(2S,4S,5S)-2-{[(2S)-2-[(1R,2R,5S,7R,10R,11R,14S,15R,16R)-5-{[(2R,4S,5S)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,4S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-16-hydroxy-2,6,6,10,11-pentamethyltetracyclo[8.7.0.02,7.011,15]heptadecan-14-yl]-6-methylhept-5-en-2-yl]oxy}-6-({[(2R,4S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxane-3,4,5-triol

• ChemBase ID: 169632
• Molecular Formular: C54H92O23
• Molecular Mass: 1109.29448
• Monoisotopic Mass: 1108.6029392
• SMILES: C1[C@@H](C([C@H]2[C@](C1)([C@@H]1[C@@](CC2)([C@]2([C@H]([C@@H](C1)O)[C@H](CC2)[C@@](O[C@@H]1OC([C@H]([C@@H](C1O)O)O)CO[C@@H]1OC([C@H]([C@@H](C1O)O)O)CO)(CCC=C(C)C)C)C)C)C)(C)C)O[C@@H]1OC([C@H]([C@@H](C1O[C@@H]1OC([C@H]([C@@H](C1O)O)O)CO)O)O)CO
• Canonical SMILES: OCC1O[C@@H](O[C@H]2CC[C@]3([C@H](C2(C)C)CC[C@@]2([C@@H]3C[C@@H](O)[C@H]3[C@@]2(C)CC[C@@H]3[C@@](O[C@@H]2OC(CO[C@@H]3OC(CO)[C@H]([C@@H](C3O)O)O)[C@H]([C@@H](C2O)O)O)(CCC=C(C)C)C)C)C)C([C@H]([C@@H]1O)O)O[C@@H]1OC(CO)[C@H]([C@@H](C1O)O)O
• InChI: InChI=1S/C54H92O23/c1-23(2)10-9-14-54(8,77-48-44(69)40(65)37(62)29(74-48)22-70-46-42(67)38(63)34(59)26(19-55)71-46)24-11-16-53(7)33(24)25(58)18-31-51(5)15-13-32(50(3,4)30(51)12-17-52(31,53)6)75-49-45(41(66)36(61)28(21-57)73-49)76-47-43(68)39(64)35(60)27(20-56)72-47/h10,24-49,55-69H,9,11-22H2,1-8H3/t24-,25+,26?,27?,28?,29?,30-,31+,32-,33-,34+,35+,36+,37+,38-,39-,40-,41-,42?,43?,44?,45?,46+,47-,48-,49-,51-,52+,53+,54-/m0/s1
• InChIKey: GZYPWOGIYAIIPV-XLVKXKOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,4S,5S)-2-{[(2S)-2-[(1R,2R,5S,7R,10R,11R,14S,15R,16R)-5-{[(2R,4S,5S)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,4S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-16-hydroxy-2,6,6,10,11-pentamethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]-6-methylhept-5-en-2-yl]oxy}-6-({[(2R,4S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxane-3,4,5-triol
• IUPAC Traditional name: (2S,4S,5S)-2-{[(2S)-2-[(1R,2R,5S,7R,10R,11R,14S,15R,16R)-5-{[(2R,4S,5S)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,4S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-16-hydroxy-2,6,6,10,11-pentamethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]-6-methylhept-5-en-2-yl]oxy}-6-({[(2R,4S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxane-3,4,5-triol
• Synonyms: (3β,12β)-20-[(6-O-β-D-Glucopyranosyl-β-D-glucopyranosyl)oxy]-12-hydroxydammar-24-en-3-yl 2-O-β-D-glucopyranosyl-β-D-glucopyranoside; Arasaponin E1; Gynosaponin C; Gypenoside III; NSC 310103; Notoginsenoside Rb1; Panaxoside Rb1; Sanchinoside E1; Sanchinoside Rb1; Ginsenoside Rb1

Database IDs

• CAS Number: 41753-43-9
• PubChem SID: 162263764
• PubChem CID: 71317070

CALCULATED PROPERTIES

• Acid pKa: 11.751606
• H Acceptors: 23
• H Donor: 15
• LogD (pH = 5.5): -1.5514051
• LogD (pH = 7.4): -1.551424
• Log P: -1.5514048
• Molar Refractivity: 266.8891 cm^3
• Polarizability: 109.40082 Å^3
• Polar Surface Area: 377.29 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - G387600

A major bioactive component of panax ginseng that promotes neurotransmitter release by modulating phosphorylation of synapsins through a cAMP-dependent protein kinase pathway. It has been reported to display immunostimulatory and anticancer effects.

REFERENCES

• Xue, J. et al.: Brain Res., 1106, 91 (2006)
• Kim, B. et al.: J. Ginseng Res., 33, 330 (2006)
• Li, B. et al.: Cancer Lett., 289, 62 (2006)