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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-07-07 20:53:58 UTC

HMDB ID

HMDB0000479

Secondary Accession Numbers

HMDB00479

Metabolite Identification

Common Name

Methylhistidine

Description

3-Methylhistidine, also known as 3-MHis, 3MH, pi-methylhistidine or pros-methylhistidine, belongs to the class of organic compounds known as histidine and derivatives. 3MH 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 “pi-methylhistidine” with the hope that the archaic term, 3-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 3MH is tau-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”. 3MH is a free amino acid arising from the proteolysis of 3MH-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. 3MH can only be generated from histidine residues through the action of methyltransferases as a protein post-translational modification event. Histidine methylation on the 3- or pi site of histidine-containing proteins is mediated by only one known enzyme – METTL9. Recent discoveries have shown that 3MH is produced in essentially all vertebrates via the methyltransferase enzyme known as METTL9 (3MH/1MH switch - PMID: 33563959 ). METTL9 is a broad-specificity S-adenosylmethionine-mediated methyltransferase that mediates the formation of the majority of 3MH present in mammalian and other vertebrate proteomes. METTL9-catalyzed methylation requires a His-x-His (HxH) motif, where 'x' is a small amino acid consisting of A, N, G, S, or T. This H[ANGST]H or HxH motif is found in a number of abundant mammalian proteins such as ARMC6, S100A9, and NDUFB3 (3MH/1MH switch - PMID: 33563959 ). In addition to these pi-His-methylated proteins, a specialized dipeptide called anserine (called beta-alanyl-3-methyl-L-histidine) that consists of beta-alanine and 3MH is also known and particularly well studied (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 mammals, birds, and fish (PMID: 24137022 ). Anserine, like its homologs ophidine 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 of its abundance in some muscle-related proteins but especially because of the high abundance of anserine found in poultry and fish, 3MH has been found to be a good biomarker for the consumption of meat (PMID: 21527577 ). Dietary studies have shown that general poultry consumption (p-trend = 0.0006) and especially chicken consumption (p-trend = 0.0003) are associated with increased levels of 3MH in human plasma (PMID: 30018457 ). The consumption of fish, especially salmon and cod, has also been shown to increase the levels of 3MH in serum and urine (3MH/1MH switch PMID: 31401679 ). 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 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 15-OCT-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-OCT-19         0                                  
HETATM    1  C   UNK     0      -1.651   1.651   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.274   4.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.274   5.930   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      -1.608   3.620   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0       1.830  -0.290   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0      -0.186   1.175   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0      -1.608   6.700   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       1.060   6.700   0.000  0.00  0.00           O+0
HETATM   13  H   UNK     0       1.060   5.160   0.000  0.00  0.00           H+0
CONECT    1   10                                                            
CONECT    2    5    6                                                       
CONECT    3    5    9                                                       
CONECT    4    9   10                                                       
CONECT    5    2    3   10                                                  
CONECT    6    2    7    8   13                                             
CONECT    7    6   11   12                                                  
CONECT    8    6                                                            
CONECT    9    3    4                                                       
CONECT   10    1    4    5                                                  
CONECT   11    7                                                            
CONECT   12    7                                                            
CONECT   13    6                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(2S)-2-Amino-3-(1-methyl-1H-imidazol-5-yl)propanoic acid	ChEBI
3-Methyl-L-histidine	ChEBI
N-pros-Methyl-L-histidine	ChEBI
(2S)-2-Amino-3-(1-methyl-1H-imidazol-5-yl)propanoate	Generator
3-N-Methyl-L-histidine	HMDB
L-3-Methylhistidine	HMDB
N(pros)-Methyl-L-histidine	HMDB
N3-Methyl-L-histidine	HMDB
3-Methylhistidine hydride	HMDB
3-Methylhistidine dihydrochloride	HMDB
3-Methylhistidine	ChEBI
Pi methylhistidine	HMDB
N(Pi)-methylhistidine	HMDB
N Pi-methylhistidine	HMDB

