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MetaCyc Compound: tryptamine

Synonyms: 3-(2-aminoethyl)indole

Chemical Formula: C10H13N2

Molecular Weight: 161.23 Daltons

Monoisotopic Molecular Weight: 161.1078734277 Daltons

tryptamine compound structure

SMILES: C([N+])CC2(=CNC1(=C(C=CC=C1)2))

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

InChIKey: InChIKey=APJYDQYYACXCRM-UHFFFAOYSA-O

Unification Links: CAS:61-54-1, ChEBI:57887, ChemSpider:3205163, HMDB:HMDB00303, KEGG:C00398, MetaboLights:MTBLC57887, PubChem:3985862

Standard Gibbs Free Energy of Formation (ΔfG in kcal/mol): 165.98352Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

beta-carboline biosynthesis :
tryptamine → harmalol

camptothecin biosynthesis , secologanin and strictosidine biosynthesis :
tryptamine + secologanin → strictosidine + H2O

hydroxycinnamic acid serotonin amides biosynthesis :
tryptamine + NAD(P)H + H+ + oxygen → serotonin + NAD(P)+ + H2O

indole-3-acetate biosynthesis II :
tryptamine + NADPH + oxygen → N-hydroxyl-tryptamine + NADP+ + H2O

L-tryptophan degradation VI (via tryptamine) , L-tryptophan degradation X (mammalian, via tryptamine) :
tryptamine + H2O + oxygen → ammonium + indole acetaldehyde + hydrogen peroxide

Reactions known to produce the compound:

beta-carboline biosynthesis , camptothecin biosynthesis , hydroxycinnamic acid serotonin amides biosynthesis , indole-3-acetate biosynthesis II , L-tryptophan degradation VI (via tryptamine) , L-tryptophan degradation X (mammalian, via tryptamine) , secologanin and strictosidine biosynthesis :
L-tryptophan + H+ → CO2 + tryptamine

Enzymes inhibited by tryptamine, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: tryptophan decarboxylase [Noe84] Inhibitor (Mechanism unknown) of: histamine N-methyltransferase [Fuhr86], tryptophan dioxygenase [Matsumura84], L-tryptophan decarboxylase [Nakazawa77], strictosidine synthase [Treimer79], deacetylvindoline 4-O-acetyltransferase [Power90]

This compound has been characterized as an alternative substrate of the following enzymes: indoleamine 2,3-dioxygenase, melatonin myeloperoxidase, tryptophan 2'-dioxygenase


References

Fuhr86: Fuhr N, Kownatzki E (1986). "Inhibition of rat kidney histamine-N-methyltransferase by biogenic amines." Pharmacology 32(2);114-20. PMID: 3952132

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Matsumura84: Matsumura M, Osada K, Aiba S (1984). "L-tryptophan 2,3-dioxygenase of a moderate thermophile, Bacillus brevis. Purification, properties and a substrate-mediated stabilization of the quaternary structure." Biochim Biophys Acta 786(1-2);9-17. PMID: 6712960

Nakazawa77: Nakazawa, H., Sano, K., Kumagai, H., Yamada, H. (1977). "Distribution and formation of aromatic L-amino acid decarboxylase in bacteria." Agric. Biol.. Chem. 41(11):2241-2247.

Noe84: Noe, W., Mollenschott, C., Berlin, J. (84). "Tryptophan decarboxylase from Catharanthus roseus cell suspension cultures: purification, molecular and kinetic data of the homogeneous protein." Plant Mol Biol 3: 281-288.

Power90: Power R, Kurz WG, De Luca V (1990). "Purification and characterization of acetylcoenzyme A: deacetylvindoline 4-O-acetyltransferase from Catharanthus roseus." Arch Biochem Biophys 279(2);370-6. PMID: 2350183

Treimer79: Treimer JF, Zenk MH (1979). "Purification and properties of strictosidine synthase, the key enzyme in indole alkaloid formation." Eur J Biochem 101(1);225-33. PMID: 510306


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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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