
aromatic amino acid transmembrane transporter activityLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
neutral L-amino acid transmembrane transporter activityLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
L-leucine transmembrane transporter activityLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
L-tryptophan transmembrane transporter activityLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
antiporter activityLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
thyroid hormone transmembrane transporter activityLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
peptide antigen bindingLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
L-amino acid transmembrane transporter activityLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (16)

Processvia Protein(s)Taxonomy
cytosolCarbonic anhydrase 1Homo sapiens (human)
extracellular exosomeCarbonic anhydrase 1Homo sapiens (human)
cytoplasmCarbonic anhydrase 2Homo sapiens (human)
cytosolCarbonic anhydrase 2Homo sapiens (human)
plasma membraneCarbonic anhydrase 2Homo sapiens (human)
myelin sheathCarbonic anhydrase 2Homo sapiens (human)
apical part of cellCarbonic anhydrase 2Homo sapiens (human)
extracellular exosomeCarbonic anhydrase 2Homo sapiens (human)
cytoplasmCarbonic anhydrase 2Homo sapiens (human)
plasma membraneCarbonic anhydrase 2Homo sapiens (human)
apical part of cellCarbonic anhydrase 2Homo sapiens (human)
Golgi membraneAdenosine receptor A2aRattus norvegicus (Norway rat)
lysosomal membraneLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
cytosolLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
plasma membraneLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
basal plasma membraneLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
membraneLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
basolateral plasma membraneLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
apical plasma membraneLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
microvillus membraneLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
intracellular membrane-bounded organelleLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
extracellular exosomeLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
external side of apical plasma membraneLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
amino acid transport complexLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (28)

Assay IDTitleYearJournalArticle
AID725228Activation of human recombinant CA1 by stopped flow CO2 hydrase method2013Bioorganic & medicinal chemistry letters, Feb-15, Volume: 23, Issue:4
The extremo-α-carbonic anhydrase (CA) from Sulfurihydrogenibium azorense, the fastest CA known, is highly activated by amino acids and amines.
AID691714Activity of human recombinant CA2 cytosolic isoform after 15 mins by phenol red staining based stopped flow CO2 hydration assay2012Bioorganic & medicinal chemistry letters, Oct-15, Volume: 22, Issue:20
The first activation study of a bacterial carbonic anhydrase (CA). The thermostable α-CA from Sulfurihydrogenibium yellowstonense YO3AOP1 is highly activated by amino acids and amines.
AID725227Activation of Sulfurihydrogenibium yellowstonense recombinant CA by stopped flow CO2 hydrase method2013Bioorganic & medicinal chemistry letters, Feb-15, Volume: 23, Issue:4
The extremo-α-carbonic anhydrase (CA) from Sulfurihydrogenibium azorense, the fastest CA known, is highly activated by amino acids and amines.
AID691713Activity of human recombinant CA1 cytosolic isoform after 15 mins by phenol red staining based stopped flow CO2 hydration assay2012Bioorganic & medicinal chemistry letters, Oct-15, Volume: 22, Issue:20
The first activation study of a bacterial carbonic anhydrase (CA). The thermostable α-CA from Sulfurihydrogenibium yellowstonense YO3AOP1 is highly activated by amino acids and amines.
AID1331210Activation of Burkholderia pseudomallei gamma carbonic anhydrase assessed as Kcat at 10 uM incubated for 15 mins prior to testing by stopped flow CO2 hydration assay2017Bioorganic & medicinal chemistry letters, 01-01, Volume: 27, Issue:1
Burkholderia pseudomallei γ-carbonic anhydrase is strongly activated by amino acids and amines.
AID1331206Activation of Burkholderia pseudomallei gamma carbonic anhydrase at 10 uM incubated for 15 mins prior to testing by stopped flow CO2 hydration assay2017Bioorganic & medicinal chemistry letters, 01-01, Volume: 27, Issue:1
Burkholderia pseudomallei γ-carbonic anhydrase is strongly activated by amino acids and amines.
AID1397321Activation of Leishmania donovani chagasi CA preincubated for 15 mins followed by CO2 addition by stopped-flow assay
AID1398361Trans-stimulation of human LAT1 expressed in TREx HEK293 cells assessed as induction of [3H]-gabapentin efflux at 200 uM after 3 mins by scintillation counting analysis relative to L-phenylalanine2018Journal of medicinal chemistry, 08-23, Volume: 61, Issue:16
Reevaluating the Substrate Specificity of the L-Type Amino Acid Transporter (LAT1).
