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CHEBI:65753 - 3,5-di-O-acetyl-1-O-[(5β,8α,9β,10α)-18-oxokaur-16-en-18-yl]-β-L-arabinofuranose

ChEBI IDCHEBI:65753
ChEBI Name3,5-di-O-acetyl-1-O-[(5β,8α,9β,10α)-18-oxokaur-16-en-18-yl]-β-L-arabinofuranose
Stars
ASCII Name3,5-di-O-acetyl-1-O-[(5beta,8alpha,9beta,10alpha)-18-oxokaur-16-en-18-yl]-beta-L-arabinofuranose
DefinitionAn ent-kaurane diterpenoid that is ent-kaur-16-en-18-oic acid substituted by a β-L-3',5'-diacetoxy-arabinofuranosyl moiety at position 18 via a glycosidic linkage. It is isolated from the whole herb of Sagittaria pygmaea and exhibits antibacterial activity against the oral pathogens.
Last Modified2 January 2013
DownloadsMolfile
FormulaC29H42O8
Net Charge0
Average Mass518.647
Monoisotopic Mass518.28797
SMILES[H][C@]12CC[C@]34CC(=C)[C@H](CC[C@@]3([H])[C@]1(C)CCC[C@@]2(C)C(=O)O[C@H]1O[C@@H](COC(C)=O)[C@H](OC(C)=O)[C@H]1O)C4
InChIInChI=1S/C29H42O8/c1-16-13-29-12-9-21-27(4,22(29)8-7-19(16)14-29)10-6-11-28(21,5)26(33)37-25-23(32)24(35-18(3)31)20(36-25)15-34-17(2)30/h19-25,32H,1,6-15H2,2-5H3/t19?,20-,21-,22-,23+,24-,25+,27+,28+,29+/m0/s1
InChIKeyNDNXVUYCJZMRRS-ABRNDMKOSA-N
Species of MetaboliteComponentSourceComments
Sagittaria pygmaea (ncbitaxon:258217) whole plant (BTO:0001461) PubMed (17315313)
Roles Classification
Biological Roles:
antibacterial agent  A substance (or active part thereof) that kills or slows the growth of bacteria.
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)
3,5-di-O-acetyl-1-O-[(5β,8α,9β,10α)-18-oxokaur-16-en-18-yl]-β-L-arabinofuranose (CHEBI:65753) has functional parent β-L-arabinofuranose (CHEBI:28272)
3,5-di-O-acetyl-1-O-[(5β,8α,9β,10α)-18-oxokaur-16-en-18-yl]-β-L-arabinofuranose (CHEBI:65753) has role antibacterial agent (CHEBI:33282)
3,5-di-O-acetyl-1-O-[(5β,8α,9β,10α)-18-oxokaur-16-en-18-yl]-β-L-arabinofuranose (CHEBI:65753) has role metabolite (CHEBI:25212)
3,5-di-O-acetyl-1-O-[(5β,8α,9β,10α)-18-oxokaur-16-en-18-yl]-β-L-arabinofuranose (CHEBI:65753) is a ent-kaurane diterpenoid (CHEBI:36760)
3,5-di-O-acetyl-1-O-[(5β,8α,9β,10α)-18-oxokaur-16-en-18-yl]-β-L-arabinofuranose (CHEBI:65753) is a acetate ester (CHEBI:47622)
IUPAC Name 
3,5-di-O-acetyl-1-O-[(5β,8α,9β,10α)-18-oxokaur-16-en-18-yl]-β-L-arabinofuranose
Synonym  Source
18-β-L-3',5'-diacetoxy-arabinofuranosyl-ent-kaur-16-eneChEBI
Citations