MiMeDB: Showing metabocard for Tryptamine (MMDBc0000096)

Plant

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-10-27 23:30:13 UTC

Update Date

2022-08-30 23:34:09 UTC

Metabolite ID

MMDBc0000096

Metabolite Identification

Common Name

Tryptamine

Description

Tryptamine, also known as TrpN, is a catabolite of tryptophan converted by the gut microbiota. After absorption through the intestinal epithelium, tryptophan catabolites enter the bloodstream and are later excreted in the urine. Both Clostridium sp. and Ruminococcus sp. have been found to convert tryptophan into tryptamine (PMID: 30120222 ). Tryptamine is a monoamine compound that is a common precursor molecule to many hormones and neurotransmitters. Biosynthesis generally proceeds from the amino acid tryptophan, with tryptamine acting as a precursor for other compounds. Substitutions to the tryptamine molecule give rise to a group of compounds collectively known as tryptamines. The most well-known tryptamines are serotonin, an important neurotransmitter, and melatonin, a hormone involved in regulating the sleep-wake cycle. Tryptamine has been detected, but not quantified in, several different foods, such as onion-family vegetables, acerola, Japanese walnuts, custard apples, and green zucchinis. This could make tryptamine a potential biomarker for the consumption of these foods.

Structure

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

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0    8661.2098665.593   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8660.7338664.128   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8661.7648662.984   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8663.2708663.304   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0    8663.4858667.247   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0    8662.7168665.913   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8663.7468664.769   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8665.1538665.395   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8664.9928666.927   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8666.4878664.625   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8667.8208665.395   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0    8669.1548664.625   0.000  0.00  0.00           N+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    7                                                       
CONECT    5    6    9                                                       
CONECT    6    7    5    1                                                  
CONECT    7    6    8    4                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8    5                                                       
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

Synonyms

Value	Source
1H-Indole-3-ethanamine	ChEBI
2-(1H-indol-3-yl)ETHANAMINE	ChEBI
2-(3-Indolyl)ethylamine	ChEBI
3-(2-Aminoethyl)indole	ChEBI
(3-Indolyl)ethylamine	HMDB
2-(1H-indol-3-yl)Ethylamine	HMDB
2-indol-3-yl-Aethylamin	HMDB
2-indol-3-yl-Ethylamine	HMDB
3-(2-Aminoethyl)-1H-indole	HMDB
3-Indoleethanamine	HMDB
3-Indoleethylamine	HMDB
Tryptamin	HMDB
2-(1H-indol-3-yl)Ethan-1-amine	HMDB
beta-(3-Indolyl)ethylamine	HMDB
Β-(3-indolyl)ethylamine	HMDB
TRPN	HMDB
Tryptamine	HMDB

Molecular Formula

C₁₀H₁₂N₂

Average Mass

160.2157

Monoisotopic Mass

160.100048394

IUPAC Name

2-(1H-indol-3-yl)ethan-1-amine

Traditional Name

tryptamine

CAS Registry Number

61-54-1

SMILES

NCCC1=CNC2=C1C=CC=C2

InChI Identifier

InChI=1S/C10H12N2/c11-6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5-6,11H2

InChI Key

APJYDQYYACXCRM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tryptamines and derivatives. Tryptamines and derivatives are compounds containing the tryptamine backbone, which is structurally characterized by an indole ring substituted at the 3-position by an ethanamine.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Tryptamines and derivatives

Direct Parent

Tryptamines and derivatives

Alternative Parents

Substituents

Tryptamine
3-alkylindole
Indole
2-arylethylamine
Aralkylamine
Substituted pyrrole
Benzenoid
Pyrrole
Heteroaromatic compound
Azacycle
Hydrocarbon derivative
Organopnictogen compound
Amine
Primary amine
Organonitrogen compound
Primary aliphatic amine
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

indole alkaloid (CHEBI:16765 )
aminoalkylindole (CHEBI:16765 )
tryptamines (CHEBI:16765 )
aralkylamino compound (CHEBI:16765 )
Indole alkaloids (C00398 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	1.34 g/L	ALOGPS
logP	1.21	ALOGPS
logP	1.49	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	17.17	ChemAxon
pKa (Strongest Basic)	9.73	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	41.81 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	50.37 m³·mol⁻¹	ChemAxon
Polarizability	18.34 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Brain
Feces
Intestine
Neuron
Platelet
Urine

