CHEBI:18002 - (−)-secologanin

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ChEBI Name (−)-secologanin
ChEBI ID CHEBI:18002
ChEBI ASCII Name (-)-secologanin
Definition An iridoid monoterpenoid that is acetaldehyde in which on of the hydrogens of the methyl group has been replaced by a 2-(β-D-glucopyranosyloxy)-3,4-dihydro-2H-pyran-4-yl group which is substituted at positions 3 and 5 by a vinyl and a methoxycarbonyl group, respectively (the 2S,3R,4S stereoisomer).
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:45549, CHEBI:9076, CHEBI:18500, CHEBI:15070
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Formulae C17H24O10
C17H24O10
Net Charge 0
Average Mass 388.367
Monoisotopic Mass 388.137
InChI InChI=1S/C17H24O10/c1-3-8-9(4-5-18)10(15(23)24-2)7-25-16(8)27-17-14(22)13(21)12(20)11(6-19)26-17/h3,5,7-9,11-14,16-17,19-22H,1,4,6H2,2H3/t8-,9+,11-,12-,13+,14-,16+,17+/m1/s1
InChIKey CSKKDSFETGLMSB-NRZPKYKESA-N
SMILES [C@H]1(O[C@@H]([C@@H](O)[C@@H]([C@H]1O)O)CO)O[C@H]2[C@@H]([C@@H](C(=CO2)C(OC)=O)CC=O)C=C
Roles Classification
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.
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ChEBI Ontology
Outgoing (−)-secologanin (CHEBI:18002) has role plant metabolite (CHEBI:76924)
(−)-secologanin (CHEBI:18002) is a β-D-glucoside (CHEBI:22798)
(−)-secologanin (CHEBI:18002) is a aldehyde (CHEBI:17478)
(−)-secologanin (CHEBI:18002) is a enoate ester (CHEBI:51702)
(−)-secologanin (CHEBI:18002) is a methyl ester (CHEBI:25248)
(−)-secologanin (CHEBI:18002) is a pyrans (CHEBI:26407)
(−)-secologanin (CHEBI:18002) is a secoiridoid glycoside (CHEBI:50274)
IUPAC Name
methyl (2S,3R,4S)-3-ethenyl-2-(β-D-glucopyranosyloxy)-4-(2-oxoethyl)-3,4-dihydro-2H-pyran-5-carboxylate
Synonyms Sources
(-)-Secologanin KEGG COMPOUND
3-Ethenyl-2-(beta-D-glucopyranosyloxy)-3,4-dihydro-4-(2-oxoethyl)-2H-pyran-5-carboxylic acid, methyl ester ChemIDplus
METHYL (2S,3R,4S)-2-(BETA-D-GLUCOPYRANOSYLOXY)-4-(2-OXOETHYL)-3-VINYL-3,4-DIHYDRO-2H-PYRAN-5-CARBOXYLATE PDBeChem
methyl (2S,3R,4S)-4-(formylmethyl)-2-(β-D-glucopyranosyloxy)-3,4-dihydro-3-vinyl-2H-pyran-5-carboxylate IUBMB
Secologanin KEGG COMPOUND
secologanin UniProt
Manual Xrefs Databases
C00003098 KNApSAcK
C01852 KEGG COMPOUND
LMPR0102070002 LIPID MAPS
SCG PDBeChem
Secologanin Wikipedia
SECOLOGANIN-CPD MetaCyc
View more database links
Registry Numbers Types Sources
1441446 Beilstein Registry Number Beilstein
1441446 Reaxys Registry Number Reaxys
19351-63-4 CAS Registry Number KEGG COMPOUND
19351-63-4 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
24104568 PubMed citation Europe PMC
26285573 PubMed citation Europe PMC
Last Modified
29 November 2017