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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:14:26 UTC

HMDB ID

HMDB0000001

Secondary Accession Numbers

HMDB00001
HMDB0004935
HMDB0006703
HMDB0006704
HMDB04935
HMDB06703
HMDB06704

Metabolite Identification

Common Name

1-Methylhistidine

Description

1-Methylhistidine, also known as 1-MHis, 1MH, tau-methylhistidine or tele-methylhistidine, belongs to the class of organic compounds known as histidine and derivatives. 1MH is also classified as a methylamino acid. Methylamino acids are primarily proteogenic amino acids (found in proteins) which have been methylated (in situ) on their side chains by various methyltransferase enzymes. Histidine can be methylated at either the N1 or N3 position of its imidazole ring, yielding the isomers 1-methylhistidine (1MH; also referred to as tau-methylhistidine, according to IUPAC) or 3-methylhistidine (3MH; pi-methylhistidine, according to IUPAC), respectively. There is considerable confusion with regard to the nomenclature of the methylated nitrogen atoms on the imidazole ring of histidine in histidine-containing proteins (such as actin and myosin) as well as histidine-containing peptides (such as anserine and ophidine/balenine). In particular, older literature (mostly prior to the year 2000) as well as most biochemists and nutrition scientists incorrectly number the imidazole nitrogen atom most proximal to the side chain beta-carbon as 1 or N1, while organic chemists correctly designate it as 3 or N3. As a result, biochemists and nutrition scientists historically designated anserine (Npi-methylated) as beta-alanyl-N1-methylhistidine (or beta-alanyl-1-methylhistidine), whereas according to standard IUPAC nomenclature, anserine is correctly named as beta-alanyl-N3-methylhistidine. As a result, for several decades, many papers incorrectly identified 1MH as a specific marker for dietary consumption or various pathophysiological effects when they really are referring to 3MH – and vice versa (PMID: 24137022 ). To help resolve this issue the IUPAC commission (PMID: 6743224 and IUPAC Compendium of Chemical Terminology, 2nd ed. (the 'Gold Book'). Compiled by A. D. McNaught and A. Wilkinson. Blackwell Scientific Publications, Oxford (1997)) revised the nomenclature for histidine and introduced the terms pi (for prox or pros – near) and tau (for tele – far) to label the imidazole nitrogens in histidine. Therefore, the pi nitrogen is the nitrogen closest to the side chain beta carbon (atom #3 or N3) while the tau nitrogen is most distant from the side chain beta carbon (atom #1 or N1). IUPAC's goal is for the global community to refer to the molecule depicted here is as 'tau-methylhistidine' with the hope that the archaic term, 1-methylhistidine will eventually disappear. Unfortunately, this has not happened and confusion still persists. Older versions of the HMDB (prior to 2022) as well as current versions of some databases, such as PubChem, KEGG, and UniProt, indicate that an acceptable synonym for 1MH is pi-methylhistidine or otherwise somehow equate 1MH and 3MH. This is incorrect and it continues to sow confusion. Indeed, a key paper that identified METTL9 as the enzyme responsible for pi-methylation of histidine in most vertebrates also incorrectly labeled the METTL9 product as 1MH (PMID: 33563959 ). Similarly, a key paper that identified METTL18 as the enzyme responsible for tau-methylation of histidine incorrectly labelled the METTL18 product as 3MH (PMID: 33693809 ). Likewise, many members of the biochemical/nutrition community still incorrectly refer to 1MH as pi-methlyhistidine and 3MH as tau-methylhistidine. This has led to even more confusion. To maintain consistency for this compound description, all papers cited herein that incorrectly refer to 3MH as 1MH and vice versa, will have their conclusions re-stated and the citation will be marked with the phrase '3MH/1MH switch'. 