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CHEBI:2622 - amarogentin

Default Structure
ChEBI IDCHEBI:2622
ChEBI Nameamarogentin
Stars
DefinitionA secoiridoid glycoside that consists of (4aS,5R,6R)-5-ethenyl-6-hydroxy-4,4a,5,6-tetrahydro-1H,3H-pyrano[3,4-c]pyran-1-one having a 2-O-[(3,3',5-trihydroxybiphenyl-2-yl)carbonyl]-β-D-glucopyranosyl group attached at position 6 via a glycosidic linkage.
Last Modified28 July 2014
DownloadsMolfile
FormulaC29H30O13
Net Charge0
Average Mass586.546
Monoisotopic Mass586.16864
SMILES[H][C@@]12CCOC(=O)C1=CO[C@@H](O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1OC(=O)c1c(O)cc(O)cc1-c1cccc(O)c1)[C@@H]2C=C
InChIInChI=1S/C29H30O13/c1-2-16-17-6-7-38-26(36)19(17)12-39-28(16)42-29-25(24(35)23(34)21(11-30)40-29)41-27(37)22-18(9-15(32)10-20(22)33)13-4-3-5-14(31)8-13/h2-5,8-10,12,16-17,21,23-25,28-35H,1,6-7,11H2/t16-,17+,21-,23-,24+,25-,28+,29+/m1/s1
InChIKeyDBOVHQOUSDWAPQ-WTONXPSSSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Swertia chirata (IPNI:60447539-2) - DOI (10.1016/S0040-4039(00)72792-4)
Swertia japonica (ncbitaxon:137129) - DOI (10.1055/s-2008-1074888)
Swertia mileensis (ncbitaxon:266086) - PubMed (8720386)
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 5.99.1.2 (DNA topoisomerase) inhibitor  A topoisomerase inhibitor that inhibits the bacterial enzymes of the DNA topoisomerases, Type I class (EC 5.99.1.2) that catalyze ATP-independent breakage of one of the two strands of DNA, passage of the unbroken strand through the break, and rejoining of the broken strand. These bacterial enzymes reduce the topological stress in the DNA structure by relaxing negatively, but not positively, supercoiled DNA.
ChEBI Ontology
Outgoing Relation(s)
amarogentin (CHEBI:2622) has role EC 5.99.1.2 (DNA topoisomerase) inhibitor (CHEBI:50276)
amarogentin (CHEBI:2622) has role metabolite (CHEBI:25212)
amarogentin (CHEBI:2622) is a monosaccharide derivative (CHEBI:63367)
amarogentin (CHEBI:2622) is a secoiridoid glycoside (CHEBI:50274)
IUPAC Name 
(4aR)-5t-ethenyl-6c-[O2-(3,5,3'-trihydroxybiphenyl-2-ylcarbonyl)-β-D-glucopyranosyloxy]-4,4ar,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-1-one
Synonyms  Source
(4aS,5R,6S)-5-ethenyl-1-oxo-4,4a,5,6-tetrahydro-1H,3H-pyrano[3,4-c]pyran-6-yl- 2-O-[(3,3',5-trihydroxybiphenyl-2-yl)carbonyl]-β-D-glucopyranosideChEBI
AmarogentinKEGG COMPOUND
sweroside-2'-(3'',5'',3'''-trihydroxydiphenyl)-2''-carboxylic acid esterChEBI
Manual XrefsDatabases
AmarogentinWikipedia
C00003070KNApSAcK
C09767KEGG COMPOUND
Registry NumbersSources
Reaxys:74677Reaxys
CAS:21018-84-8KEGG COMPOUND
CAS:21018-84-8ChemIDplus
Citations