Metabolic Modeling Tutorial
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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: indole

Superclasses: an aromatic compound an indole

Chemical Formula: C8H7N

Molecular Weight: 117.15 Daltons

Monoisotopic Molecular Weight: 117.0578492299 Daltons

SMILES: C2(C=CC1(=C(C=CN1)C=2))

InChI: InChI=1S/C8H7N/c1-2-4-8-7(3-1)5-6-9-8/h1-6,9H

InChIKey: InChIKey=SIKJAQJRHWYJAI-UHFFFAOYSA-N

Unification Links: CAS:120-72-9 , ChEBI:16881 , ChemSpider:776 , DrugBank:DB04532 , HMDB:HMDB00738 , IAF1260:35045 , KEGG:C00463 , PubChem:798

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): 125.38785 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

DIBOA-glucoside biosynthesis :
indole + NAD(P)H + oxygen + H+ → indolin-2-one + NAD(P)+ + H2O

indican biosynthesis , indigo biosynthesis :
indole + 2 NADH + oxygen → cis-indole-2,3-dihydrodiol + 2 NAD+

indole degradation to anthranil and anthranilate :
indole + oxygen → 2-formylaminobenzaldehyde

tryptophan biosynthesis :
L-serine + indole → L-tryptophan + H2O

Not in pathways:
indole + NADH + oxygen + H+ → indoxyl + NAD+ + H2O

Reactions known to both consume and produce the compound:

DIBOA-glucoside biosynthesis , tryptophan biosynthesis :
(1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate ↔ indole + D-glyceraldehyde 3-phosphate

tryptophan degradation II (via pyruvate) :
L-tryptophan ↔ indole + 2-aminoprop-2-enoate + H+

Not in pathways:
indole-3-carboxylate + H+indole + CO2

In Reactions of unknown directionality:

Not in pathways:
L-tryptophan + H2O = indole + pyruvate + ammonium
indole + acetate = indole-3-acetate + 2 H+

In Transport reactions:
indole[cytosol]indole[periplasmic space] ,
indole[periplasmic space] + H+[periplasmic space]indole[cytosol] + H+[cytosol]

Enzymes activated by indole, sorted by the type of activation, are:

Activator (Allosteric) of: tryptophanase [Hoch66]

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

Inhibitor (Mechanism unknown) of: tryptophan dioxygenase [Matsumura84]


References

Hoch66: Hoch JA, Simpson FJ, DeMoss RD (1966). "Purification and some properties of tryptophanase from Bacillus alvei." Biochemistry 5(7);2229-37. PMID: 4959960

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


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, BIOCYC14B.