AID1751498Antibiofilm activity against Staphylococcus aureus assessed as inhibition of biofilm formation at 100 uM2021Bioorganic & medicinal chemistry letters, 09-15, Volume: 48Discovery of non-proteinogenic amino acids inhibiting biofilm formation by S. aureus and methicillin-resistant S. aureus.
AID464322Activation of Candida glabrata recombinant carbonic anhydrase by stopped flow CO2 hydration method2010Bioorganic & medicinal chemistry letters, Mar-01, Volume: 20, Issue:5
Carbonic anhydrase activators: Activation of the beta-carbonic anhydrase from the pathogenic yeast Candida glabrata with amines and amino acids.
AID1397320Activation of human CA2 by stopped-flow CO2 hydration assay
AID1331203Activation of recombinant human carbonic anhydrase 1 at 10 uM incubated for 15 mins prior to testing by stopped flow CO2 hydration assay2017Bioorganic & medicinal chemistry letters, 01-01, Volume: 27, Issue:1
Burkholderia pseudomallei γ-carbonic anhydrase is strongly activated by amino acids and amines.
AID464321Activation of Saccharomyces cerevisiae recombinant Nce103p by stopped flow CO2 hydration method2010Bioorganic & medicinal chemistry letters, Mar-01, Volume: 20, Issue:5
Carbonic anhydrase activators: Activation of the beta-carbonic anhydrase from the pathogenic yeast Candida glabrata with amines and amino acids.
AID691715Activity of Sulfurihydrogenibium yellowstonense YO3AOP1 recombinant CA expressed in Escherichia coli BL21(DE3) after 15 mins by phenol red staining based stopped flow CO2 hydration assay2012Bioorganic & medicinal chemistry letters, Oct-15, Volume: 22, Issue:20
The first activation study of a bacterial carbonic anhydrase (CA). The thermostable α-CA from Sulfurihydrogenibium yellowstonense YO3AOP1 is highly activated by amino acids and amines.
AID725226Activation of Sulfurihydrogenibium azorense recombinant alpha carbonic anhydrase by stopped flow CO2 hydrase method2013Bioorganic & medicinal chemistry letters, Feb-15, Volume: 23, Issue:4
The extremo-α-carbonic anhydrase (CA) from Sulfurihydrogenibium azorense, the fastest CA known, is highly activated by amino acids and amines.
AID464319Activation of human recombinant carbonic anhydrase isoenzyme 2 by stopped flow CO2 hydration method2010Bioorganic & medicinal chemistry letters, Mar-01, Volume: 20, Issue:5
Carbonic anhydrase activators: Activation of the beta-carbonic anhydrase from the pathogenic yeast Candida glabrata with amines and amino acids.
AID1398360Cis-inhibition of human LAT1 expressed in TREx HEK293 cells at 200 uM assessed as inhibition of [3H]-gabapentin uptake at 200 uM preincubated for 3 mins at 37 degC followed by washing with choline buffer and measured after 3 hrs by scintillation counting 2018Journal of medicinal chemistry, 08-23, Volume: 61, Issue:16
Reevaluating the Substrate Specificity of the L-Type Amino Acid Transporter (LAT1).
AID1398359Cis-inhibition of human LAT1 expressed in TREx HEK293 cells at 200 uM assessed as inhibition of [3H]-gabapentin uptake preincubated for 3 mins at 37 degC followed by washing with choline buffer and measured after 3 hrs by scintillation counting analysis r2018Journal of medicinal chemistry, 08-23, Volume: 61, Issue:16
Reevaluating the Substrate Specificity of the L-Type Amino Acid Transporter (LAT1).
AID725229Activation of human recombinant CA2 by stopped flow CO2 hydrase method2013Bioorganic & medicinal chemistry letters, Feb-15, Volume: 23, Issue:4
The extremo-α-carbonic anhydrase (CA) from Sulfurihydrogenibium azorense, the fastest CA known, is highly activated by amino acids and amines.