1MH is a free amino acid arising from the proteolysis of 1MH-containing proteins and peptides. It is not synthesized on its own, nor can it be incorporated into proteins as an amino acid. However, it can be incorporated into certain dipeptides through the action of the enzyme known as carnosine synthase I. 1MH can only be generated from histidine residues through the action of methyltransferases as a protein post-translational modification event. Histidine methylation on the 1- or tau site of histidine-containing proteins is mediated by at least two enzymes: SETD3 (PMID: 30526847 ) and METTL18 (3MH/1MH switch - PMID: 33693809 ). SETD3, or SET domain-containing protein 3, is a protein-histidine N-methyltransferase that specifically mediates 1-methylhistidine (tau-methylhistidine) methylation of actin at 'His-73' (PMID: 30526847 ; 3MH/1MH switch - PMID: 30626964 ). SETD3 is a methyltransferase that uses S-adenosyl-L-methionine to transfer the methyl group to histidine at the tau position. Histidine methylation of actin His-73 is required for smooth muscle contraction of the laboring uterus during delivery (3MH/1MH switch - PMID: 30626964 ). It also reduces the nucleotide exchange rate on actin monomers and modestly accelerates actin filament assembly (3MH/1MH switch - PMID: 30626964 ). SETD3-mediated histidine methylation appears to occur in all higher eukaryotes with actin, from plants to insects to vertebrates. Within cells, SETD3 is found in the cytoplasm and nucleus. In contrast to SETD3, METTL18 is a nuclear methyltransferase protein that contains a functional nuclear localization signal and accumulates in nucleoli. Specifically, METTL18 is a seven β-strand (7BS) methyltransferase that uses S-adenosyl-L-methionine to transfer the methyl group to the tau position of His-245 on ribosomal protein L3, RPL3 (3MH/1MH switch - PMID: 33693809 ). METTL18 is highly conserved and found in essentially all eukaryotes (from yeast to humans). METTL18-mediated methylation of RPL3 is important for optimal ribosome biogenesis and function (3MH/1MH switch - PMID: 33693809 ). Other proteins that are known to have 1MH modifications include myosin and myosin kinase. In addition to these tau-His-methylated proteins, a specialized dipeptide called ophidine (balenine) that consists of beta-alanine and 1MH is also known (PMID: 24137022 ). This methylated analog of carnosine, which is naturally produced in the liver via the enzyme carnosine synthase I (PMID: 20097752 ), is especially abundant in the skeletal muscles and brains of whales and dolphins but almost completely absent in other vertebrates (PMID: 24137022 ). Ophidine, like its homologs anserine and carnosine, is believed to act as a pH buffer (for lactic acid generated by muscles), an antiglycating agent, and an antioxidant. Neither ophidine nor anserine are produced in humans, with humans being the only vertebrate not producing (or producing very little) methylated histidine versions of carnosine (PMID: 24137022 ). Because 1MH is so abundant in skeletal muscle tissues (being found in the main myofibrillar proteins actin and myosin), the urinary concentrations of 1-methylhistidine can be used as a biomarker for skeletal muscle protein breakdown, especially for those who have been subject to muscle injury (3MH/1MH switch - PMID: 16079625 ). During protein catabolism, 1-methylhistidine is released but cannot be reutilized. Therefore, the plasma concentration and urine excretion of 1-methylhistidine serve as sensitive markers of myofibrillar protein degradation (3MH/1MH switch - PMID: 32235743 ). Approximately 75% of 1-methylhistidine in the human body is estimated to originate from skeletal muscle (3MH/1MH switch - PMID: 32235743 ). In addition to the degradation of muscle proteins, the 1-methylhistidine level can be moderately affected by the degradation of intestinal proteins and meat intake. 1-Methylhistidine has been found to be associated with several diseases such as Alzheimer's disease, preeclampsia, obesity, kidney disease. The normal concentration of 1-methylhistidine in the urine of healthy adult humans has been detected and quantified in a range of 17.7-153.8 micromoles per millimole (umol/mmol) of creatinine, with most studies reporting the average urinary concentration between 25-40 umol/mmol of creatinine. The average concentration of 1-methylhistidine in human blood plasma has been detected and quantified at 12.7 micromolar (uM) with a range of 9.8-15.6 uM. As a general rule, urinary 3MH is associated with white meat intake (p< 0.001), whereas urinary 1MH is associated with red meat intake (p< 0.001) (3MH/1MH switch - PMID: 34091671 ).

