Identification

Name
L-Histidine
Accession Number
DB00117  (NUTR00030)
Type
Small Molecule
Groups
Approved, Nutraceutical
Description

An essential amino acid that is required for the production of histamine. [PubChem]

Structure
Thumb
Synonyms
  • (S)-4-(2-Amino-2-carboxyethyl)imidazole
  • (S)-a-Amino-1H-imidazole-4-propanoic acid
  • (S)-alpha-amino-1H-Imidazole-4-propanoic acid
  • (S)-alpha-Amino-1H-imidazole-4-propionic acid
  • (S)-α-amino-1H-Imidazole-4-propanoic acid
  • H
  • His
  • Histidine
  • L-(-)-Histidine
  • L-(−)-histidine
  • L-Histidin
  • L-Histidine
External IDs
FEMA NO. 3694
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
2.5% Travasol Amino Acid Injection With Electrolytes In 10% DextroseL-Histidine (120 mg) + Dipotassium phosphate (130.5 mg) + Glucose (10 g) + Glycine (260 mg) + L-Alanine (520 mg) + L-Arginine (290 mg) + L-Isoleucine (150 mg) + L-Leucine (182.5 mg) + L-Lysine (145 mg) + L-Methionine (100 mg) + L-Phenylalanine (140 mg) + L-Proline (170 mg) + L-Serine (125 mg) + L-Threonine (105 mg) + L-Tryptophan (45 mg) + L-Tyrosine (10 mg) + L-Valine (145 mg) + Magnesium chloride (25.5 mg) + Sodium Chloride (29.3 mg) + Sodium acetate (170 mg)SolutionIntravenousBaxter Corporation Clintec Nutrition Division1996-12-312015-08-05Canada
2.5% Travasol Amino Acid Injection With Electrolytes In 10% Dextrose ClinimixL-Histidine (110 mg) + Dipotassium phosphate (130.5 mg) + Glucose (10 g) + Glycine (520 mg) + L-Alanine (520 mg) + L-Arginine (260 mg) + L-Isoleucine (120 mg) + L-Leucine hydrochloride (155 mg) + L-Lysine hydrochloride (145 mg) + L-Methionine (145 mg) + L-Phenylalanine hydrochloride (155 mg) + L-Proline (105 mg) + L-Threonine (105 mg) + L-Tryptophan (45 mg) + L-Tyrosine (10 mg) + L-Valine (115 mg) + Magnesium chloride (25.5 mg) + Sodium Chloride (29.3 mg) + Sodium acetate (170 mg)SolutionIntravenousBaxter Corporation Clintec Nutrition Division1993-12-312015-08-05Canada
2.5% Travasol Amino Acid Injection Without Electrolytes In 10% Dextrose QuickmixL-Histidine (110 mg) + Glucose (10 g) + Glycine (520 mg) + L-Alanine (520 mg) + L-Arginine (260 mg) + L-Isoleucine (120 mg) + L-Leucine hydrochloride (155 mg) + L-Lysine hydrochloride (195 mg) + L-Methionine (195 mg) + L-Phenylalanine hydrochloride (155 mg) + L-Proline (105 mg) + L-Threonine (105 mg) + L-Tryptophan (45 mg) + L-Tyrosine (10 mg) + L-Valine (115 mg)SolutionIntravenousBaxter Corporation Clintec Nutrition Division1995-12-312007-08-02Canada
2.5%travasol Amino Acid InJ.W.eleC.W.25%dexL-Histidine (120 mg) + Dipotassium phosphate (130.5 mg) + Glucose (25 g) + Glycine (260 mg) + L-Alanine (520 mg) + L-Arginine (290 mg) + L-Isoleucine (150 mg) + L-Leucine (182.5 mg) + L-Lysine (145 mg) + L-Methionine (100 mg) + L-Phenylalanine (140 mg) + L-Proline (170 mg) + L-Serine (125 mg) + L-Threonine (105 mg) + L-Tryptophan (45 mg) + L-Tyrosine (10 mg) + L-Valine (145 mg) + Magnesium chloride (25.5 mg) + Sodium Chloride (29.3 mg) + Sodium acetate (170 mg)LiquidIntravenousClintec Nutrition Company1996-07-301998-08-13Canada
2.75% Travas. Amino Acid InJ.W.elecw.25%dexL-Histidine (132 mg) + Dipotassium phosphate (261 mg) + Glucose (25 g) + Glycine (283 mg) + L-Alanine (570 mg) + L-Arginine (316 mg) + L-Isoleucine (165 mg) + L-Leucine (201 mg) + L-Lysine (159.5 mg) + L-Methionine (110 mg) + L-Phenylalanine (154 mg) + L-Proline (187 mg) + L-Serine (137.5 mg) + L-Threonine (115.5 mg) + L-Tryptophan (49.5 mg) + L-Tyrosine (11 mg) + L-Valine (159.5 mg) + Magnesium chloride (51 mg) + Sodium Chloride (112 mg) + Sodium acetate (215.5 mg)LiquidIntravenousClintec Nutrition Company1996-07-301998-08-13Canada
