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CHEBI:18002 - (−)-secologanin

ChEBI IDCHEBI:18002
ChEBI Name(−)-secologanin
Stars
ASCII Name(-)-secologanin
DefinitionAn iridoid monoterpenoid that is acetaldehyde in which on of the hydrogens of the methyl group has been replaced by a 2-(β-D-glucopyranosyloxy)-3,4-dihydro-2H-pyran-4-yl group which is substituted at positions 3 and 5 by a vinyl and a methoxycarbonyl group, respectively (the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).
Secondary ChEBI IDsCHEBI:9076, CHEBI:15070, CHEBI:18500, CHEBI:45549
Last Modified29 November 2017
DownloadsMolfile
FormulaC17H24O10
Net Charge0
Average Mass388.369
Monoisotopic Mass388.13695
SMILESC=C[C@H]1[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)OC=C(C(=O)OC)[C@H]1CC=O
InChIInChI=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
InChIKeyCSKKDSFETGLMSB-NRZPKYKESA-N
Wikipedia
Roles Classification
Biological Role:
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
ChEBI Ontology
Outgoing Relation(s)
(−)-secologanin (CHEBI:18002) has role plant metabolite (CHEBI:76924)
(−)-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)
(−)-secologanin (CHEBI:18002) is a β-D-glucoside (CHEBI:22798)
IUPAC Name 
methyl (2S,3R,4S)-3-ethenyl-2-(β-D-glucopyranosyloxy)-4-(2-oxoethyl)-3,4-dihydro-2H-pyran-5-carboxylate
Synonyms  Source
3-Ethenyl-2-(beta-D-glucopyranosyloxy)-3,4-dihydro-4-(2-oxoethyl)-2H-pyran-5-carboxylic acid, methyl esterChemIDplus
methyl (2S,3R,4S)-4-(formylmethyl)-2-(β-D-glucopyranosyloxy)-3,4-dihydro-3-vinyl-2H-pyran-5-carboxylateIUBMB
METHYL (2S,3R,4S)-2-(BETA-D-GLUCOPYRANOSYLOXY)-4-(2-OXOETHYL)-3-VINYL-3,4-DIHYDRO-2H-PYRAN-5-CARBOXYLATEPDBeChem
(-)-SecologaninKEGG COMPOUND
SecologaninKEGG COMPOUND
UniProt Name  Source
secologaninUniProt
Manual XrefsDatabases
C00003098KNApSAcK
C01852KEGG COMPOUND
LMPR0102070002LIPID MAPS
SCGPDBeChem
SecologaninWikipedia
SECOLOGANIN-CPDMetaCyc
Registry NumbersSources
Reaxys:1441446Reaxys
Beilstein:1441446Beilstein
CAS:19351-63-4ChemIDplus
CAS:19351-63-4KEGG COMPOUND
Citations