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MetaCyc Compound: shisonin

Superclasses: an aromatic compoundan organic aromatic compounda phenylpropanoida flavonoidan anthocyaninan anthocyanidin-3-O-beta-D-glucosidean anthocyanidin 3,5-di-O-beta-D-glucoside
an aromatic compoundan organic aromatic compounda phenylpropanoida flavonoidan anthocyaninan anthocyanidin-5-O-beta-D-glucosidean anthocyanidin 3,5-di-O-beta-D-glucoside
an organic heterocyclic compoundan organic heterobicyclic compounda benzopyrana 1-benzopyrana chromenea flavonoidan anthocyaninan anthocyanidin-3-O-beta-D-glucosidean anthocyanidin 3,5-di-O-beta-D-glucoside
an organic heterocyclic compoundan organic heterobicyclic compounda benzopyrana 1-benzopyrana chromenea flavonoidan anthocyaninan anthocyanidin-5-O-beta-D-glucosidean anthocyanidin 3,5-di-O-beta-D-glucoside

Chemical Formula: C36H36O18

Molecular Weight: 756.67 Daltons

Monoisotopic Molecular Weight: 757.1979893855 Daltons

shisonin compound structure

SMILES: C(C6(OC(OC1(=CC(=CC2([O+]=C(C(=CC1=2)OC3(OC(C(C(C3O)O)O)COC(C=CC4(C=CC(=CC=4)O))=O))C5(=CC(=C(C=C5)O)O)))[O-]))C(C(C6O)O)O))O

InChI: InChI=1S/C36H36O18/c37-13-25-28(43)30(45)32(47)35(53-25)51-23-11-18(39)10-22-19(23)12-24(34(50-22)16-4-7-20(40)21(41)9-16)52-36-33(48)31(46)29(44)26(54-36)14-49-27(42)8-3-15-1-5-17(38)6-2-15/h1-12,25-26,28-33,35-37,43-48H,13-14H2,(H3-,38,39,40,41,42)/t25-,26-,28-,29-,30+,31+,32-,33-,35-,36-/m1/s1

InChIKey: InChIKey=YPXWWSJGANMFFQ-AQAMAIGXSA-N

Unification Links: KEGG:C12096, PubChem:90657172

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -129.26862Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

shisonin biosynthesis , superpathway of anthocyanin biosynthesis (from cyanidin and cyanidin 3-O-glucoside) :
shisonin + malonyl-CoA → malonylshisonin + coenzyme A

Not in pathways:
a flavonoid + NADPH + oxygen + H+ → a 3'-hydroxy-flavonoid + NADP+ + H2O

Reactions known to produce the compound:

shisonin biosynthesis :
4-coumaryl-CoA + cyanidin 3,5-di-O-β-D-glucoside → shisonin + coenzyme A
UDP-α-D-glucose + cyanidin 3-(p-coumaroyl)-glucoside → shisonin + UDP

superpathway of anthocyanin biosynthesis (from cyanidin and cyanidin 3-O-glucoside) :
4-coumaryl-CoA + cyanidin 3,5-di-O-β-D-glucoside → shisonin + coenzyme A
UDP-α-D-glucose + cyanidin 3-(p-coumaroyl)-glucoside → shisonin + UDP

In Reactions of unknown directionality:

Not in pathways:
an anthocyanidin 3,5-di-O-β-D-glucoside + 4-coumaryl-CoA = an anthocyanidin 3-glucoside-5-(4-hydroxycinnamoyl)glucoside + coenzyme A
UDP-α-D-glucose + an anthocyanidin-3-O-β-D-glucoside = UDP + an anthocyanidin 3,5-di-O-β-D-glucoside + H+

Not in pathways:
malonyl-CoA + an anthocyanidin-3-O-β-D-glucoside + H+ = an anthocyanidin-3-O-(6-O-malonyl-β-D-glucoside) + coenzyme A
4-coumaryl-CoA + an anthocyanidin-3-O-β-D-glucoside + H+ = an anthocyanidin-3-O-[6-O-(hydroxycinnamoyl)-β-D-glucoside] + coenzyme A + H+
UDP-α-D-xylose + an anthocyanidin-3-O-β-D-glucoside = UDP + an anthocyanidin 3-O-β-D-sambubioside + H+
UDP-α-D-glucose + an anthocyanidin-3-O-β-D-glucoside = UDP + an anthocyanidin 3,5-di-O-β-D-glucoside + H+
UDP-α-D-glucose + an anthocyanidin-3-O-β-D-glucoside = UDP + an anthocyanidin 3-O-sophoroside + H+
UDP-α-D-glucose + an anthocyanidin = an anthocyanidin-3-O-β-D-glucoside + UDP
an anthocyanidin + UDP-α-D-glucose = an anthocyanidin-3-O-β-D-glucoside + UDP + H+


References

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


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 Pathway Tools version 19.5 (software by SRI International) on Sun Feb 7, 2016, biocyc11.