AFCDB: L-Histidine (FDB011856)

Record Information

Version

1.0

Creation date

2010-04-08 22:09:52 UTC

Update date

2019-11-26 03:05:35 UTC

Primary ID

FDB011856

Secondary Accession Numbers

Not Available

Chemical Information

FooDB 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
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	62 g/L	ALOGPS
logP	-3.1	ALOGPS
logP	-3.6	ChemAxon
logS	-0.4	ALOGPS
pKa (Strongest Acidic)	1.85	ChemAxon
pKa (Strongest Basic)	9.44	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	92 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	38.06 m³·mol⁻¹	ChemAxon
Polarizability	14.8 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

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

Classification

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 )

Ontology

No ontology term

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 46.45%; H 5.85%; N 27.08%; O 20.62%	DFC
Melting Point	Mp 277° dec.	DFC
Boiling Point	Not Available
Experimental Water Solubility	45.6 mg/mL at 25 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP	-3.32	CHMELIK,J ET AL. (1991)
Experimental pKa	2.76
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]25D +18.3 (+11.8) (5M HCl)	DFC
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-001i-9100000000-ae0a0b81669663b3b4a5	2014-09-20	View Spectrum
Predicted GC-MS	L-Histidine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-001i-9400000000-5e6963983298535b27d8	Spectrum
Predicted GC-MS	L-Histidine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Histidine, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Histidine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Histidine, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Histidine, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Histidine, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Histidine, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-053r-9000000000-1478106116309658fadd	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-001i-9200000000-c7bde7fc68c95b650666	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-0bt9-0900000000-5ae6a574e7140a379bbd	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 25V, Positive	splash10-03di-4900000000-1236c6813216a3650ccc	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 25V, Positive	splash10-03di-3900000000-7eed8a793aebb339a1a1	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-053r-9000000000-2dd5486f7b3241685315	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0gw0-0900000000-a0cbbe99d0c71d0ff5c7	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-39864028be32b684b6b8	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0900000000-c792e4d6040e598120d3	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-08g0-0900000000-9089f7d82f3446b94c4f	2018-04-06	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-7900000000-717ec4c802609a81cf53	2018-04-06	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f89-9000000000-03526fc1a092a64548b9	2018-04-06	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-1900000000-b23127c1801c4cf851ed	2018-04-06	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0ul9-8900000000-c5317c32047bfd386dae	2018-04-06	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-007o-9000000000-e9c8ee81851c24c3bc0d	2018-04-06	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-08fr-0900000000-2c5b01f968746b87ab67	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03dl-6900000000-ab46f486b2b76d433d32	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-053u-9000000000-e3d5332f624d684d2d2a	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udr-1900000000-4ca598739f604c4fdd39	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9300000000-4ce447c349d8c431928b	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kf-9000000000-cafb1c651f51cab7cf44	2021-10-12	View Spectrum

NMR

Type	Description		View
1D NMR	¹³C NMR Spectrum (1D, 22.53 MHz, D₂O, experimental)		Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

15971

Phenol-Explorer ID

Not Available

DrugBank ID

DB00117

HMDB ID

HMDB00177

CRC / DFC (Dictionary of Food Compounds) ID

HBB51-Y:HBB61-B

EAFUS ID

1701

Dr. Duke ID

L-HISTIDINE|HISTIDINE

BIGG ID

33985

KNApSAcK ID

C00001363

HET ID

1KAH

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1037461

SuperScent ID

Not Available

Wikipedia ID

L-Histidine

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
anti arteriosclerotic	38070	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 nephritic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
antioxidant	22586	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 ulcer	49201	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 uremic			DUKE
essential			DUKE
oxidant	63248	A substance that removes electrons from another reactant in a redox reaction.	DUKE

Enzymes

Name	Gene Name	UniProt ID
Aromatic-L-amino-acid decarboxylase	DDC	P20711
Histidine decarboxylase	HDC	P19113
Histidine ammonia-lyase	HAL	P42357
Probable histidine--tRNA ligase, mitochondrial	HARS2	P49590
Histidine--tRNA ligase, cytoplasmic	HARS	P12081

Pathways

Name	SMPDB Link	KEGG Link
Ammonia Recycling	SMP00009	map00910
Histidine Metabolism	SMP00044	map00340
Transcription/Translation	SMP00019	Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
odorless	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
bitter	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

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not 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.

L-Histidine (FDB011856)

Structure for FDB011856 (L-Histidine)