Livestock Metabolome Database: Showing metabocard for 3-Methylhistidine (LMDB00163)

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

Record Information

Version

1.0

Creation Date

2016-07-13 19:43:44 UTC

Update Date

2016-07-20 20:27:44 UTC

Lmdb

LMDB00163

Secondary Accession Numbers

None

Metabolite Identification

Common Name

3-Methylhistidine

Description

3-Methylhistidine 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. 3-Methylhistidine is a very strong basic compound (based on its pKa). 3-Methylhistidine exists in all eukaryotes, ranging from yeast to humans. In humans, 3-methylhistidine is involved in methylhistidine metabolism. A L-histidine derivative that is L-histidine substituted by a methyl group at position 3 on the imidazole ring.

Structure

MOL SDF PDB SMILES InChI

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

CN1C=NC=C1C[C@H](N)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

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	-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	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dm-9500000000-ab7d6324146b8775fe50	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00fr-9400000000-42443c78fdfca9db1926	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 (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)	splash10-014i-2900000000-15f0e43eb0d06e7f3ef3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0002-9200000000-5a1ab4d052e6ba4a76e4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0002-9000000000-c1951c88c84885804fb6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-00di-0900000000-4e0fea0fe9b1142db07b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-0592-4900000000-ee1bce969d650e9fcfbe	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-0002-9200000000-1ad733cdcfa4db4fe3b9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-0002-9000000000-a87ff5cc0642ea3af69c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-0002-9000000000-28a73708493f968c2ac6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0002-9800000000-6565ccf96757ef3bc08f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-014i-0900000000-3cbd02f5b6c4e6e64eb9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-0udi-0900000000-e6ce7548fd6f09e2098f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-014i-0900000000-3cbd02f5b6c4e6e64eb9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-00di-0900000000-2d351351f285b2188710	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0592-4900000000-ee1bce969d650e9fcfbe	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0002-9200000000-1ad733cdcfa4db4fe3b9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0002-9000000000-2ed34e7b458d9f8c092f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0002-9000000000-c1b8a62adc15b80955c3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0002-9800000000-6565ccf96757ef3bc08f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-00di-6900000000-acc4a08855924a8bf5a1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-1ca24429b22e547d10d9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-1900000000-4cafc4698b6e3649ce7a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-9300000000-ef0c8b716935df30c508	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-1900000000-8a91a6a64bb07285c36d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01b9-4900000000-4ad91c6f55caf69120e9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05di-9300000000-ea67f38340a4b7ef8e11	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
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

Follicular Fluid
Milk
Plasma
Serum

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Follicular Fluid	Detected and Quantified	44 +/- 1-5+/-2 uM	Not Available	Porcine	183842	details
Milk	Detected and Quantified	103-151 uM	Not Available	Bovine	20338431	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Bovine	24440255	details
Plasma	Detected and Quantified	5 +/- 0-9+/-2 uM	Not Available	Porcine	22513987	details
Plasma	Detected and Quantified	6 +/- 1-8+/-1 uM	Not Available	Porcine	22513987	details
Plasma	Detected and Quantified	7 +/- 0-6+/-0 uM	Not Available	Porcine	22513987	details
Serum	Detected and Quantified	2.187 uM	Not Available	Porcine	26020888	details
Serum	Detected and Quantified	2.483 uM	Not Available	Porcine	26020888	details
Serum	Detected and Quantified	2.00968 uM	Not Available	Porcine	26020888	details
Serum	Detected and Quantified	2.719 uM	Not Available	Porcine	26020888	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Porcine	18989615	details
Serum	Detected and Quantified	46 +/- 6 uM	Not Available	Porcine	183842	details