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

• ChemBase ID: 157798
• Molecular Formular: C17H26O10
• Molecular Mass: 390.38234
• Monoisotopic Mass: 390.15259703
• SMILES: C[C@H]1[C@H](C[C@H]2[C@@H]1[C@@H](OC=C2C(=O)OC)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)O
• Canonical SMILES: OC[C@H]1O[C@@H](O[C@@H]2OC=C([C@@H]3[C@H]2[C@@H](C)[C@H](C3)O)C(=O)OC)[C@@H]([C@H]([C@@H]1O)O)O
• 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
• InChIKey: AMBQHHVBBHTQBF-UOUCRYGSSA-N

NAMES AND DATABASE IDS

Names

• 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}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-4-carboxylate
• IUPAC Traditional name: loganin
• Synonyms: Loganin; (1S,4aS,6S,7R,7aS)-1-(β-D-Glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-6-hydroxy-7-methylcyclopenta[c]pyran-4-carboxylic Acid Methyl Ester; (-)-Loganin; Loganoside; (1S)-1α-(β-D-Glucopyranosyloxy)-1,4aα,5,6,7,7aα-hexahydro-6α-hydroxy-7α-methylcyclopenta[c]pyran-4-carboxylic Acid Methyl Ester; 7-Hydroxy-6-desoxyverbenalin; NSC 606403; Loganin; 马钱子苷

Database IDs

• CAS Number: 18524-94-2
• EC Number: 242-398-0
• MDL Number: MFCD00075645
• Beilstein Number: 55724
• PubChem SID: 162251935; 24862459
• PubChem CID: 87691

CALCULATED PROPERTIES

• Acid pKa: 12.20619
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -1.8371456
• LogD (pH = 7.4): -1.8371522
• Log P: -1.8371454
• Molar Refractivity: 87.4744 cm^3
• Polarizability: 35.872616 Å^3
• Polar Surface Area: 155.14 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Powder

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥97.0% (HPLC); 95+%; 97%
• Grade: analytical standard
• Empirical Formula (Hill Notation): C17H26O10

DETAILS

Sigma Aldrich - 36483

Other Notes
Iridoid glycoside isolated from various plants. Substrate for cytochrome P4501
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 36483.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - L469405

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. A potential an

REFERENCES

• Yamabe, N. et al.: Eur. J. Pharmmacol., 648, 179 (2010)
• de Carman Recio, M. et al.: Planta Medica, 3, 232 (2010)
• Kwon, S. et al.: Eur. J. Pharmacol., 619, 44 (2010)