Loganin
PubChem CID: 87691
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| Compound Synonyms | Loganin, 18524-94-2, Loganoside, 7-Hydroxy-6-desoxyverbenalin, CHEBI:15771, UNII-H7WJ16Q93C, H7WJ16Q93C, EINECS 242-398-0, NSC 606403, LOGANIN, (-)-, NSC-606403, Cyclopenta[c]pyran-4-carboxylic acid,1-(b-D-glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-6-hydroxy-7-methyl-, methyl ester, (1S,4aS,6S,7R,7aS)-, methyl (1S,4aS,6S,7R,7aS)-6-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate, MFCD00075645, (1S,4aS,6S,7R,7aS)-Methyl 6-hydroxy-7-methyl-1-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate, methyl (1S,4aS,6S,7R,7aS)-6-hydroxy-7-methyl-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-4-carboxylate, (-)-Loganin, C17H26O10, 1-(beta-D-glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-6-hydroxy-7-methylcyclopenta(c)pyran-4-carboxylic acid methyl ester, 1-(beta-D-glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-6-hydroxy-7-methylcyclopenta[c]pyran-4-carboxylic acid methyl ester, methyl (1S,4aS,6S,7R,7aS)-1-(beta-D-glucopyranosyloxy)-6-hydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta(c)pyran-4-carboxylate, methyl (1S,4aS,6S,7R,7aS)-1-(beta-D-glucopyranosyloxy)-6-hydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate, Loganin (Standard), Spectrum_001503, SpecPlus_000563, LOGANIN [MI], Spectrum2_001637, Spectrum3_001875, Spectrum4_001914, Spectrum5_000628, Loganin, analytical standard, BSPBio_003350, KBioGR_002535, KBioSS_001983, DivK1c_006659, SCHEMBL307017, SPECTRUM1504066, SPBio_001733, MEGxp0_000723, CHEMBL1081584, ACon1_001749, HY-N0512R, KBio1_001603, KBio2_001983, KBio2_004551, KBio2_007119, KBio3_002852, CYCLOPENTA(C)PYRAN-4-CARBOXYLIC ACID, 1-(.BETA.-D-GLUCOPYRANOSYLOXY)-1,4A,5,6,7,7A-HEXAHYDRO-6-HYDROXY-7-METHYL-, METHYL ESTER, CYCLOPENTA(C)PYRAN-4-CARBOXYLIC ACID, 1-(.BETA.-D-GLUCOPYRANOSYLOXY)-1,4A,5,6,7,7A-HEXAHYDRO-6-HYDROXY-7-METHYL-, METHYL ESTER, (1S-(1.ALPHA.,4A.ALPHA.,6.ALPHA.,7.ALPHA.,7A.ALPHA.))-, HY-N0512, BDBM50279529, CCG-38757, s3835, AKOS022190418, CS-5019, LMPR0102070001, ML11578, SDCCGMLS-0066747.P001, NCGC00178124-01, NCGC00178124-02, NCGC00178124-03, NCGC00178124-04, NCGC00178124-08, AC-34479, AS-75232, cyclopenta(c)pyran-4-carboxylic acid, 1-(beta-D-glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-6-hydroxy-7-methyl-, methyl ester, (1S, 4aS, 6S, 7R, 7aS)-, Cyclopenta(c)pyran-4-carboxylic acid, 1-(beta-D-glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-6-hydroxy-7-methyl-, methyl ester, (1S-(1alpha,4aalpha,6alpha,7alpha,7aalpha))-, C01433, 5A5AFFBA-93AB-4635-A071-FC87B9DC023D, Q15426222, (1S)-1.ALPHA.-(.BETA.-D-GLUCOPYRANOSYLOXY)-1,4A.ALPHA.,5,6,7,7A.ALPHA.-HEXAHYDRO-6.ALPHA.-HYDROXY-7.ALPHA.-METHYLCYCLOPENTA(C)PYRAN-4-CARBOXYLIC ACID METHYL ESTER, (1S)-1alpha-(beta-D-GLUCOPYRANOSYLOXY)-1,4Aalpha,5,6,7,7Aalpha-HEXAHYDRO-6alpha-HYDROXY-7alpha-METHYLCYCLOPENTA(C)PYRAN-4-CARBOXYLIC ACID METHYL ESTER, (1S,4aS,6S,7R,7aS)-methyl 6-hydroxy-7-methyl-1-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate, (1S,4aS,6S,7R,7aS)-Methyl6-hydroxy-7-methyl-1-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate, 242-398-0, CYCLOPENTA(C)PYRAN-4-CARBOXYLIC ACID, 1-(.BETA.