(3R,5R)-3-hydroxy-3-[(3S,5S,8R,9R,10R,13R,14R,17S)-3-[(2R,3R,4S,5R,6R)-5-hydroxy-6-(hydroxymethyl)-3-[(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]oxy-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-5-(2-methylprop-1-enyl)oxolan-2-one

Details

• Internal ID: a6ab3bd6-6a9c-49e3-be00-5ab0c51bbb18
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: (3R,5R)-3-hydroxy-3-[(3S,5S,8R,9R,10R,13R,14R,17S)-3-[(2R,3R,4S,5R,6R)-5-hydroxy-6-(hydroxymethyl)-3-[(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]oxy-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-5-(2-methylprop-1-enyl)oxolan-2-one
• 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)CO)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)CO)O)O[C@H]8[C@@H]([C@H]([C@@H](CO8)O)O)O)O)O)O
• InChI: InChI=1S/C47H76O17/c1-21(2)17-23-18-47(57,42(56)60-23)25-11-15-45(7)24(25)9-10-29-44(6)14-13-30(43(4,5)28(44)12-16-46(29,45)8)62-41-38(64-40-36(55)34(53)31(50)22(3)59-40)37(33(52)27(19-48)61-41)63-39-35(54)32(51)26(49)20-58-39/h17,22-41,48-55,57H,9-16,18-20H2,1-8H3/t22-,23-,24+,25-,26+,27+,28+,29+,30-,31-,32-,33+,34+,35+,36+,37-,38+,39-,40-,41-,44-,45+,46+,47+/m0/s1
• InChI Key: FYSVMXWLJSUANI-KMVQHFQESA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₇H₇₆O₁₇
• Molecular Weight: 913.10 g/mol
• Exact Mass: 912.50825095 g/mol
• Topological Polar Surface Area (TPSA): 264.00 Ų
• XlogP: 3.20
• Atomic LogP (AlogP): 1.18
• H-Bond Acceptor: 17
• H-Bond Donor: 9
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8592	85.92%
Caco-2	-	0.8871	88.71%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.8477	84.77%
OATP2B1 inhibitior	-	0.8790	87.90%
OATP1B1 inhibitior	+	0.8213	82.13%
OATP1B3 inhibitior	+	0.8897	88.97%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.7781	77.81%
P-glycoprotein inhibitior	+	0.7622	76.22%
P-glycoprotein substrate	+	0.5402	54.02%
CYP3A4 substrate	+	0.7498	74.98%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8723	87.23%
CYP3A4 inhibition	-	0.8944	89.44%
CYP2C9 inhibition	-	0.8559	85.59%
CYP2C19 inhibition	-	0.9065	90.65%
CYP2D6 inhibition	-	0.9285	92.85%
CYP1A2 inhibition	-	0.9109	91.09%
CYP2C8 inhibition	+	0.6568	65.68%
CYP inhibitory promiscuity	-	0.9128	91.28%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5806	58.06%
Eye corrosion	-	0.9898	98.98%
Eye irritation	-	0.9066	90.66%
Skin irritation	-	0.5693	56.93%
Skin corrosion	-	0.9422	94.22%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7693	76.93%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	-	0.7625	76.25%
skin sensitisation	-	0.9035	90.35%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	-	0.6000	60.00%
Nephrotoxicity	-	0.9053	90.53%
Acute Oral Toxicity (c)	I	0.7858	78.58%
Estrogen receptor binding	+	0.8067	80.67%
Androgen receptor binding	+	0.7480	74.80%
Thyroid receptor binding	-	0.5704	57.04%
Glucocorticoid receptor binding	+	0.7207	72.07%
Aromatase binding	+	0.6618	66.18%
PPAR gamma	+	0.7806	78.06%
Honey bee toxicity	-	0.5578	55.78%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.6400	64.00%
Fish aquatic toxicity	+	0.9609	96.09%

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	96.13%	91.11%
CHEMBL1937	Q92769	Histone deacetylase 2	93.29%	94.75%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.89%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	91.28%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.08%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.54%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.29%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.08%	89.00%
CHEMBL218	P21554	Cannabinoid CB1 receptor	89.70%	96.61%
CHEMBL2581	P07339	Cathepsin D	89.39%	98.95%
CHEMBL3714130	P46095	G-protein coupled receptor 6	88.00%	97.36%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.84%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.62%	95.89%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.78%	97.25%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	84.84%	96.77%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.53%	94.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.32%	97.14%
CHEMBL226	P30542	Adenosine A1 receptor	83.38%	95.93%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	82.85%	93.00%
CHEMBL5103	Q969S8	Histone deacetylase 10	82.32%	90.08%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	82.24%	92.88%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.23%	92.94%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	82.20%	100.00%
CHEMBL4105786	P41182	B-cell lymphoma 6 protein	81.87%	92.86%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	81.87%	91.24%
CHEMBL325	Q13547	Histone deacetylase 1	81.73%	95.92%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.22%	95.89%

Plants that contains it

• Gynostemma pentaphyllum

Cross-Links

• PubChem: 162934804
• LOTUS: LTS0028316
• wikiData: Q105004695