(2S,3S,4S,5R,6R)-6-[[(3S,4S,4aR,6aS,6aR,6bR,8R,8aR,9R,10R,12aS,14aR,14bR)-8a-(acetyloxymethyl)-8,9-dihydroxy-4-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-10-[(E)-2-methylbut-2-enoyl]oxy-1,2,3,4a,5,6,6a,7,8,9,10,12,12a,13,14,14a-hexadecahydropicen-3-yl]oxy]-4-hydroxy-3,5-bis[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]oxane-2-carboxylic acid

Details

• Internal ID: 9e20f744-f2b4-47f8-bfba-241069c139d1
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: (2S,3S,4S,5R,6R)-6-[[(3S,4S,4aR,6aS,6aR,6bR,8R,8aR,9R,10R,12aS,14aR,14bR)-8a-(acetyloxymethyl)-8,9-dihydroxy-4-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-10-[(E)-2-methylbut-2-enoyl]oxy-1,2,3,4a,5,6,6a,7,8,9,10,12,12a,13,14,14a-hexadecahydropicen-3-yl]oxy]-4-hydroxy-3,5-bis[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]oxane-2-carboxylic acid
• SMILES (Canonical): CC=C(C)C(=O)OC1C(C2(C(CC1(C)C)C3CCC4C5(CCC(C(C5CCC4(C3(CC2O)C)C)(C)CO)OC6C(C(C(C(O6)C(=O)O)OC7C(C(C(C(O7)CO)O)O)O)O)OC8C(C(C(C(O8)CO)O)O)O)C)COC(=O)C)O
• SMILES (Isomeric): C/C=C(\C)/C(=O)O[C@H]1[C@@H]([C@@]2([C@@H](C[C@@]3([C@H]([C@@H]2CC1(C)C)CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H]([C@]5(C)CO)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)C(=O)O)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)O)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)C)C)C)O)COC(=O)C)O
• InChI: InChI=1S/C55H88O24/c1-10-23(2)46(71)79-44-43(68)55(22-72-24(3)59)26(17-50(44,4)5)25-11-12-30-51(6)15-14-32(52(7,21-58)29(51)13-16-53(30,8)54(25,9)18-31(55)60)75-49-41(77-48-38(66)36(64)34(62)28(20-57)74-48)39(67)40(42(78-49)45(69)70)76-47-37(65)35(63)33(61)27(19-56)73-47/h10,25-44,47-49,56-58,60-68H,11-22H2,1-9H3,(H,69,70)/b23-10+/t25-,26-,27+,28+,29+,30+,31+,32-,33+,34+,35-,36-,37+,38+,39-,40-,41+,42-,43-,44-,47-,48-,49+,51-,52+,53+,54+,55-/m0/s1
• InChI Key: VQDUTOWWPYHRSC-VWBFFQSWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₅H₈₈O₂₄
• Molecular Weight: 1133.30 g/mol
• Exact Mass: 1132.56655367 g/mol
• Topological Polar Surface Area (TPSA): 388.00 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): -1.24
• H-Bond Acceptor: 23
• H-Bond Donor: 13
• Rotatable Bonds: 14

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6914	69.14%
Caco-2	-	0.8714	87.14%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.8437	84.37%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8312	83.12%
OATP1B3 inhibitior	-	0.3175	31.75%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.5276	52.76%
BSEP inhibitior	+	0.8944	89.44%
P-glycoprotein inhibitior	+	0.7471	74.71%
P-glycoprotein substrate	+	0.5640	56.40%
CYP3A4 substrate	+	0.7452	74.52%
CYP2C9 substrate	-	0.7978	79.78%
CYP2D6 substrate	-	0.8976	89.76%
CYP3A4 inhibition	-	0.8434	84.34%
CYP2C9 inhibition	-	0.8601	86.01%
CYP2C19 inhibition	-	0.9074	90.74%
CYP2D6 inhibition	-	0.9486	94.86%
CYP1A2 inhibition	-	0.8960	89.60%
CYP2C8 inhibition	+	0.7711	77.11%
CYP inhibitory promiscuity	-	0.9730	97.30%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6550	65.50%
Eye corrosion	-	0.9905	99.05%
Eye irritation	-	0.8993	89.93%
Skin irritation	-	0.6049	60.49%
Skin corrosion	-	0.9482	94.82%
Ames mutagenesis	-	0.6978	69.78%
Human Ether-a-go-go-Related Gene inhibition	+	0.7445	74.45%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	-	0.7584	75.84%
skin sensitisation	-	0.8989	89.89%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	-	0.6000	60.00%
Nephrotoxicity	+	0.4658	46.58%
Acute Oral Toxicity (c)	III	0.7630	76.30%
Estrogen receptor binding	+	0.7641	76.41%
Androgen receptor binding	+	0.7618	76.18%
Thyroid receptor binding	+	0.5725	57.25%
Glucocorticoid receptor binding	+	0.7954	79.54%
Aromatase binding	+	0.6336	63.36%
PPAR gamma	+	0.8119	81.19%
Honey bee toxicity	-	0.6144	61.44%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9535	95.35%

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	96.61%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.14%	91.11%
CHEMBL2782	P35610	Acyl coenzyme A:cholesterol acyltransferase 1	94.10%	91.65%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.06%	94.45%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	91.84%	93.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	90.94%	97.36%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.71%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.38%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.05%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.38%	97.25%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	87.42%	91.24%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	87.17%	81.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.50%	99.17%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	86.30%	94.33%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	85.58%	95.71%
CHEMBL2096618	P11274	Bcr/Abl fusion protein	85.57%	85.83%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	85.15%	91.07%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.82%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.71%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.40%	97.09%
CHEMBL4227	P25090	Lipoxin A4 receptor	84.33%	100.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	83.89%	95.50%
CHEMBL4302	P08183	P-glycoprotein 1	83.75%	92.98%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	83.50%	100.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.96%	95.50%
CHEMBL5028	O14672	ADAM10	82.20%	97.50%
CHEMBL221	P23219	Cyclooxygenase-1	81.68%	90.17%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.78%	92.62%
CHEMBL5255	O00206	Toll-like receptor 4	80.67%	92.50%

Plants that contains it

• Aesculus chinensis

Cross-Links

• PubChem: 163106333
• LOTUS: LTS0046632
• wikiData: Q105291191