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MetaCyc Compound: shisonin

Superclasses: an aromatic compound an organic aromatic compound a phenylpropanoid a flavonoid an anthocyanin an anthocyanidin-3-O-beta-D-glucoside an anthocyanidin 3,5-di-O-beta-D-glucoside
an aromatic compound an organic aromatic compound a phenylpropanoid a flavonoid an anthocyanin an anthocyanidin-5-O-beta-D-glucoside an anthocyanidin 3,5-di-O-beta-D-glucoside
an organic heterocyclic compound an organic heterobicyclic compound a benzopyran a 1-benzopyran a chromene a flavonoid an anthocyanin an anthocyanidin-3-O-beta-D-glucoside an anthocyanidin 3,5-di-O-beta-D-glucoside
an organic heterocyclic compound an organic heterobicyclic compound a benzopyran a 1-benzopyran a chromene a flavonoid an anthocyanin an anthocyanidin-5-O-beta-D-glucoside an anthocyanidin 3,5-di-O-beta-D-glucoside

Chemical Formula: C36H36O18

Molecular Weight: 756.67 Daltons

Monoisotopic Molecular Weight: 757.1979893855 Daltons

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:5282068

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -129.26862 Inferred 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 + H+

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 + H+

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+


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 SRI International Pathway Tools version 18.5 on Fri Dec 19, 2014, biocyc14.