2.75% Travasol Amino Acid Injection With Electrolytes In 25% Dextrose QuickmixL-Histidine (120.5 mg) + Dipotassium phosphate (261 mg) + Glucose (25 g) + Glycine (570 mg) + L-Alanine (570 mg) + L-Arginine (285 mg) + L-Isoleucine (131.5 mg) + L-Leucine hydrochloride (170 mg) + L-Lysine hydrochloride (159 mg) + L-Methionine (159 mg) + L-Phenylalanine hydrochloride (170 mg) + L-Proline (115 mg) + L-Threonine (115 mg) + L-Tryptophan (49.5 mg) + L-Tyrosine (11 mg) + L-Valine (126 mg) + Magnesium chloride (51 mg) + Sodium Chloride (112 mg) + Sodium acetate (215.5 mg)SolutionIntravenousBaxter Corporation Clintec Nutrition Division1996-02-022007-08-02Canada
2.75% Travasol Amino Acid Injection With Electrolytes In 5% Dextrose QuickmixL-Histidine (120.5 mg) + Dipotassium phosphate (215.5 mg) + Glucose (5 g) + Glycine (570 mg) + L-Alanine (570 mg) + L-Arginine (285 mg) + L-Isoleucine (131.5 mg) + L-Leucine hydrochloride (170 mg) + L-Lysine hydrochloride (159 mg) + L-Methionine (159 mg) + L-Phenylalanine hydrochloride (170 mg) + L-Proline (115 mg) + L-Threonine (115 mg) + L-Tryptophan (49.5 mg) + L-Tyrosine (11 mg) + L-Valine (126 mg) + Magnesium chloride (51 mg) + Sodium Chloride (112 mg) + Sodium acetate (256 mg)SolutionIntravenousBaxter Corporation Clintec Nutrition Division1993-12-312007-08-02Canada
2.75%travasol Amino Acid InJ.W.eleC.W.5%dex.L-Histidine (132 mg) + Dipotassium phosphate (261 mg) + Glucose (5 g) + Glycine (283 mg) + L-Alanine (570 mg) + L-Arginine (316 mg) + L-Isoleucine (165 mg) + L-Leucine (201 mg) + L-Lysine (159.5 mg) + L-Methionine (110 mg) + L-Phenylalanine (154 mg) + L-Proline (187 mg) + L-Serine (137.5 mg) + L-Threonine (115.5 mg) + L-Tryptophan (49.5 mg) + L-Tyrosine (11 mg) + L-Valine (159.5 mg) + Magnesium chloride (51 mg) + Sodium Chloride (112 mg) + Sodium acetate (215 mg)LiquidIntravenousClintec Nutrition Company1996-12-311999-08-10Canada
4.25% Amino Acid Injection Without Electrolytes In 20% Dextrose QuickmixL-Histidine (186 mg) + Glucose (20 g) + Glycine (880 mg) + L-Alanine (880 mg) + L-Arginine (440 mg) + L-Isoleucine (203 mg) + L-Leucine hydrochloride (263 mg) + L-Lysine hydrochloride (246 mg) + L-Methionine (246 mg) + L-Phenylalanine hydrochloride (263 mg) + L-Proline (178 mg) + L-Threonine (178 mg) + L-Tryptophan (76 mg) + L-Tyrosine (17 mg) + L-Valine (195 mg)SolutionIntravenousBaxter Corporation Clintec Nutrition Division1995-12-312007-08-02Canada
4.25% Travasol Amino Acid Injection With Electrolytes In 10% DextroseL-Histidine (204 mg) + Dipotassium phosphate (261 mg) + Glucose (10 g) + Glycine (438 mg) + L-Alanine (880 mg) + L-Arginine (489 mg) + L-Isoleucine (255 mg) + L-Leucine (310 mg) + L-Lysine hydrochloride (246.5 mg) + L-Methionine (170 mg) + L-Phenylalanine (238 mg) + L-Proline (289 mg) + L-Serine (212.5 mg) + L-Threonine (178.5 mg) + L-Tryptophan (76.5 mg) + L-Tyrosine (17 mg) + L-Valine (246.5 mg) + Magnesium chloride (51 mg) + Sodium Chloride (77 mg) + Sodium acetate (297 mg)SolutionIntravenousBaxter Corporation Clintec Nutrition Division1996-12-312015-08-05Canada
Categories
UNII
4QD397987E
CAS number
71-00-1
Weight
Average: 155.1546
Monoisotopic: 155.069476547
Chemical Formula
C6H9N3O2
InChI Key
HNDVDQJCIGZPNO-YFKPBYRVSA-N
InChI
InChI=1S/C6H9N3O2/c7-5(6(10)11)1-4-2-8-3-9-4/h2-3,5H,1,7H2,(H,8,9)(H,10,11)/t5-/m0/s1
IUPAC Name
(2S)-2-amino-3-(1H-imidazol-5-yl)propanoic acid
SMILES
N[[email protected]@H](CC1=CN=CN1)C(O)=O