Structure

MOL SDF PDB SMILES InChI

HEADER    PROTEIN                                 15-AUG-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-AUG-22         0                                  
HETATM    1  C   UNK     0       0.142   0.957   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.476   0.188   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.807   0.957   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.142   0.188   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       2.807   2.496   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0       1.476  -1.350   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      -4.142  -2.496   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      -2.441   1.111   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      -3.687   0.205   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      -3.211  -1.259   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      -1.671  -1.259   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.195   0.205   0.000  0.00  0.00           C+0
CONECT    1    2   12                                                       
CONECT    2    1    3    6                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    2                                                            
CONECT    7   10                                                            
CONECT    8    9   12                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11    7                                                  
CONECT   11   12   10                                                       
CONECT   12   11    8    1                                                  
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(2S)-2-Amino-3-(1-methyl-1H-imidazol-4-yl)propanoic acid	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	HMDB
1-Methylhistidine	ChEBI
Tau methylhistidine	HMDB
N(Tau)-methylhistidine	HMDB
Tau-methyl-L-histidine	HMDB
N Tau-methylhistidine	HMDB

Chemical Formula

C₇H₁₁N₃O₂

Average Molecular Weight

169.1811

Monoisotopic Molecular Weight

169.085126611

IUPAC Name

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

Traditional Name

4-methyl-histidine hydrate

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

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
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

Digestive system disorder

Hepatobiliary disorder

Hepatic disorder

Liver damage (PMID: 31434538)

Nervous system disorder

Nerve damage (PMID: 31434538)

Disposition

Biological location

Cellular substructure

Organelle

Nucleus (HMDB: HMDB0000001)
Myofibril (HMDB: HMDB0000001)

Nucleoli (HMDB: HMDB0000001)
Cytoplasm (HMDB: HMDB0000001)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 17031479)
Saliva (PMID: 1819935)
Cerebrospinal Fluid (CSF) (PMID: 17031479)

Tissue

Muscle tissue

Skeletal muscle (HMDB: HMDB0000001)

Excreta

Biofluid or Excreta

Urine (PMID: 15899597)
Feces (PMID: 25486321)

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)

Equine

Horse (FooDB: FOOD00378)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Lean meat (HMDB: HMDB0000001)
Red meat (HMDB: HMDB0000001)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Histidine Metabolism (PathBank: SMP0000044)
Purine Nucleotides De Novo Biosynthesis (PathBank: SMP0000927)

Disease pathway

Histidinemia (PathBank: SMP0000191)

Role

Biological role

Waste product (PMID: 35448883)

Industrial application

Pharmaceutical industry

Biomarker

Preeclampsia/Eclampsia (MarkerDB: MDB00000001)
Alzheimer's Disease (MarkerDB: MDB00000001)
Pregnancy (MarkerDB: MDB00000001)
Obesity (MarkerDB: MDB00000001)
Kidney disease (MarkerDB: MDB00000001)
Chronic kidney disease (MarkerDB: MDB00000001)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	249 °C	http://download.cappchem.com/data/Properties-of-Amino-Acids.pdf
Boiling Point	Not Available	Not Available
Water Solubility	200 g/kg	http://download.cappchem.com/data/Properties-of-Amino-Acids.pdf
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	MetCCS_train_neg	139.639	30932474
[M+H]+	Astarita_pos	129.0	30932474
[M+H]+	MetCCS_test_pos	133.103	30932474
[M-H]-	Not Available	139.639	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000001
[M+H]+	Not Available	133.594	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000001