Tissue Locations

Brain
Intestine
Neuron
Platelet

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191706	Serotonin N-acetyltransferase	Enzyme	Q16613	Homo_sapiens
MMDBp0191832	Amine oxidase [flavin-containing] B	Unknown	P27338	Homo_sapiens
MMDBp0191840	Amine oxidase [flavin-containing] A	Unknown	P21397	Homo_sapiens
MMDBp0191948	Aromatic-L-amino-acid decarboxylase	Enzyme	P20711	Homo_sapiens
MMDBp0192057	Amiloride-sensitive amine oxidase [copper-containing]	Unknown	P19801	Homo_sapiens
MMDBp0192081	Indolethylamine N-methyltransferase	Unknown	O95050	Homo_sapiens
MMDBp0193303	Aryl hydrocarbon receptor	Unknown	P35869	Homo_sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
colorectal cancer				HMDB	21330412
Inflammatory bowel disease				HMDB	27275383

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Bacteroidetes	9	Human feces	Microbial culture; Metabolic reconstruction
Bacteria	Firmicutes	107	Human ; Human feces; Pig ; Cattle	Microbial culture; Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria	Proteobacteria	209	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab	Metabolic reconstruction
Bacteria	Actinobacteria	92	Human feces; Human	Metabolic reconstruction
Archaea	Euryarchaeota	2	Human feces	Metabolic reconstruction
Bacteria	Fusobacteria	2	Human ; Human feces	Metabolic reconstruction
Bacteria	Planctomycetes	2	Human feces	Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	1	Human feces
Eukaryota/Fungi	Basidiomycota	2

Exposure Sources

Food Exposures

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Min	Max	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified							HMDB
Human	Detected and Quantified	0.026			Adult (>18 years old)	Both	Normal	HMDB	19309105
Human	Detected and Quantified	0.02	0.02	0.03	Adult (>18 years old)	Female	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human	Detected and Quantified	0.03	0.01	0.049	Adult (>18 years old)	Male	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human	Detected and Quantified	0.098	0.03	0.15	Children (1-13 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Brain	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Intestine	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Neuron	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Platelet	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Feces	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	21330412
Human Feces	Detected but not Quantified				Infant (0-1 year old)	NULL	Normal	HMDB	24628373
Human Feces	Detected but not Quantified				Infant (0-1 year old)	Not Specified	Normal	HMDB	24628373
Human Feces	Detected but not Quantified				Infant (0-1 year old)	Not Specified	Normal	HMDB	24628373
Human Feces	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	29808030
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