AID1331204Activation of recombinant human carbonic anhydrase 2 at 10 uM incubated for 15 mins prior to testing by stopped flow CO2 hydration assay2017Bioorganic & medicinal chemistry letters, 01-01, Volume: 27, Issue:1
Burkholderia pseudomallei γ-carbonic anhydrase is strongly activated by amino acids and amines.
AID1397322Activation of Trypanosoma cruzi CA preincubated for 15 mins followed by CO2 addition by stopped-flow assay
AID1751482Antibacterial activity in Staphylococcus aureus assessed as bacterial growth rate at 100 uM measured by UV absorbance based analysis2021Bioorganic & medicinal chemistry letters, 09-15, Volume: 48Discovery of non-proteinogenic amino acids inhibiting biofilm formation by S. aureus and methicillin-resistant S. aureus.
AID1751483Antibiofilm activity against Staphylococcus aureus assessed as biofilm formation at 100 uM measured by crystal violet staining based microplate reader assay2021Bioorganic & medicinal chemistry letters, 09-15, Volume: 48Discovery of non-proteinogenic amino acids inhibiting biofilm formation by S. aureus and methicillin-resistant S. aureus.
AID681113TP_TRANSPORTER: inhibition of L-tryptophan uptake in Xenopus laevis oocytes2001The Journal of biological chemistry, May-18, Volume: 276, Issue:20
Expression cloning of a Na+-independent aromatic amino acid transporter with structural similarity to H+/monocarboxylate transporters.
AID464320Activation of archaea Methanobacterium thermoautotrophicum recombinant carbonic anhydrase by stopped flow CO2 hydration method2010Bioorganic & medicinal chemistry letters, Mar-01, Volume: 20, Issue:5
Carbonic anhydrase activators: Activation of the beta-carbonic anhydrase from the pathogenic yeast Candida glabrata with amines and amino acids.
AID1281543Activation of Malassezia globosa beta-carbonic anhydrase incubated for 15 mins prior to testing by stopped flow CO2 hydrase method2016Bioorganic & medicinal chemistry letters, Mar-01, Volume: 26, Issue:5
Carbonic anhydrase activators: Activation of the β-carbonic anhydrase from Malassezia globosa with amines and amino acids.
AID1331205Activation of recombinant Methanosarcina thermophila gamma carbonic anhydrase at 10 uM incubated for 15 mins prior to testing by stopped flow CO2 hydration assay2017Bioorganic & medicinal chemistry letters, 01-01, Volume: 27, Issue:1
Burkholderia pseudomallei γ-carbonic anhydrase is strongly activated by amino acids and amines.
AID1397319Activation of human CA1 by stopped-flow CO2 hydration assay
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (9)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's1 (11.11)29.6817
2010's7 (77.78)24.3611
2020's1 (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: 34.04

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.

MetricThis Compound (vs All)
Research Demand Index34.04 (24.57)
Research Supply Index2.30 (2.92)
Research Growth Index4.88 (4.65)
Search Engine Demand Index39.83 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (34.04)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other9 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
catechol
[no description available]		2.3110catecholsallelochemical;
genotoxin;
plant metabolite
glycine
[no description available]		2.4620alpha-amino acid;
amino acid zwitterion;
proteinogenic amino acid;
serine family amino acid		EC 2.1.2.1 (glycine hydroxymethyltransferase) inhibitor;
fundamental metabolite;
hepatoprotective agent;
micronutrient;
neurotransmitter;
NMDA receptor agonist;
nutraceutical
histamine
[no description available]		3.1950aralkylamino compound;
imidazoles		human metabolite;
mouse metabolite;
neurotransmitter
pyruvic acid
Pyruvic Acid: An intermediate compound in the metabolism of carbohydrates, proteins, and fats. In thiamine deficiency, its oxidation is retarded and it accumulates in the tissues, especially in nervous structures. (From Stedman, 26th ed). pyruvic acid : A 2-oxo monocarboxylic acid that is the 2-keto derivative of propionic acid. It is a metabolite obtained during glycolysis.		2102-oxo monocarboxylic acidcofactor;
fundamental metabolite
tyramine
