3alpha,11alpha-Dihydroxylup-20(29)-ene-23,28-dioic acid 28-[6-O-[4-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranosyl]-beta-D-glucopyranosyl] ester

Details

• Internal ID: 359bb7e6-d1de-4a77-a44a-cfc2023365f1
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: (1R,3aS,5aR,5bR,7aR,8S,9R,11aS,11bR,12R,13aR,13bR)-3a-[(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]oxycarbonyl-9,12-dihydroxy-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-8-carboxylic acid
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(OC(C(C2O)O)OCC3C(C(C(C(O3)OC(=O)C45CCC(C4C6CC(C7C8(CCC(C(C8CCC7(C6(CC5)C)C)(C)C(=O)O)O)C)O)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]6C[C@H]([C@@H]7[C@]8(CC[C@H]([C@@]([C@@H]8CC[C@]7([C@@]6(CC5)C)C)(C)C(=O)O)O)C)O)C(=C)C)O)O)O)CO)O)O)O
• InChI: InChI=1S/C48H76O20/c1-19(2)21-8-13-48(15-14-45(5)22(28(21)48)16-23(50)38-44(4)11-10-27(51)47(7,42(60)61)26(44)9-12-46(38,45)6)43(62)68-41-35(58)32(55)30(53)25(66-41)18-63-39-36(59)33(56)37(24(17-49)65-39)67-40-34(57)31(54)29(52)20(3)64-40/h20-41,49-59H,1,8-18H2,2-7H3,(H,60,61)/t20-,21-,22+,23+,24+,25+,26+,27+,28+,29-,30+,31+,32-,33+,34+,35+,36+,37+,38+,39+,40-,41-,44-,45+,46+,47-,48-/m0/s1
• InChI Key: JYJSDPJHFJZKFG-CRNRAUGNSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₈H₇₆O₂₀
• Molecular Weight: 973.10 g/mol
• Exact Mass: 972.49299481 g/mol
• Topological Polar Surface Area (TPSA): 332.00 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): -0.94
• H-Bond Acceptor: 19
• H-Bond Donor: 12
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6584	65.84%
Caco-2	-	0.8814	88.14%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.7734	77.34%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8286	82.86%
OATP1B3 inhibitior	+	0.8845	88.45%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6298	62.98%
BSEP inhibitior	+	0.8921	89.21%
P-glycoprotein inhibitior	+	0.7431	74.31%
P-glycoprotein substrate	+	0.6182	61.82%
CYP3A4 substrate	+	0.7388	73.88%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8776	87.76%
CYP3A4 inhibition	-	0.8497	84.97%
CYP2C9 inhibition	-	0.9019	90.19%
CYP2C19 inhibition	-	0.9180	91.80%
CYP2D6 inhibition	-	0.9525	95.25%
CYP1A2 inhibition	-	0.9138	91.38%
CYP2C8 inhibition	+	0.7490	74.90%
CYP inhibitory promiscuity	-	0.9681	96.81%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6641	66.41%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.9044	90.44%
Skin irritation	+	0.5458	54.58%
Skin corrosion	-	0.9395	93.95%
Ames mutagenesis	-	0.7470	74.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7502	75.02%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	-	0.7598	75.98%
skin sensitisation	-	0.9206	92.06%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.9319	93.19%
Acute Oral Toxicity (c)	I	0.4943	49.43%
Estrogen receptor binding	+	0.8424	84.24%
Androgen receptor binding	+	0.7525	75.25%
Thyroid receptor binding	-	0.4921	49.21%
Glucocorticoid receptor binding	+	0.7280	72.80%
Aromatase binding	+	0.6400	64.00%
PPAR gamma	+	0.8124	81.24%
Honey bee toxicity	-	0.6090	60.90%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	+	0.9713	97.13%

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	98.47%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.24%	96.09%
CHEMBL233	P35372	Mu opioid receptor	96.11%	97.93%
CHEMBL3714130	P46095	G-protein coupled receptor 6	93.82%	97.36%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.20%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.75%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.66%	97.25%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	90.27%	96.38%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	90.00%	97.33%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	89.72%	95.50%
CHEMBL340	P08684	Cytochrome P450 3A4	87.91%	91.19%
CHEMBL226	P30542	Adenosine A1 receptor	87.90%	95.93%
CHEMBL218	P21554	Cannabinoid CB1 receptor	87.66%	96.61%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	87.48%	95.89%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	87.25%	89.05%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.15%	89.00%
CHEMBL5255	O00206	Toll-like receptor 4	87.12%	92.50%
CHEMBL1914	P06276	Butyrylcholinesterase	85.87%	95.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.65%	100.00%
CHEMBL4618	P09960	Leukotriene A4 hydrolase	84.70%	97.86%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	84.44%	93.04%
CHEMBL5028	O14672	ADAM10	83.95%	97.50%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	83.07%	96.77%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	83.01%	82.50%
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	82.43%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.09%	94.45%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.74%	100.00%
CHEMBL1871	P10275	Androgen Receptor	81.33%	96.43%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.00%	92.94%
CHEMBL2581	P07339	Cathepsin D	80.80%	98.95%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.65%	95.83%

Plants that contains it

• Diospyros dendo
• Heptapleurum heptaphyllum
• Narcissus tazetta
• Podophyllum grayi
• Primula veris
• Solanum tuberosum

Cross-Links

• PubChem: 101606374
• NPASS: NPC7645
• LOTUS: LTS0145359
• wikiData: Q105137062