-D-GLUCOPYRANOSYLOXY)-1,4A,5,6,7,7A-HEXAHYDRO-6-HYDROXY-7-METHYL-, METHYL ESTER, (1S,4AS,6S,7R,7AS)-, CYCLOPENTA(C)PYRAN-4-CARBOXYLIC ACID, 1-(beta-D-GLUCOPYRANOSYLOXY)-1,4A,5,6,7,7A-HEXAHYDRO-6-HYDROXY-7-METHYL-, METHYL ESTER, CYCLOPENTA(C)PYRAN-4-CARBOXYLIC ACID, 1-(beta-D-GLUCOPYRANOSYLOXY)-1,4A,5,6,7,7A-HEXAHYDRO-6-HYDROXY-7-METHYL-, METHYL ESTER, (1S,4AS,6S,7R,7AS)-, methyl (1S,4aS,6S,7R,7aS)-6-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate, METHYL (1S-(1.ALPHA.,4A.ALPHA.,6.ALPHA.,7.ALPHA.,7A.ALPHA.))-1-(.BETA.-D-GLUCOPYRANOSYLOXY)-1,4A,5,6,7,7A-HEXAHYDRO-6-HYDROXY-7-METHYLCYCLOPENTA(C)PYRAN-4-CARBOXYLATE, Methyl (1S-(1alpha,4aalpha,6alpha,7alpha,7aalpha))-1-(beta-D-glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-6-hydroxy-7-methylcyclopenta(c)pyran-4-carboxylate, Methyl 6-hydroxy-7-methyl-1-((3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-1,4a,5 |
|---|---|
| Ghose Rule | False |
| Classyfire Kingdom | Organic compounds |
| Topological Polar Surface Area | 155.0 |
| Hydrogen Bond Donor Count | 5.0 |
| Pfizer 3 75 Rule | True |
| Scaffold Graph Level | C1CCC(CC2CCCC3CCCC32)CC1 |
| Np Classifier Class | Iridoids monoterpenoids |
| Deep Smiles | OC[C@H]O[C@@H]O[C@@H]OC=C[C@@H][C@H]6[C@@H]C)[C@H]C5)O)))))C=O)OC))))))))[C@@H][C@H][C@@H]6O))O))O |
| Heavy Atom Count | 27.0 |
| Classyfire Class | Prenol lipids |
| Description | Loganin, also known as loganoside, is a member of the class of compounds known as iridoid o-glycosides. Iridoid o-glycosides are iridoid monoterpenes containing a glycosyl (usually a pyranosyl) moiety linked to the iridoid skeleton. Thus, loganin is considered to be an isoprenoid lipid molecule. Loganin is soluble (in water) and a very weakly acidic compound (based on its pKa). Loganin can be found in a number of food items such as groundcherry, annual wild rice, muscadine grape, and broad bean, which makes loganin a potential biomarker for the consumption of these food products. Loganin is one of the best-known of the iridoid glycosides.It is named for the Loganiaceae,having first been isolated from the seeds of a member of that plant family, namely those of Strychnos nux-vomica. It also occurs in Alstonia boonei (Apocynaceae), a medicinal tree of West Africa and in the medicinal/entheogenic shrub Desfontainia spinosa (Columelliaceae) native to Central America and South America . |
| Scaffold Graph Node Level | C1CCC(OC2OCCC3CCCC32)OC1 |
| Classyfire Subclass | Terpene glycosides |
| Isotope Atom Count | 0.0 |
| Molecular Complexity | 580.0 |
| Database Name | cmaup_ingredients;fooddb_chem_all;imppat_phytochem;npass_chem_all;pubchem |
| Defined Atom Stereocenter Count | 10.0 |
| Uniprot Id | Q9Y6L6, Q9NPD5, P23219, P35354, P40763 |
| Iupac Name | methyl (1S,4aS,6S,7R,7aS)-6-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate |
| Prediction Hob | 0.0 |
| Veber Rule | False |
| Classyfire Superclass | Lipids and lipid-like molecules |
| Target Id | NPT38 |
| Xlogp | -1.4 |
| Gsk 4 400 Rule | True |
| Molecular Formula | C17H26O10 |
| Scaffold Graph Node Bond Level | C1=CC2CCCC2C(OC2CCCCO2)O1 |
| Prediction Swissadme | 0.0 |
