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CHEBI:66052 - hyemaloside C

Default Structure
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:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
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.
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