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Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
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MetaCyc Compound: tryptamine

Synonyms: 3-(2-aminoethyl)indole

Chemical Formula: C10H13N2

Molecular Weight: 161.23 Daltons

Monoisotopic Molecular Weight: 160.1000483956 Daltons

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 Change Formation (ΔfG in kcal/mol): 165.98352 Inferred 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

tryptophan degradation VI (via tryptamine) , 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 , secologanin and strictosidine biosynthesis , tryptophan degradation VI (via tryptamine) , tryptophan degradation X (mammalian, via tryptamine) :
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]


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


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 18.5 on Sun Nov 23, 2014, BIOCYC13A.