FComEx: L-Histidine (PC000093)

Record Information

Version

1.0

Creation date

2015-10-09 22:28:12 UTC

Update date

2017-01-19 02:36:12 UTC

FoodComEx ID

PC000093

FoodDB Record

FDB011856

Chemical Information

Name

L-Histidine

Description

Flavouring 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 Number

71-00-1

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(2S)-2-amino-3-(1H-imidazol-4-yl)propanoic acid	biospider
(2S)-2-amino-3-(3H-imidazol-4-yl)propanoic acid	biospider
(l)-histidine	biospider
(S)-1H-Imidazole-4-alanine	biospider
(S)-2-Amino-3-(4-imidazolyl)propionic acid	biospider
(S)-2-amino-3-(4-Imidazolyl)propionsaeure	HMDB
(S)-4-(2-Amino-2-carboxyethyl)imidazole	biospider
(S)-a-Amino-1H-imidazole-4-propanoate	biospider
(S)-a-Amino-1H-imidazole-4-propanoic acid	biospider
(S)-a-amino-1H-Imidazole-4-propionate	Generator
(S)-a-amino-1H-Imidazole-4-propionic acid	Generator
(S)-alpha-Amino-1H-imidazole-4-propanoate	biospider
(S)-alpha-Amino-1H-imidazole-4-propanoic acid	biospider
(S)-alpha-Amino-1H-imidazole-4-propionate	biospider
(S)-alpha-Amino-1H-imidazole-4-propionic acid	biospider
(s)-histidine	biospider
(S)-α-amino-1H-imidazole-4-propanoate	Generator
(S)-α-amino-1H-imidazole-4-propanoic acid	Generator
(S)-α-amino-1H-imidazole-4-propionate	Generator
(S)-α-amino-1H-imidazole-4-propionic acid	Generator
(S)1H-Imidazole-4-alanine	biospider
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-Alanine	biospider
4-(2-Amino-2-carboxyethyl)imidazole	biospider
alpha-Amino-1H-imidazole-4-propionic acid, (S)-	biospider
alpha-Amino-4(or 5)-imidazolepropionic acid	biospider
amino-1H-imidazole-4-propanoate	biospider
amino-1H-imidazole-4-propanoic acid	biospider
amino-4-imidazoleproprionate	biospider
amino-4-imidazoleproprionic acid	biospider
FEMA 3694	db_source
Glyoxaline-5-alanine	biospider
H	ChEBI
His	ChEBI
HISTIDINE	ChEBI
Histidine (usp/inn)	biospider
Histidine (van)	biospider
Histidine [usan:inn]	biospider
Histidine, INN, USAN; L-form	db_source
Histidine, l-	biospider
L-(-)-histidine	biospider
L-Alanine, 3-(1H-imidazol-4-yl)-	biospider
L-beta-(4-Imidazolyl)-alpha-alanin	biospider
L-beta-(4-Imidazolyl)alanin	biospider
L-histidin	biospider
L-Histidine	biospider
S-histidine	biospider

Chemical Formula

C6H9N3O2

IUPAC name

2-amino-3-(1H-imidazol-5-yl)propanoic acid

InChI Identifier

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)

InChI Key

HNDVDQJCIGZPNO-UHFFFAOYSA-N

Isomeric SMILES

NC(CC1=CN=CN1)C(O)=O

Average Molecular Weight

155.1546

Monoisotopic Molecular Weight

155.069476547

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as histidine and derivatives. Histidine and derivatives 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

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 Framework

Aromatic heteromonocyclic compounds

External Descriptors

imidazoles (CHEBI:27570 )
alpha-amino acid (CHEBI:27570 )

Physico-Chemical Properties - Experimental

Property	Value	Reference
Experimental logP	-3.32	CHMELIK,J ET AL. (1991)
Experimental Water Solubility	45.6 mg/mL at 25 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Melting Point	Mp 277° dec.	DFC

Foods of Origin