[(2R,3R,4S,5R,6R)-3-hydroxy-6-[[(3S,5S,8R,9R,10R,13R,14R,17S)-17-[(3S,5S)-3-hydroxy-5-(2-methylprop-1-enyl)-2-oxooxolan-3-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]-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]methyl acetate

Details

• Internal ID: 31c45b80-e904-41ce-9872-223d048dc69a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: [(2R,3R,4S,5R,6R)-3-hydroxy-6-[[(3S,5S,8R,9R,10R,13R,14R,17S)-17-[(3S,5S)-3-hydroxy-5-(2-methylprop-1-enyl)-2-oxooxolan-3-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]-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]methyl acetate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(C(OC2OC3CCC4(C5CCC6C(CCC6(C5(CCC4C3(C)C)C)C)C7(CC(OC7=O)C=C(C)C)O)C)COC(=O)C)O)OC8C(C(C(CO8)O)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]3CC[C@@]4([C@H]5CC[C@@H]6[C@H](CC[C@]6([C@@]5(CC[C@@H]4C3(C)C)C)C)[C@]7(C[C@H](OC7=O)C=C(C)C)O)C)COC(=O)C)O)O[C@H]8[C@@H]([C@H]([C@@H](CO8)O)O)O)O)O)O
• InChI: InChI=1S/C49H78O18/c1-22(2)18-25-19-49(59,44(58)63-25)27-12-16-47(8)26(27)10-11-31-46(7)15-14-32(45(5,6)30(46)13-17-48(31,47)9)65-43-40(67-42-38(57)36(55)33(52)23(3)62-42)39(35(54)29(64-43)21-60-24(4)50)66-41-37(56)34(53)28(51)20-61-41/h18,23,25-43,51-57,59H,10-17,19-21H2,1-9H3/t23-,25+,26+,27-,28+,29+,30+,31+,32-,33-,34-,35+,36+,37+,38+,39-,40+,41-,42-,43-,46-,47+,48+,49-/m0/s1
• InChI Key: AXBJYHWXSQPRFA-WUTAAGMLSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₉H₇₈O₁₈
• Molecular Weight: 955.10 g/mol
• Exact Mass: 954.51881563 g/mol
• Topological Polar Surface Area (TPSA): 270.00 Ų
• XlogP: 3.20
• Atomic LogP (AlogP): 1.76
• H-Bond Acceptor: 18
• H-Bond Donor: 8
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8719	87.19%
Caco-2	-	0.8824	88.24%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.8672	86.72%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8215	82.15%
OATP1B3 inhibitior	+	0.9240	92.40%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.8643	86.43%
P-glycoprotein inhibitior	+	0.7571	75.71%
P-glycoprotein substrate	+	0.5956	59.56%
CYP3A4 substrate	+	0.7537	75.37%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8976	89.76%
CYP3A4 inhibition	-	0.8789	87.89%
CYP2C9 inhibition	-	0.8273	82.73%
CYP2C19 inhibition	-	0.9032	90.32%
CYP2D6 inhibition	-	0.9392	93.92%
CYP1A2 inhibition	-	0.9287	92.87%
CYP2C8 inhibition	+	0.7043	70.43%
CYP inhibitory promiscuity	-	0.9311	93.11%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5530	55.30%
Eye corrosion	-	0.9894	98.94%
Eye irritation	-	0.9045	90.45%
Skin irritation	-	0.5494	54.94%
Skin corrosion	-	0.9384	93.84%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7035	70.35%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	-	0.7375	73.75%
skin sensitisation	-	0.9012	90.12%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	-	0.9392	93.92%
Acute Oral Toxicity (c)	I	0.8216	82.16%
Estrogen receptor binding	+	0.8108	81.08%
Androgen receptor binding	+	0.7492	74.92%
Thyroid receptor binding	-	0.5486	54.86%
Glucocorticoid receptor binding	+	0.7840	78.40%
Aromatase binding	+	0.6723	67.23%
PPAR gamma	+	0.7942	79.42%
Honey bee toxicity	-	0.5889	58.89%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.6600	66.00%
Fish aquatic toxicity	+	0.9846	98.46%

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	95.57%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.24%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.78%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.99%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.55%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.54%	86.33%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	91.45%	96.77%
CHEMBL218	P21554	Cannabinoid CB1 receptor	91.03%	96.61%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.44%	100.00%
CHEMBL1937	Q92769	Histone deacetylase 2	89.08%	94.75%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.35%	95.56%
CHEMBL2581	P07339	Cathepsin D	87.44%	98.95%
CHEMBL3714130	P46095	G-protein coupled receptor 6	87.23%	97.36%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	86.28%	93.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.05%	97.09%
CHEMBL5255	O00206	Toll-like receptor 4	85.85%	92.50%
CHEMBL226	P30542	Adenosine A1 receptor	85.77%	95.93%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.92%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.13%	94.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.49%	94.33%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	81.46%	95.71%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.44%	95.89%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	81.02%	100.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.82%	97.14%
CHEMBL340	P08684	Cytochrome P450 3A4	80.29%	91.19%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	80.13%	82.69%

Plants that contains it

• Gynostemma pentaphyllum

Cross-Links

• PubChem: 162969728
• LOTUS: LTS0149548
• wikiData: Q104920414