Human Metabolome Database: Showing metabocard for 1-Methylhistidine (HMDB0000001)

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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

enzymes (2) Show 2 proteins

Record Information

Version

4.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2018-04-16 17:00:02 UTC

HMDB ID

HMDB0000001

Secondary Accession Numbers

HMDB00001
HMDB0004935
HMDB0006703
HMDB0006704
HMDB04935
HMDB06703
HMDB06704

Metabolite Identification

Common Name

1-Methylhistidine

Description

One-methylhistidine (1-MHis) is derived mainly from the anserine of dietary flesh sources, especially poultry. The enzyme, carnosinase, splits anserine into b-alanine and 1-MHis. High levels of 1-MHis tend to inhibit the enzyme carnosinase and increase anserine levels. Conversely, genetic variants with deficient carnosinase activity in plasma show increased 1-MHis excretions when they consume a high meat diet. Reduced serum carnosinase activity is also found in patients with Parkinson's disease and multiple sclerosis and patients following a cerebrovascular accident. Vitamin E deficiency can lead to 1-methylhistidinuria from increased oxidative effects in skeletal muscle. 1-Methylhistidine is a biomarker for the consumption of meat, especially red meat.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
(2S)-2-amino-3-(1-Methyl-1H-imidazol-4-yl)propanoic acid	ChEBI
1-Methylhistidine	ChEBI
Pi-methylhistidine	ChEBI
(2S)-2-amino-3-(1-Methyl-1H-imidazol-4-yl)propanoate	Generator
1 Methylhistidine	HMDB
1-Methyl histidine	HMDB
1-Methyl-histidine	HMDB
1-Methyl-L-histidine	HMDB
1-MHis	HMDB
1-N-Methyl-L-histidine	HMDB
L-1-Methylhistidine	HMDB
N1-Methyl-L-histidine	HMDB
1-Methylhistidine dihydrochloride	MeSH

Chemical Formula

C₇H₁₁N₃O₂

Average Molecular Weight

169.1811

Monoisotopic Molecular Weight

169.085126611

IUPAC Name

(2S)-2-amino-3-(1-methyl-1H-imidazol-4-yl)propanoic acid

Traditional Name

1 methylhistidine

CAS Registry Number

332-80-9

SMILES

CN1C=NC(C[C@H](N)C(O)=O)=C1

InChI Identifier

InChI=1S/C7H11N3O2/c1-10-3-5(9-4-10)2-6(8)7(11)12/h3-4,6H,2,8H2,1H3,(H,11,12)/t6-/m0/s1

InChI Key

BRMWTNUJHUMWMS-LURJTMIESA-N

Chemical 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

Substituents

Histidine or derivatives
Alpha-amino acid
L-alpha-amino acid
Imidazolyl carboxylic acid derivative
Aralkylamine
N-substituted imidazole
Azole
Imidazole
Heteroaromatic compound
Amino acid
Carboxylic acid
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Primary amine
Primary aliphatic amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Amine
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

non-proteinogenic L-alpha-amino acid (CHEBI:50599 )
L-histidine derivative (CHEBI:50599 )

Ontology

Physiological effect

Health effect:

Health condition:

Metabolism and nutrition disorders:

Obesity

Disposition

Source:

Endogenous

Biological location:

Tissue and substructures:

Biofluid and excreta:

Subcellular:

Cytoplasm

Process

Naturally occurring process:

Biological process:

Biochemical pathway:

Histidine Metabolism

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	249	http://download.cappchem.com/data/Properties-of-Amino-Acids.pdf
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	6.93 g/L	ALOGPS
logP	-3.1	ChemAxon
pKa (Strongest Acidic)	1.96	ChemAxon
pKa (Strongest Basic)	9.25	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	81.14 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	42.39 m³·mol⁻¹	ChemAxon
Polarizability	17.11 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-0002-9610000000-d0147d3e28362f91174a	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-0gbd-4941000000-cee19577c72eecd95aec	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0002-9610000000-d0147d3e28362f91174a	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0gbd-4941000000-cee19577c72eecd95aec	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dm-9500000000-e50450f2dc8a5d4b3655	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9310000000-d6f7eb07e6f5ecb74263	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00di-0900000000-037d24a7d65676b7e356	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00di-0900000000-03e99316bd6c098f5d11	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-00ea-9800000000-a33c82a1c91f56d372fe	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-695bcc2d0a01df2d7521	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0900000000-4eea9cf6f12f18d06f98	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05us-9300000000-072d6fe7a7a03cd7390b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-1900000000-57f1e30ae8b606ea5f5c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01b9-5900000000-ff71b6d300a9ee595b3c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0adj-9300000000-e045823003ab541d5b1e	View in MoNA
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Saliva
Urine