Pharmacology

Indication

The actions of supplemental L-histidine are entirely unclear. It may have some immunomodulatory as well as antioxidant activity. L-histidine may be indicated for use in some with rheumatoid arthritis. It is not indicated for treatment of anemia or uremia or for lowering serum cholesterol.

Structured Indications
Not Available
Pharmacodynamics

Is found abundantly in hemoglobin; has been used in the treatment of rheumatoid arthritis, allergic diseases, ulcers and anemia. A deficiency can cause poor hearing.

Mechanism of action

Since the actions of supplemental L-histidine are unclear, any postulated mechanism is entirely speculative. However, some facts are known about L-histidine and some of its metabolites, such as histamine and trans-urocanic acid, which suggest that supplemental L-histidine may one day be shown to have immunomodulatory and/or antioxidant activities. Low free histidine has been found in the serum of some rheumatoid arthritis patients. Serum concentrations of other amino acids have been found to be normal in these patients. L-histidine is an excellent chelating agent for such metals as copper, iron and zinc. Copper and iron participate in a reaction (Fenton reaction) that generates potent reactive oxygen species that could be destructive to tissues, including joints.
L-histidine is the obligate precursor of histamine, which is produced via the decarboxylation of the amino acid. In experimental animals, tissue histamine levels increase as the amount of dietary L-histidine increases. It is likely that this would be the case in humans as well. Histamine is known to possess immunomodulatory and antioxidant activity. Suppressor T cells have H2 receptors, and histamine activates them. Promotion of suppressor T cell activity could be beneficial in rheumatoid arthritis. Further, histamine has been shown to down-regulate the production of reactive oxygen species in phagocytic cells, such as monocytes, by binding to the H2 receptors on these cells. Decreased reactive oxygen species production by phagocytes could play antioxidant, anti-inflammatory and immunomodulatory roles in such diseases as rheumatoid arthritis.
This latter mechanism is the rationale for the use of histamine itself in several clinical trials studying histamine for the treatment of certain types of cancer and viral diseases. In these trials, down-regulation by histamine of reactive oxygen species formation appears to inhibit the suppression of natural killer (NK) cells and cytotoxic T lymphocytes, allowing these cells to be more effective in attacking cancer cells and virally infected cells.

TargetActionsOrganism
UHistidine decarboxylaseNot AvailableHuman
UHistidine--tRNA ligase, cytoplasmicNot AvailableHuman
USodium-coupled neutral amino acid transporter 3Not AvailableHuman
UHistidine ammonia-lyaseNot AvailableHuman
Absorption

Absorbed from the small intestine via an active transport mechanism requiring the presence of sodium.

Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity

ORL-RAT LD50 > 15000 mg/kg, IPR-RAT LD50 > 8000 mg/kg, ORL-MUS LD50 > 15000 mg/kg, IVN-MUS LD50 > 2000 mg/kg; Mild gastrointestinal side effects.

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Tobramycin Action PathwayDrug action
Arbekacin Action PathwayDrug action
Methacycline Action PathwayDrug action
Histidine MetabolismMetabolic
Amikacin Action PathwayDrug action
Spectinomycin Action PathwayDrug action
GABA-Transaminase DeficiencyDisease
Ureidopropionase DeficiencyDisease
Beta-Alanine MetabolismMetabolic
Clindamycin Action PathwayDrug action
Gentamicin Action PathwayDrug action
Netilmicin Action PathwayDrug action
Doxycycline Action PathwayDrug action
Minocycline Action PathwayDrug action
Lymecycline Action PathwayDrug action
Tigecycline Action PathwayDrug action
HistidinemiaDisease
Clarithromycin Action PathwayDrug action
Erythromycin Action PathwayDrug action
Roxithromycin Action PathwayDrug action
Kanamycin Action PathwayDrug action
Neomycin Action PathwayDrug action
Clomocycline Action PathwayDrug action
Paromomycin Action PathwayDrug action
Rolitetracycline Action PathwayDrug action
Chloramphenicol Action PathwayDrug action
Ammonia RecyclingMetabolic
Azithromycin Action PathwayDrug action
Telithromycin Action PathwayDrug action
Streptomycin Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference

Kazumi Araki, Tetsuro Kuga, "Process for producing L-histidine by fermentation." U.S. Patent US4495283, issued April, 1975.

