2-O-methyl 4a-O-[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (2S,4aR,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2S,3R,4S,5S)-4-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3,5-dihydroxyoxan-2-yl]oxy-2,6a,6b,9,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-2,4a-dicarboxylate

Details

• Internal ID: a7114d3f-7440-4452-992e-9e7c37668035
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: 2-O-methyl 4a-O-[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (2S,4aR,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2S,3R,4S,5S)-4-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3,5-dihydroxyoxan-2-yl]oxy-2,6a,6b,9,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-2,4a-dicarboxylate
• SMILES (Canonical): CC1(C2CCC3(C(C2(CCC1OC4C(C(C(CO4)O)OC5C(C(C(C(O5)CO)O)O)OC6C(C(C(C(O6)CO)O)O)O)O)C)CC=C7C3(CCC8(C7CC(CC8)(C)C(=O)OC)C(=O)OC9C(C(C(C(O9)CO)O)O)O)C)C)C
• SMILES (Isomeric): C[C@@]1(CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)O[C@H]6[C@@H]([C@H]([C@H](CO6)O)O[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)O)O)O)O)C)C)[C@@H]2C1)C)C(=O)O[C@H]9[C@H]([C@@H]([C@H]([C@@H](O9)CO)O)O)O)C(=O)OC
• InChI: InChI=1S/C54H86O24/c1-49(2)29-10-13-53(6)30(9-8-23-24-18-50(3,47(68)70-7)14-16-54(24,17-15-52(23,53)5)48(69)78-45-39(66)36(63)33(60)27(20-56)73-45)51(29,4)12-11-31(49)75-43-40(67)41(25(58)22-71-43)76-46-42(37(64)34(61)28(21-57)74-46)77-44-38(65)35(62)32(59)26(19-55)72-44/h8,24-46,55-67H,9-22H2,1-7H3/t24-,25-,26+,27-,28+,29-,30+,31-,32+,33-,34+,35-,36+,37-,38+,39-,40+,41-,42+,43-,44-,45-,46-,50-,51-,52+,53+,54-/m0/s1
• InChI Key: DKWLTFMGAHQIEP-SDQXEYELSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₅₄H₈₆O₂₄
• Molecular Weight: 1119.20 g/mol
• Exact Mass: 1118.55090361 g/mol
• Topological Polar Surface Area (TPSA): 380.00 Ų
• XlogP: -0.40
• Atomic LogP (AlogP): -2.24
• H-Bond Acceptor: 24
• H-Bond Donor: 13
• Rotatable Bonds: 12

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	-	0.8756	87.56%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.8446	84.46%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.6920	69.20%
OATP1B3 inhibitior	-	0.3173	31.73%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	+	0.9075	90.75%
P-glycoprotein inhibitior	+	0.7467	74.67%
P-glycoprotein substrate	-	0.6764	67.64%
CYP3A4 substrate	+	0.7397	73.97%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8587	85.87%
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	+	0.7257	72.57%
CYP inhibitory promiscuity	-	0.9771	97.71%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5934	59.34%
Eye corrosion	-	0.9888	98.88%
Eye irritation	-	0.9000	90.00%
Skin irritation	-	0.6306	63.06%
Skin corrosion	-	0.9434	94.34%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7756	77.56%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.9375	93.75%
skin sensitisation	-	0.8954	89.54%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	-	0.6125	61.25%
Nephrotoxicity	-	0.8049	80.49%
Acute Oral Toxicity (c)	III	0.7499	74.99%
Estrogen receptor binding	+	0.7518	75.18%
Androgen receptor binding	+	0.7440	74.40%
Thyroid receptor binding	+	0.5767	57.67%
Glucocorticoid receptor binding	+	0.7694	76.94%
Aromatase binding	+	0.6338	63.38%
PPAR gamma	+	0.8049	80.49%
Honey bee toxicity	-	0.6530	65.30%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
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	99.30%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.81%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.57%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.01%	97.09%
CHEMBL3714130	P46095	G-protein coupled receptor 6	90.20%	97.36%
CHEMBL2581	P07339	Cathepsin D	89.06%	98.95%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	87.70%	94.33%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	87.53%	96.21%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	86.38%	95.50%
CHEMBL5255	O00206	Toll-like receptor 4	86.32%	92.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.47%	95.56%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	85.16%	96.77%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.12%	99.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.11%	95.89%
CHEMBL5028	O14672	ADAM10	80.72%	97.50%
CHEMBL3922	P50579	Methionine aminopeptidase 2	80.39%	97.28%

Plants that contains it

• Chenopodium quinoa

Cross-Links

• PubChem: 163067043
• LOTUS: LTS0072254
• wikiData: Q104983840