20S-protopanaxadiol (aPPD) is a metabolite of ginsenosides that can inhibit Akt activity and causes apoptosis in a variety of tumor cells [1].

Physicochemical Properties

Molecular Formula	C30H52O3
Molecular Weight	460.73208
Exact Mass	460.391
CAS #	30636-90-9
PubChem CID	11213350
Appearance	White to off-white solid powder
Density	1.0±0.1 g/cm3
Boiling Point	559.5±40.0 °C at 760 mmHg
Melting Point	211 °C
Flash Point	226.1±21.9 °C
Vapour Pressure	0.0±3.5 mmHg at 25°C
Index of Refraction	1.529
LogP	7.59
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	4
Heavy Atom Count	33
Complexity	783
Defined Atom Stereocenter Count	10
SMILES	CC(=CCC[C@@](C)([C@H]1CC[C@@]2([C@@H]1[C@@H](C[C@H]3[C@]2(CC[C@@H]4[C@@]3(CC[C@@H](C4(C)C)O)C)C)O)C)O)C
InChi Key	PYXFVCFISTUSOO-HKUCOEKDSA-N
InChi Code	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
Chemical Name	(3S,5R,8R,9R,10R,12R,13R,14R,17S)-17-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,12-diol
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

Targets	(20S)-Protopanaxadiol targets raft-associated Akt signaling pathway[1]
ln Vitro	In N2a cell rafts, 20S-protopanaxadiol treatment increased flotillin-1 levels to 142.91±10.71% of control. Depending on the type of cell, 20S-protopanaxadiol may have different effects on the raft-resident protein flotillin-1 [1]. (20S)-Protopanaxadiol regulates raft-associated Akt phosphorylation in a cell-type-specific manner; it enhances Akt Ser473 phosphorylation in HeLa and MCF-7 cells, while inhibiting it in PC12 and Neuro-2a cells[1] (20S)-Protopanaxadiol modulates the association of Akt with lipid rafts; it increases Akt recruitment to lipid rafts in HeLa/MCF-7 cells and reduces this recruitment in PC12/Neuro-2a cells, thereby altering downstream signaling (e.g., GSK-3β phosphorylation)[1] (20S)-Protopanaxadiol does not affect total Akt protein levels, only the raft-localized fraction and its phosphorylation status[1]
Cell Assay	For lipid raft isolation and Akt association assay: Culture HeLa, MCF-7, PC12, and Neuro-2a cells in DMEM medium supplemented with fetal bovine serum; treat cells with (20S)-Protopanaxadiol (10 μM) for 24 hours; lyse cells with ice-cold lysis buffer containing detergent; separate lipid rafts via sucrose density gradient centrifugation; detect Akt and raft marker proteins (flotillin-1) in raft and non-raft fractions via Western blot[1] For Akt phosphorylation assay: Culture target cells in DMEM medium; treat cells with (20S)-Protopanaxadiol (5-20 μM) for 12-48 hours; lyse cells and extract total protein; perform Western blot to detect phosphorylated Akt (Ser473), total Akt, and downstream target GSK-3β (phosphorylated and total forms); quantify band intensities via densitometry[1] For cell viability assay: Culture cells in 96-well plates; treat with (20S)-Protopanaxadiol (1-50 μM) for 48 hours; add MTT reagent and incubate for 4 hours; dissolve formazan crystals with DMSO; measure absorbance at 570 nm to evaluate cell viability[1]
References	[1]. Cell-type-specific regulation of raft-associated Akt signaling. Cell Death Dis. 2011;2(4):e145. Published 2011 Apr 14.
Additional Infomation	(20S)-protopanaxadiol is a diastereomer of protopanaxadiol in which the 20-hydroxy substituent has been introduced at the pro-S position. (20S)-Protopanaxadiol has been reported in Gynostemma pentaphyllum, Panax ginseng, and Aralia elata with data available. (20S)-Protopanaxadiol is a major metabolite of ginsenosides, a class of active compounds isolated from Panax ginseng[1] The cell-type-specific regulation of raft-associated Akt signaling by (20S)-Protopanaxadiol is attributed to differences in lipid raft composition and downstream signaling networks between cell types[1] (20S)-Protopanaxadiol may exert cell-type-specific biological effects (e.g., proliferation promotion in cancer cells vs. neuroprotection in neuronal cells) via modulating raft-dependent Akt signaling[1]

Solubility Data

Solubility (In Vitro)

DMSO : ≥ 100 mg/mL (~217.05 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (5.43 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	2.1705 mL	10.8523 mL	21.7047 mL
	5 mM	0.4341 mL	2.1705 mL	4.3409 mL
	10 mM	0.2170 mL	1.0852 mL	2.1705 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.