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

Details

• Internal ID: cdf44b92-568a-47f5-8f9e-196233f8de34
• 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,9R,10S,12aR,14bS)-10-[(2R,3R,4R,5S,6R)-5-[(2S,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-9-(hydroxymethyl)-2,6a,6b,9,12a-pentamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-2,4a-dicarboxylate
• SMILES (Canonical): CC1(CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)CO)OC6C(C(C(C(O6)CO)OC7C(C(C(C(O7)CO)OC8C(C(C(C(O8)CO)O)O)O)O)O)O)O)C)C)C2C1)C)C(=O)OC9C(C(C(C(O9)CO)O)O)O)C(=O)OC
• 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]([C@@]5(C)CO)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)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/C55H88O26/c1-50(48(71)73-6)13-15-55(49(72)81-47-39(68)35(64)33(62)26(19-57)75-47)16-14-53(4)23(24(55)17-50)7-8-30-51(2)11-10-31(52(3,22-60)29(51)9-12-54(30,53)5)78-44-40(69)36(65)42(27(20-58)76-44)80-46-41(70)37(66)43(28(21-59)77-46)79-45-38(67)34(63)32(61)25(18-56)74-45/h7,24-47,56-70H,8-22H2,1-6H3/t24-,25+,26-,27+,28+,29+,30+,31-,32+,33-,34-,35+,36+,37+,38+,39-,40+,41+,42+,43+,44-,45-,46-,47-,50-,51-,52-,53+,54+,55-/m0/s1
• InChI Key: ZMLVLPRCOMEBRP-AIXAMXRESA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₅H₈₈O₂₆
• Molecular Weight: 1165.30 g/mol
• Exact Mass: 1164.55638291 g/mol
• Topological Polar Surface Area (TPSA): 421.00 Ų
• XlogP: -2.80
• Atomic LogP (AlogP): -3.91
• 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	+	0.6450	64.50%
Caco-2	-	0.8735	87.35%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.8410	84.10%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8502	85.02%
OATP1B3 inhibitior	-	0.2591	25.91%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.5021	50.21%
BSEP inhibitior	+	0.9377	93.77%
P-glycoprotein inhibitior	+	0.7454	74.54%
P-glycoprotein substrate	-	0.6940	69.40%
CYP3A4 substrate	+	0.7272	72.72%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8587	85.87%
CYP3A4 inhibition	-	0.9325	93.25%
CYP2C9 inhibition	-	0.9274	92.74%
CYP2C19 inhibition	-	0.9129	91.29%
CYP2D6 inhibition	-	0.9549	95.49%
CYP1A2 inhibition	-	0.8851	88.51%
CYP2C8 inhibition	+	0.7024	70.24%
CYP inhibitory promiscuity	-	0.9658	96.58%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6068	60.68%
Eye corrosion	-	0.9889	98.89%
Eye irritation	-	0.8995	89.95%
Skin irritation	-	0.6260	62.60%
Skin corrosion	-	0.9468	94.68%
Ames mutagenesis	-	0.7800	78.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8177	81.77%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	-	0.8125	81.25%
skin sensitisation	-	0.9199	91.99%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	+	0.5116	51.16%
Acute Oral Toxicity (c)	III	0.6420	64.20%
Estrogen receptor binding	+	0.7700	77.00%
Androgen receptor binding	+	0.7523	75.23%
Thyroid receptor binding	+	0.5996	59.96%
Glucocorticoid receptor binding	+	0.7584	75.84%
Aromatase binding	+	0.6372	63.72%
PPAR gamma	+	0.8055	80.55%
Honey bee toxicity	-	0.6986	69.86%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9298	92.98%

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	98.94%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.72%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.38%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.55%	97.09%
CHEMBL3714130	P46095	G-protein coupled receptor 6	90.11%	97.36%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	89.01%	94.33%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	86.37%	95.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.00%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.42%	95.56%
CHEMBL5255	O00206	Toll-like receptor 4	84.35%	92.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.75%	99.17%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.84%	91.07%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.41%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.63%	89.00%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	80.52%	96.90%

Plants that contains it

• Chenopodium quinoa

Cross-Links

• PubChem: 162924871
• LOTUS: LTS0265472
• wikiData: Q105379509