Bovine Metabolome Database: Showing metabocard for 1-Methylhistamine (BMDB0000898)

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

Record Information

Version

1.0

Creation Date

2016-09-30 22:38:16 UTC

Update Date

2020-05-21 16:28:38 UTC

BMDB ID

BMDB0000898

Secondary Accession Numbers

BMDB00898

Metabolite Identification

Common Name

1-Methylhistamine

Description

1-1-1-methylhistamine belongs to the class of organic compounds known as 2-arylethylamines. These are primary amines that have the general formula RCCNH2, where R is an organic group. 1-1-1-methylhistamine is possibly soluble (in water) and a very strong basic compound (based on its pKa). 1-1-1-methylhistamine exists in all living organisms, ranging from bacteria to humans. 1-1-1-methylhistamine participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and 1-1-methylhistamine can be biosynthesized from S-adenosylmethionine and histamine through its interaction with the enzyme histamine N-methyltransferase. In addition, 1-1-1-methylhistamine can be converted into methylimidazole acetaldehyde through the action of the enzyme amine oxidase [flavin-containing] a. In cattle, 1-1-methylhistamine is involved in the metabolic pathway called the histidine metabolism pathway. 1-1-1-methylhistamine is a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Methyl-1H-imidazole-4-ethanamine	ChEBI
1-Methyl-4-(2-aminoethyl)imidazole	ChEBI
3-Methylhistamine	ChEBI
4-(1-Aminoethyl)-1-methyl-1H-imidazole	ChEBI
Methylhistamine	ChEBI
N-Methylhistamine	ChEBI
N(1)-Methylhistamine	ChEBI
Ntau-methylhistamine	ChEBI
tele-Methylhistamine	ChEBI
tele-Methylhistamine dihydrochloride	HMDB
1-Methyl-4-(beta-aminoethyl)imidazole	HMDB
1,4-Methylhistamine	HMDB
N-tele Methylhistamine	HMDB
1-Methyl-4-(b-aminoethyl)imidazole	HMDB
1-Methyl-4-histamine	HMDB
2-(1-Methyl-1H-imidazol-4-yl)ethanamine	HMDB
2-(1-Methyl-1H-imidazol-4-yl)ethylamine	HMDB
4-(2-Aminoethyl)-1-methyl-imidazole	HMDB
4-(2-Aminoethyl)-1-methylimidazole	HMDB
H137	HMDB
N( 1)-Methylhistamine	HMDB
N(T)-Methylhistamine	HMDB
N-tele-Methylhistamine	HMDB
N-Telle-methylhistamine	HMDB
N1-Methylhistamine	HMDB
NT-Methylhistamine	HMDB

Chemical Formula

C₆H₁₁N₃

Average Molecular Weight

125.1716

Monoisotopic Molecular Weight

125.095297367

IUPAC Name

2-(1-methyl-1H-imidazol-4-yl)ethan-1-amine

Traditional Name

methylhistamine

CAS Registry Number

501-75-7

SMILES

CN1C=NC(CCN)=C1

InChI Identifier

InChI=1S/C6H11N3/c1-9-4-6(2-3-7)8-5-9/h4-5H,2-3,7H2,1H3

InChI Key

FHQDWPCFSJMNCT-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as 2-arylethylamines. These are primary amines that have the general formula RCCNH2, where R is an organic group.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Amines

Direct Parent

2-arylethylamines

Alternative Parents

Substituents

2-arylethylamine
Aralkylamine
N-substituted imidazole
Heteroaromatic compound
Imidazole
Azole
Azacycle
Organoheterocyclic compound
Organopnictogen compound
Hydrocarbon derivative
Primary aliphatic amine
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

imidazoles (CHEBI:29009 )
primary amino compound (CHEBI:29009 )

Ontology

Status

Expected but not Quantified

Origin

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cytoplasm

Physical Properties

State

Solid

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	-0.57	ALOGPS
logP	-0.48	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Basic)	9.57	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	43.84 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	36.56 m³·mol⁻¹	ChemAxon
Polarizability	14.24 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
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-0fki-3900000000-8197b65f233a917f6f5d	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-00dr-3900000000-4a05dead99e371226a6c	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-00di-9700000000-b8108f1cb31c26ab942f	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-0fe0-5900000000-c04c884eec0846197eb8	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00di-2910000000-3458f7def44a74d73f7b	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0fki-3900000000-8197b65f233a917f6f5d	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00dr-3900000000-4a05dead99e371226a6c	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9700000000-b8108f1cb31c26ab942f	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0fe0-5900000000-c04c884eec0846197eb8	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-001j-9200000000-f6dbf3d86200b3f6be5f	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0a4i-0900000000-b77c6433a2a8bdb852dd	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0aor-9600000000-a2a8c75c945ca81ded8a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-001i-9200000000-fa9fad79e09f38a3450d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-004i-0900000000-b9f4341a558b04495c54	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-004i-0900000000-b9f4341a558b04495c54	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-056r-0900000000-b9f2ff9fde6f1a170d38	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-1900000000-0ad300b172fcdc68e104	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0le9-9000000000-fe751072b0ecf7a0d5bf	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0900000000-c7b86cf59142756c4f91	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-3900000000-0bed565bcfefeb389d2b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0arv-9100000000-fc2c7dc356034fe098ae	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0900000000-317df42b1c6c53a3cd83	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-6900000000-e29c16ae4d103e7eaa01	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-066u-9000000000-2d8cc6d1c8601ed4eed0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-1900000000-c5c45bb41ea05838fa94	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-5900000000-68ef55e857c894f92309	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-9000000000-434d60e1525fedada46a	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Bone Marrow
Brain
Leukocyte

Pathways

Name	SMPDB/Pathwhiz	KEGG
Histidine Metabolism		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Bone Marrow	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Brain	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Leukocyte	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0000898

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022306

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

29009

References

Synthesis Reference

Rothschild, Zuleika; Schayer, Richard W. Synthesis and metabolism of a histamine metabolite, 1-methyl-4-(b-aminoethyl)imidazole. Biochimica et Biophysica Acta (1958), 30 23-7.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Histamine N-methyltransferase

General function:: Involved in histamine N-methyltransferase activity
Specific function:: Inactivates histamine by N-methylation. Plays an important role in degrading histamine and in regulating the airway response to histamine.
Gene Name:: HNMT
Uniprot ID:: Q58DV7
Molecular weight:: 33646.0

Reactions

S-Adenosylmethionine + Histamine → S-Adenosylhomocysteine + 1-Methylhistamine	details

Enzyme Details

2. Amine oxidase [flavin-containing] A

General function:: Amino acid transport and metabolism
Specific function:: Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:: MAOA
Uniprot ID:: P21398
Molecular weight:: 59758.0

Reactions

1-Methylhistamine + Water + Oxygen → Methylimidazole acetaldehyde + Ammonia + Hydrogen peroxide	details

Showing metabocard for 1-Methylhistamine (BMDB0000898)

Structure for BMDB0000898 (1-Methylhistamine)

Enzymes

Reactions

Reactions