CHEBI:66052 - hyemaloside C

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ChEBI Name hyemaloside C
ChEBI ID CHEBI:66052
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C40H30O23
Net Charge 0
Average Mass 878.65240
Monoisotopic Mass 878.11779
InChI InChI=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
InChIKey BIUWKTLZFMHRQE-RYQQTUIDSA-N
SMILES Oc1ccc(O[C@@H]2O[C@@H]3COC(=O)c4cc(O)c(O)c(O)c4-c4c(O)c(O)c(O)cc4C(=O)O[C@H]3[C@H](OC(=O)c3cc(O)c(O)c(O)c3)[C@H]2OC(=O)c2cc(O)c(O)c(O)c2)cc1
Metabolite of Species Details
Eugenia hyemalis (IPNI:594680-1) Found in whole plant (BTO:0001461). Whole plant without roots See: PubMed
Roles Classification
Biological Role(s): 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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 β-D-glucoside (CHEBI:22798)
hyemaloside C (CHEBI:66052) is a gallate ester (CHEBI:37576)
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 Number Type Source
19205164 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
18763827 PubMed citation Europe PMC
Last Modified
26 February 2013