| Inchi Key | AMBQHHVBBHTQBF-UOUCRYGSSA-N |
| Silicos It Class | Soluble |
| Fcsp3 | 0.8235294117647058 |
| Logs | -1.009 |
| Rotatable Bond Count | 5.0 |
| Logd | 0.131 |
| Synonyms | loganin |
| Esol Class | Very soluble |
| Functional Groups | CO, COC(=O)C1=CO[C@@H](O[C@@H](C)OC)CC1 |
| Compound Name | Loganin |
| Prediction Hob Swissadme | 0.0 |
| Exact Mass | 390.153 |
| Formal Charge | 0.0 |
| Monoisotopic Mass | 390.153 |
| Hydrogen Bond Acceptor Count | 10.0 |
| Molecular Weight | 390.4 |
| Gi Absorption | False |
| Covalent Unit Count | 1.0 |
| Total Atom Stereocenter Count | 10.0 |
| Total Bond Stereocenter Count | 0.0 |
| Lipinski Rule Of 5 | True |
| Esol | -1.0546870000000008 |
| Inchi | InChI=1S/C17H26O10/c1-6-9(19)3-7-8(15(23)24-2)5-25-16(11(6)7)27-17-14(22)13(21)12(20)10(4-18)26-17/h5-7,9-14,16-22H,3-4H2,1-2H3/t6-,7+,9-,10+,11+,12+,13-,14+,16-,17-/m0/s1 |
| Smiles | C[C@H]1[C@H](C[C@H]2[C@@H]1[C@@H](OC=C2C(=O)OC)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O |
| Nring | 3.0 |
| Np Classifier Biosynthetic Pathway | Terpenoids |
| Defined Bond Stereocenter Count | 0.0 |
| Egan Rule | False |
| Np Classifier Superclass | Monoterpenoids |
- 1. Outgoing r'ship
FOUND_INto/from Acacia Aulacocarpa (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 2. Outgoing r'ship
FOUND_INto/from Anemone Flaccida (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 3. Outgoing r'ship
FOUND_INto/from Ardisia Neriifolia (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 4. Outgoing r'ship
FOUND_INto/from Aspidosperma Subincanum (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 5. Outgoing r'ship
FOUND_INto/from Avicennia Officinalis (Plant) Rel Props:Reference:ISBN:9770972795006 - 6. Outgoing r'ship
FOUND_INto/from Catharanthus Roseus (Plant) Rel Props:Reference:https://www.ncbi.nlm.nih.gov/pubmed/19722248 - 7. Outgoing r'ship
FOUND_INto/from Cerbera Manghas (Plant) Rel Props:Reference:ISBN:9788185042145 - 8. Outgoing r'ship
FOUND_INto/from Cornus Officinalis (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 9. Outgoing r'ship
FOUND_INto/from Cryptocarya Aschersoniana (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 10. Outgoing r'ship
FOUND_INto/from Dimocarpus Fumatus (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 11. Outgoing r'ship
FOUND_INto/from Dipsacus Asper (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 12. Outgoing r'ship
FOUND_INto/from Dipsacus Asperoides (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 13. Outgoing r'ship
FOUND_INto/from Dipsacus Fullonum (Plant) Rel Props:Reference:https://doi.org/10.15482/usda.adc/1239279 - 14. Outgoing r'ship
FOUND_INto/from Dipsacus Inermis (Plant) Rel Props:Reference:ISBN:9788185042145 - 15. Outgoing r'ship
FOUND_INto/from Eucommia Ulmoides (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 16. Outgoing r'ship
FOUND_INto/from Eupatorium Argentinum (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 17. Outgoing r'ship
FOUND_INto/from Gentiana Crassicaulis (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 18. Outgoing r'ship
FOUND_INto/from Gentiana Dahurica (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 19. Outgoing r'ship
