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编号: 157798
• 分子式: C17H26O10
• 平均质量: 390.38234
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 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传统名: loganin
• 别名: 马钱子苷; 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

登记号

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

理论计算性质

• Acid pKa: 12.20619
• 质子受体: 9
• 质子供体: 5
• LogD (pH = 5.5): -1.8371456
• LogD (pH = 7.4): -1.8371522
• Log P: -1.8371454
• 摩尔折射率: 87.4744 cm^3
• 极化性: 35.872616 Å^3
• 极化表面积: 155.14 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: true

分子性质

理化性质

• 外观: Powder

安全信息

• 德国WGK号: 3
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

产品相关信息

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

详细说明

Sigma Aldrich - 36483

Other Notes
从各种植物中分离的环烯醚萜苷。用作细胞色素 P4501 的底物
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

参考文献

• 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)