methyl (2S,3S,4S,5R,6R)-6-[[(3S,4S,6aR,8aR,10R,12aS,14bR)-7,8-dihydroxy-8a-(hydroxymethyl)-4-methoxycarbonyl-4,6a,6b,11,11,14b-hexamethyl-9,10-bis[[(Z)-2-methylbut-2-enoyl]oxy]-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,5-dihydroxy-4-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxane-2-carboxylate

Details

• Internal ID: 48d238b9-257c-42f5-8124-eba311fc1a4a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: methyl (2S,3S,4S,5R,6R)-6-[[(3S,4S,6aR,8aR,10R,12aS,14bR)-7,8-dihydroxy-8a-(hydroxymethyl)-4-methoxycarbonyl-4,6a,6b,11,11,14b-hexamethyl-9,10-bis[[(Z)-2-methylbut-2-enoyl]oxy]-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,5-dihydroxy-4-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxane-2-carboxylate
• SMILES (Canonical): CC=C(C)C(=O)OC1C(C2(C(CC1(C)C)C3=CCC4C5(CCC(C(C5CCC4(C3(C(C2O)O)C)C)(C)C(=O)OC)OC6C(C(C(C(O6)C(=O)OC)O)OC7C(C(C(CO7)O)O)O)O)C)CO)OC(=O)C(=CC)C
• SMILES (Isomeric): C/C=C(/C)\C(=O)O[C@H]1C([C@]2([C@@H](CC1(C)C)C3=CCC4[C@]5(CC[C@@H]([C@@](C5CC[C@]4(C3(C(C2O)O)C)C)(C)C(=O)OC)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)C(=O)OC)O)O[C@H]7[C@@H]([C@H]([C@H](CO7)O)O)O)O)C)CO)OC(=O)/C(=C\C)/C
• InChI: InChI=1S/C53H80O20/c1-13-24(3)42(62)72-40-41(73-43(63)25(4)14-2)53(23-54)27(21-48(40,5)6)26-15-16-29-49(7)19-18-31(51(9,47(65)67-12)30(49)17-20-50(29,8)52(26,10)38(60)39(53)61)69-46-35(59)36(34(58)37(71-46)44(64)66-11)70-45-33(57)32(56)28(55)22-68-45/h13-15,27-41,45-46,54-61H,16-23H2,1-12H3/b24-13-,25-14-/t27-,28-,29?,30?,31-,32-,33+,34-,35+,36-,37-,38?,39?,40-,41?,45-,46+,49+,50+,51-,52?,53-/m0/s1
• InChI Key: QCMIZNQBGXTSJB-ZEYACDJTSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₃H₈₀O₂₀
• Molecular Weight: 1037.20 g/mol
• Exact Mass: 1036.52429494 g/mol
• Topological Polar Surface Area (TPSA): 304.00 Ų
• XlogP: 3.70
• Atomic LogP (AlogP): 1.68
• H-Bond Acceptor: 20
• H-Bond Donor: 8
• Rotatable Bonds: 11

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7524	75.24%
Caco-2	-	0.8647	86.47%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.8446	84.46%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8008	80.08%
OATP1B3 inhibitior	-	0.3173	31.73%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	+	0.9456	94.56%
P-glycoprotein inhibitior	+	0.7503	75.03%
P-glycoprotein substrate	+	0.6405	64.05%
CYP3A4 substrate	+	0.7470	74.70%
CYP2C9 substrate	-	0.8006	80.06%
CYP2D6 substrate	-	0.8956	89.56%
CYP3A4 inhibition	-	0.8504	85.04%
CYP2C9 inhibition	-	0.8702	87.02%
CYP2C19 inhibition	-	0.9017	90.17%
CYP2D6 inhibition	-	0.9473	94.73%
CYP1A2 inhibition	-	0.9011	90.11%
CYP2C8 inhibition	+	0.7591	75.91%
CYP inhibitory promiscuity	-	0.9771	97.71%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5934	59.34%
Eye corrosion	-	0.9888	98.88%
Eye irritation	-	0.8997	89.97%
Skin irritation	-	0.6306	63.06%
Skin corrosion	-	0.9434	94.34%
Ames mutagenesis	-	0.5948	59.48%
Human Ether-a-go-go-Related Gene inhibition	+	0.7282	72.82%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.6834	68.34%
skin sensitisation	-	0.8954	89.54%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	-	0.6125	61.25%
Nephrotoxicity	+	0.4889	48.89%
Acute Oral Toxicity (c)	III	0.7499	74.99%
Estrogen receptor binding	+	0.7480	74.80%
Androgen receptor binding	+	0.7605	76.05%
Thyroid receptor binding	+	0.6155	61.55%
Glucocorticoid receptor binding	+	0.8060	80.60%
Aromatase binding	+	0.6482	64.82%
PPAR gamma	+	0.8322	83.22%
Honey bee toxicity	-	0.6632	66.32%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9235	92.35%

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	99.52%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.51%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.59%	96.09%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	93.70%	91.07%
CHEMBL221	P23219	Cyclooxygenase-1	89.73%	90.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.86%	95.89%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	88.84%	94.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.82%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.11%	86.33%
CHEMBL1871	P10275	Androgen Receptor	87.51%	96.43%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	86.65%	96.77%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.16%	92.62%
CHEMBL2581	P07339	Cathepsin D	85.75%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.67%	100.00%
CHEMBL4208	P20618	Proteasome component C5	84.85%	90.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.73%	97.25%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.27%	97.14%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.50%	99.17%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	82.46%	95.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.45%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	81.97%	94.73%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	81.82%	91.24%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.39%	95.50%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	80.93%	96.90%
CHEMBL5028	O14672	ADAM10	80.61%	97.50%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	80.51%	91.03%

Plants that contains it

• Atractylodes lancea
• Camellia sinensis
• Isatis tinctoria
• Lycium chinense

Cross-Links

• PubChem: 11969009
• NPASS: NPC154016
• LOTUS: LTS0202329
• wikiData: Q105218328