Chemical Formula

C₇H₁₁N₃O₂

Average Molecular Weight

169.1811

Monoisotopic Molecular Weight

169.085126611

IUPAC Name

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

Traditional Name

3,methylhistidine

CAS Registry Number

368-16-1

SMILES

[H][C@](N)(CC1=CN=CN1C)C(O)=O

InChI Identifier

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

InChI Key

JDHILDINMRGULE-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:27596 )
L-histidine derivative (CHEBI:27596 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 4017235)
Cerebrospinal Fluid (CSF) (PMID: 17031479)
Saliva (HMDB: HMDB0000479)

Tissue

Muscle tissue

Skeletal muscle (HMDB: HMDB0000479)

Excreta

Biofluid or Excreta

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

Cellular substructure

Cytoplasm (HMDB: HMDB0000479)

Source

Endogenous

Endogenous (HMDB: HMDB0000479)

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)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

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)

Equine

Horse (FooDB: FOOD00378)

Lean meat (HMDB: HMDB0000479)

Aquatic origin

Fish

Fish (HMDB: HMDB0000479)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Histidine Metabolism (PathBank: SMP0063632)
Beta-Alanine metabolism (PathBank: SMP0087180)
Methylhistidine Metabolism (PathBank: SMP0063638)

Disease pathway

GABA-Transaminase Deficiency (PathBank: SMP0120478)
Histidinemia (PathBank: SMP0120493)
Carnosinuria, Carnosinemia (PathBank: SMP0120558)

Role

Industrial application

Pharmaceutical industry

Biomarker

Preeclampsia/Eclampsia (MarkerDB: MDB00000170)
Alzheimer's Disease (MarkerDB: MDB00000170)
Pregnancy (MarkerDB: MDB00000170)
Kidney disease (MarkerDB: MDB00000170)
Chronic kidney disease (MarkerDB: MDB00000170)
Propionic acidemia (MarkerDB: MDB00000170)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	200 mg/mL at 25 °C	BEILSTEIN
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	134.37	30932474
[M+H]+	MetCCS_train_pos	134.085	30932474
[M-H]-	Not Available	137.9	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000016
[M+H]+	Not Available	134.5	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000016