HMDB0000303

DrugBank ID

DB08653

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Tryptamine

METLIN ID

Not Available

PubChem Compound

1150

PDB ID

Not Available

ChEBI ID

16765

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Radulovacki P, Djuricic-Nedelson M, Chen EH, Radulovacki M: Human tryptamine metabolism decreases during night sleep. Brain Res Bull. 1983 Jan;10(1):43-5. doi: 10.1016/0361-9230(83)90072-2. [PubMed:6186344 ]
Mathew RJ, Ho BT, Kralik P, Weinman M, Claghorn JL: Anxiety and platelet MAO levels after relaxation training. Am J Psychiatry. 1981 Mar;138(3):371-3. doi: 10.1176/ajp.138.3.371. [PubMed:7008633 ]
Gilboa-Garber N, Katz-Bergman Y, Pinsky A: Comparative study of the sensitivity of acetylcholinesterases and cholinesterases from animal and bacterial sources to inhibition by serotonin and its derivatives. Experientia. 1978 Aug 15;34(8):992-3. doi: 10.1007/BF01915306. [PubMed:100343 ]
Tsuchiya H, Ohtani S, Yamada K, Tajima K, Sato M: Formation of tetrahydro-beta-carbolines in human saliva. Biochem Pharmacol. 1995 Dec 22;50(12):2109-12. doi: 10.1016/0006-2952(95)02068-3. [PubMed:8849340 ]
Tam WY, Chan MY, Lee PH: The menstrual cycle and platelet 5-HT uptake. Psychosom Med. 1985 Jul-Aug;47(4):352-62. doi: 10.1097/00006842-198507000-00005. [PubMed:4023163 ]
Friedl W, Kruger J, Propping P: Intraindividual stability and extent of genetic determination of platelet monoamine oxidase activity. Pharmacopsychiatria. 1981 May;14(3):83-6. doi: 10.1055/s-2007-1019575. [PubMed:7196052 ]
Sullivan JP, McDonnell L, Hardiman OM, Farrell MA, Phillips JP, Tipton KF: The oxidation of tryptamine by the two forms of monoamine oxidase in human tissues. Biochem Pharmacol. 1986 Oct 1;35(19):3255-60. doi: 10.1016/0006-2952(86)90421-1. [PubMed:3094536 ]
al Mardini H, Harrison EJ, Ince PG, Bartlett K, Record CO: Brain indoles in human hepatic encephalopathy. Hepatology. 1993 Jun;17(6):1033-40. [PubMed:7685732 ]
Young SN, Gauthier S: Effect of tryptophan administration on tryptophan, 5-hydroxyindoleacetic acid and indoleacetic acid in human lumbar and cisternal cerebrospinal fluid. J Neurol Neurosurg Psychiatry. 1981 Apr;44(4):323-8. doi: 10.1136/jnnp.44.4.323. [PubMed:6165809 ]
Siwers B, Ringberger VA, Tuck JR, Sjoqvist F: Initial clinical trial based on biochemical methodology of zimelidine (a serotonin uptake inhibitor) in depressed patients. Clin Pharmacol Ther. 1977 Feb;21(2):194-200. doi: 10.1002/cpt1977212194. [PubMed:837638 ]
Sullivan JL, Coffey CE, Basuk B, Cavenar JO, Maltbie AA, Zung WW: Urinary tryptamine excretion in chronic schizophrenics with low platelet MAO activity. Biol Psychiatry. 1980 Feb;15(1):113-20. [PubMed:7357050 ]
Tsuchiya H, Hayashi T, Tatsumi M, Hoshino Y, Ohtani S, Takagi N: High-performance liquid-chromatographic analysis for serotonin and tryptamine excreted in urine after oral loading with L-tryptophan. Clin Chem. 1989 Jan;35(1):43-7. [PubMed:2910580 ]
Anderson GM, Gerner RH, Cohen DJ, Fairbanks L: Central tryptamine turnover in depression, schizophrenia, and anorexia: measurement of indoleacetic acid in cerebrospinal fluid. Biol Psychiatry. 1984 Oct;19(10):1427-35. [PubMed:6518200 ]
Gaszner P, Miklya I: The use of the synthetic enhancer substances (-)-deprenyl and (-)-BPAP in major depression. Neuropsychopharmacol Hung. 2004 Dec;6(4):210-20. [PubMed:15825677 ]
Dolusic E, Kowalczyk M, Magnus V, Sandberg G, Normanly J: Biotinylated indoles as probes for indole-binding proteins. Bioconjug Chem. 2001 Mar-Apr;12(2):152-62. doi: 10.1021/bc000035o. [PubMed:11312675 ]
Demisch L, von der Muhlen H, Bochnik HJ, Seiler N: Substrate-typic changes of platelet monoamine oxidase activity in sub-types of schizophrenia. Arch Psychiatr Nervenkr (1970). 1977 Dec 28;224(4):319-29. doi: 10.1007/BF00341614. [PubMed:606205 ]
Gaszner P, Miklya I: Major depression and the synthetic enhancer substances, (-)-deprenyl and R-(-)-1-(benzofuran-2-yl)-2-propylaminopentane. Prog Neuropsychopharmacol Biol Psychiatry. 2006 Jan;30(1):5-14. doi: 10.1016/j.pnpbp.2005.06.004. Epub 2005 Jul 14. [PubMed:16023777 ]
Mousseau DD, Layrargues GP, Butterworth RF: Region-selective decreases in densities of [3H]tryptamine binding sites in autopsied brain tissue from cirrhotic patients with hepatic encephalopathy. J Neurochem. 1994 Feb;62(2):621-5. doi: 10.1046/j.1471-4159.1994.62020621.x. [PubMed:8294925 ]
Anthenelli RM, Tipp J, Li TK, Magnes L, Schuckit MA, Rice J, Daw W, Nurnberger JI Jr: Platelet monoamine oxidase activity in subgroups of alcoholics and controls: results from the Collaborative Study on the Genetics of Alcoholism. Alcohol Clin Exp Res. 1998 May;22(3):598-604. doi: 10.1111/j.1530-0277.1998.tb04298.x. [PubMed:9622437 ]
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 ]
Roager HM, Licht TR: Microbial tryptophan catabolites in health and disease. Nat Commun. 2018 Aug 17;9(1):3294. doi: 10.1038/s41467-018-05470-4. [PubMed:30120222 ]

Showing metabocard for Tryptamine (MMDBc0000096)

MOL for #<Metabolite:0x00007f120cd4ff10>

3D MOL for #<Metabolite:0x00007f120cd4ff10>

3D SDF for #<Metabolite:0x00007f120cd4ff10>

3D-SDF for #<Metabolite:0x00007f120cd4ff10>

PDB for #<Metabolite:0x00007f120cd4ff10>

3D PDB for #<Metabolite:0x00007f120cd4ff10>

SMILES for #<Metabolite:0x00007f120cd4ff10>

INCHI for #<Metabolite:0x00007f120cd4ff10>

Structure for #<Metabolite:0x00007f120cd4ff10>

3D Structure for #<Metabolite:0x00007f120cd4ff10>