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CHEBI:66052 - hyemaloside C

ChEBI IDCHEBI:66052
ChEBI Namehyemaloside C
Stars
DefinitionA β-D-glucoside compound having a a hexahydroxydiphenoyl (HHDP) group bridging over positions 4 and 6, galloyl groups at positions 2 and 3 and a 4-hydroxyphenyl substituent at the 1-position. Isolated from Eugenia hyemalis, it exhibits inhibitory activity against HIV-1.
Last Modified26 February 2013
DownloadsMolfile
FormulaC40H30O23
Net Charge0
Average Mass878.657
Monoisotopic Mass878.11779
SMILESO=C(O[C@@H]1[C@@H](OC(=O)c2cc(O)c(O)c(O)c2)[C@H](Oc2ccc(O)cc2)O[C@@H]2COC(=O)c3cc(O)c(O)c(O)c3-c3c(cc(O)c(O)c3O)C(=O)O[C@@H]12)c1cc(O)c(O)c(O)c1
InChIInChI=1S/C40H30O23/c41-14-1-3-15(4-2-14)59-40-35(63-37(55)13-7-20(44)28(49)21(45)8-13)34(62-36(54)12-5-18(42)27(48)19(43)6-12)33-24(60-40)11-58-38(56)16-9-22(46)29(50)31(52)25(16)26-17(39(57)61-33)10-23(47)30(51)32(26)53/h1-10,24,33-35,40-53H,11H2/t24-,33-,34+,35-,40-/m1/s1
InChIKeyBIUWKTLZFMHRQE-RYQQTUIDSA-N
Species of MetaboliteComponentSourceComments
Eugenia hyemalis (IPNI:594680-1) whole plant (BTO:0001461) PubMed (18763827) Whole plant without roots
Roles Classification
Biological Roles:
EC 3.1.26.13 (retroviral ribonuclease H) inhibitor  An inhibitor of ribonuclease H (EC 3.1.26.13), an enzyme required for specific hydrolysis of the RNA strand of an RNA/DNA hybrid.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
ChEBI Ontology
Outgoing Relation(s)
hyemaloside C (CHEBI:66052) has functional parent hydroquinone O-β-D-glucopyranoside (CHEBI:18305)
hyemaloside C (CHEBI:66052) has role EC 3.1.26.13 (retroviral ribonuclease H) inhibitor (CHEBI:52629)
hyemaloside C (CHEBI:66052) has role metabolite (CHEBI:25212)
hyemaloside C (CHEBI:66052) is a gallate ester (CHEBI:37576)
hyemaloside C (CHEBI:66052) is a β-D-glucoside (CHEBI:22798)
IUPAC Name 
(11aR,13S,14R,15S,15aR)-2,3,4,5,6,7-hexahydroxy-13-(4-hydroxyphenoxy)-9,17-dioxo-9,11,11a,13,14,15,15a,17-octahydrodibenzo[g,i]pyrano[3,2-b][1,5]dioxacycloundecine-14,15-diyl bis(3,4,5-trihydroxybenzoate)
Registry NumbersSources
Reaxys:19205164Reaxys
Citations