Predicted Molecular Properties

Property	Value	Source
Water Solubility	6.93 g/L	ALOGPS
logP	-2.9	ALOGPS
logP	-3.4	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	1.96	ChemAxon
pKa (Strongest Basic)	9.43	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	42.96 m³·mol⁻¹	ChemAxon
Polarizability	16.58 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]+	137.427	31661259
DarkChem	[M-H]-	132.692	31661259
AllCCS	[M+H]+	137.938	32859911
AllCCS	[M-H]-	134.371	32859911
DeepCCS	[M+H]+	131.068	30932474
DeepCCS	[M-H]-	128.451	30932474
DeepCCS	[M-2H]-	164.528	30932474
DeepCCS	[M+Na]+	139.256	30932474
AllCCS	[M+H]+	137.9	32859911
AllCCS	[M+H-H2O]+	133.7	32859911
AllCCS	[M+NH4]+	141.9	32859911
AllCCS	[M+Na]+	143.0	32859911
AllCCS	[M-H]-	134.4	32859911
AllCCS	[M+Na-2H]-	135.6	32859911
AllCCS	[M+HCOO]-	136.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Methylhistidine	[H][C@](N)(CC1=CN=CN1C)C(O)=O	2814.7	Standard polar	33892256
3-Methylhistidine	[H][C@](N)(CC1=CN=CN1C)C(O)=O	1666.3	Standard non polar	33892256
3-Methylhistidine	[H][C@](N)(CC1=CN=CN1C)C(O)=O	1982.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Methylhistidine,1TMS,isomer #1	CN1C=NC=C1C[C@H](N)C(=O)O[Si](C)(C)C	1761.5	Semi standard non polar	33892256
3-Methylhistidine,1TMS,isomer #2	CN1C=NC=C1C[C@H](N[Si](C)(C)C)C(=O)O	1862.9	Semi standard non polar	33892256
3-Methylhistidine,2TMS,isomer #1	CN1C=NC=C1C[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1861.2	Semi standard non polar	33892256
3-Methylhistidine,2TMS,isomer #1	CN1C=NC=C1C[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1797.2	Standard non polar	33892256
3-Methylhistidine,2TMS,isomer #1	CN1C=NC=C1C[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	2267.1	Standard polar	33892256
3-Methylhistidine,2TMS,isomer #2	CN1C=NC=C1C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1995.6	Semi standard non polar	33892256
3-Methylhistidine,2TMS,isomer #2	CN1C=NC=C1C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1919.9	Standard non polar	33892256
3-Methylhistidine,2TMS,isomer #2	CN1C=NC=C1C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2428.2	Standard polar	33892256
3-Methylhistidine,3TMS,isomer #1	CN1C=NC=C1C[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2044.1	Semi standard non polar	33892256
3-Methylhistidine,3TMS,isomer #1	CN1C=NC=C1C[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1954.1	Standard non polar	33892256
3-Methylhistidine,3TMS,isomer #1	CN1C=NC=C1C[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2157.3	Standard polar	33892256
3-Methylhistidine,1TBDMS,isomer #1	CN1C=NC=C1C[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C	2018.0	Semi standard non polar	33892256
3-Methylhistidine,1TBDMS,isomer #2	CN1C=NC=C1C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O	2110.9	Semi standard non polar	33892256
3-Methylhistidine,2TBDMS,isomer #1	CN1C=NC=C1C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2304.8	Semi standard non polar	33892256
3-Methylhistidine,2TBDMS,isomer #1	CN1C=NC=C1C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2268.3	Standard non polar	33892256
3-Methylhistidine,2TBDMS,isomer #1	CN1C=NC=C1C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2437.1	Standard polar	33892256
3-Methylhistidine,2TBDMS,isomer #2	CN1C=NC=C1C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2437.4	Semi standard non polar	33892256
3-Methylhistidine,2TBDMS,isomer #2	CN1C=NC=C1C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2357.5	Standard non polar	33892256
3-Methylhistidine,2TBDMS,isomer #2	CN1C=NC=C1C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2521.6	Standard polar	33892256
3-Methylhistidine,3TBDMS,isomer #1	CN1C=NC=C1C[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	2667.8	Semi standard non polar	33892256
3-Methylhistidine,3TBDMS,isomer #1	CN1C=NC=C1C[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	2596.9	Standard non polar	33892256
