Structure Database (LMSD)
Common Name
Protopanaxadiol
Systematic Name
24-Dammarene-3β,12β-20S-triol
Synonyms
3D model of Protopanaxadiol
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
Level 4 Class
Biological Context
(20)R-Protopanaxadiol is a sapogenin that has been found in P. ginseng and has anticancer and antibacterial activities.1,2,3 It has a cytotoxic concentration (CC50) value of 6.1 µM in MT-4 human T cell leukemia cells and inhibits the growth of several additional cancer cell lines, including A549 human lung carcinoma, SKOV3 human ovarian adenocarcinoma, SK-Mel-2 human melanoma, P388 and L1210 murine leukemia, and K562 human chronic leukemia cells (ED50s = 11-26 µM).1,2 (20)R-protopanaxadiol also inhibits the growth of H. pylori in vitro (MICs = 50-100 µg/ml).3
This information has been provided by Cayman Chemical
References
1. Bae, E.A., Han, M.J., Choo, M.K., et al. Metabolism of 20(S)- and 20(R)-ginsenoside Rg3 by human intestinal bacteria and its relation to in vitro biological activities. Biol. Pharm. Bull. 25(1), 58-63 (2002).
2. Hasegawa, H., Matsumiya, S., Uchiyama, M., et al. Inhibitory effect of some triterpenoid saponins on glucose transport in tumor cells and its application to in vitro cytotoxic and antiviral activities. Planta Med. 60(3), 240-243 (1994).
3. Nam-In, B., Kim, D.S., Lee, Y.H., et al. Cytotoxicities of ginseng saponins and their degradation products against some cancer cell lines. Arch. Pharm. Res. 18(3), 164-168 (1995).
References
String Representations
InChiKey (Click to copy)
PYXFVCFISTUSOO-VUFVRDRTSA-N
InChi (Click to copy)
InChI=1S/C30H52O3/c1-19(2)10-9-14-30(8,33)20-11-16-29(7)25(20)21(31)18-23-27(5)15-13-24(32)26(3,4)22(27)12-17-28(23,29)6/h10,20-25,31-33H,9,11-18H2,1-8H3/t20-,21+,22-,23+,24-,25-,27-,28+,29+,30+/m0/s1
SMILES (Click to copy)
C1C[C@]2(C)[C@@]3([H])C[C@@H](O)[C@]4([H])[C@@]([H])([C@@](O)(C)CC/C=C(\C)/C)CC[C@@]4(C)[C@]3(C)CC[C@@]2([H])C(C)(C)[C@H]1O
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
33
Rings
4
Aromatic Rings
0
Rotatable Bonds
4
Van der Waals Molecular Volume
501.85
Topological Polar Surface Area
60.69
Hydrogen Bond Donors
3
Hydrogen Bond Acceptors
3
logP
7.36
Molar Refractivity
137.22
Admin
Created at
-
Updated at
11th Mar 2025