[no description available]		210monoamine molecular messenger;
primary amino compound;
tyramines		EC 3.1.1.8 (cholinesterase) inhibitor;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
neurotransmitter
thyroxine
Thyroxine: The major hormone derived from the thyroid gland. Thyroxine is synthesized via the iodination of tyrosines (MONOIODOTYROSINE) and the coupling of iodotyrosines (DIIODOTYROSINE) in the THYROGLOBULIN. Thyroxine is released from thyroglobulin by proteolysis and secreted into the blood. Thyroxine is peripherally deiodinated to form TRIIODOTHYRONINE which exerts a broad spectrum of stimulatory effects on cell metabolism.. thyroxine : An iodothyronine compound having iodo substituents at the 3-, 3'-, 5- and 5'-positions.		2102-halophenol;
iodophenol;
L-phenylalanine derivative;
non-proteinogenic L-alpha-amino acid;
thyroxine zwitterion;
thyroxine		antithyroid drug;
human metabolite;
mouse metabolite;
thyroid hormone
cysteine
[no description available]		210cysteine zwitterion;
cysteine;
L-alpha-amino acid;
proteinogenic amino acid;
serine family amino acid		EC 4.3.1.3 (histidine ammonia-lyase) inhibitor;
flour treatment agent;
human metabolite
triiodothyronine
Triiodothyronine: A T3 thyroid hormone normally synthesized and secreted by the thyroid gland in much smaller quantities than thyroxine (T4). Most T3 is derived from peripheral monodeiodination of T4 at the 5' position of the outer ring of the iodothyronine nucleus. The hormone finally delivered and used by the tissues is mainly T3.. 3,3',5-triiodo-L-thyronine : An iodothyronine compound having iodo substituents at the 3-, 3'- and 5-positions. Although some is produced in the thyroid, most of the 3,3',5-triiodo-L-thyronine in the body is generated by mono-deiodination of L-thyroxine in the peripheral tissues. Its metabolic activity is about 3 to 5 times that of L-thyroxine. The sodium salt is used in the treatment of hypothyroidism.		2102-halophenol;
amino acid zwitterion;
iodophenol;
iodothyronine		human metabolite;
mouse metabolite;
thyroid hormone
alanine
Alanine: A non-essential amino acid that occurs in high levels in its free state in plasma. It is produced from pyruvate by transamination. It is involved in sugar and acid metabolism, increases IMMUNITY, and provides energy for muscle tissue, BRAIN, and the CENTRAL NERVOUS SYSTEM.. alanine : An alpha-amino acid that consists of propionic acid bearing an amino substituent at position 2.		210alanine zwitterion;
alanine;
L-alpha-amino acid;
proteinogenic amino acid;
pyruvate family amino acid		EC 4.3.1.15 (diaminopropionate ammonia-lyase) inhibitor;
fundamental metabolite
serine
Serine: A non-essential amino acid occurring in natural form as the L-isomer. It is synthesized from GLYCINE or THREONINE. It is involved in the biosynthesis of PURINES; PYRIMIDINES; and other amino acids.. serine : An alpha-amino acid that is alanine substituted at position 3 by a hydroxy group.		210L-alpha-amino acid;
proteinogenic amino acid;
serine family amino acid;
serine zwitterion;
serine		algal metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
aspartic acid
Aspartic Acid: One of the non-essential amino acids commonly occurring in the L-form. It is found in animals and plants, especially in sugar cane and sugar beets. It may be a neurotransmitter.. aspartic acid : An alpha-amino acid that consists of succinic acid bearing a single alpha-amino substituent. L-aspartic acid : The L-enantiomer of aspartic acid.		2.4620aspartate family amino acid;
aspartic acid;
L-alpha-amino acid;
proteinogenic amino acid		Escherichia coli metabolite;
mouse metabolite;
neurotransmitter
glutamine
Glutamine: A non-essential amino acid present abundantly throughout the body and is involved in many metabolic processes. It is synthesized from GLUTAMIC ACID and AMMONIA. It is the principal carrier of NITROGEN in the body and is an important energy source for many cells.. L-glutamine : An optically active form of glutamine having L-configuration.. glutamine : An alpha-amino acid that consists of butyric acid bearing an amino substituent at position 2 and a carbamoyl substituent at position 4.		210amino acid zwitterion;
