Methyl-[1S-(1α,4aα,6α,7α,7aα)]-1-(β-D-glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-6-hydroxy-7-methylcyclopenta[c]pyran-4-carboxylat
(-)-Loganin
Grundinformationen
- 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- Summenformel
- C17H26O10
- Durchschnittliche Molmasse
- 390,4 g/mol
- Monoisotopische Masse
- 390,15259702
Überblick
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.
Namen und Bezeichner
- Bevorzugter 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
- Lokaler Name
- Methyl-[1S-(1α,4aα,6α,7α,7aα)]-1-(β-D-glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-6-hydroxy-7-methylcyclopenta[c]pyran-4-carboxylat
- Englischer Name
- Loganin
- Summenformel
- C17H26O10
- Molmasse
- 390.38
Namen und Synonyme
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)-
Weitere Namen anzeigen
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
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- -1,4
- Polarare Oberfläche (TPSA)
- 155 Ų
- H-Brücken-Donoren
- 5
- H-Brücken-Akzeptoren
- 10
- Frei drehbare Bindungen
- 5
- Schwere Atome
- 27
- Formalladung
- 0
- Komplexität
- 580
Experimentelle und physikochemische Eigenschaften
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]+
Physikochemische Eigenschaften
- Schmelzpunkt
- 222 °C · 222°C
- Siedepunkt
- 608.8 · 608.8±55.0 °C(Predicted)
- Dichte
- 1.5 · 1.50±0.1 g/cm3(Predicted)
- storage temp.
- Sealed in dry,Room Temperature
- Wasserlöslichkeit
- Completely soluble in water
- Löslichkeit
- 15 mg/ml; · DMF: 15 mg/ml; DMSO: 10 mg/ml; PBS (pH 7.2): 10 mg/ml
- Aggregatzustand
- Solid
- pka
- 12.8 · 12.80±0.70(Predicted)
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS ClassificationNot Classified
Gefahrenhinweise
Hazard Classes and CategoriesNot Classified
Sicherheitsdaten
- F
- 3-10-23
- wgk
- 3
- ridadr
- 1544
- hs_code
- 29389090
- risk_code
- 22
- safety_code
- 22-45-24/25
- Speicherklasse
- 11 - Combustible Solids
Chemie und Industrie
Anwendungen
VerwendenLoganin 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.
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