Tissue Location

Muscle
Skeletal Muscle

Pathways

Name	SMPDB/Pathwhiz	KEGG
Histidine Metabolism
Histidinemia		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	7.7 +/- 1.9 uM	Adult (>18 years old)	Both	Normal	7061274	details
Blood	Detected and Quantified	14.4 +/- 2.3 uM	Adult (>18 years old)	Both	Normal	7061274	details
Blood	Detected and Quantified	19.6 +/- 2.6 uM	Adult (>18 years old)	Both	Normal	7061274	details
Blood	Detected and Quantified	12.7 +/- 2.9 uM	Adult (>18 years old)	Both	Normal	7061274	details
Blood	Detected and Quantified	20.2 +/- 4.0 uM	Adult (>18 years old)	Both	Normal	7061274	details
Blood	Detected and Quantified	9.1 +/- 7.2 uM	Children (1-13 years old)	Not Specified	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	4.0 +/- 8.0 uM	Adult (>18 years old)	Both	Normal	Geigy Scientific ...	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	4.0 +/- 1.74 uM	Adult (>18 years old)	Both	Normal	17031479	details
Feces	Detected but not Quantified		Not Specified	Both	Normal	25486321	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Normal	27543620	details
Saliva	Detected and Quantified	26.34 uM	Adult (>18 years old)	Both	Normal	1819935	details
Urine	Detected and Quantified	10-17 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	27012787	details
Urine	Detected but not Quantified		Not Available	Male	Normal	22932811	details
Urine	Detected and Quantified	17.74-153.77 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	David F. Putnam C...	details
Urine	Detected and Quantified	8.3 (2.4-28.4) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	15.9 +/- 19.5 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	11052553	details
Urine	Detected and Quantified	46.0833 +/- 53.432 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	11052553	details
Urine	Detected and Quantified	11-16 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	27012787	details
Urine	Detected and Quantified	45.473 +/- 41.617 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	11052553	details
Urine	Detected and Quantified	15.919 +/- 19.503 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	11052553	details
Urine	Detected and Quantified	4.635 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	11052553	details
Urine	Detected and Quantified	33.624 +/- 36.360 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	11052553	details
Urine	Detected and Quantified	28.0954 +/- 31.826 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	11052553	details
Urine	Detected and Quantified	2.340 +/- 5.0764 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	11052553	details
Urine	Detected and Quantified	1.334 +/- 2.759 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	11052553	details
Urine	Detected and Quantified	30.0 +/- 43.0 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	15899597	details
Urine	Detected and Quantified	4.6 +/- 2.7 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	11052553	details
Urine	Detected and Quantified	2.3 +/- 5.1 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	11052553	details
Urine	Detected and Quantified	46.1 +/- 53.5 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	11052553	details
Urine	Detected and Quantified	15.9 +/- 19.5 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	11052553	details
Urine	Detected and Quantified	28.1 +/- 31.8 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	11052553	details
Urine	Detected and Quantified	1.3 +/- 2.76 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	11052553	details
Urine	Detected and Quantified	45.5 +/- 41.6 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	11052553	details
Urine	Detected and Quantified	33.6 +/- 36.4 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	11052553	details
Urine	Detected and Quantified	21.329 +/- 12.971 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Mordechai, Hien, ...	details
Urine	Detected but not Quantified		Adult (>18 years old)	Male	Normal	17022649	details
Urine	Detected but not Quantified		Adult (>18 years old)	Both	Normal	21736852	details
Urine	Detected but not Quantified		Adult (>18 years old)	Both	Normal	23269817	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	51.2 +/- 17.6 uM	Adult (>18 years old)	Female	Pregnancy with fetuses with trisomy 18	23535240	details
Blood	Detected and Quantified	43.4 +/- 22.3 uM	Adult (>18 years old)	Female	Pregnancy	23535240	details
Blood	Detected and Quantified	50.7 (12.9) uM	Adult (>18 years old)	Female	Early preeclampsia	22494326	details
Blood	Detected and Quantified	50.0 (14.6) uM	Adult (>18 years old)	Female	Pregnancy	22494326	details
Blood	Detected and Quantified	28.8 +/- 18.2 uM	Adult (>18 years old)	Both	Kidney disease	10838467	details
Blood	Detected and Quantified	83.1 +/- 21.7 uM	Adult (>18 years old)	Both	Kidney disease	10838467	details
Blood	Detected and Quantified	70.3 (40.0) uM	Adult (>18 years old)	Female	Late-onset preeclampsia	23159745	details
Blood	Detected and Quantified	38.9 (20.3) uM	Adult (>18 years old)	Female	Pregnancy	23159745	details
Blood	Detected and Quantified	10.66 +/- 2.68 uM	Elderly (>65 years old)	Both	Alzheimer's disease	17031479	details
Blood	Detected and Quantified	40.4 (12.3) uM	Adult (>18 years old)	Female	Down syndrome pregnancy	23313728	details
Blood	Detected and Quantified	32.7 (13.7) uM	Adult (>18 years old)	Female	Pregnancy	23313728	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	2.6 +/- 1.13 uM	Adult (>18 years old)	Both	Alzheimer's disease	17031479	details
Urine	Detected and Quantified	10.9 +/- 10.1 umol/mmol creatinine	Adult (>18 years old)	Both	Obesity	15899597	details
Urine	Detected and Quantified	17.5 +/- 25.7 umol/mmol creatinine	Adult (>18 years old)	Both	Diabetes	15899597	details
Urine	Detected and Quantified	15.7 +/- 4.04 umol/mmol creatinine	Adult (>18 years old)	Both	Alzheimer's disease	17031479	details
Urine	Detected and Quantified	18.299 +/- 16.521 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Mordechai, Hien, ...	details
Urine	Detected and Quantified	40 +/- 2.6 umol/mmol creatinine	Adult (>18 years old)	Both	Propionic acidemia	19551947	details
Urine	Detected and Quantified	31 +/- 11 umol/mmol creatinine	Adult (>18 years old)	Both	Maple syrup urine disease	19551947	details
Urine	Detected and Quantified	50.3 +/- 9.9 umol/mmol creatinine	Adult (>18 years old)	Both	Aminoaciduria	19551947	details