Predicted Molecular Properties

Property	Value	Source
Water Solubility	6.93 g/L	ALOGPS
logP	-3	ALOGPS
logP	-3.1	ChemAxon
logS	-1.4	ALOGPS
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	17.1 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	138.634	31661259
DarkChem	[M-H]-	139.484	31661259
AllCCS	[M+H]+	138.137	32859911
AllCCS	[M-H]-	135.509	32859911
DeepCCS	[M+H]+	139.671	30932474
DeepCCS	[M-H]-	137.517	30932474
DeepCCS	[M-2H]-	171.187	30932474
DeepCCS	[M+Na]+	145.583	30932474
AllCCS	[M+H]+	138.1	32859911
AllCCS	[M+H-H2O]+	133.9	32859911
AllCCS	[M+NH4]+	142.0	32859911
AllCCS	[M+Na]+	143.2	32859911
AllCCS	[M-H]-	135.5	32859911
AllCCS	[M+Na-2H]-	136.7	32859911
AllCCS	[M+HCOO]-	138.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1-Methylhistidine	CN1C=NC(C[C@H](N)C(O)=O)=C1	2786.8	Standard polar	33892256
1-Methylhistidine	CN1C=NC(C[C@H](N)C(O)=O)=C1	1704.0	Standard non polar	33892256
1-Methylhistidine	CN1C=NC(C[C@H](N)C(O)=O)=C1	1882.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
1-Methylhistidine,1TMS,isomer #1	CN1C=NC(C[C@H](N)C(=O)O[Si](C)(C)C)=C1	1756.4	Semi standard non polar	33892256
1-Methylhistidine,1TMS,isomer #1	CN1C=NC(C[C@H](N)C(=O)O[Si](C)(C)C)=C1	1722.8	Standard non polar	33892256
1-Methylhistidine,1TMS,isomer #1	CN1C=NC(C[C@H](N)C(=O)O[Si](C)(C)C)=C1	2700.3	Standard polar	33892256
1-Methylhistidine,1TMS,isomer #2	CN1C=NC(C[C@H](N[Si](C)(C)C)C(=O)O)=C1	1822.4	Semi standard non polar	33892256
1-Methylhistidine,1TMS,isomer #2	CN1C=NC(C[C@H](N[Si](C)(C)C)C(=O)O)=C1	1778.9	Standard non polar	33892256
1-Methylhistidine,1TMS,isomer #2	CN1C=NC(C[C@H](N[Si](C)(C)C)C(=O)O)=C1	2717.7	Standard polar	33892256
1-Methylhistidine,2TMS,isomer #1	CN1C=NC(C[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)=C1	1829.7	Semi standard non polar	33892256
1-Methylhistidine,2TMS,isomer #1	CN1C=NC(C[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)=C1	1805.4	Standard non polar	33892256
1-Methylhistidine,2TMS,isomer #1	CN1C=NC(C[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)=C1	2309.2	Standard polar	33892256
1-Methylhistidine,2TMS,isomer #2	CN1C=NC(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)=C1	1982.1	Semi standard non polar	33892256
1-Methylhistidine,2TMS,isomer #2	CN1C=NC(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)=C1	1928.0	Standard non polar	33892256
1-Methylhistidine,2TMS,isomer #2	CN1C=NC(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)=C1	2475.5	Standard polar	33892256
1-Methylhistidine,3TMS,isomer #1	CN1C=NC(C[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)=C1	2034.9	Semi standard non polar	33892256
1-Methylhistidine,3TMS,isomer #1	CN1C=NC(C[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)=C1	1962.9	Standard non polar	33892256
1-Methylhistidine,3TMS,isomer #1	CN1C=NC(C[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)=C1	2190.2	Standard polar	33892256
1-Methylhistidine,1TBDMS,isomer #1	CN1C=NC(C[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C)=C1	2006.1	Semi standard non polar	33892256
1-Methylhistidine,1TBDMS,isomer #1	CN1C=NC(C[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C)=C1	1955.4	Standard non polar	33892256
1-Methylhistidine,1TBDMS,isomer #1	CN1C=NC(C[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C)=C1	2783.2	Standard polar	33892256
1-Methylhistidine,1TBDMS,isomer #2	CN1C=NC(C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O)=C1	2057.6	Semi standard non polar	33892256
1-Methylhistidine,1TBDMS,isomer #2	CN1C=NC(C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O)=C1	2027.5	Standard non polar	33892256
1-Methylhistidine,1TBDMS,isomer #2	CN1C=NC(C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O)=C1	2753.7	Standard polar	33892256
1-Methylhistidine,2TBDMS,isomer #1	CN1C=NC(C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)=C1	2267.7	Semi standard non polar	33892256
1-Methylhistidine,2TBDMS,isomer #1	CN1C=NC(C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)=C1	2257.2	Standard non polar	33892256
1-Methylhistidine,2TBDMS,isomer #1	CN1C=NC(C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)=C1	2465.1	Standard polar	33892256
1-Methylhistidine,2TBDMS,isomer #2	CN1C=NC(C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	2421.6	Semi standard non polar	33892256
1-Methylhistidine,2TBDMS,isomer #2	CN1C=NC(C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	2352.3	Standard non polar	33892256
1-Methylhistidine,2TBDMS,isomer #2	CN1C=NC(C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	2557.0	Standard polar	33892256
1-Methylhistidine,3TBDMS,isomer #1	CN1C=NC(C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	2660.0	Semi standard non polar	33892256
