Livestock Metabolome Database: Showing metabocard for 1-Methylhistidine (LMDB00001)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:22:06 UTC

Update Date

2021-04-30 20:57:56 UTC

Lmdb

LMDB00001

Secondary Accession Numbers

None

Metabolite Identification

Common Name

1-Methylhistidine

Description

1-Methylhistidine, also known as 1-mhis, 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. 1-Methylhistidine exists in all living organisms, ranging from bacteria to humans. In humans, 1-methylhistidine is involved in the histidine metabolism pathway. 1-Methylhistidine has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make 1-methylhistidine a potential biomarker for the consumption of these foods. 1-Methylhistidine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. 1-Methylhistidine, with regard to humans, has been found to be associated with several diseases such as alzheimer's disease, eosinophilic esophagitis, and diabetes mellitus type 2; 1-methylhistidine has also been linked to several inborn metabolic disorders including maple syrup urine disease and propionic acidemia. Based on a literature review a significant number of articles have been published on 1-Methylhistidine.

Structure

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

Synonyms

Value	Source
(2S)-2-Amino-3-(1-methyl-1H-imidazol-4-yl)propanoic acid	ChEBI
(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

Status

Detected and Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-0002-9610000000-d0147d3e28362f91174a	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-0gbd-4941000000-cee19577c72eecd95aec	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0002-9610000000-d0147d3e28362f91174a	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0gbd-4941000000-cee19577c72eecd95aec	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dm-9500000000-e50450f2dc8a5d4b3655	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9310000000-d6f7eb07e6f5ecb74263	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00di-0900000000-037d24a7d65676b7e356	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00di-0900000000-03e99316bd6c098f5d11	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-00ea-9800000000-a33c82a1c91f56d372fe	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-695bcc2d0a01df2d7521	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0900000000-4eea9cf6f12f18d06f98	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05us-9300000000-072d6fe7a7a03cd7390b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-1900000000-57f1e30ae8b606ea5f5c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01b9-5900000000-ff71b6d300a9ee595b3c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0adj-9300000000-e045823003ab541d5b1e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-8b15275d24e410674982	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0592-5900000000-9af09354b313cccd21ae	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a5a-9500000000-6fff2b3f74fb49f4b389	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-a2577f99286255ceb6f8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-05fr-2900000000-39dfca8cd6f4c3e15a96	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001l-9100000000-de4522e3df03361bc39a	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Colostrum
Plasma
Serum

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Colostrum	Detected but not Quantified	Not Applicable	Not Available	Bovine	22436164	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Bovine	24440255	details
Plasma	Detected and Quantified	17 +/- 1-19+/-2 uM	Not Available	Porcine	22513987	details
Plasma	Detected and Quantified	25 +/- 1-24+/-4 uM	Not Available	Porcine	22513987	details
Plasma	Detected and Quantified	29 +/- 6-20+/-2 uM	Not Available	Porcine	22513987	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Porcine	21942754	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Porcine	18989615	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Porcine	21584308	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Porcine	21429726	details
Serum	Detected and Quantified	61 uM	Not Available	Porcine	26020888	details
Serum	Detected and Quantified	72.644 uM	Not Available	Porcine	26020888	details
Serum	Detected and Quantified	50.124 uM	Not Available	Porcine	26020888	details
Serum	Detected and Quantified	62.182 uM	Not Available	Porcine	26020888	details
Serum	Detected and Quantified	83.7017 +/- 26.5027 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	78.3264 +/- 20.9583 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	64.3864 +/- 25.6295 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	65.9809 +/- 31.5215 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	38.85 +/- 17.67 uM	Not Available	Ovine	Candidate serum m...	details
Serum	Detected and Quantified	76.8997 +/- 14.1496 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Equine	Lucia Pappalardo,...	details
Serum	Detected and Quantified	60.5854 +/- 17.4741 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	78.8319 +/- 26.1811 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	84.7309 +/- 26.0394 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	69.0192 +/- 19.186 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	67.678 +/- 25.7615 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	76.5402 +/- 29.5597 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	85.9343 +/- 29.1249 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	76.1201 +/- 20.9519 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	71.1698 +/- 32.2155 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	71.8906 +/- 34.956 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	84.9698 +/- 34.2423 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	88.3722 +/- 21.1699 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	66.9318 +/- 18.2983 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	59.3064 +/- 21.9801 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	59.0153 +/- 20.9635 uM	Normal	Ovine	Goldansaz et al.,...	details