[(2R,3R,4S,5R,6R)-6-[[(2S,3R,4S,5S,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-[[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl] (4aS,5S,6aS,6aS,6bS,8aS,10R,12aS,14bR)-5-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-10-sulfooxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate

Details

• Internal ID: eaf5dabe-fca5-4b8e-99ad-78df75c9e154
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: [(2R,3R,4S,5R,6R)-6-[[(2S,3R,4S,5S,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-[[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl] (4aS,5S,6aS,6aS,6bS,8aS,10R,12aS,14bR)-5-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-10-sulfooxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
• SMILES (Canonical): CC1(CCC2(C(C1)C3=CCC4C5(CCC(C(C5CCC4(C3(CC2O)C)C)(C)C)OS(=O)(=O)O)C)C(=O)OC6C(C(C(C(O6)COC7C(C(C(C(O7)CO)O)O)OC8C(C(C(C(O8)COC9C(C(C(C(O9)CO)O)O)O)O)O)O)O)O)O)C
• SMILES (Isomeric): C[C@@]12CC[C@H](C([C@H]1CC[C@]3([C@H]2CC=C4[C@]3(C[C@@H]([C@]5([C@@H]4CC(CC5)(C)C)C(=O)O[C@@H]6[C@@H]([C@H]([C@H]([C@H](O6)CO[C@@H]7[C@@H]([C@H]([C@@H]([C@@H](O7)CO)O)O)O[C@@H]8[C@H]([C@@H]([C@@H]([C@@H](O8)CO[C@H]9[C@H]([C@H]([C@H]([C@H](O9)CO)O)O)O)O)O)O)O)O)O)O)C)C)(C)C)OS(=O)(=O)O
• InChI: InChI=1S/C54H88O27S/c1-49(2)14-15-54(23(16-49)22-8-9-29-51(5)12-11-31(81-82(70,71)72)50(3,4)28(51)10-13-52(29,6)53(22,7)17-30(54)57)48(69)80-46-42(68)38(64)35(61)27(78-46)21-74-47-43(39(65)33(59)25(19-56)76-47)79-45-41(67)37(63)34(60)26(77-45)20-73-44-40(66)36(62)32(58)24(18-55)75-44/h8,23-47,55-68H,9-21H2,1-7H3,(H,70,71,72)/t23-,24-,25+,26+,27-,28-,29+,30+,31-,32+,33-,34-,35+,36+,37-,38+,39+,40+,41+,42-,43-,44-,45-,46-,47+,51-,52+,53-,54+/m1/s1
• InChI Key: OXAWPYDAXHYZTK-CYJPXSHUSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₄H₈₈O₂₇S
• Molecular Weight: 1201.30 g/mol
• Exact Mass: 1200.52336870 g/mol
• Topological Polar Surface Area (TPSA): 446.00 Ų
• XlogP: -1.20
• Atomic LogP (AlogP): -3.24
• H-Bond Acceptor: 26
• H-Bond Donor: 15
• Rotatable Bonds: 14

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8165	81.65%
Caco-2	-	0.8691	86.91%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.5813	58.13%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7453	74.53%
OATP1B3 inhibitior	+	0.9055	90.55%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.7026	70.26%
BSEP inhibitior	+	0.8822	88.22%
P-glycoprotein inhibitior	+	0.7443	74.43%
P-glycoprotein substrate	-	0.5827	58.27%
CYP3A4 substrate	+	0.7309	73.09%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8692	86.92%
CYP3A4 inhibition	-	0.8014	80.14%
CYP2C9 inhibition	-	0.7532	75.32%
CYP2C19 inhibition	-	0.7218	72.18%
CYP2D6 inhibition	-	0.8699	86.99%
CYP1A2 inhibition	-	0.7442	74.42%
CYP2C8 inhibition	+	0.7045	70.45%
CYP inhibitory promiscuity	-	0.9302	93.02%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.6100	61.00%
Carcinogenicity (trinary)	Non-required	0.5719	57.19%
Eye corrosion	-	0.9790	97.90%
Eye irritation	-	0.8988	89.88%
Skin irritation	-	0.7513	75.13%
Skin corrosion	-	0.9060	90.60%
Ames mutagenesis	-	0.8288	82.88%
Human Ether-a-go-go-Related Gene inhibition	+	0.7424	74.24%
Micronuclear	+	0.5800	58.00%
Hepatotoxicity	-	0.8348	83.48%
skin sensitisation	-	0.8341	83.41%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	-	0.9036	90.36%
Acute Oral Toxicity (c)	III	0.6098	60.98%
Estrogen receptor binding	+	0.8034	80.34%
Androgen receptor binding	+	0.7490	74.90%
Thyroid receptor binding	+	0.5953	59.53%
Glucocorticoid receptor binding	+	0.7647	76.47%
Aromatase binding	+	0.6327	63.27%
PPAR gamma	+	0.8148	81.48%
Honey bee toxicity	-	0.6892	68.92%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5405	54.05%
Fish aquatic toxicity	+	0.9873	98.73%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.24%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.18%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.14%	94.45%
CHEMBL226	P30542	Adenosine A1 receptor	93.68%	95.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.40%	97.09%
CHEMBL5255	O00206	Toll-like receptor 4	90.26%	92.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.91%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.65%	95.56%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	88.96%	95.50%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.82%	97.25%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	87.74%	96.77%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	86.12%	94.33%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	84.46%	96.21%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.26%	94.00%
CHEMBL340	P08684	Cytochrome P450 3A4	84.10%	91.19%
CHEMBL2581	P07339	Cathepsin D	83.94%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.65%	89.00%
CHEMBL218	P21554	Cannabinoid CB1 receptor	83.09%	96.61%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.38%	95.89%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.75%	95.83%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.75%	86.33%
CHEMBL5028	O14672	ADAM10	81.37%	97.50%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.54%	86.92%

Plants that contains it

• Bupleurum rotundifolium

Cross-Links

• PubChem: 163013493
• LOTUS: LTS0102786
• wikiData: Q105202461