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Secologanin

PubChem CID: 161276

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Compound Synonyms Secologanin, 19351-63-4, loniceroside, (-)-Secologanin, NK7B26K93T, methyl (2S,3R,4S)-3-ethenyl-4-(2-oxoethyl)-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carboxylate, CHEBI:18002, tert-butyl 3-[[5-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-4,5-dihydro-1,2-oxazole-3-carbonyl]amino]butanoate, methyl (2S,3R,4S)-3-ethenyl-2-(beta-D-glucopyranosyloxy)-4-(2-oxoethyl)-3,4-dihydro-2H-pyran-5-carboxylate, NSC-640525, Loniceroside (iridoid), Secologanin (Standard), UNII-NK7B26K93T, SCHEMBL431171, Secologanin, analytical standard, CHEMBL1235867, DTXSID30941033, AKOS040753996, FS65469, HY-125598R, LMPR0102070002, NCGC00384550-01, METHYL (2S,3R,4S)-2-(BETA-D-GLUCOPYRANOSYLOXY)-4-(2-OXOETHYL)-3-VINYL-3,4-DIHYDRO-2H-PYRAN-5-CARBOXYLATE, MS-26429, HY-125598, CS-0092439, NS00074296, C01852, G13893, Q1531155, F19BE380-C97E-46CC-89C6-F6BCAFC793EC, 2H-Pyran-5-carboxylic acid, 3-ethenyl-2-(beta-D-glucopyranosyloxy)-3,4-dihydro-4-(2-oxoethyl)-, methyl ester, (2S,3R,4S)-, 3-Ethenyl-2-(beta-D-glucopyranosyloxy)-3,4-dihydro-4-(2-oxoethyl)-2H-pyran-5-carboxylic acid, methyl ester, methyl (2S,3R,4S)-4-(formylmethyl)-2-(beta-D-glucopyranosyloxy)-3,4-dihydro-3-vinyl-2H-pyran-5-carboxylate, NCGC00384550-01_C17H24O10_Methyl (2S,3R,4S)-2-(beta-D-glucopyranosyloxy)-4-(2-oxoethyl)-3-vinyl-3,4-dihydro-2H-pyran-5-carboxylate
Ghose Rule False
Classyfire Kingdom Organic compounds
Topological Polar Surface Area 152.0
Hydrogen Bond Donor Count 4.0
Pfizer 3 75 Rule True
Scaffold Graph Level C1CCC(CC2CCCCC2)CC1
Np Classifier Class Secoiridoid monoterpenoids
Deep Smiles O=CC[C@H][C@@H]C=C))[C@@H]OC=C6C=O)OC))))))O[C@@H]O[C@H]CO))[C@H][C@@H][C@H]6O))O))O
Heavy Atom Count 27.0
Classyfire Class Prenol lipids
Description Secologanin is a member of the class of compounds known as terpene glycosides. Terpene glycosides are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone. Thus, secologanin is considered to be an isoprenoid lipid molecule. Secologanin is soluble (in water) and a very weakly acidic compound (based on its pKa). Secologanin can be found in a number of food items such as oyster mushroom, flaxseed, nectarine, and cereals and cereal products, which makes secologanin a potential biomarker for the consumption of these food products. Secologanin is a secoiridoid monoterpene synthesized from geranyl pyrophosphate in the mevalonate pathway. Secologanin then proceeds with dopamine or tryptamine to form ipecac and terpene indole alkaloids, respectively .
Scaffold Graph Node Level C1CCC(OC2CCCCO2)OC1
Classyfire Subclass Terpene glycosides
Isotope Atom Count 0.0
Molecular Complexity 576.0
Database Name cmaup_ingredients;fooddb_chem_all;imppat_phytochem;npass_chem_all;pubchem
Defined Atom Stereocenter Count 8.0
Iupac Name methyl (2S,3R,4S)-3-ethenyl-4-(2-oxoethyl)-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carboxylate
Prediction Hob 0.0
Veber Rule False
Classyfire Superclass Lipids and lipid-like molecules
Xlogp -1.6
Gsk 4 400 Rule True
Molecular Formula C17H24O10
Scaffold Graph Node Bond Level C1=COC(OC2CCCCO2)CC1
Prediction Swissadme 0.0
Inchi Key CSKKDSFETGLMSB-NRZPKYKESA-N
Silicos It Class Soluble
Fcsp3 0.6470588235294118
Rotatable Bond Count 8.0
Synonyms loniceroside, secologanin
Esol Class Very soluble
Functional Groups C=CC, CC=O, CO, COC(=O)C1=CO[C@@H](O[C@@H](C)OC)CC1
Compound Name Secologanin
Prediction Hob Swissadme 0.0
Exact Mass 388.137
Formal Charge 0.0
Monoisotopic Mass 388.137
Hydrogen Bond Acceptor Count 10.0
Molecular Weight 388.4
Gi Absorption False
Covalent Unit Count 1.0
Total Atom Stereocenter Count 8.0
Total Bond Stereocenter Count 0.0
Lipinski Rule Of 5 True
Esol -0.6992878000000005
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
Smiles COC(=O)C1=CO[C@H]([C@@H]([C@@H]1CC=O)C=C)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
Np Classifier Biosynthetic Pathway Terpenoids
Defined Bond Stereocenter Count 0.0
Egan Rule False
Np Classifier Superclass Monoterpenoids

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