Record Information
Version1.0
Creation date2010-04-08 22:09:52 UTC
Update date2018-01-23 19:18:34 UTC
Primary IDFDB011856
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameL-Histidine
DescriptionFlavouring ingredient; dietary supplement, nutrient Histidine (abbreviated as His or H) is one of the 20 standard amino acids present in proteins. Nutritionally, histidine is considered an essential amino acid in human infants. After reaching several years of age, humans begin to synthesize it and it thus becomes a non-essential amino acid. Its codons are CAU and CAC.; Is found abundantly in hemoglobin; The amino acid is a precursor for histamine and carnosine biosynthesis.; The imidazole sidechain of histidine is a common coordinating ligand in metalloproteins and is a part of catalytic sites in certain enzymes. In catalytic triads, the basic nitrogen of histidine is used to abstract a proton from serine, threonine or cysteine to activate it as a nucleophile. In a histidine proton shuttle, histidine is used to quickly shuttle protons, it can do this by abstracting a proton with its basic nitrogen to make a positively-charged intermediate and then use another molecule, a buffer, to extract the proton from its acidic nitrogen. In carbonic anhydrases, a histidine proton shuttle is utilized to rapidly shuttle protons away from a zinc-bound water molecule to quickly regenerate the active form of the enzyme.; histidine is an essential amino acid for infants but not adults. Infants four to six months old require 33 mg/kg of histidine. It is not clear how adults make small amounts of histidine, and dietary sources probably account for most of the histidine in the body. Inborn errors of histidine metabolism exist and are marked by increased histidine levels in the blood. Elevated blood histidine is accompanied by a wide range of symptoms, from mental and physical retardation to poor intellectual functioning, emotional instability, tremor, ataxia and psychosis. histidine in medical therapies has its most promising trials in rheumatoid arthritis where up to 4.5 g daily have been used effectively in severely affected patients. Arthritis patients have been found to have low serum histidine levels, apparently because of too-rapid removal of histidine from their blood. histidine and other imidazole compounds have anti-inflammatory properties. histidine may accomplish this function through a complex interaction with threonine or cysteine and possibly copper. However, copper is usually elevated in rheumatoid arthritis patients and worsens the disease. Other patients besides arthritis patients that have been found to be low in serum histidine are those with chronic renal failure. histidine has been claimed to have been useful in hypertension because of its vasodilatory effects. Claims of its use to improve libido and counteract allergy are without proof at present. histidine may have many other possible functions because it is the precursor of the ubiquitous neurohormone-neurotransmitter histamine. histidine increases histamine in the blood and probably in the brain. Low blood histamine with low serum histidine occurs in rheumatoid arthritis patients. Low blood histamine also occurs in some manic, schizophrenic, high copper and hyperactive groups of psychiatric patients. histidine is a useful therapy in all low histamine patients. ( http://www.dcnutrition.com ). L-Histidine is found in many foods, some of which are lemon verbena, sparkleberry, rowanberry, and walleye.
CAS Number71-00-1
Structure
Thumb
Synonyms
SynonymSource
alpha-amino-1H-Imidazole-4-propionic acidChEBI
DL-HistidineChEBI
HistidinChEBI
HistidinaChEBI
a-amino-1H-Imidazole-4-propionateGenerator
a-amino-1H-Imidazole-4-propionic acidGenerator
alpha-amino-1H-Imidazole-4-propionateGenerator
α-amino-1H-imidazole-4-propionateGenerator
α-amino-1H-imidazole-4-propionic acidGenerator
(2S)-2-amino-3-(1H-imidazol-4-yl)propanoic acidbiospider
(2S)-2-amino-3-(3H-imidazol-4-yl)propanoic acidbiospider
(l)-histidinebiospider
(S)-1H-Imidazole-4-alaninebiospider
(S)-2-Amino-3-(4-imidazolyl)propionic acidbiospider
(S)-2-amino-3-(4-Imidazolyl)propionsaeureHMDB
(S)-4-(2-Amino-2-carboxyethyl)imidazolebiospider
(S)-a-Amino-1H-imidazole-4-propanoatebiospider
(S)-a-Amino-1H-imidazole-4-propanoic acidbiospider
(S)-a-amino-1H-Imidazole-4-propionateGenerator
