3beta-[2-O-(alpha-L-Rhamnopyranosyl)-4-O-[4-O-(beta-D-glucopyranosyl)-beta-D-glucopyranosyl]-alpha-L-arabinopyranosyloxy]-23-hydroxylupan-20(29)-en-28-oic acid 6-O-[4-O-(alpha-L-rhamnopyranosyl)-beta-D-glucopyranosyl]-beta-D-glucopyranosyl ester

Details

• Internal ID: 252ae16e-5330-4c6e-8eb5-59341ad3d782
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: [(2S,3R,4S,5S,6R)-6-[[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl] (1R,3aS,5aR,5bR,7aR,8R,9S,11aR,11bR,13aR,13bR)-9-[(2S,3R,4S,5S)-5-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-4-hydroxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-8-(hydroxymethyl)-5a,5b,8,11a-tetramethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(OC(C(C2O)O)OCC3C(C(C(C(O3)OC(=O)C45CCC(C4C6CCC7C8(CCC(C(C8CCC7(C6(CC5)C)C)(C)CO)OC9C(C(C(CO9)OC1C(C(C(C(O1)CO)OC1C(C(C(C(O1)CO)O)O)O)O)O)O)OC1C(C(C(C(O1)C)O)O)O)C)C(=C)C)O)O)O)CO)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H](O[C@H]([C@@H]([C@H]2O)O)OC[C@@H]3[C@H]([C@@H]([C@H]([C@@H](O3)OC(=O)[C@]45CC[C@H]([C@@H]4[C@H]6CC[C@@H]7[C@]8(CC[C@@H]([C@@]([C@@H]8CC[C@]7([C@@]6(CC5)C)C)(C)CO)O[C@H]9[C@@H]([C@H]([C@H](CO9)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)O)O)O)O[C@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)C)O)O)O)C)C(=C)C)O)O)O)CO)O)O)O
• InChI: InChI=1S/C71H116O36/c1-25(2)28-11-16-71(66(93)107-64-53(90)47(84)42(79)33(101-64)22-94-59-54(91)48(85)56(31(20-73)99-59)104-60-50(87)44(81)39(76)26(3)96-60)18-17-69(7)29(38(28)71)9-10-36-67(5)14-13-37(68(6,24-75)35(67)12-15-70(36,69)8)103-65-58(106-61-51(88)45(82)40(77)27(4)97-61)43(80)34(23-95-65)102-62-55(92)49(86)57(32(21-74)100-62)105-63-52(89)46(83)41(78)30(19-72)98-63/h26-65,72-92H,1,9-24H2,2-8H3/t26-,27-,28-,29+,30+,31+,32+,33+,34-,35+,36+,37-,38+,39-,40-,41+,42+,43-,44+,45+,46-,47-,48+,49+,50+,51+,52+,53+,54+,55+,56+,57+,58+,59+,60-,61-,62-,63-,64-,65-,67-,68-,69+,70+,71-/m0/s1
• InChI Key: NWWQLXKEDLLKBI-JXJHENQESA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₇₁H₁₁₆O₃₆
• Molecular Weight: 1545.70 g/mol
• Exact Mass: 1544.7246300 g/mol
• Topological Polar Surface Area (TPSA): 571.00 Ų
• XlogP: -5.00
• Atomic LogP (AlogP): -7.04
• H-Bond Acceptor: 36
• H-Bond Donor: 21
• Rotatable Bonds: 20

