[(2R,3S,4S,5R,6R)-6-[[(3S,5R,6S,8R,9R,10R,12R,13R,14R,17S)-3,12-dihydroxy-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-6-yl]oxy]-3,4,5-trihydroxyoxan-2-yl]methyl acetate

Details

• Internal ID: 1a53a32e-ea2a-49e4-84f2-0b203b7525dc
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: [(2R,3S,4S,5R,6R)-6-[[(3S,5R,6S,8R,9R,10R,12R,13R,14R,17S)-3,12-dihydroxy-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-6-yl]oxy]-3,4,5-trihydroxyoxan-2-yl]methyl acetate
• SMILES (Canonical): CC(=CCCC(C)(C1CCC2(C1C(CC3C2(CC(C4C3(CCC(C4(C)C)O)C)OC5C(C(C(C(O5)COC(=O)C)O)O)O)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(C[C@@H]([C@@H]4[C@@]3(CC[C@@H](C4(C)C)O)C)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)COC(=O)C)O)O)O)C)O)C)O)C
• InChI: InChI=1S/C38H64O10/c1-20(2)11-10-14-38(9,45)22-12-16-36(7)28(22)23(40)17-26-35(6)15-13-27(41)34(4,5)32(35)24(18-37(26,36)8)47-33-31(44)30(43)29(42)25(48-33)19-46-21(3)39/h11,22-33,40-45H,10,12-19H2,1-9H3/t22-,23+,24-,25+,26+,27-,28-,29+,30-,31+,32-,33+,35+,36+,37+,38-/m0/s1
• InChI Key: SMHMKYWUENKQRV-VXJKQVLXSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₈H₆₄O₁₀
• Molecular Weight: 680.90 g/mol
• Exact Mass: 680.44994823 g/mol
• Topological Polar Surface Area (TPSA): 166.00 Ų
• XlogP: 4.30
• Atomic LogP (AlogP): 3.87
• H-Bond Acceptor: 10
• H-Bond Donor: 6
• Rotatable Bonds: 8

Synonyms

• CHEMBL3634636
• 20(S)-ginsenoside Rh1 6'-acetate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8958	89.58%
Caco-2	-	0.8555	85.55%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.8312	83.12%
OATP2B1 inhibitior	-	0.7238	72.38%
OATP1B1 inhibitior	+	0.8251	82.51%
OATP1B3 inhibitior	+	0.8651	86.51%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7318	73.18%
BSEP inhibitior	+	0.7531	75.31%
P-glycoprotein inhibitior	+	0.7447	74.47%
P-glycoprotein substrate	-	0.6950	69.50%
CYP3A4 substrate	+	0.7337	73.37%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8900	89.00%
CYP3A4 inhibition	-	0.9099	90.99%
CYP2C9 inhibition	-	0.7775	77.75%
CYP2C19 inhibition	-	0.8530	85.30%
CYP2D6 inhibition	-	0.9298	92.98%
CYP1A2 inhibition	-	0.8005	80.05%
CYP2C8 inhibition	+	0.6472	64.72%
CYP inhibitory promiscuity	-	0.9049	90.49%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7080	70.80%
Eye corrosion	-	0.9923	99.23%
Eye irritation	-	0.9133	91.33%
Skin irritation	+	0.5248	52.48%
Skin corrosion	-	0.9476	94.76%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7001	70.01%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	+	0.5984	59.84%
skin sensitisation	-	0.8833	88.33%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	-	0.7329	73.29%
Acute Oral Toxicity (c)	I	0.4485	44.85%
Estrogen receptor binding	+	0.6770	67.70%
Androgen receptor binding	+	0.7154	71.54%
Thyroid receptor binding	-	0.6012	60.12%
Glucocorticoid receptor binding	+	0.6781	67.81%
Aromatase binding	+	0.7050	70.50%
PPAR gamma	+	0.7076	70.76%
Honey bee toxicity	-	0.5990	59.90%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.6100	61.00%
Fish aquatic toxicity	+	0.9780	97.80%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.96%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.29%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.24%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.16%	96.09%
CHEMBL1914	P06276	Butyrylcholinesterase	92.73%	95.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.42%	94.45%
CHEMBL2179	P04062	Beta-glucocerebrosidase	90.79%	85.31%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.70%	86.33%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	88.64%	97.21%
CHEMBL226	P30542	Adenosine A1 receptor	88.28%	95.93%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.03%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.89%	100.00%
CHEMBL218	P21554	Cannabinoid CB1 receptor	87.78%	96.61%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	85.33%	96.77%
CHEMBL5255	O00206	Toll-like receptor 4	84.82%	92.50%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.29%	85.14%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.78%	100.00%
CHEMBL3401	O75469	Pregnane X receptor	83.42%	94.73%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	83.14%	94.33%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	82.88%	96.90%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	82.70%	82.50%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	82.50%	95.50%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.26%	96.95%
CHEMBL5028	O14672	ADAM10	82.19%	97.50%
CHEMBL2581	P07339	Cathepsin D	81.86%	98.95%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	81.44%	100.00%

Plants that contains it

• Panax ginseng

Cross-Links

• PubChem: 122196265
• LOTUS: LTS0086605
• wikiData: Q105255932