Associated Disorders and Diseases

Disease References

Alzheimer's disease
Fonteh AN, Harrington RJ, Tsai A, Liao P, Harrington MG: Free amino acid and dipeptide changes in the body fluids from Alzheimer's disease subjects. Amino Acids. 2007 Feb;32(2):213-24. Epub 2006 Oct 10. [PubMed:17031479 ]
Diabetes mellitus type 2
Tuma P, Samcova E, Balinova P: Determination of 3-methylhistidine and 1-methylhistidine in untreated urine samples by capillary electrophoresis. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Jul 5;821(1):53-9. [PubMed:15899597 ]
Kidney disease
Raj DS, Ouwendyk M, Francoeur R, Pierratos A: Plasma amino acid profile on nocturnal hemodialysis. Blood Purif. 2000;18(2):97-102. [PubMed:10838467 ]
Obesity
Tuma P, Samcova E, Balinova P: Determination of 3-methylhistidine and 1-methylhistidine in untreated urine samples by capillary electrophoresis. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Jul 5;821(1):53-9. [PubMed:15899597 ]

Associated OMIM IDs

104300 (Alzheimer's disease)
601665 (Obesity)
125853 (Diabetes mellitus type 2)

External Links

DrugBank ID

DB04151

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB012119

KNApSAcK ID

Not Available

Chemspider ID

83153

KEGG Compound ID

C01152

BioCyc ID

CPD-1823

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

PubChem Compound

PDB ID

ChEBI ID

References

Synthesis Reference

Jain, Rahul; Cohen, Louis A. Regiospecific alkylation of histidine and histamine at N-1 (t).Tetrahedron (1996), 52(15), 5363-70.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Colombani PC, Kovacs E, Frey-Rindova P, Frey W, Langhans W, Arnold M, Wenk C: Metabolic effects of a protein-supplemented carbohydrate drink in marathon runners. Int J Sport Nutr. 1999 Jun;9(2):181-201. [PubMed:10362454 ]
Nicholson JK, Foxall PJ, Spraul M, Farrant RD, Lindon JC: 750 MHz 1H and 1H-13C NMR spectroscopy of human blood plasma. Anal Chem. 1995 Mar 1;67(5):793-811. [PubMed:7762816 ]
Myint T, Fraser GE, Lindsted KD, Knutsen SF, Hubbard RW, Bennett HW: Urinary 1-methylhistidine is a marker of meat consumption in Black and in White California Seventh-day Adventists. Am J Epidemiol. 2000 Oct 15;152(8):752-5. [PubMed:11052553 ]
Giesecke K, Magnusson I, Ahlberg M, Hagenfeldt L, Wahren J: Protein and amino acid metabolism during early starvation as reflected by excretion of urea and methylhistidines. Metabolism. 1989 Dec;38(12):1196-200. [PubMed:2593832 ]
Vranic L, Granic P, Rajic Z: Basic amino acid in the pathogenesis of caries. Acta Stomatol Croat. 1991;25(2):71-6. [PubMed:1819935 ]