3-Methylhistidine,3TBDMS,isomer #1	CN1C=NC=C1C[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	2457.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Methylhistidine GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dm-9500000000-ab7d6324146b8775fe50	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methylhistidine GC-MS (1 TMS) - 70eV, Positive	splash10-00fr-9400000000-42443c78fdfca9db1926	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methylhistidine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methylhistidine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methylhistidine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methylhistidine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 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 - Methylhistidine LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOF	splash10-014i-0900000000-3cbd02f5b6c4e6e64eb9	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methylhistidine LC-ESI-IT , negative-QTOF	splash10-0udi-0900000000-e6ce7548fd6f09e2098f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methylhistidine LC-ESI-QTOF , negative-QTOF	splash10-014i-0900000000-3cbd02f5b6c4e6e64eb9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methylhistidine 35V, Negative-QTOF	splash10-014i-2900000000-77f55ec21b9e637c0148	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methylhistidine 35V, Negative-QTOF	splash10-014i-0900000000-25e42ab3c1bd0832a7fe	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methylhistidine 20V, Negative-QTOF	splash10-0ab9-3900000000-fb4a45b41e8cb903c156	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methylhistidine 35V, Negative-QTOF	splash10-014i-0900000000-0a98679ff9db2f56925a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methylhistidine 10V, Negative-QTOF	splash10-014i-1900000000-7b29b213a49dfa3c0f7d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methylhistidine 40V, Negative-QTOF	splash10-00di-0900000000-5a4990ec47e6292c0f7f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methylhistidine 10V, Negative-QTOF	splash10-014i-0900000000-993e2b71358969de5168	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methylhistidine 20V, Negative-QTOF	splash10-00di-9500000000-1817d9d8adbfaf0595f9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methylhistidine 40V, Negative-QTOF	splash10-014i-9100000000-2e05be86f146c22455ce	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methylhistidine Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-014i-2900000000-15f0e43eb0d06e7f3ef3	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methylhistidine Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-0002-9200000000-5a1ab4d052e6ba4a76e4	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methylhistidine Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-0002-9000000000-c1951c88c84885804fb6	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methylhistidine LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOF	splash10-00di-0900000000-4e0fea0fe9b1142db07b	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methylhistidine LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOF	splash10-0592-4900000000-ee1bce969d650e9fcfbe	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methylhistidine LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOF	splash10-0002-9200000000-1ad733cdcfa4db4fe3b9	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methylhistidine LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOF	splash10-0002-9000000000-a87ff5cc0642ea3af69c	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methylhistidine LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive-QTOF	splash10-0002-9000000000-28a73708493f968c2ac6	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methylhistidine LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOF	splash10-0002-9800000000-6565ccf96757ef3bc08f	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methylhistidine LC-ESI-QQ , positive-QTOF	splash10-00di-0900000000-2d351351f285b2188710	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methylhistidine LC-ESI-QQ , positive-QTOF	splash10-0592-4900000000-ee1bce969d650e9fcfbe	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methylhistidine LC-ESI-QQ , positive-QTOF	splash10-0002-9200000000-1ad733cdcfa4db4fe3b9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methylhistidine LC-ESI-QQ , positive-QTOF	splash10-0002-9000000000-2ed34e7b458d9f8c092f	2017-09-14	HMDB team, MONA	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	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Experimental 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)	2021-10-10	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	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