FOUND_INto/from Gentiana Macrophylla (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 20. Outgoing r'ship
FOUND_INto/from Gentiana Pedicellata (Plant) Rel Props:Reference:ISBN:9788185042138 - 21. Outgoing r'ship
FOUND_INto/from Gentiana Straminea (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 22. Outgoing r'ship
FOUND_INto/from Guatteria Boliviana (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 23. Outgoing r'ship
FOUND_INto/from Juniperus Brevifolia (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 24. Outgoing r'ship
FOUND_INto/from Lamium Album (Plant) Rel Props:Source_db:npass_chem_all - 25. Outgoing r'ship
FOUND_INto/from Lonicera Angustifolia (Plant) Rel Props:Reference:ISBN:9770972795006 - 26. Outgoing r'ship
FOUND_INto/from Lonicera Confusa (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 27. Outgoing r'ship
FOUND_INto/from Lonicera Fulvotomentosa (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 28. Outgoing r'ship
FOUND_INto/from Lonicera Hypoglauca (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 29. Outgoing r'ship
FOUND_INto/from Lonicera Japonica (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 30. Outgoing r'ship
FOUND_INto/from Lonicera Macranthoides (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 31. Outgoing r'ship
FOUND_INto/from Lonicera Quinquelocularis (Plant) Rel Props:Reference:ISBN:9770972795006 - 32. Outgoing r'ship
FOUND_INto/from Menyanthes Trifoliata (Plant) Rel Props:Reference:ISBN:9788172361150; ISBN:9788185042138 - 33. Outgoing r'ship
FOUND_INto/from Mitragyna Parvifolia (Plant) Rel Props:Reference:ISBN:9770972795006 - 34. Outgoing r'ship
FOUND_INto/from Peritassa Compta (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 35. Outgoing r'ship
FOUND_INto/from Phlomoides Rotata (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 36. Outgoing r'ship
FOUND_INto/from Psiadia Dentata (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 37. Outgoing r'ship
FOUND_INto/from Pterocephalus Hookeri (Plant) Rel Props:Source_db:npass_chem_all - 38. Outgoing r'ship
FOUND_INto/from Rheedia Acuminata (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 39. Outgoing r'ship
FOUND_INto/from Scaevola Frutescens (Plant) Rel Props:Reference:ISBN:9780387706375 - 40. Outgoing r'ship
FOUND_INto/from Scaevola Taccada (Plant) Rel Props:Reference:ISBN:9788185042145 - 41. Outgoing r'ship
FOUND_INto/from Scutellaria Lateriflora (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 42. Outgoing r'ship
FOUND_INto/from Stephania Viridiflavens (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 43. Outgoing r'ship
FOUND_INto/from Strychnos Ignatii (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 44. Outgoing r'ship
FOUND_INto/from Strychnos Nux-Vomica (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 45. Outgoing r'ship
FOUND_INto/from Strychnos Potatorum (Plant) Rel Props:Reference:ISBN:9788172361150 - 46. Outgoing r'ship
FOUND_INto/from Uncaria Cordata (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 47. Outgoing r'ship
FOUND_INto/from Verbena Officinalis (Plant) Rel Props:Reference:ISBN:9780387706375