1-Methylhistidine,3TBDMS,isomer #1	CN1C=NC(C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	2590.7	Standard non polar	33892256
1-Methylhistidine,3TBDMS,isomer #1	CN1C=NC(C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	2475.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 1-Methylhistidine GC-MS (2 TMS)	splash10-0002-9610000000-d0147d3e28362f91174a	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 1-Methylhistidine GC-MS (3 TMS)	splash10-0gbd-4941000000-cee19577c72eecd95aec	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 1-Methylhistidine GC-MS (Non-derivatized)	splash10-0002-9610000000-d0147d3e28362f91174a	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 1-Methylhistidine GC-MS (Non-derivatized)	splash10-0gbd-4941000000-cee19577c72eecd95aec	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-Methylhistidine GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dm-9500000000-e50450f2dc8a5d4b3655	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-Methylhistidine GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9310000000-d6f7eb07e6f5ecb74263	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-Methylhistidine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-Methylhistidine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-Methylhistidine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-Methylhistidine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1-Methylhistidine Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-00di-0900000000-037d24a7d65676b7e356	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1-Methylhistidine Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-00di-0900000000-03e99316bd6c098f5d11	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1-Methylhistidine Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-00ea-9800000000-a33c82a1c91f56d372fe	2012-07-24	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methylhistidine 10V, Positive-QTOF	splash10-00di-0900000000-695bcc2d0a01df2d7521	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methylhistidine 20V, Positive-QTOF	splash10-00di-0900000000-4eea9cf6f12f18d06f98	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methylhistidine 40V, Positive-QTOF	splash10-05us-9300000000-072d6fe7a7a03cd7390b	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methylhistidine 10V, Negative-QTOF	splash10-014i-1900000000-57f1e30ae8b606ea5f5c	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methylhistidine 20V, Negative-QTOF	splash10-01b9-5900000000-ff71b6d300a9ee595b3c	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methylhistidine 40V, Negative-QTOF	splash10-0adj-9300000000-e045823003ab541d5b1e	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methylhistidine 10V, Positive-QTOF	splash10-00di-0900000000-8b15275d24e410674982	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methylhistidine 20V, Positive-QTOF	splash10-0592-5900000000-9af09354b313cccd21ae	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methylhistidine 40V, Positive-QTOF	splash10-0a5a-9500000000-6fff2b3f74fb49f4b389	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methylhistidine 10V, Negative-QTOF	splash10-014i-0900000000-a2577f99286255ceb6f8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methylhistidine 20V, Negative-QTOF	splash10-05fr-2900000000-39dfca8cd6f4c3e15a96	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methylhistidine 40V, Negative-QTOF	splash10-001l-9100000000-de4522e3df03361bc39a	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-14	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-14	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-14	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-14	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-14	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-14	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-14	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-14	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-14	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-14	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-14	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-14	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-14	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-14	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-14	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-14	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-14	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-14	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-14	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-14	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Nucleus
Myofibril
Nucleoli