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Saliva
Urine

Tissue Locations

Skeletal Muscle

Pathways

Name	SMPDB/PathBank	KEGG
beta-Alanine metabolism	Not Available
GABA-Transaminase Deficiency		Not Available
Ureidopropionase Deficiency		Not Available
Carnosinuria, carnosinemia		Not Available
Histidine metabolism

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	2.7 (0.0-5.9) uM	Adult (>18 years old)	Both	Normal	0721679757	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	3.0 (2.7 - 5.9) uM	Adult (>18 years old)	Not Specified	Normal	4017235	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	3.82 +/- 2.43 uM	Adult (>18 years old)	Not Specified	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	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Saliva	Detected and Quantified	0.00950 +/- 0.0494 uM	Adult (>18 years old)	Male	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	0.0982 +/- 0.128 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	0.126 +/- 0.139 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	0.134 +/- 0.110 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	27.68 +/- 28.12 uM	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details
Urine	Detected and Quantified	32.79 +/- 20.35 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	19468821	details
Urine	Detected and Quantified	39.57 +/- 15.83 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	19468821	details
Urine	Detected and Quantified	8.71-29.41 umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	Mayo Clinic	details
Urine	Detected and Quantified	5.26 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	19309105	details
Urine	Detected and Quantified	39.57 +/- 23.74 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	19468821	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
Urine	Detected and Quantified	5.8-50 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	27012787	details
Urine	Detected and Quantified	5.32-29.64 umol/mmol creatinine	Adolescent (13-18 years old)	Not Specified	Normal	Mayo Clinic	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	7.92-27.83 umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	Mayo Clinic	details
Urine	Detected and Quantified	9.95-39.59 umol/mmol creatinine	Infant (0-1 year old)	Not Specified	Normal	Mayo Clinic	details
Urine	Detected and Quantified	5.4-35 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	27012787	details
Urine	Detected and Quantified	69.27 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	Shaykhutdinov RA,...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	16.5 (2.8-59.8) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	9.73-37.33 umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	Mayo Clinic	details
Urine	Detected and Quantified	12.5 +/- 4.2 umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	15899597	details
Urine	Detected and Quantified	44.944 +/- 41.318 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details
Urine	Detected and Quantified	6.33-35.75 umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	Mayo Clinic	details
Urine	Detected and Quantified	42.76 +/- 22.84 umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	2026685	details
Urine	Detected and Quantified	42.71 (31.68-56.08) umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	Analysis of 40 NI...	details
Urine	Detected and Quantified	17.977 +/- 5.902 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	11052553	details
Urine	Detected and Quantified	18.191 +/- 7.0323 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	11052553	details
Urine	Detected and Quantified	15.806 +/- 5.404 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	11052553	details
Urine	Detected and Quantified	13.556 +/- 2.487 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	11052553	details
Urine	Detected and Quantified	18.203 +/- 6.512 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	11052553	details
Urine	Detected and Quantified	17.705 +/- 6.00349 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	11052553	details
Urine	Detected and Quantified	16.0206 +/- 4.895 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	11052553	details
Urine	Detected and Quantified	17.0268 +/- 1.572 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	11052553	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	13.0 +/- 10.4 uM	Adult (>18 years old)	Both	Kidney disease	10838467	details
Blood	Detected and Quantified	23.7 +/- 18.6 uM	Adult (>18 years old)	Both	Kidney disease	10838467	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	5.16 +/- 1.27 uM	Elderly (>65 years old)	Both	Alzheimer's disease	17031479	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	2.48 +/- 1.58 uM	Adult (>18 years old)	Not Specified	Alzheimer's disease	17031479	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Urine	Detected and Quantified	24.0 +/- 1.7 umol/mmol creatinine	Adult (>18 years old)	Both	Alzheimer's disease	17031479	details
Urine	Detected and Quantified	11.6 +/- 6.6 umol/mmol creatinine	Adult (>18 years old)	Not Specified	Diabetes mellitus	15899597	details
Urine	Detected and Quantified	16.0 +/- 9.0 umol/mmol creatinine	Adult (>18 years old)	Not Specified	Obesity	15899597	details
Urine	Detected and Quantified	57.778 +/- 73.153 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details
Urine	Detected and Quantified	44.5 +/- 1.3 umol/mmol creatinine	Adult (>18 years old)	Both	Propionic acidemia	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 ]
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 ]
Colorectal cancer
Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
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 ]
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 ]
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 ]
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)
114500 (Colorectal cancer)
125853 (Diabetes mellitus type 2)
601665 (Obesity)
606054 (Propionic acidemia)
610247 (Eosinophilic esophagitis)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB093613