glutamine family amino acid;
glutamine;
L-alpha-amino acid;
polar amino acid zwitterion;
proteinogenic amino acid		EC 1.14.13.39 (nitric oxide synthase) inhibitor;
Escherichia coli metabolite;
human metabolite;
metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
Saccharomyces cerevisiae metabolite
lysine
Lysine: An essential amino acid. It is often added to animal feed.. lysine : A diamino acid that is caproic (hexanoic) acid bearing two amino substituents at positions 2 and 6.. L-lysine : An L-alpha-amino acid; the L-isomer of lysine.		2.4620aspartate family amino acid;
L-alpha-amino acid zwitterion;
L-alpha-amino acid;
lysine;
organic molecular entity;
proteinogenic amino acid		algal metabolite;
anticonvulsant;
Escherichia coli metabolite;
human metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
plant metabolite;
Saccharomyces cerevisiae metabolite
levodopa
Levodopa: The naturally occurring form of DIHYDROXYPHENYLALANINE and the immediate precursor of DOPAMINE. Unlike dopamine itself, it can be taken orally and crosses the blood-brain barrier. It is rapidly taken up by dopaminergic neurons and converted to DOPAMINE. It is used for the treatment of PARKINSONIAN DISORDERS and is usually given with agents that inhibit its conversion to dopamine outside of the central nervous system.. L-dopa : An optically active form of dopa having L-configuration. Used to treat the stiffness, tremors, spasms, and poor muscle control of Parkinson's disease		3.4770amino acid zwitterion;
dopa;
L-tyrosine derivative;
non-proteinogenic L-alpha-amino acid		allelochemical;
antidyskinesia agent;
antiparkinson drug;
dopaminergic agent;
hapten;
human metabolite;
mouse metabolite;
neurotoxin;
plant growth retardant;
plant metabolite;
prodrug
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.		3.4670amino 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
leucine
Leucine: An essential branched-chain amino acid important for hemoglobin formation.. leucine : A branched-chain amino acid that consists of glycine in which one of the hydrogens attached to the alpha-carbon is substituted by an isobutyl group.		2.4620amino acid zwitterion;
L-alpha-amino acid;
leucine;
proteinogenic amino acid;
pyruvate family amino acid		algal metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
plant metabolite;
Saccharomyces cerevisiae metabolite
methionine
Methionine: A sulfur-containing essential L-amino acid that is important in many body functions.. methionine : A sulfur-containing amino acid that is butyric acid bearing an amino substituent at position 2 and a methylthio substituent at position 4.		2.4620aspartate family amino acid;
L-alpha-amino acid;
methionine zwitterion;
methionine;
proteinogenic amino acid		antidote to paracetamol poisoning;
human metabolite;
micronutrient;
mouse metabolite;
nutraceutical
phenylalanine
Phenylalanine: An essential aromatic amino acid that is a precursor of MELANIN; DOPAMINE; noradrenalin (NOREPINEPHRINE), and THYROXINE.. L-phenylalanine : The L-enantiomer of phenylalanine.. phenylalanine : An aromatic amino acid that is alanine in which one of the methyl hydrogens is substituted by a phenyl group.		3.4670amino acid zwitterion;
erythrose 4-phosphate/phosphoenolpyruvate family amino acid;
L-alpha-amino acid;
phenylalanine;
proteinogenic amino acid		algal metabolite;
EC 3.1.3.1 (alkaline phosphatase) inhibitor;
Escherichia coli metabolite;
human xenobiotic metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
plant metabolite;
Saccharomyces cerevisiae metabolite
asparagine
Asparagine: A non-essential amino acid that is involved in the metabolic control of cell functions in nerve and brain tissue. It is biosynthesized from ASPARTIC ACID and AMMONIA by asparagine synthetase. (From Concise Encyclopedia Biochemistry and Molecular Biology, 3rd ed). asparagine : An alpha-amino acid in which one of the hydrogens attached to the alpha-carbon of glycine is substituted by a 2-amino-2-oxoethyl group.		210amino acid zwitterion;
asparagine;
aspartate family amino acid;
