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

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ChEBI Name 3,5-di-O-acetyl-1-O-[(5β,8α,9β,10α)-18-oxokaur-16-en-18-yl]-β-L-arabinofuranose
ChEBI ID CHEBI:65753
ChEBI ASCII Name 3,5-di-O-acetyl-1-O-[(5beta,8alpha,9beta,10alpha)-18-oxokaur-16-en-18-yl]-beta-L-arabinofuranose
Definition An 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C29H42O8
Net Charge 0
Average Mass 518.63900
Monoisotopic Mass 518.28797
InChI InChI=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
InChIKey NDNXVUYCJZMRRS-ABRNDMKOSA-N
SMILES [H][C@]12CC[C@@]34C[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)C(=C)C4
Metabolite of Species Details
Sagittaria pygmaea (NCBI:txid258217) Found in whole plant (BTO:0001461). See: PubMed
Roles Classification
Biological Role(s): 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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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-ene
Note: (2013-01-02) The synonym is a misnomer as it fails to suggest an ester linkage between the sugar and the aglycone.
 ChEBI
Citation Waiting for Citations Type Source
17315313 PubMed citation Europe PMC
Last Modified
02 January 2013