KNApSAcK ID

Not Available

Chemspider ID

58494

KEGG Compound ID

C01152

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

3-Methylhistidine

METLIN ID

5466

PubChem Compound

64969

PDB ID

Not Available

ChEBI ID

27596

Food Biomarker Ontology

Not Available

VMH ID

3MHIS

MarkerDB ID

MDB00000170

Good Scents ID

Not Available

References

Synthesis Reference

Ohba, Masashi; Mukaihira, Takafumi; Fujii, Tozo. Preparatory study for the synthesis of the starfish alkaloid imbricatine. Syntheses of 5-arylthio-3-methyl-L-histidines. Chemical & Pharmaceutical Bulletin (1994), 42(9), 1784-90.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

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 ]
Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
Bucciante G, Mencini A, Boninsegna A, Branca D, Scutari A, Scutari G: 3-Methylhistidine urinary excretion as an index of skeletal muscle protein metabolism: reference values. G Clin Med. 1985 Nov-Dec;66(11-12):451-8. [PubMed:3835089 ]
Schmitz JE: [Effect of metabolism-oriented substrate administration on energy and protein metabolism in polytraumatized artificial respiration patients]. Infusionsther Klin Ernahr. 1984 Aug;11(4):205-18. [PubMed:6434422 ]
McKeran RO, Halliday D, Purkiss P: Comparison of human myofibrillar protein catabolic rate derived from 3-methylhistidine excretion with synthetic rate from muscle biopsies during L-[alpha-15N]lysine infusion. Clin Sci Mol Med. 1978 May;54(5):471-5. [PubMed:750147 ]
Teahon K, Rideout JM: A sensitive and specific high performance liquid chromatographic assay for imidazole dipeptides and 3-methylhistidine in human muscle biopsies, serum and urine. Biomed Chromatogr. 1992 Jan-Feb;6(1):16-9. [PubMed:1600369 ]
Adlerberth A, Jagenburg R, Lindstedt G, Stenstrom G, Hasselgren PO: Effects of thyroid hormone and beta-adrenoceptor blocking agents on urinary excretion of 3-methylhistidine and plasma amino acids in man. Eur J Clin Invest. 1986 Aug;16(4):316-20. [PubMed:3093243 ]
Wang Z, Deurenberg P, Matthews DE, Heymsfield SB: Urinary 3-methylhistidine excretion: association with total body skeletal muscle mass by computerized axial tomography. JPEN J Parenter Enteral Nutr. 1998 Mar-Apr;22(2):82-6. [PubMed:9527964 ]
Nygren J, Thorell A, Brismar K, Essen P, Wernerman J, McNurlan MA, Garlick PJ, Ljungqvist O: Glucose flux is normalized by compensatory hyperinsulinaemia in growth hormone-induced insulin resistance in healthy subjects, while skeletal muscle protein synthesis remains unchanged. Clin Sci (Lond). 2002 Apr;102(4):457-64. [PubMed:11914108 ]
Elia M, Carter A, Bacon S, Winearls CG, Smith R: Clinical usefulness of urinary 3-methylhistidine excretion in indicating muscle protein breakdown. Br Med J (Clin Res Ed). 1981 Jan 31;282(6261):351-4. [PubMed:6780020 ]
Rathmacher JA, Flakoll PJ, Nissen SL: A compartmental model of 3-methylhistidine metabolism in humans. Am J Physiol. 1995 Jul;269(1 Pt 1):E193-8. [PubMed:7631776 ]
Lunyong VE, Friedman Z: Myofibrillar protein degradation in premature infants with respiratory distress as assessed by 3-methylhistidine and creatinine excretions. Am J Clin Nutr. 1982 Sep;36(3):485-91. [PubMed:7113954 ]
Buchholz-Wimmer GB, Wimmer W, Herbertz L, Reinauer H: [3-Methylhistidine as a parameter for the determination of muscle proteolysis in the post-stress syndrome and in diabetes mellitus]. Infusionsther Klin Ernahr. 1984 Jun;11(3):168-74. [PubMed:6434416 ]
Vesali RF, Klaude M, Thunblad L, Rooyackers OE, Wernerman J: Contractile protein breakdown in human leg skeletal muscle as estimated by [2H3]-3-methylhistidine: a new method. Metabolism. 2004 Aug;53(8):1076-80. [PubMed:15281022 ]
Bird SP, Tarpenning KM, Marino FE: Independent and combined effects of liquid carbohydrate/essential amino acid ingestion on hormonal and muscular adaptations following resistance training in untrained men. Eur J Appl Physiol. 2006 May;97(2):225-38. Epub 2006 Mar 24. [PubMed:16456674 ]
Lamisse F, May MA, Couet C, Constans T, Bacq Y, Delarue J, Lamagnere JP, Colombat P, Garrigue MA: [Changes in nutritional status at the initial phase of treatment of cancers and malignant hemopathies]. Rev Med Interne. 1987 May-Jun;8(3):257-61. [PubMed:3616232 ]
Neuhauser M, Bergstrom J, Chao L, Holmstrom J, Nordlund L, Vinnars E, Furst P: Urinary excretion of 3-methylhistidine as an index of muscle protein catabolism in postoperative trauma: the effect of parenteral nutrition. Metabolism. 1980 Dec;29(12):1206-13. [PubMed:6779092 ]
Emery PW, Rennie MJ: Elimination by formaldehyde of interference with 3-methylhistidine determination: application of the method to the study of muscle protein degradation. Anal Biochem. 1982 Oct;126(1):67-73. [PubMed:7181118 ]
Tomas FM, Ballard FJ, Pope LM: Age-dependent changes in the rate of myofibrillar protein degradation in humans as assessed by 3-methylhistidine and creatinine excretion. Clin Sci (Lond). 1979 Apr;56(4):341-6. [PubMed:477219 ]
Long CL, Dillard DR, Bodzin JH, Geiger JW, Blakemore WS: Validity of 3-methylhistidine excretion as an indicator of skeletal muscle protein breakdown in humans. Metabolism. 1988 Sep;37(9):844-9. [PubMed:3138511 ]
Young VR, Munro HN: Ntau-methylhistidine (3-methylhistidine) and muscle protein turnover: an overview. Fed Proc. 1978 Jul;37(9):2291-300. [PubMed:350635 ]
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 ]
Boldyrev AA, Aldini G, Derave W: Physiology and pathophysiology of carnosine. Physiol Rev. 2013 Oct;93(4):1803-45. doi: 10.1152/physrev.00039.2012. [PubMed:24137022 ]
Chinkes DL: Methods for measuring tissue protein breakdown rate in vivo. Curr Opin Clin Nutr Metab Care. 2005 Sep;8(5):534-7. doi: 10.1097/01.mco.0000170754.25372.37. [PubMed:16079625 ]
Holecek M: Histidine in Health and Disease: Metabolism, Physiological Importance, and Use as a Supplement. Nutrients. 2020 Mar 22;12(3). pii: nu12030848. doi: 10.3390/nu12030848. [PubMed:32235743 ]
Said MY, Rodriguez-Nino A, Post A, Schutten JC, Kieneker LM, Gomes-Neto AW, van Londen M, Oste MC, Borgonjen-van den Berg KJ, Nolte IM, van den Berg E, de Blaauw P, van der Krogt J, Heiner-Fokkema MR, Navis G, Yard BA, Bakker SJ: Meat intake and risk of mortality and graft failure in kidney transplant recipients. Am J Clin Nutr. 2021 Jun 5. pii: 6294068. doi: 10.1093/ajcn/nqab185. [PubMed:34091671 ]