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Urine

Tissue Locations

Skeletal Muscle

Pathways

Name	SMPDB/PathBank	KEGG
Histidine metabolism
Histidinemia		Not Available
1-Methylhistidine Metabolism		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	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 Quantified	Not Specified	Both	Normal	25486321	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Urine	Detected and Quantified	2.15-162.32 umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	Mayo Clinic	details
Urine	Detected and Quantified	10-17 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	27012787	details
Urine	Detected but not Quantified	Not Quantified	Not Available	Male	Normal	22932811	details
Urine	Detected and Quantified	1.36-175.22 umol/mmol creatinine	Adolescent (13-18 years old)	Not Specified	Normal	Mayo Clinic	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	2.60-151.46 umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	Mayo Clinic	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	1.92-47.39 umol/mmol creatinine	Infant (0-1 year old)	Not Specified	Normal	Mayo Clinic	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	2.036-184.27 umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	Mayo Clinic	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	18.55-145.2 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	32340350	details
Urine	Detected and Quantified	21.329 +/- 12.971 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details
Urine	Detected and Quantified	53.18(22.81-139.9) umol/mmol creatinine	Newborn (0-30 days old)	Female	Normal	32340350	details
Urine	Detected and Quantified	47.06(17.31-146.8) umol/mmol creatinine	Newborn (0-30 days old)	Male	Normal	32340350	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	1.13-166.96 umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	Mayo Clinic	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	17022649	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	21736852	details
Urine	Detected but not Quantified	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	Analysis of 30 no...	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

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 ]
Early preeclampsia
Bahado-Singh RO, Akolekar R, Mandal R, Dong E, Xia J, Kruger M, Wishart DS, Nicolaides K: Metabolomics and first-trimester prediction of early-onset preeclampsia. J Matern Fetal Neonatal Med. 2012 Oct;25(10):1840-7. doi: 10.3109/14767058.2012.680254. Epub 2012 Apr 28. [PubMed:22494326 ]
Pregnancy
Bahado-Singh RO, Akolekar R, Mandal R, Dong E, Xia J, Kruger M, Wishart DS, Nicolaides K: Metabolomics and first-trimester prediction of early-onset preeclampsia. J Matern Fetal Neonatal Med. 2012 Oct;25(10):1840-7. doi: 10.3109/14767058.2012.680254. Epub 2012 Apr 28. [PubMed:22494326 ] Bahado-Singh RO, Akolekar R, Mandal R, Dong E, Xia J, Kruger M, Wishart DS, Nicolaides K: First-trimester metabolomic detection of late-onset preeclampsia. Am J Obstet Gynecol. 2013 Jan;208(1):58.e1-7. doi: 10.1016/j.ajog.2012.11.003. Epub 2012 Nov 13. [PubMed:23159745 ] Bahado-Singh RO, Akolekar R, Mandal R, Dong E, Xia J, Kruger M, Wishart DS, Nicolaides K: Metabolomic analysis for first-trimester Down syndrome prediction. Am J Obstet Gynecol. 2013 May;208(5):371.e1-8. doi: 10.1016/j.ajog.2012.12.035. Epub 2013 Jan 8. [PubMed:23313728 ] Bahado-Singh RO, Akolekar R, Chelliah A, Mandal R, Dong E, Kruger M, Wishart DS, Nicolaides K: Metabolomic analysis for first-trimester trisomy 18 detection. Am J Obstet Gynecol. 2013 Jul;209(1):65.e1-9. doi: 10.1016/j.ajog.2013.03.028. Epub 2013 Mar 25. [PubMed:23535240 ]
Late-onset preeclampsia
Bahado-Singh RO, Akolekar R, Mandal R, Dong E, Xia J, Kruger M, Wishart DS, Nicolaides K: First-trimester metabolomic detection of late-onset preeclampsia. Am J Obstet Gynecol. 2013 Jan;208(1):58.e1-7. doi: 10.1016/j.ajog.2012.11.003. Epub 2012 Nov 13. [PubMed:23159745 ]
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 ]
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 ]
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 ]
Propionic acidemia
Gronwald W, Klein MS, Kaspar H, Fagerer SR, Nurnberger N, Dettmer K, Bertsch T, Oefner PJ: Urinary metabolite quantification employing 2D NMR spectroscopy. Anal Chem. 2008 Dec 1;80(23):9288-97. doi: 10.1021/ac801627c. [PubMed:19551947 ]
Maple syrup urine disease
Gronwald W, Klein MS, Kaspar H, Fagerer SR, Nurnberger N, Dettmer K, Bertsch T, Oefner PJ: Urinary metabolite quantification employing 2D NMR spectroscopy. Anal Chem. 2008 Dec 1;80(23):9288-97. doi: 10.1021/ac801627c. [PubMed:19551947 ]
Eosinophilic esophagitis
Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.