Synonyms

• DTXSID201098020
• 366814-44-0
• 3beta-[2-O-(alpha-L-Rhamnopyranosyl)-4-O-[4-O-(beta-D-glucopyranosyl)-beta-D-glucopyranosyl]-alpha-L-arabinopyranosyloxy]-23-hydroxylupan-20(29)-en-28-oic acid 6-O-[4-O-(alpha-L-rhamnopyranosyl)-beta-D-glucopyranosyl]-beta-D-glucopyranosyl ester
• O-6-Deoxy-alpha-L-mannopyranosyl-(1-->4)-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl (3beta,4alpha)-3-[(O-6-deoxy-alpha-L-mannopyranosyl-(1-->2)-O-[O-beta-D-glucopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->4)]-alpha-L-arabinopyranosyl)oxy]-23-hydroxylup-20(29)-en-28-oate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6500	65.00%
Caco-2	-	0.8682	86.82%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.7713	77.13%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8702	87.02%
OATP1B3 inhibitior	+	0.8155	81.55%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.7526	75.26%
BSEP inhibitior	+	0.9505	95.05%
P-glycoprotein inhibitior	+	0.7437	74.37%
P-glycoprotein substrate	+	0.6491	64.91%
CYP3A4 substrate	+	0.7503	75.03%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8587	85.87%
CYP3A4 inhibition	-	0.9527	95.27%
CYP2C9 inhibition	-	0.9059	90.59%
CYP2C19 inhibition	-	0.8980	89.80%
CYP2D6 inhibition	-	0.9476	94.76%
CYP1A2 inhibition	-	0.8816	88.16%
CYP2C8 inhibition	+	0.7849	78.49%
CYP inhibitory promiscuity	-	0.9276	92.76%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6833	68.33%
Eye corrosion	-	0.9899	98.99%
Eye irritation	-	0.8976	89.76%
Skin irritation	-	0.5278	52.78%
Skin corrosion	-	0.9457	94.57%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7818	78.18%
Micronuclear	-	0.9100	91.00%
Hepatotoxicity	-	0.7625	76.25%
skin sensitisation	-	0.9142	91.42%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	-	0.9015	90.15%
Acute Oral Toxicity (c)	I	0.4430	44.30%
Estrogen receptor binding	+	0.7672	76.72%
Androgen receptor binding	+	0.7635	76.35%
Thyroid receptor binding	+	0.6322	63.22%
Glucocorticoid receptor binding	+	0.7738	77.38%
Aromatase binding	+	0.6744	67.44%
PPAR gamma	+	0.8196	81.96%
Honey bee toxicity	-	0.5838	58.38%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9729	97.29%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3714130	P46095	G-protein coupled receptor 6	95.88%	97.36%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.84%	91.11%
CHEMBL233	P35372	Mu opioid receptor	93.91%	97.93%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	92.18%	91.24%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.53%	96.09%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	91.47%	97.33%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	91.09%	92.86%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.44%	97.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	90.17%	92.94%
CHEMBL2581	P07339	Cathepsin D	90.13%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.65%	86.33%
CHEMBL226	P30542	Adenosine A1 receptor	89.32%	95.93%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.81%	89.00%
CHEMBL218	P21554	Cannabinoid CB1 receptor	88.77%	96.61%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	88.49%	95.50%
CHEMBL1974	P36888	Tyrosine-protein kinase receptor FLT3	86.67%	91.83%
CHEMBL4618	P09960	Leukotriene A4 hydrolase	86.45%	97.86%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.23%	97.25%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.72%	95.89%
CHEMBL5255	O00206	Toll-like receptor 4	85.60%	92.50%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.87%	94.00%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	84.80%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	84.69%	91.19%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.46%	94.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.44%	100.00%
CHEMBL5028	O14672	ADAM10	84.38%	97.50%
CHEMBL2096618	P11274	Bcr/Abl fusion protein	84.08%	85.83%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.58%	94.45%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	83.53%	89.05%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	83.04%	100.00%
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	82.95%	96.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	82.94%	96.77%
CHEMBL2243	O00519	Anandamide amidohydrolase	82.89%	97.53%
CHEMBL4302	P08183	P-glycoprotein 1	82.72%	92.98%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.54%	99.17%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	82.47%	96.90%
CHEMBL2095194	P08709	Coagulation factor VII/tissue factor	82.15%	99.17%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	81.75%	93.10%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	81.58%	93.04%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.35%	95.83%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	81.19%	96.38%
CHEMBL1075317	P61964	WD repeat-containing protein 5	80.72%	96.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.60%	95.89%
CHEMBL1871	P10275	Androgen Receptor	80.11%	96.43%
CHEMBL2072	P35499	Sodium channel protein type IV alpha subunit	80.05%	92.32%

Plants that contains it

• Pulsatilla chinensis

Cross-Links

• PubChem: 10866203
• NPASS: NPC115219