CHEBI:132712 - secoxyloganin

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ChEBI Name secoxyloganin
ChEBI ID CHEBI:132712
Definition A secoiridoid glycoside that is [(2R,3R,4S)-2-hydroxy-5-(methoxycarbonyl)-3-vinyl-3,4-dihydro-2H-pyran-4-yl]acetic acid in which the anometric hydroxy group has been converted to the corresponding β-D-glucoside. It has been isolated from several plant species and exhibits antioxidant and anti-allergic properties.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter qingping liu
Supplier Information
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Formula C17H24O11
Net Charge 0
Average Mass 404.367
Monoisotopic Mass 404.13186
InChI InChI=1S/C17H24O11/c1-3-7-8(4-11(19)20)9(15(24)25-2)6-26-16(7)28-17-14(23)13(22)12(21)10(5-18)27-17/h3,6-8,10,12-14,16-18,21-23H,1,4-5H2,2H3,(H,19,20)/t7-,8+,10-,12-,13+,14-,16+,17+/m1/s1
InChIKey MQLSOVRLZHTATK-PEYNGXJCSA-N
SMILES O1[C@@H](O[C@@H]2OC=C([C@H]([C@H]2C=C)CC(O)=O)C(OC)=O)[C@H](O)[C@@H](O)[C@H](O)[C@H]1CO
Metabolite of Species Details
Lonicera japonica (NCBI:txid105884) Found in flower (BTO:0000469). See: PubMed
Lonicera japonica (NCBI:txid105884) Found in leaf (BTO:0000713). See: PubMed
Manulea altissima (NCBI:txid292437) See: PubMed
Guettarda pohliana (NCBI:txid336043) Found in leaf (BTO:0000713). See: PubMed
Guettarda pohliana (NCBI:txid336043) Found in root (BTO:0001188). See: PubMed
Guettarda platypoda (NCBI:txid339301) Found in Root (BTO:0001188). See: PubMed
Catharanthus roseus (NCBI:txid4058) See: PubMed
Olea europaea (NCBI:txid4146) Found in leaf (BTO:0000713). See: PubMed
Olea europaea (NCBI:txid4146) Found in fruit (BTO:0000486). See: PubMed
Lonicera fragrantissima (NCBI:txid486666) Found in flower (BTO:0000469). See: PubMed
Lonicera macranthoides (NCBI:txid638627) Found in flower bud (BTO:0000470). See: PubMed
Lonicera caerulea var. kamtschatica (NCBI:txid760126) Found in fruit (BTO:0000486). See: PubMed
Palicourea rigida (NCBI:txid96266) Found in root (BTO:0001188). See: PubMed
Palicourea rigida (NCBI:txid96266) Found in flower (BTO:0000469). See: PubMed
Palicourea rigida (NCBI:txid96266) Found in leaf (BTO:0000713). See: PubMed
Roles Classification
Chemical Role(s): antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Application(s): anti-allergic agent
A drug used to treat allergic reactions.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing secoxyloganin (CHEBI:132712) has role anti-allergic agent (CHEBI:50857)
secoxyloganin (CHEBI:132712) has role antioxidant (CHEBI:22586)
secoxyloganin (CHEBI:132712) has role plant metabolite (CHEBI:76924)
secoxyloganin (CHEBI:132712) is a β-D-glucoside (CHEBI:22798)
secoxyloganin (CHEBI:132712) is a dicarboxylic acid monoester (CHEBI:36244)
secoxyloganin (CHEBI:132712) is a enoate ester (CHEBI:51702)
secoxyloganin (CHEBI:132712) is a methyl ester (CHEBI:25248)
secoxyloganin (CHEBI:132712) is a monosaccharide derivative (CHEBI:63367)
secoxyloganin (CHEBI:132712) is a pyrans (CHEBI:26407)
secoxyloganin (CHEBI:132712) is a secoiridoid glycoside (CHEBI:50274)
secoxyloganin (CHEBI:132712) is conjugate acid of secoxyloganin(1−) (CHEBI:192364)
Incoming secoxyloganin(1−) (CHEBI:192364) is conjugate base of secoxyloganin (CHEBI:132712)
IUPAC Name
[(2S,3R,4S)-3-ethenyl-2-(β-D-glucopyranosyloxy)-5-(methoxycarbonyl)-3,4-dihydro-2H-pyran-4-yl]acetic acid
Synonyms Sources
(2S,3R,4S)-3-ethenyl-2-(β-D-glucopyranosyloxy)-3,4-dihydro-5-(methoxycarbonyl)-2H-pyran-4-acetic acid ChEBI
secoxy-loganin ChemIDplus
Manual Xrefs Databases
C00031346 KNApSAcK
HMDB0258204 HMDB
LMPR01020139 LIPID MAPS
View more database links
Registry Numbers Types Sources
5458989 Reaxys Registry Number Reaxys
58822-47-2 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
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Last Modified
07 July 2022