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
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
twitter

MetaCyc Compound: fumigaclavine A

Synonyms: isofumigaclavine A, (2R,3S,4S,7R)-3-(acetyloxy)-4,6-dimethyl-6,11-diazatetracyclo[7.6.1.02,7.012,16]hexadeca-1(16),9,12,14-tetraen-6-ium, 6,8β-dimethylergolin-9β-yl acetate

Superclasses: a secondary metabolite an alkaloid

Citations: [Rigbers08, Matuschek11]

Chemical Formula: C18H23N2O2

Molecular Weight: 299.39 Daltons

Monoisotopic Molecular Weight: 298.1681279608 Daltons

SMILES: CC1(C[N+](C)[CH]2(CC4(C3(=C([CH](C(OC(C)=O)1)2)C=CC=C3NC=4))))

InChI: InChI=1S/C18H22N2O2/c1-10-9-20(3)15-7-12-8-19-14-6-4-5-13(16(12)14)17(15)18(10)22-11(2)21/h4-6,8,10,15,17-19H,7,9H2,1-3H3/p+1/t10-,15+,17+,18-/m0/s1

InChIKey: InChIKey=GJSSYQDXZLZOLR-IMKJFWDFSA-O

Unification Links: ChEBI:67145 , PubChem:46173279

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): 230.58372 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

fumigaclavine biosynthesis :
fumigaclavine A + dimethylallyl diphosphate → fumigaclavine C + diphosphate

Reactions known to produce the compound:

fumigaclavine biosynthesis :
fumigaclavine B + acetyl-CoA → fumigaclavine A + coenzyme A

Credits:
Created 01-Jun-2012 by Caspi R , SRI International


References

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

Matuschek11: Matuschek M, Wallwey C, Xie X, Li SM (2011). "New insights into ergot alkaloid biosynthesis in Claviceps purpurea: an agroclavine synthase EasG catalyses, via a non-enzymatic adduct with reduced glutathione, the conversion of chanoclavine-I aldehyde to agroclavine." Org Biomol Chem 9(11);4328-35. PMID: 21494745

Rigbers08: Rigbers O, Li SM (2008). "Ergot alkaloid biosynthesis in Aspergillus fumigatus. Overproduction and biochemical characterization of a 4-dimethylallyltryptophan N-methyltransferase." J Biol Chem 283(40);26859-68. PMID: 18678866


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 Fri Dec 19, 2014, biocyc14.