US4495283
General References
Not Available
External Links
Human Metabolome Database
HMDB00177
KEGG Drug
D00032
KEGG Compound
C00135
ChemSpider
6038
BindingDB
7953
ChEBI
15971
ChEMBL
CHEMBL17962
PharmGKB
PA449882
IUPHAR
3310
Guide to Pharmacology
GtP Drug Page
HET
HIS
PDRhealth
PDRhealth Drug Page
Wikipedia
L-Histidine
AHFS Codes
  • 40:20.00 — Caloric Agents
  • 88:28.01* — Vitamins & Minerals
MSDS
Download (72.7 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingSupportive CareProtein Feeding in Post-traumatic Injury Patients1
1RecruitingTreatmentTuberculosis1
2Active Not RecruitingTreatmentCarcinoid Tumors / Medulloblastomas / Neuroblastomas / Neuroendocrine Tumors1
2RecruitingPreventionMuscle Wasting / Quality of Life1
3CompletedTreatmentCritical Illness1
3CompletedTreatmentInfant, Low Birth Weight / Infant, Small for Gestational Age / Infants, Premature / Newborn Infants / Sepsis1
3CompletedTreatmentInfection, Human Immunodeficiency Virus I1
3CompletedTreatmentLeukemias1
4CompletedTreatmentDyslipidemias / Human Immunodeficiency Virus (HIV)1
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
Not AvailableCompletedTreatmentMyocardial Infarction (MI)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Dosage forms
FormRouteStrength
Injection, solutionIntravenous
Injection, solution, concentrateIntravenous
EmulsionIntravenous
SolutionIntravenous
LiquidIntravenous
InjectionIntravenous
Kit
Prices
Unit descriptionCostUnit
L-histidine mhc crystals0.32USD g
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)287 dec °CPhysProp
water solubility4.56E+004 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP-3.32CHMELIK,J ET AL. (1991)
logS-0.53ADME Research, USCD
pKa2.76 (at 0 °C)KORTUM,G ET AL (1961)
Predicted Properties
PropertyValueSource
Water Solubility62.0 mg/mLALOGPS
logP-3.1ALOGPS
logP-3.6ChemAxon
logS-0.4ALOGPS
pKa (Strongest Acidic)1.85ChemAxon
pKa (Strongest Basic)9.44ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area92 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity38.06 m3·mol-1ChemAxon
Polarizability14.67 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.8921
Blood Brain Barrier+0.7546
Caco-2 permeable-0.6669
P-glycoprotein substrateNon-substrate0.6143
P-glycoprotein inhibitor INon-inhibitor0.9889
P-glycoprotein inhibitor IINon-inhibitor0.9923
Renal organic cation transporterNon-inhibitor0.907
CYP450 2C9 substrateNon-substrate0.8647
CYP450 2D6 substrateNon-substrate0.8235
CYP450 3A4 substrateNon-substrate0.8363
CYP450 1A2 substrateNon-inhibitor0.9815
CYP450 2C9 inhibitorNon-inhibitor0.9646
CYP450 2D6 inhibitorNon-inhibitor0.9566
CYP450 2C19 inhibitorNon-inhibitor0.9656
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9798
Ames testNon AMES toxic0.7016
CarcinogenicityNon-carcinogens0.9206
BiodegradationNot ready biodegradable0.569
Rat acute toxicity1.7719 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9893
hERG inhibition (predictor II)Non-inhibitor0.9551
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (7.24 KB)
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)GC-MSsplash10-0udi-0940000000-43b9b035189af65e19cb
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)GC-MSsplash10-0udi-0910000000-fc3ecec9d4ff3aa8cb09
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-0udi-0910000000-8284a673a35f7ac2241f
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)GC-MSsplash10-0fk9-8910000000-a3231b1a418b5798ecac
GC-MS Spectrum - GC-MS (3 TMS)GC-MSsplash10-0udi-1920000000-227e8116769731104e82
GC-MS Spectrum - GC-MS (4 TMS)GC-MSsplash10-0ufu-2942100000-31605fd50ecc1f5be0ed
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0udi-0940000000-43b9b035189af65e19cb
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0udi-0910000000-fc3ecec9d4ff3aa8cb09
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0udi-0910000000-8284a673a35f7ac2241f
GC-MS Spectrum - GC-EI-QQGC-MSsplash10-0002-2901100000-ae0f3865934743de764c
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0fk9-8910000000-a3231b1a418b5798ecac
GC-MS Spectrum - GC-MSGC-MSsplash10-0udi-1920000000-227e8116769731104e82
GC-MS Spectrum - GC-MSGC-MSsplash10-0ufu-2942100000-31605fd50ecc1f5be0ed
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0ue9-0900000000-75e38a3f347210c301b0
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0udi-0910000000-c54bd92cc112eec7e509
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-0a4i-0900000000-21530fac9975dc1edc7c
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-053r-9300000000-a946c375931adb366aae
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-053r-9000000000-61a3602d80bc0d54c579
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-0a4i-0900000000-7d63b501889c2628f4f0
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-001i-0900000000-d4ccd4e44ca818b4cb17
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-0a4i-0900000000-811aee5724fe0999c134
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-0a4i-2900000000-052753eb699ae7cb4cb9
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-0a4i-0900000000-3e145a05e6a71a0a2f56
