(2S,3R,4R,5R,6S)-2-[(2R,3R,4S,5S,6R)-2-[[(3S,5R,6S,8R,9R,10R,12R,13R,14R,17S)-3,12-dihydroxy-4,4,8,10,14-pentamethyl-17-[(2E)-6-methylhepta-2,5-dien-2-yl]-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-6-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-6-methyloxane-3,4,5-triol

Details

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Internal ID 94991fe0-f87a-47c0-9842-0bb86057c87a
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
IUPAC Name (2S,3R,4R,5R,6S)-2-[(2R,3R,4S,5S,6R)-2-[[(3S,5R,6S,8R,9R,10R,12R,13R,14R,17S)-3,12-dihydroxy-4,4,8,10,14-pentamethyl-17-[(2E)-6-methylhepta-2,5-dien-2-yl]-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-6-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-6-methyloxane-3,4,5-triol
SMILES (Canonical) CC1C(C(C(C(O1)OC2C(C(C(OC2OC3CC4(C(CC(C5C4(CCC5C(=CCC=C(C)C)C)C)O)C6(C3C(C(CC6)O)(C)C)C)C)CO)O)O)O)O)O
SMILES (Isomeric) C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2O[C@H]3C[C@@]4([C@H](C[C@H]([C@H]5[C@]4(CC[C@@H]5/C(=C/CC=C(C)C)/C)C)O)[C@@]6([C@@H]3C([C@H](CC6)O)(C)C)C)C)CO)O)O)O)O)O
InChI InChI=1S/C42H70O12/c1-20(2)11-10-12-21(3)23-13-16-41(8)29(23)24(44)17-27-40(7)15-14-28(45)39(5,6)36(40)25(18-42(27,41)9)52-38-35(33(49)31(47)26(19-43)53-38)54-37-34(50)32(48)30(46)22(4)51-37/h11-12,22-38,43-50H,10,13-19H2,1-9H3/b21-12+/t22-,23+,24+,25-,26+,27+,28-,29-,30-,31+,32+,33-,34+,35+,36-,37-,38+,40+,41+,42+/m0/s1
InChI Key QOMBXPYXWGTFNR-PWAOTOFHSA-N
Popularity 4 references in papers

Physical and Chemical Properties

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Molecular Formula C42H70O12
Molecular Weight 767.00 g/mol
Exact Mass 766.48672766 g/mol
Topological Polar Surface Area (TPSA) 199.00 Ų
XlogP 4.50
Atomic LogP (AlogP) 2.95
H-Bond Acceptor 12
H-Bond Donor 8
Rotatable Bonds 8

Synonyms

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Ginsenoside RG4
181225-33-2
(E)-GINSENOSIDE F4
CHEMBL3634728
126223-28-7
HY-N2503
MS-31384
CS-0022774

2D Structure

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2D Structure of (2S,3R,4R,5R,6S)-2-[(2R,3R,4S,5S,6R)-2-[[(3S,5R,6S,8R,9R,10R,12R,13R,14R,17S)-3,12-dihydroxy-4,4,8,10,14-pentamethyl-17-[(2E)-6-methylhepta-2,5-dien-2-yl]-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-6-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-6-methyloxane-3,4,5-triol

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.7734 77.34%
Caco-2 - 0.8712 87.12%
Blood Brain Barrier - 0.5750 57.50%
Human oral bioavailability - 0.8429 84.29%
Subcellular localzation Mitochondria 0.7358 73.58%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8518 85.18%
OATP1B3 inhibitior + 0.8280 82.80%
MATE1 inhibitior - 0.9612 96.12%
OCT2 inhibitior - 0.6250 62.50%
BSEP inhibitior + 0.5727 57.27%
P-glycoprotein inhibitior + 0.7583 75.83%
P-glycoprotein substrate - 0.5982 59.82%
CYP3A4 substrate + 0.7310 73.10%
CYP2C9 substrate - 0.8025 80.25%
CYP2D6 substrate - 0.8264 82.64%
CYP3A4 inhibition - 0.9174 91.74%
CYP2C9 inhibition - 0.8394 83.94%
CYP2C19 inhibition - 0.9148 91.48%
CYP2D6 inhibition - 0.9377 93.77%
CYP1A2 inhibition - 0.8896 88.96%
CYP2C8 inhibition + 0.6369 63.69%
CYP inhibitory promiscuity - 0.9159 91.59%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.6603 66.03%
Eye corrosion - 0.9911 99.11%
Eye irritation - 0.9138 91.38%
Skin irritation - 0.5364 53.64%
Skin corrosion - 0.9481 94.81%
Ames mutagenesis - 0.8154 81.54%
Human Ether-a-go-go-Related Gene inhibition + 0.8591 85.91%
Micronuclear - 0.8700 87.00%
Hepatotoxicity - 0.7302 73.02%
skin sensitisation - 0.9023 90.23%
Respiratory toxicity + 0.6444 64.44%
Reproductive toxicity + 0.8889 88.89%
Mitochondrial toxicity - 0.5250 52.50%
Nephrotoxicity - 0.8936 89.36%
Acute Oral Toxicity (c) I 0.5477 54.77%
Estrogen receptor binding + 0.7222 72.22%
Androgen receptor binding + 0.7359 73.59%
Thyroid receptor binding - 0.5569 55.69%
Glucocorticoid receptor binding + 0.6349 63.49%
Aromatase binding + 0.6849 68.49%
PPAR gamma + 0.7244 72.44%
Honey bee toxicity - 0.5831 58.31%
Biodegradation - 0.7250 72.50%
Crustacea aquatic toxicity + 0.5300 53.00%
Fish aquatic toxicity + 0.9339 93.39%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
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 98.82% 91.11%
CHEMBL3137262 O60341 LSD1/CoREST complex 93.65% 97.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 93.02% 86.33%
CHEMBL6136 O60341 Lysine-specific histone demethylase 1 92.18% 95.58%
CHEMBL1994 P08235 Mineralocorticoid receptor 90.70% 100.00%
CHEMBL226 P30542 Adenosine A1 receptor 90.67% 95.93%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 89.87% 96.09%
CHEMBL218 P21554 Cannabinoid CB1 receptor 89.80% 96.61%
CHEMBL4187 Q99250 Sodium channel protein type II alpha subunit 89.40% 95.50%
CHEMBL5608 Q16288 NT-3 growth factor receptor 88.79% 95.89%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 88.20% 94.45%
CHEMBL241 Q14432 Phosphodiesterase 3A 87.42% 92.94%
CHEMBL3714130 P46095 G-protein coupled receptor 6 87.18% 97.36%
CHEMBL3476 O15111 Inhibitor of nuclear factor kappa B kinase alpha subunit 84.39% 95.83%
CHEMBL1937 Q92769 Histone deacetylase 2 84.16% 94.75%
CHEMBL3589 P55263 Adenosine kinase 81.84% 98.05%
CHEMBL2274 Q9H228 Sphingosine 1-phosphate receptor Edg-8 80.62% 100.00%
CHEMBL3430907 Q96GD4 Aurora kinase B/Inner centromere protein 80.22% 97.50%
CHEMBL1806 P11388 DNA topoisomerase II alpha 80.08% 89.00%
CHEMBL1977 P11473 Vitamin D receptor 80.06% 99.43%
CHEMBL4227 P25090 Lipoxin A4 receptor 80.01% 100.00%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.
Panax ginseng

Cross-Links

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PubChem 102179726
NPASS NPC288694
LOTUS LTS0076661
wikiData Q105269667