L-alpha-amino acid;
proteinogenic amino acid		Escherichia coli metabolite;
human metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
plant metabolite;
Saccharomyces cerevisiae metabolite
histidine
Histidine: An essential amino acid that is required for the production of HISTAMINE.. L-histidine : The L-enantiomer of the amino acid histidine.. histidine : An alpha-amino acid that is propanoic acid bearing an amino substituent at position 2 and a 1H-imidazol-4-yl group at position 3.		3.4670amino acid zwitterion;
histidine;
L-alpha-amino acid;
polar amino acid zwitterion;
proteinogenic amino acid		algal metabolite;
Escherichia coli metabolite;
human metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
Saccharomyces cerevisiae metabolite
valine
Valine: A branched-chain essential amino acid that has stimulant activity. It promotes muscle growth and tissue repair. It is a precursor in the penicillin biosynthetic pathway.. valine : A branched-chain amino acid that consists of glycine in which one of the hydrogens attached to the alpha-carbon is substituted by an isopropyl group.. L-valine : The L-enantiomer of valine.		2.4620L-alpha-amino acid zwitterion;
L-alpha-amino acid;
proteinogenic amino acid;
pyruvate family amino acid;
valine		algal metabolite;
Escherichia coli metabolite;
human metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
Saccharomyces cerevisiae metabolite
threonine
Threonine: An essential amino acid occurring naturally in the L-form, which is the active form. It is found in eggs, milk, gelatin, and other proteins.. threonine : An alpha-amino acid in which one of the hydrogens attached to the alpha-carbon of glycine is substituted by a 1-hydroxyethyl group.		210amino acid zwitterion;
aspartate family amino acid;
L-alpha-amino acid;
proteinogenic amino acid;
threonine		algal metabolite;
Escherichia coli metabolite;
human metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
plant metabolite;
Saccharomyces cerevisiae metabolite
tryptophan
Tryptophan: An essential amino acid that is necessary for normal growth in infants and for NITROGEN balance in adults. It is a precursor of INDOLE ALKALOIDS in plants. It is a precursor of SEROTONIN (hence its use as an antidepressant and sleep aid). It can be a precursor to NIACIN, albeit inefficiently, in mammals.. tryptophan : An alpha-amino acid that is alanine bearing an indol-3-yl substituent at position 3.		3.4670erythrose 4-phosphate/phosphoenolpyruvate family amino acid;
L-alpha-amino acid zwitterion;
L-alpha-amino acid;
proteinogenic amino acid;
tryptophan zwitterion;
tryptophan		antidepressant;
Escherichia coli metabolite;
human metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
plant metabolite;
Saccharomyces cerevisiae metabolite
isoleucine
Isoleucine: An essential branched-chain aliphatic amino acid found in many proteins. It is an isomer of LEUCINE. It is important in hemoglobin synthesis and regulation of blood sugar and energy levels.. isoleucine : A 2-amino-3-methylpentanoic acid having either (2R,3R)- or (2S,3S)-configuration.. L-isoleucine : The L-enantiomer of isoleucine.		2.4620aspartate family amino acid;
isoleucine;
L-alpha-amino acid zwitterion;
L-alpha-amino acid;
proteinogenic amino acid		algal metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
plant metabolite;
Saccharomyces cerevisiae metabolite
arginine
Arginine: An essential amino acid that is physiologically active in the L-form.. arginine : An alpha-amino acid that is glycine in which the alpha-is substituted by a 3-guanidinopropyl group.		2.4620arginine;
glutamine family amino acid;
L-alpha-amino acid;
proteinogenic amino acid		biomarker;
Escherichia coli metabolite;
micronutrient;
mouse metabolite;
nutraceutical
aminoethylpiperazine
aminoethylpiperazine: RN given refers to parent cpd with specified locant		3.1950
D-proline
[no description available]		2.3110D-alpha-amino acid zwitterion;
D-alpha-amino acid;
proline		mouse metabolite
D-tryptophan
[no description available]		3.4670D-alpha-amino acid;
tryptophan zwitterion;
tryptophan		bacterial metabolite
3-methoxytyrosine