(S)-a-amino-1H-Imidazole-4-propionic acidGenerator
(S)-alpha-Amino-1H-imidazole-4-propanoatebiospider
(S)-alpha-Amino-1H-imidazole-4-propanoic acidbiospider
(S)-alpha-Amino-1H-imidazole-4-propionatebiospider
(S)-alpha-Amino-1H-imidazole-4-propionic acidbiospider
(s)-histidinebiospider
(S)-α-amino-1H-imidazole-4-propanoateGenerator
(S)-α-amino-1H-imidazole-4-propanoic acidGenerator
(S)-α-amino-1H-imidazole-4-propionateGenerator
(S)-α-amino-1H-imidazole-4-propionic acidGenerator
(S)1H-Imidazole-4-alaninebiospider
1H-Imidazole-4-alanine, (S)-biospider
1H-Imidazole-4-propanoic acid, α-amino-, (S)-biospider
1H-Imidazole-4-propanoic acid, alpha-amino-, (S)-biospider
3-(1H-imidazol-4-yl)-L-Alaninebiospider
4-(2-Amino-2-carboxyethyl)imidazolebiospider
alpha-Amino-1H-imidazole-4-propionic acid, (S)-biospider
alpha-Amino-4(or 5)-imidazolepropionic acidbiospider
amino-1H-imidazole-4-propanoatebiospider
amino-1H-imidazole-4-propanoic acidbiospider
amino-4-imidazoleproprionatebiospider
amino-4-imidazoleproprionic acidbiospider
FEMA 3694db_source
Glyoxaline-5-alaninebiospider
HChEBI
HisChEBI
HISTIDINEChEBI
Histidine (usp/inn)biospider
Histidine (van)biospider
Histidine [usan:inn]biospider
Histidine, INN, USAN; L-formdb_source
Histidine, l-biospider
L-(-)-histidinebiospider
L-Alanine, 3-(1H-imidazol-4-yl)-biospider
L-beta-(4-Imidazolyl)-alpha-alaninbiospider
L-beta-(4-Imidazolyl)alaninbiospider
L-histidinbiospider
L-Histidinebiospider
S-histidinebiospider
Predicted Properties
PropertyValueSource
Water Solubility62 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity38.06 m³·mol⁻¹ChemAxon
Polarizability14.8 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC6H9N3O2
IUPAC name2-amino-3-(1H-imidazol-5-yl)propanoic acid
InChI IdentifierInChI=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)
InChI KeyHNDVDQJCIGZPNO-UHFFFAOYSA-N
Isomeric SMILESNC(CC1=CN=CN1)C(O)=O
Average Molecular Weight155.1546
Monoisotopic Molecular Weight155.069476547
Classification
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentHistidine and derivatives
Alternative Parents
Substituents
  • Histidine or derivatives
  • Alpha-amino acid
  • Imidazolyl carboxylic acid derivative
  • Aralkylamine
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Amino acid
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic nitrogen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organic oxide
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Amine
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 46.45%; H 5.85%; N 27.08%; O 20.62%DFC
Melting PointMp 277° dec.DFC
Boiling PointNot Available
Experimental Water Solubility45.6 mg/mL at 25 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP-3.32CHMELIK,J ET AL. (1991)
Experimental pKa2.76
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]25D +18.3 (+11.8) (5M HCl)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
ChemSpider ID6038
ChEMBL IDCHEMBL17962
KEGG Compound IDC00135
Pubchem Compound ID6274
Pubchem Substance IDNot Available
ChEBI ID15971
Phenol-Explorer IDNot Available
DrugBank IDDB00117
HMDB IDHMDB00177
CRC / DFC (Dictionary of Food Compounds) IDHBB51-Y:HBB61-B
EAFUS ID1701
Dr. Duke IDL-HISTIDINE|HISTIDINE
BIGG ID33985
KNApSAcK IDC00001363
HET ID1KAH
Flavornet IDNot Available
GoodScent IDrw1037461
SuperScent IDNot Available
Wikipedia IDL-Histidine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti arteriosclerotic38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
anti nephritic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
anti ulcer49201 One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract.DUKE
anti uremicDUKE
essentialDUKE
oxidant63248 A substance that removes electrons from another reactant in a redox reaction.DUKE
Enzymes
NameGene NameUniProt ID
Aromatic-L-amino-acid decarboxylaseDDCP20711
Histidine decarboxylaseHDCP19113
Histidine ammonia-lyaseHALP42357
Probable histidine--tRNA ligase, mitochondrialHARS2P49590
Histidine--tRNA ligase, cytoplasmicHARSP12081
Pathways
NameSMPDB LinkKEGG Link
Ammonia RecyclingSMP00009 map00910
Histidine MetabolismSMP00044 map00340
Transcription/TranslationSMP00019 Not Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
odorless
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
bitter
  1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).
— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.