Sjolin J, Stjernstrom H, Henneberg S, Hambraeus L, Friman G: Evaluation of urinary 3-methylhistidine excretion in infection by measurements of 1-methylhistidine and the creatinine ratios. Am J Clin Nutr. 1989 Jan;49(1):62-70. [PubMed:2912013 ]
COCKS DH, DENNIS PO, NELSON TH: ISOLATION OF 3-METHYL HISTIDINE FROM WHALEMEAT EXTRACT AND THE PREPARATION OF SOME DERIVATIVES. Nature. 1964 Apr 11;202:184-5. [PubMed:14156296 ]
Dohm GL, Williams RT, Kasperek GJ, van Rij AM: Increased excretion of urea and N tau -methylhistidine by rats and humans after a bout of exercise. J Appl Physiol Respir Environ Exerc Physiol. 1982 Jan;52(1):27-33. [PubMed:7061274 ]
Garlick PJ, McNurlan MA, Bark T, Lang CH, Gelato MC: Hormonal regulation of protein metabolism in relation to nutrition and disease. J Nutr. 1998 Feb;128(2 Suppl):356S-359S. [PubMed:9478024 ]
Tuma P, Samcova E, Balinova P: Determination of 3-methylhistidine and 1-methylhistidine in untreated urine samples by capillary electrophoresis. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Jul 5;821(1):53-9. [PubMed:15899597 ]
Dunnett M, Harris RC: High-performance liquid chromatographic determination of imidazole dipeptides, histidine, 1-methylhistidine and 3-methylhistidine in equine and camel muscle and individual muscle fibres. J Chromatogr B Biomed Sci Appl. 1997 Jan 10;688(1):47-55. [PubMed:9029312 ]
Betto P, Ricciarello G, Pichini S, Dello Strologo L, Rizzoni G: High-performance liquid chromatography-electrochemical detection of 3-methylhistidine in human urine. J Chromatogr. 1992 Dec 23;584(2):256-60. [PubMed:1484110 ]

Enzymes

Enzyme Details

1. Beta-Ala-His dipeptidase

General function:: Involved in metallopeptidase activity
Specific function:: Preferential hydrolysis of the beta-Ala-|-His dipeptide (carnosine), and also anserine, Xaa-|-His dipeptides and other dipeptides including homocarnosine
Gene Name:: CNDP1
Uniprot ID:: Q96KN2
Molecular weight:: 56691.6

References

Fleisher LD, Rassin DK, Wisniewski K, Salwen HR: Carnosinase deficiency: a new variant with high residual activity. Pediatr Res. 1980 Apr;14(4 Pt 1):269-71. [PubMed:7375183 ]

Enzyme Details

2. Protein arginine N-methyltransferase 3

General function:: Involved in protein methyltransferase activity
Specific function:: Methylates (mono and asymmetric dimethylation) the guanidino nitrogens of arginyl residues in some proteins
Gene Name:: PRMT3
Uniprot ID:: O60678
Molecular weight:: 59902.7

References

Raghavan M, Lindberg U, Schutt C: The use of alternative substrates in the characterization of actin-methylating and carnosine-methylating enzymes. Eur J Biochem. 1992 Nov 15;210(1):311-8. [PubMed:1446680 ]

Showing metabocard for 1-Methylhistidine (HMDB0000001)

Structure for HMDB0000001 (1-Methylhistidine)

Enzymes

References

References