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-0a4i-0900000000-143a4b9d88183bc5abe7
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-03di-0900000000-a8c213472da676a241f2
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-001i-0900000000-dfdf9562f155abb5fdeb
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-0uk9-0879331100-8434b5b9e7e5700c2353
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-000i-0900000000-aaaaadcecd4cd7c94e1e
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-0udi-0900000000-90c4cbd09d7abc003013
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-0udi-0900000000-1381708d18c24486773d
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-0w29-0696321100-eb62fc608270d1151707
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-000i-0900000000-3450566ff38e6506a70f
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-01q9-7900000000-124509a66476629ce10a
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-0udi-0900000000-efa6a21b1be16fda0802
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-0udi-0900000000-137840e69da48c6114e4
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-0udu-3900000000-06d50e90c797793a72d7
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-0006-9100000000-de7c9eb8068ef4f39f85
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, NegativeLC-MS/MSsplash10-00l6-9000000000-ebf778679d4c6d6a6057
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, NegativeLC-MS/MSsplash10-014i-9000000000-08d0188684283d1b2372
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, PositiveLC-MS/MSsplash10-0a4i-0900000000-46c2f608d27f0381a039
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, PositiveLC-MS/MSsplash10-03di-1900000000-93b0baded5b5f54aca17
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, PositiveLC-MS/MSsplash10-03e9-9800000000-a3c782d1535ae8b0d1c1
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, PositiveLC-MS/MSsplash10-001i-9100000000-c7c31b7ea6894d3b0a6e
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, PositiveLC-MS/MSsplash10-001i-9000000000-ffcb71d851f251f1292f
MS/MS Spectrum - CE-ESI-TOF (CE-system connected to 6210 Time-of-Flight MS, Agilent) , PositiveLC-MS/MSsplash10-0a4i-0900000000-dac9566873944f51ac90
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-0a4i-0900000000-3f6e71a4367fbb22d3e2
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, PositiveLC-MS/MSsplash10-0a4i-0900000000-23a17624cb20e8b396c8
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-03di-2900000000-51c690b17a1f55dc7c19
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-0udi-3900000000-e4fa4911c4ebd02263b9
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-0udi-2900000000-6287a186f043aec33ef3
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/MSsplash10-0udi-0900000000-137840e69da48c6114e4
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0udu-3900000000-88bbc00d1f044650dd14
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0006-9100000000-de7c9eb8068ef4f39f85
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-00l6-9000000000-ebf778679d4c6d6a6057
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-014i-9000000000-08d0188684283d1b2372
LC-MS/MS Spectrum - LC-ESI-IT , negativeLC-MS/MSsplash10-000i-0900000000-4b93103dfe83a33375e1
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-000i-0900000000-aaaaadcecd4cd7c94e1e
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-000i-0900000000-3450566ff38e6506a70f
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0udi-3900000000-e4fa4911c4ebd02263b9
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0udi-2900000000-fe149448da604682a5a4
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0a4i-0900000000-46c2f608d27f0381a039
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-03di-1900000000-93b0baded5b5f54aca17
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-03e9-9800000000-a3c782d1535ae8b0d1c1
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-001i-9100000000-7aeaadf1d0b73479e267
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-001i-9000000000-ffcb71d851f251f1292f
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4i-0900000000-3f6e71a4367fbb22d3e2
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4i-0900000000-23a17624cb20e8b396c8
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-03di-2900000000-51c690b17a1f55dc7c19
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as histidine and derivatives. These are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Histidine and derivatives
Alternative Parents
L-alpha-amino acids / Imidazolyl carboxylic acids and derivatives / Aralkylamines / Heteroaromatic compounds / Amino acids / Monocarboxylic acids and derivatives / Carboxylic acids / Azacyclic compounds / Organopnictogen compounds / Organic oxides
show 3 more
Substituents
Histidine or derivatives / Alpha-amino acid / L-alpha-amino acid / Imidazolyl carboxylic acid derivative / Aralkylamine / Azole / Imidazole / Heteroaromatic compound / Amino acid / Carboxylic acid
show 15 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