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

Enzyme Details

2. Carnosine synthase 1

General function:: Involved in catalytic activity
Specific function:: Catalyzes the synthesis of carnosine and homocarnosine. Carnosine is synthesized more efficiently than homocarnosine.
Gene Name:: CARNS1
Uniprot ID:: A5YM72
Molecular weight:: 101318.725

Reactions

Adenosine triphosphate + Methylhistidine + beta-Alanine → Adenosine monophosphate + Pyrophosphate + Anserine	details

Enzyme Details

3. HemK methyltransferase family member 1

General function:: Not Available
Specific function:: N5-glutamine methyltransferase responsible for the methylation of the GGQ triplet of the mitochondrial translation release factor MTRF1L.
Gene Name:: HEMK1
Uniprot ID:: Q9Y5R4
Molecular weight:: Not Available

Reactions

Histidine + S-Adenosylmethionine → Methylhistidine + S-Adenosylhomocysteine	details

Enzyme Details

4. Methyltransferase-like protein 2B

General function:: Not Available
Specific function:: Probable methyltransferase (By similarity).
Gene Name:: METTL2B
Uniprot ID:: Q6P1Q9
Molecular weight:: Not Available

Reactions

Histidine + S-Adenosylmethionine → Methylhistidine + S-Adenosylhomocysteine	details

Enzyme Details

5. Methyltransferase-like protein 6

General function:: Not Available
Specific function:: Probable methyltransferase (By similarity).
Gene Name:: METTL6
Uniprot ID:: Q8TCB7
Molecular weight:: Not Available

Reactions

Histidine + S-Adenosylmethionine → Methylhistidine + S-Adenosylhomocysteine	details

Enzyme Details

6. Uncharacterized methyltransferase WBSCR22

General function:: Not Available
Specific function:: Methyltransferase that may act on DNA.
Gene Name:: WBSCR22
Uniprot ID:: O43709
Molecular weight:: Not Available

Reactions

Histidine + S-Adenosylmethionine → Methylhistidine + S-Adenosylhomocysteine	details

Enzyme Details

7. Histidine protein methyltransferase 1 homolog

General function:: Involved in methyltransferase activity
Specific function:: Protein-L-histidine N-tele-methyltransferase that specifically monomethylates RPL3. Through the methylation of RPL3 regulates the dynamics of pre-rRNA processing, ribosome biogenesis, and translation .
Gene Name:: METTL18
Uniprot ID:: O95568
Molecular weight:: 42.0

Showing metabocard for Methylhistidine (HMDB0000479)

MOL for HMDB0000479 (Methylhistidine)

3D MOL for HMDB0000479 (Methylhistidine)

3D SDF for HMDB0000479 (Methylhistidine)

3D-SDF for HMDB0000479 (Methylhistidine)

PDB for HMDB0000479 (Methylhistidine)

3D PDB for HMDB0000479 (Methylhistidine)

SMILES for HMDB0000479 (Methylhistidine)

INCHI for HMDB0000479 (Methylhistidine)

Structure for HMDB0000479 (Methylhistidine)

3D Structure for HMDB0000479 (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

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