(2S,3R,4S,5S,6R)-2-{[(2S)-2-[(1R,3R,5S,7R,10R,11R,14S,15R,16R)-5-{[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-16-hydroxy-3,6,6,10,11-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-6-methylhept-5-en-2-yl]oxy}-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxane-3,4,5-triol

• ChemBase ID: 4470
• Molecular Formular: C54H92O23
• Molecular Mass: 1109.29448
• Monoisotopic Mass: 1108.6029392
• SMILES: C(=CCC[C@@](O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O)O)O)(C)[C@@H]1[C@H]2[C@@H](C[C@@H]3C4[C@@H](C[C@@H](C([C@@H]4CC[C@]3([C@@]2(CC1)C)C)(C)C)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)C)O)(C)C
• Canonical SMILES: OC[C@H]1O[C@@H](O[C@H]2C[C@@H](C)C3[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]2O[C@H](CO[C@@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O)[C@H]([C@@H]([C@H]2O)O)O)(CCC=C(C)C)C)C)[C@@H]([C@H]([C@@H]1O)O)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O
• InChI: InChI=1S/C54H92O23/c1-22(2)10-9-13-54(8,77-49-45(69)41(65)38(62)31(74-49)21-70-47-43(67)39(63)35(59)28(18-55)71-47)25-12-15-53(7)34(25)27(58)17-26-33-23(3)16-32(51(4,5)24(33)11-14-52(26,53)6)75-50-46(42(66)37(61)30(20-57)73-50)76-48-44(68)40(64)36(60)29(19-56)72-48/h10,23-50,55-69H,9,11-21H2,1-8H3/t23-,24-,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+,50+,52-,53-,54+/m1/s1
• InChIKey: JRZQHNRYHFRTFZ-MHMDWUMYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R,4S,5S,6R)-2-{[(2S)-2-[(1R,3R,5S,7R,10R,11R,14S,15R,16R)-5-{[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-16-hydroxy-3,6,6,10,11-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-6-methylhept-5-en-2-yl]oxy}-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxane-3,4,5-triol
• IUPAC Traditional name: (2S,3R,4S,5S,6R)-2-{[(2S)-2-[(1R,3R,5S,7R,10R,11R,14S,15R,16R)-5-{[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-16-hydroxy-3,6,6,10,11-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-6-methylhept-5-en-2-yl]oxy}-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxane-3,4,5-triol
• Synonyms: Arasaponin E1; GRb 1; Gynosaponin c; Gypenoside III; Panax saponin e; Pseudoginsenoside d; Sanchinoside E1; ginsenoside Rb1

Database IDs

• CAS Number: 41753-43-9
• PubChem SID: 99443285; 160967902
• PubChem CID: 46937026

CALCULATED PROPERTIES

JChem

• Acid pKa: 11.751606
• H Acceptors: 23
• H Donor: 15
• LogD (pH = 5.5): -1.5644331
• LogD (pH = 7.4): -1.564452
• Log P: -1.5644329
• Molar Refractivity: 266.9626 cm^3
• Polarizability: 109.40082 Å^3
• Polar Surface Area: 377.29 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -0.34
• LOG S: -2.97
• Solubility (Water): 1.18e+00 g/l

DETAILS

DrugBank - DB06749

• Drug Groups: nutraceutical
• Description: Ginsenosides are a class of steroid glycosides, and triterpene saponins, found exclusively in the plant genus Panax (ginseng). Ginsenosides have been the target of research, as they are viewed as the active compounds behind the claims of ginseng's efficacy. Because ginsenosides appear to affect multiple pathways, their effects are complex and difficult to isolate. Rb1 appears to be most abundant in Panax quinquefolius (American Ginseng). Rb1 seems to affect the reproductive system in animal testicles. Recent research shows that Rb1 affects rat embryo development and has teratogenic effects, causing birth defects. Another study shows that Rb1 may increase testosterone production in male rats indirectly through the stimulation of the luteinizing hormone. Traditional Chinese medicine asserts that Panax quinquefolius promotes yin in the body. It also inhibits chemoinvasion and angiogenesis.