(-)-Loganin
Basic information
- CAS
18524-94-2- Standard SMILES
COC(=O)C1=CO[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H]2[C@@H](C)[C@@H](O)C[C@H]12- InChIKey
AMBQHHVBBHTQBF-UOUCRYGSSA-N- Molecular formula
- C17H26O10
- Average molar mass
- 390.4 g/mol
- Monoisotopic mass
- 390.15259702
Overview
Loganin is an iridoid monoterpenoid with formula C17H26O10 that is isolated from several plant species and exhibits neuroprotective and anti-inflammatory properties. It has a role as an EC 3.1.1.7 (acetylcholinesterase) inhibitor, a neuroprotective agent, an anti-inflammatory agent, an EC 3.2.1.20 (alpha-glucosidase) inhibitor, an EC 3.4.23.46 (memapsin 2) inhibitor and a plant metabolite. It is a beta-D-glucoside, a methyl ester, a secondary alcohol, a cyclopentapyran, an iridoid monoterpenoid, an enoate ester and a monosaccharide derivative. It is functionally related to a loganetin.
Names & identifiers
- Preferred name
- (-)-Loganin
- IUPAC
- 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
- English name
- Loganin
- Molecular formula
- C17H26O10
- Molecular weight
- 390.38
Names & synonyms
Loganin18524-94-2Loganoside(-)-LoganinH7WJ16Q93CCHEBI:15771NSC-606403methyl (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-carboxylatemethyl (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-carboxylateRefChem:41672242-398-0cyclopenta(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)-
Show more names
LoganicCuchilosideMethyl 6-hydroxy-7-methyl-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[d]pyran-4-carboxylateMeliatinLoganinlLOGANINENSC 606403
7-Hydroxy-6-desoxyverbenalinMFCD00075645C17H26O10(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-carboxylatemethyl (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-carboxylateCyclopenta[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)tetrahydropyran-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylatelaganin
Properties
Computed structural properties
- XLogP
- -1.4
- Topological polar surface area
- 155 Ų
- Hydrogen bond donors
- 5
- Hydrogen bond acceptors
- 10
- Rotatable bonds
- 5
- Heavy atoms
- 27
- Formal charge
- 0
- Complexity
- 580
Experimental & physicochemical properties
LipidsLipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C10 isoprenoids (monoterpenes) [PR0102]
SpringerMaterials PropertiesChemical shift
Collision Cross Section
195.65 Ų [M+Na]+ [CCS Type: DT; Method: stepped-field]
194.4 Ų [M+Na]+
Physicochemical properties
- Melting point
- 222 °C · 222°C
- alpha
- 20 · D20 -82.1° (water)
- Boiling point
- 608.8 · 608.8±55.0 °C(Predicted)
- Density
- 1.5 · 1.50±0.1 g/cm3(Predicted)
- storage temp.
- Sealed in dry,Room Temperature
- Water Solubility
- Completely soluble in water
- solubility
- 15 mg/ml; · DMF: 15 mg/ml; DMSO: 10 mg/ml; PBS (pH 7.2): 10 mg/ml
- form
- Solid
- pka
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS ClassificationNot Classified
Hazard information
Hazard Classes and CategoriesNot Classified
Safety data
- F
- 3-10-23
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- ridadr
- 1544
- hs_code
- 29389090
- risk_code
- 22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 22-45-24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319
- Precautionary statements
- P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313
Chemistry & industry
Applications
UsesLoganin is an iridoid glycoside that exhibits protective effects against hepatic injury and other diabetic complications associated with abnormal metabolic states and inflammation caused by oxidative stress and advanced glycation endproduct formation.
Additional notes
DefinitionChEBI: An iridoid monoterpenoid isolated from the plant species of the genus Cornus.
Related reactions
1 records
Compound notes
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