CHEBI:2622 - amarogentin

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ChEBI Name amarogentin
ChEBI ID CHEBI:2622
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C29H30O13
Net Charge 0
Average Mass 586.54070
Monoisotopic Mass 586.169
InChI InChI=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
InChIKey DBOVHQOUSDWAPQ-WTONXPSSSA-N
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
Metabolite of Species Details
Swertia chirata (IPNI:60447539-2) See: DOI
Swertia japonica (NCBI:txid137129) See: DOI
Swertia mileensis (NCBI:txid266086) See: PubMed
Roles Classification
Biological Role(s): 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.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
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ChEBI Ontology
Outgoing 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 Sources
(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-glucopyranoside ChEBI
Amarogentin KEGG COMPOUND
sweroside-2'-(3'',5'',3'''-trihydroxydiphenyl)-2''-carboxylic acid ester ChEBI
Manual Xrefs Databases
Amarogentin Wikipedia
C00003070 KNApSAcK
C09767 KEGG COMPOUND
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Registry Numbers Types Sources
21018-84-8 CAS Registry Number KEGG COMPOUND
21018-84-8 CAS Registry Number ChemIDplus
74677 Reaxys Registry Number Reaxys
74677 Beilstein Registry Number Beilstein
Citation Waiting for Citations Type Source
8720386 PubMed citation Europe PMC
Last Modified
28 July 2014