3-O-methyldopa : A L-tyrosine derivative that is the 3-methoxy derivative of L-dopa.		2.4720aromatic L-alpha-amino acid zwitterion;
L-tyrosine derivative;
monomethoxybenzene;
non-proteinogenic L-alpha-amino acid		human metabolite
3,5-dibromotyrosine
3,5-dibromotyrosine: used to synthesize various secondary metabolites from marine sponges		2.3110monocarboxylic acid
2-(aminomethyl)pyridine
[no description available]		3.1950pyridines
glutamic acid
Glutamic Acid: A non-essential amino acid naturally occurring in the L-form. Glutamic acid is the most common excitatory neurotransmitter in the CENTRAL NERVOUS SYSTEM.. glutamic acid : An alpha-amino acid that is glutaric acid bearing a single amino substituent at position 2.		2.4620glutamic acid;
glutamine family amino acid;
L-alpha-amino acid;
proteinogenic amino acid		Escherichia coli metabolite;
ferroptosis inducer;
micronutrient;
mouse metabolite;
neurotransmitter;
nutraceutical
methyldopa
Methyldopa: An alpha-2 adrenergic agonist that has both central and peripheral nervous system effects. Its primary clinical use is as an antihypertensive agent.. alpha-methyl-L-dopa : A derivative of L-tyrosine having a methyl group at the alpha-position and an additional hydroxy group at the 3-position on the phenyl ring.		210L-tyrosine derivative;
non-proteinogenic L-alpha-amino acid		alpha-adrenergic agonist;
antihypertensive agent;
hapten;
peripheral nervous system drug;
sympatholytic agent
d-lactic acid
(R)-lactic acid : An optically active form of lactic acid having (R)-configuration.		2102-hydroxypropanoic acidEscherichia coli metabolite;
human metabolite
n-acetyltyrosine
N-acetyl-L-tyrosine : An N-acetyltyrosine in which the chiral centre has L configuration.		210N-acetyltyrosine;
N-acyl-L-tyrosine		biomarker;
EC 2.1.1.4 (acetylserotonin O-methyltransferase) inhibitor;
human urinary metabolite
tyrosine methyl ester
tyrosine methyl ester: RN given refers to (L)-isomer. methyl L-tyrosinate : An L-tyrosyl ester that is the methyl ester of L-tyrosine.		210L-tyrosyl ester;
methyl ester
D-serine
[no description available]		2.4720D-alpha-amino acid;
serine zwitterion;
serine		Escherichia coli metabolite;
human metabolite;
NMDA receptor agonist
D-alanine
[no description available]		210alanine zwitterion;
alanine;
D-alpha-amino acid		EC 4.3.1.15 (diaminopropionate ammonia-lyase) inhibitor;
Escherichia coli metabolite;
human metabolite
copper histidine
[no description available]		3.3560D-alpha-amino acid;
histidine;
polar amino acid zwitterion		Saccharomyces cerevisiae metabolite
D-valine
D-valine : The D-enantiomer of valine.		2.1710D-alpha-amino acid zwitterion;
D-alpha-amino acid;
valine
phenylalanine
[no description available]		3.5980D-alpha-amino acid zwitterion;
D-alpha-amino acid;
phenylalanine
n-myristoylglycine
N-myristoylglycine: RN given refers to parent cpd. N-myristoylglycine : An N-acylglycine in which the acyl group is specified as myristoyl (tetradecanoyl).		2.3110fatty amide;
N-acylglycine		human blood serum metabolite;
human urinary metabolite
2-(2-aminoethyl)pyridine
2-(2-aminoethyl)pyridine: histamine H1 receptor agonist inducing cross-tolerance to histamine; RN given refers to parent cpd; structure		3.1950aminoalkylpyridine;
primary amine		histamine agonist;
metabolite
methyl tryptophan, (l-trp)-isomer
[no description available]		210
1-methylhistidine
1-methylhistidine: found in muscle proteins; RN given refers to (L)-isomer. 1-methylhistidine : A methylhistidine in which the methyl group is located at N-1.. N(tele)-methyl-L-histidine : A L-histidine derivative in which the methyl group is at N(tele)-position.		2.1710L-histidine derivative;
non-proteinogenic L-alpha-amino acid;
zwitterion		human metabolite
D-dopa
D-dopa : The D-enantiomer of dopa.		3.1950amino acid zwitterion;
D-tyrosine derivative;
dopa
droxidopa
Droxidopa: A synthetic precursor of norepinephrine that is used in the treatment of PARKINSONIAN DISORDERS and ORTHOSTATIC HYPOTENSION.. droxidopa : A serine derivative that is L-serine substituted at the beta-position by a 3,4-dihydroxyphenyl group. A prodrug for noradrenalone, it is used for treatment of neurogenic orthostatic hypotension		210catechols;
