MiMeDB: Showing metabocard for N-Methyltyramine (MMDBc0047941)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-23 23:17:34 UTC

Update Date

2024-04-30 20:33:10 UTC

Metabolite ID

MMDBc0047941

Metabolite Identification

Common Name

N-Methyltyramine

Description

N-methyltyramine (NMT) is a phenolic amine. NMT is a potent stimulant of gastrin release present in alcoholic beverages produced by alcoholic fermentation, but not by distillation (i.e.: beer.). NMT is well absorbed in the small intestine, especially in the duodenum and jejunum. NMT is metabolized in the liver (the site of first-pass metabolism), but not in the small-intestinal mucosa. NMT is occasionally present in the stools of children and infants. Satisfactory results have been obtained in treating infective shock with injection of natural Fructus Aurantii immaturus (nat-FAI); the anti-shock effective compositions in FAI have been proved to be synephrine and NMT. (PMID: 10772638 , 2570680 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

Synonyms

Value	Source
4-Hydroxy-N-methylphenethylamine	ChEBI
Methyl-4-tyramine	ChEBI
p-(2-Methylaminoethyl)phenol	ChEBI
4-(2-(Methylamino)ethyl)-phenol	HMDB
4-(2-Methylaminoethyl)phenol	HMDB
4-[2-(Methylamino)ethyl]-phenol	HMDB
4-[2-(Methylamino)ethyl]phenol	HMDB
Methyl tyramine	HMDB
N-Methyl-p-tyramine	HMDB
N-Methyltyraminium	HMDB
NMT	HMDB
p-(2-(Methylamino)ethyl)phenol	HMDB
p-[2-(Methylamino)ethyl]-phenol	HMDB
{p-[2-(methylamino)ethyl]phenol}	HMDB
N-Methyltyrosamine	HMDB
Methyl-4-tyramine hydrochloride	HMDB
Methyl-4-tyramine hydrobromide	HMDB

Molecular Formula

C₉H₁₃NO

Average Mass

151.2056

Monoisotopic Mass

151.099714043

IUPAC Name

4-[2-(methylamino)ethyl]phenol

Traditional Name

N-methyltyramine

CAS Registry Number

370-98-9

SMILES

CNCCC1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C9H13NO/c1-10-7-6-8-2-4-9(11)5-3-8/h2-5,10-11H,6-7H2,1H3

InChI Key

AXVZFRBSCNEKPQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenethylamines. Phenethylamines are compounds containing a phenethylamine moiety, which consists of a phenyl group substituted at the second position by an ethan-1-amine.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenethylamines

Direct Parent

Phenethylamines

Alternative Parents

Substituents

Phenethylamine
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Phenol
Secondary amine
Secondary aliphatic amine
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

tyramines (CHEBI:17458 )
Tyramine derivatives (C02442 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	3.4 g/L	ALOGPS
logP	0.48	ALOGPS
logP	0.96	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	10.54	ChemAxon
pKa (Strongest Basic)	9.82	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	32.26 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	46.04 m³·mol⁻¹	ChemAxon
Polarizability	17.42 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9200000000-14293e75666be4e27019	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00xr-7920000000-4709651ba3c22c23b463	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0uk9-0900000000-0f335d13104342fdeed5	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0fk9-2900000000-037595c7cc0c504058c6	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0kk9-9500000000-376efc98f806aac30929	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-27ea78b166d8b3172ce1	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-1900000000-fb693eca1267a0ba9685	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05al-6900000000-6d964137e90c9e3293d1	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-1900000000-6ac9e0419aa31060260b	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dl-7900000000-7fd4cbc25b6ff2a2bf1e	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004l-9100000000-7021336d37b527e2e5fd	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-1c71ef4ed8c1b09fb863	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0900000000-4f21e6ca90b01b880bf4	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kf-9600000000-4a0119f5c8223bec2ae4	2021-09-22	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0006-9000000000-89ff5a43bc3e7737bcb6	2015-03-01	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-24	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192132	Protein arginine N-methyltransferase 3	Unknown	O60678	Homo sapiens
MMDBp0196837	HemK methyltransferase family member 1	Unknown	Q9Y5R4
MMDBp0196881	Methyltransferase-like protein 2B	Unknown	Q6P1Q9
MMDBp0196882	Methyltransferase-like protein 6	Unknown	Q8TCB7
MMDBp0197020	Uncharacterized methyltransferase WBSCR22	Unknown	O43709

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0004176	S-Adenosylmethionine	S-Adenosylhomocysteine	Not Available		VMH	10552930 9813302
MMDBr0010422	S-Adenosylmethionine	S-Adenosylhomocysteine	Not Available		VMH; KEGG	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Firmicutes	15	Human feces; Human	Metabolic reconstruction
Bacteria	Proteobacteria	9	Human feces; Human	Metabolic reconstruction
Bacteria	Fusobacteria	1	Human ; Human feces	Metabolic reconstruction
Bacteria	Bacteroidetes	2	Human ; Human feces	Metabolic reconstruction
Bacteria	Actinobacteria	2	Human feces; Human	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Plant	Leaves	Citrus limon	FooDB	31437929
Plant	Fruit	Citrus sinensis	FooDB	31437929
Plant	Fruit	Citrus reticulata	FooDB	31437929

Host Biospecimen and Location

Host and Biospecimen	Status	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified				HMDB
Human Urine	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0003633

DrugBank ID

Not Available

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

N-Methyltyramine

METLIN ID

Not Available

PubChem Compound

9727

PDB ID

Not Available

ChEBI ID

17458

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Zhao XW, Li JX, Zhu ZR, Sun DQ, Liu SC: Anti-shock effects of synthetic effective compositions of fructus aurantii immaturus. Experimental study and clinical observation. Chin Med J (Engl). 1989 Feb;102(2):91-3. [PubMed:2570680 ]
Kimura T, Iwasaki N, Yokoe JI, Haruta S, Yokoo Y, Ogawara KI, Higaki K: Analysis and prediction of absorption profile including hepatic first-pass metabolism of N-methyltyramine, a potent stimulant of gastrin release present in beer, after oral ingestion in rats by gastrointestinal-transit-absorption model. Drug Metab Dispos. 2000 May;28(5):577-81. [PubMed:10772638 ]
Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3. [PubMed:23455439 ]

Showing metabocard for N-Methyltyramine (MMDBc0047941)

MOL for #<Metabolite:0x00007fece0858688>

3D MOL for #<Metabolite:0x00007fece0858688>

3D SDF for #<Metabolite:0x00007fece0858688>

3D-SDF for #<Metabolite:0x00007fece0858688>

PDB for #<Metabolite:0x00007fece0858688>

3D PDB for #<Metabolite:0x00007fece0858688>

SMILES for #<Metabolite:0x00007fece0858688>

INCHI for #<Metabolite:0x00007fece0858688>

Structure for #<Metabolite:0x00007fece0858688>

3D Structure for #<Metabolite:0x00007fece0858688>