Associated OMIM IDs

104300 (Alzheimer's disease)
601665 (Obesity)
125853 (Diabetes mellitus type 2)
606054 (Propionic acidemia)
248600 (Maple syrup urine disease)
610247 (Eosinophilic esophagitis)

External Links

DrugBank ID

DB04151

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Methylhistidine

METLIN ID

3741

PubChem Compound

92105

PDB ID

Not Available

ChEBI ID

50599

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

MDB00000001

Good Scents ID

Not Available

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

Drozak J, Veiga-da-Cunha M, Vertommen D, Stroobant V, Van Schaftingen E: Molecular identification of carnosine synthase as ATP-grasp domain-containing protein 1 (ATPGD1). J Biol Chem. 2010 Mar 26;285(13):9346-56. doi: 10.1074/jbc.M109.095505. Epub 2010 Jan 22. [PubMed:20097752 ]
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 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
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Davydova E, Shimazu T, Schuhmacher MK, Jakobsson ME, Willemen HLDM, Liu T, Moen A, Ho AYY, Malecki J, Schroer L, Pinto R, Suzuki T, Gronsberg IA, Sohtome Y, Akakabe M, Weirich S, Kikuchi M, Olsen JV, Dohmae N, Umehara T, Sodeoka M, Siino V, McDonough MA, Eijkelkamp N, Schofield CJ, Jeltsch A, Shinkai Y, Falnes PO: The methyltransferase METTL9 mediates pervasive 1-methylhistidine modification in mammalian proteomes. Nat Commun. 2021 Feb 9;12(1):891. doi: 10.1038/s41467-020-20670-7. [PubMed:33563959 ]
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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 ]

Enzyme Details

3. Protein-L-histidine N-pros-methyltransferase

General function:: Involved in methyltransferase activity
Specific function:: Protein-histidine N-methyltransferase that specifically catalyzes 1-methylhistidine (pros-methylhistidine) methylation of target proteins. Mediates methylation of proteins with a His-x-His (HxH) motif (where 'x' is preferably a small amino acid). Catalyzes methylation of target proteins such as S100A9, NDUFB3, SLC39A5, SLC39A7, ARMC6 and DNAJB12; 1-methylhistidine modification may affect the binding of zinc and other metals to its target proteins. Constitutes the main methyltransferase for the 1-methylhistidine modification in cell.
Gene Name:: METTL9
Uniprot ID:: Q9H1A3
Molecular weight:: 36.0

Showing metabocard for 1-Methylhistidine (HMDB0000001)

MOL for HMDB0000001 (1-Methylhistidine)

3D MOL for HMDB0000001 (1-Methylhistidine)

3D SDF for HMDB0000001 (1-Methylhistidine)

3D-SDF for HMDB0000001 (1-Methylhistidine)

PDB for HMDB0000001 (1-Methylhistidine)

3D PDB for HMDB0000001 (1-Methylhistidine)

SMILES for HMDB0000001 (1-Methylhistidine)

INCHI for HMDB0000001 (1-Methylhistidine)

Structure for HMDB0000001 (1-Methylhistidine)

3D Structure for HMDB0000001 (1-Methylhistidine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

References

References