L-tyrosine derivative		antihypertensive agent;
prodrug;
vasoconstrictor agent
beta-hydroxyphenylalanine
beta-hydroxyphenylalanine: RN given refers to beta cpd		2.3110
dehydroabietic acid
dehydroabietic acid: major aquatic toxicant in effluent of pulp and paper mills. dehydroabietic acid : An abietane diterpenoid that is abieta-8,11,13-triene substituted at position 18 by a carboxy group.. dehydroabietate : A monocarboxylic acid anion that is the conjugate base of dehydroabietic acid, obtained by deprotonation of the carboxy group.		2.3110abietane diterpenoid;
carbotricyclic compound;
monocarboxylic acid		allergen;
metabolite
2,2-dimethyl-beta-alanine
[no description available]		210
3,4-dihydroxybenzyl alcohol
3,4-dihydroxybenzyl alcohol: structure given in first source		2.3110
2-aminobicyclo(2,2,1)heptane-2-carboxylic acid
2-aminobicyclo(2,2,1)heptane-2-carboxylic acid: amino acid analog; releases insulin; RN given refers to unlabeled cpd without isomeric designation		210monoterpenoid
proline
Proline: A non-essential amino acid that is synthesized from GLUTAMIC ACID. It is an essential component of COLLAGEN and is important for proper functioning of joints and tendons.. proline : An alpha-amino acid that is pyrrolidine bearing a carboxy substituent at position 2.		210amino acid zwitterion;
glutamine family amino acid;
L-alpha-amino acid;
proline;
proteinogenic amino acid		algal metabolite;
compatible osmolytes;
Escherichia coli metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
Saccharomyces cerevisiae metabolite
4-aminophenylalanine
4-aminophenylalanine: RN given refers to cpd without isomeric designation. 4-amino-L-phenylalanine : The L-enantiomer of 4-aminophenylalanine.. 4-aminophenylalanine : A phenylalanine derivative that is phenylalanine carrying an amino group at position 4 on the benzene ring.		3.19504-aminophenylalanine;
amino acid zwitterion
4-methylphenylalanine
4-methylphenylalanine: RN given refers to cpd without isomeric designation; structure given in first source		2.1710
abrine
abrine: from seeds of Abrus precatorius; structure in first source. N(alpha)-methyl-L-tryptophan : A N-methyl-L-alpha-amino acid that is the N(alpha)-methyl derivative of L-tryptophan.		210L-tryptophan derivative;
N-methyl-L-alpha-amino acid zwitterion;
N-methyl-L-alpha-amino acid		Escherichia coli metabolite
epitrate
(S)-adrenaline : The S-enantiomer of adrenaline.		2.76304-[1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol
4-2-Aminoethyl-morpholine
[no description available]		3.1950morpholines
D-leucine
[no description available]		2.4620D-alpha-amino acid zwitterion;
D-alpha-amino acid;
leucine		bacterial metabolite;
Saccharomyces cerevisiae metabolite
n-acetyltryptophan
N-acetyl-L-tryptophan : A N-acetyl-L-amino acid that is the N-acetyl derivative of L-tryptophan.		210L-tryptophan derivative;
N-acetyl-L-amino acid		metabolite
phenylalanine methyl ester
phenylalanine methyl ester: RN given refers to (L)-isomer. methyl L-phenylalaninate : An alpha-amino acid ester that is the methyl ester of L-phenylalanine.		210alpha-amino acid ester;
L-phenylalanine derivative
quercetin
[no description available]		2.31107-hydroxyflavonol;
pentahydroxyflavone		antibacterial agent;
antineoplastic agent;
antioxidant;
Aurora kinase inhibitor;
chelator;
EC 1.10.99.2 [ribosyldihydronicotinamide dehydrogenase (quinone)] inhibitor;
geroprotector;
phytoestrogen;
plant metabolite;
protein kinase inhibitor;
radical scavenger
3-tyrosine
3-tyrosine: RN given refers to cpd with unspecified isomeric designation. L-m-tyrosine : A hydroxyphenylalanine that is L-phenylalanine with a substituent hydroxy group at position 3.		2.1710hydroxyphenylalanine;
L-alpha-amino acid zwitterion;
L-phenylalanine derivative;
non-proteinogenic L-alpha-amino acid;
phenols		plant metabolite
ConditionIndicatedRelationship StrengthStudiesTrials
Scurf
[description not available]		02.1310
Dandruff
Excessive shedding of dry scaly material from the scalp in humans.		02.1310
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