Ginsenoside Rg3

Details

• Internal ID: ede00223-1d30-4412-baa3-c449053f701a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: (2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-2-[[(3S,5R,8R,9R,10R,12R,13R,14R,17S)-12-hydroxy-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]phenanthren-3-yl]oxy]-6-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): CC(=CCCC(C)(C1CCC2(C1C(CC3C2(CCC4C3(CCC(C4(C)C)OC5C(C(C(C(O5)CO)O)O)OC6C(C(C(C(O6)CO)O)O)O)C)C)O)C)O)C
• SMILES (Isomeric): 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@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)C)C)O)C)O)C
• InChI: InChI=1S/C42H72O13/c1-21(2)10-9-14-42(8,51)22-11-16-41(7)29(22)23(45)18-27-39(5)15-13-28(38(3,4)26(39)12-17-40(27,41)6)54-37-35(33(49)31(47)25(20-44)53-37)55-36-34(50)32(48)30(46)24(19-43)52-36/h10,22-37,43-51H,9,11-20H2,1-8H3/t22-,23+,24+,25+,26-,27+,28-,29-,30+,31+,32-,33-,34+,35+,36-,37-,39-,40+,41+,42-/m0/s1
• InChI Key: RWXIFXNRCLMQCD-JBVRGBGGSA-N
• Popularity: 460 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₂H₇₂O₁₃
• Molecular Weight: 785.00 g/mol
• Exact Mass: 784.49729235 g/mol
• Topological Polar Surface Area (TPSA): 219.00 Ų
• XlogP: 4.00
• Atomic LogP (AlogP): 2.15
• H-Bond Acceptor: 13
• H-Bond Donor: 9
• Rotatable Bonds: 10

