MetaCyc Compound: fumigaclavine A

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

Superclasses: a secondary metabolitean alkaloid

Citations: [Rigbers08, Matuschek11]

Chemical Formula: C18H23N2O2

Molecular Weight: 299.39 Daltons

Monoisotopic Molecular Weight: 299.17595299289997 Daltons

fumigaclavine A compound structure

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


Unification Links: ChEBI:67145, PubChem:70678801

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): 230.58372Inferred 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

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


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

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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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