proteinogenic amino acid, L-alpha-amino acid, histidine (CHEBI:15971) / Common amino acids (C00135)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Pyridoxal phosphate binding
Specific Function
Catalyzes the biosynthesis of histamine from histidine.
Gene Name
HDC
Uniprot ID
P19113
Uniprot Name
Histidine decarboxylase
Molecular Weight
74139.825 Da
References
  1. Landete JM, Pardo I, Ferrer S: Histamine, histidine, and growth-phase mediated regulation of the histidine decarboxylase gene in lactic acid bacteria isolated from wine. FEMS Microbiol Lett. 2006 Jul;260(1):84-90. [PubMed:16790022]
  2. Fernandez M, del Rio B, Linares DM, Martin MC, Alvarez MA: Real-time polymerase chain reaction for quantitative detection of histamine-producing bacteria: use in cheese production. J Dairy Sci. 2006 Oct;89(10):3763-9. [PubMed:16960050]
  3. Nitta Y, Kikuzaki H, Ueno H: Food components inhibiting recombinant human histidine decarboxylase activity. J Agric Food Chem. 2007 Jan 24;55(2):299-304. [PubMed:17227057]
  4. Kitamura Y, Das AK, Murata Y, Maeyama K, Dev S, Wakayama Y, Kalubi B, Takeda N, Fukui H: Dexamethasone suppresses histamine synthesis by repressing both transcription and activity of HDC in allergic rats. Allergol Int. 2006 Sep;55(3):279-86. [PubMed:17075268]
  5. Castellani ML, Kempuraj D, Frydas S, Theoharides TC, Simeonidou I, Conti P, Vecchiet J: Inhibitory effect of quercetin on tryptase and MCP-1 chemokine release, and histidine decarboxylase mRNA transcription by human mast cell-1 cell line. Neuroimmunomodulation. 2006;13(3):179-86. Epub 2006 Dec 21. [PubMed:17191019]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Histidine-trna ligase activity
Specific Function
Not Available
Gene Name
HARS
Uniprot ID
P12081
Uniprot Name
Histidine--tRNA ligase, cytoplasmic
Molecular Weight
57409.97 Da
References
  1. Nagatoyo Y, Iwaki J, Suzuki S, Kuno A, Hasegawa T: Molecular recognition of histidine tRNA by histidyl-tRNA synthetase from hyperthermophilic archaeon, Aeropyrum pernix K1. Nucleic Acids Symp Ser (Oxf). 2005;(49):307-8. [PubMed:17150756]
  2. Rosen AE, Brooks BS, Guth E, Francklyn CS, Musier-Forsyth K: Evolutionary conservation of a functionally important backbone phosphate group critical for aminoacylation of histidine tRNAs. RNA. 2006 Jul;12(7):1315-22. Epub 2006 Jun 1. [PubMed:16741232]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Symporter activity
Specific Function
Sodium-dependent amino acid/proton antiporter. Mediates electrogenic cotransport of glutamine and sodium ions in exchange for protons. Also recognizes histidine, asparagine and alanine. May mediate...
Gene Name
SLC38A3
Uniprot ID
Q99624
Uniprot Name
Sodium-coupled neutral amino acid transporter 3
Molecular Weight
55772.405 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. Eppig JJ, Pendola FL, Wigglesworth K, Pendola JK: Mouse oocytes regulate metabolic cooperativity between granulosa cells and oocytes: amino acid transport. Biol Reprod. 2005 Aug;73(2):351-7. Epub 2005 Apr 20. [PubMed:15843493]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Histidine ammonia-lyase activity
Specific Function
Not Available
Gene Name
HAL
Uniprot ID
P42357
Uniprot Name
Histidine ammonia-lyase
Molecular Weight
72696.9 Da
References
  1. Viergutz S, Retey J: Kinetic analysis of the reactions catalyzed by histidine and phenylalanine ammonia lyases. Chem Biodivers. 2004 Feb;1(2):296-302. [PubMed:17191848]
  2. Lambrecht NW, Yakubov I, Sachs G: Fasting-induced changes in ECL cell gene expression. Physiol Genomics. 2007 Oct 22;31(2):183-92. Epub 2007 May 29. [PubMed:17536021]
  3. Watts KT, Mijts BN, Lee PC, Manning AJ, Schmidt-Dannert C: Discovery of a substrate selectivity switch in tyrosine ammonia-lyase, a member of the aromatic amino acid lyase family. Chem Biol. 2006 Dec;13(12):1317-26. [PubMed:17185227]
  4. Katona A, Tosa MI, Paizs C, Retey J: Inhibition of histidine ammonia lyase by heteroaryl-alanines and acrylates. Chem Biodivers. 2006 May;3(5):502-8. [PubMed:17193285]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Transporter activity
Specific Function
Sodium-independent transporter that mediates the update of aromatic acid. Can function as a net efflux pathway for aromatic amino acids in the basosolateral epithelial cells (By similarity).
Gene Name
SLC16A10
Uniprot ID
Q8TF71
Uniprot Name
Monocarboxylate transporter 10
Molecular Weight
55492.07 Da
References
  1. Kim DK, Kanai Y, Chairoungdua A, Matsuo H, Cha SH, Endou H: Expression cloning of a Na+-independent aromatic amino acid transporter with structural similarity to H+/monocarboxylate transporters. J Biol Chem. 2001 May 18;276(20):17221-8. Epub 2001 Feb 20. [PubMed:11278508]
  2. Kim DK, Kanai Y, Matsuo H, Kim JY, Chairoungdua A, Kobayashi Y, Enomoto A, Cha SH, Goya T, Endou H: The human T-type amino acid transporter-1: characterization, gene organization, and chromosomal location. Genomics. 2002 Jan;79(1):95-103. [PubMed:11827462]

Drug created on June 13, 2005 07:24 / Updated on October 21, 2017 19:19