Synonyms

• 14197-60-5
• 20(S)-Ginsenoside Rg3
• (20S)-Propanaxadiol
• 20s-ginsenoside rg3
• 20S-propanaxadiol
• (20S)-ginsenoside Rg3
• S-Ginsenoside Rg3
• 20(S)-Ginsenoside-Rg3
• 20(S)-Propanaxidiol
• CHEMBL398412
• CHEBI:67991
• UNII-227D367Y57
• 227D367Y57
• (2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-2-[[(3S,5R,8R,9R,10R,12R,13R,14R,17S)-12-hydroxy-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]phenanthren-3-yl]oxy]-6-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• 11019-45-7
• ginsenoside 20-rg3
• ginsenoside rg3, (s)-
• ginsenoside rg3, (+)-
• 20(S)-Propanaxadiol;S-ginsenoside Rg3
• C42-H72-O13
• Dammar-24-ene-12-beta,20-diol, 3-beta-((2-O-beta-D-glucopyranosyl-beta-D-glucopyransoyl)oxy)-
• Rg3
• MFCD06410950
• (R)Ginsenoside-Rg3
• Ginsenoside Rg3,(S)
• D01BKS
• GTPL7658
• GINSENOSIDE RG3 [WHO-DD]
• RWXIFXNRCLMQCD-JBVRGBGGSA-N
• DTXSID101316982
• GLXC-19139
• HMS3886B14
• BDBM50317537
• Ginsenoside Rg3, analytical standard
• s9022
• Ginsenoside Rg3, >=98% (HPLC)
• AKOS037514674
• CCG-270472
• (3beta,12beta)-12,20-dihydroxydammar-24-en-3-yl 2-O-beta-D-glucopyranosyl-beta-D-glucopyranoside
• AS-56617
• C20778
• Q-100154
• Q27077807
• .BETA.-D-GLUCOPYRANOSIDE, (3.BETA.,12.BETA.)-12,20-DIHYDROXYDAMMAR-24-EN-3-YL 2-O-.BETA.-D-GLUCOPYRANOSYL-
• 3-O-.BETA.-D-GLUCOPYRANOSYL-(1->2)-.BETA.-D-GLUCOPYRANOSYLDAMMAR-24-ENE-3.BETA.,12.BETA.,20S-TRIOL
• dammar-24-ene-12beta,20-diol, 3-beta-((2-O-beta-D-glucopyranosyl-beta-D-glucopyransoyl)oxy)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6877	68.77%
Caco-2	-	0.8840	88.40%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.7251	72.51%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7934	79.34%
OATP1B3 inhibitior	+	0.8189	81.89%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	-	0.4911	49.11%
P-glycoprotein inhibitior	+	0.8063	80.63%
P-glycoprotein substrate	-	0.9036	90.36%
CYP3A4 substrate	+	0.7234	72.34%
CYP2C9 substrate	-	0.7890	78.90%
CYP2D6 substrate	-	0.8406	84.06%
CYP3A4 inhibition	-	0.9502	95.02%
CYP2C9 inhibition	-	0.8671	86.71%
CYP2C19 inhibition	-	0.9036	90.36%
CYP2D6 inhibition	-	0.9380	93.80%
CYP1A2 inhibition	-	0.9057	90.57%
CYP2C8 inhibition	+	0.6241	62.41%
CYP inhibitory promiscuity	-	0.9413	94.13%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6474	64.74%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.9095	90.95%
Skin irritation	-	0.5956	59.56%
Skin corrosion	-	0.9488	94.88%
Ames mutagenesis	-	0.7600	76.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8437	84.37%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	-	0.5436	54.36%
skin sensitisation	-	0.8991	89.91%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	-	0.7155	71.55%
Acute Oral Toxicity (c)	I	0.5677	56.77%
Estrogen receptor binding	+	0.7418	74.18%
Androgen receptor binding	+	0.7407	74.07%
Thyroid receptor binding	-	0.5905	59.05%
Glucocorticoid receptor binding	+	0.6369	63.69%
Aromatase binding	+	0.6823	68.23%
PPAR gamma	+	0.7336	73.36%
Honey bee toxicity	-	0.5274	52.74%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.9172	91.72%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.42%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.48%	97.25%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	94.40%	95.58%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.84%	97.09%
CHEMBL2996	Q05655	Protein kinase C delta	91.54%	97.79%
CHEMBL5608	Q16288	NT-3 growth factor receptor	91.15%	95.89%
CHEMBL241	Q14432	Phosphodiesterase 3A	90.23%	92.94%
CHEMBL226	P30542	Adenosine A1 receptor	89.68%	95.93%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.61%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.39%	86.33%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	88.22%	100.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.16%	100.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	87.15%	97.36%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	84.88%	95.50%
CHEMBL1977	P11473	Vitamin D receptor	84.66%	99.43%
CHEMBL1937	Q92769	Histone deacetylase 2	84.51%	94.75%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.95%	94.45%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.85%	97.14%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.71%	92.62%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	81.71%	100.00%
CHEMBL2581	P07339	Cathepsin D	81.56%	98.95%
CHEMBL237	P41145	Kappa opioid receptor	81.36%	98.10%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.85%	100.00%

Plants that contains it

• Achillea clypeolata
• Athanasia crithmifolia
• Berberis julianae
• Bridelia ferruginea
• Bystropogon origanifolius
• Cardamine heptaphylla
• Centella asiatica
• Cerbera odollam
• Cneorum pulverulentum
• Codonocarpus attenuatus
• Crateva magna
• Diospyros verrucosa
• Euonymus nanoides
• Jacobaea subalpina
• Nepeta multifida
• Panax ginseng
• Panax japonicus
• Panax notoginseng
• Panax quinquefolius
• Pleogyne australis
• Polygala amara
• Pyrola decorata
• Quercus serrata
• Rubus allegheniensis
• Salvia abrotanoides
• Stephania sutchuenensis
• Swertia japonica
• Tetraneuris acaulis
• Unonopsis glaucopetala
• Zieria smithii

Cross-Links

• PubChem: 9918693
• NPASS: NPC120123
• LOTUS: LTS0174795
• wikiData: Q27077807