Esculentoside N

Details

• Internal ID: f0df34ae-8c85-4fa0-be80-bcca6c834631
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: 2-O-methyl 4a-O-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (2R,4aR,6aR,6aS,6bR,9R,10R,11S,12aR,14bR)-11-hydroxy-10-[(2R,3R,4S,5R,6R)-5-hydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-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(CC(C(C5(C)CO)OC6C(C(C(C(O6)CO)O)OC7C(C(C(C(O7)CO)O)O)O)OC8C(C(C(CO8)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(CCC5[C@@]4(C[C@@H]([C@@H]([C@@]5(C)CO)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)O[C@H]8[C@@H]([C@H]([C@@H](CO8)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/C54H86O26/c1-49(47(70)72-6)11-13-54(48(71)80-45-39(69)36(66)33(63)27(18-56)75-45)14-12-52(4)22(23(54)15-49)7-8-30-50(2)16-24(59)42(51(3,21-58)29(50)9-10-53(30,52)5)79-46-41(78-43-37(67)31(61)25(60)20-73-43)40(34(64)28(19-57)76-46)77-44-38(68)35(65)32(62)26(17-55)74-44/h7,23-46,55-69H,8-21H2,1-6H3/t23-,24+,25-,26-,27-,28-,29?,30-,31+,32-,33-,34-,35+,36+,37-,38-,39-,40+,41-,42+,43+,44+,45+,46+,49-,50+,51+,52-,53-,54+/m1/s1
• InChI Key: WVJDSQFWFCCTAH-BKWLPVKJSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₅₄H₈₆O₂₆
• Molecular Weight: 1151.20 g/mol
• Exact Mass: 1150.54073284 g/mol
• Topological Polar Surface Area (TPSA): 421.00 Ų
• XlogP: -2.60
• Atomic LogP (AlogP): -4.30
• H-Bond Acceptor: 26
• H-Bond Donor: 15
• Rotatable Bonds: 13

Synonyms

• 141890-69-9
• 3-O-(Glucopyranosyl(1-4)-xylopyranosyl(1-4)-glucopyranosyl)-28-O-glucopyranosylphytolaccagenin
• Olean-12-ene-28,29-dioic-acid, 3-((O-beta-D-glucopyranosyl-(1-4)-O-beta-D-xylopyranosyl-(1-4)-beta-D-glucopyranosyl)oxy)-2,23-dihydroxy-, 28-beta-D-glucopyranosyl 29-methyl ester, (2beta,3beta,4alpha,20beta)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6877	68.77%
Caco-2	-	0.8793	87.93%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.8112	81.12%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8320	83.20%
OATP1B3 inhibitior	-	0.2293	22.93%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.5771	57.71%
BSEP inhibitior	+	0.9088	90.88%
P-glycoprotein inhibitior	+	0.7466	74.66%
P-glycoprotein substrate	+	0.5102	51.02%
CYP3A4 substrate	+	0.7306	73.06%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8587	85.87%
CYP3A4 inhibition	-	0.8833	88.33%
CYP2C9 inhibition	-	0.9285	92.85%
CYP2C19 inhibition	-	0.9205	92.05%
CYP2D6 inhibition	-	0.9538	95.38%
CYP1A2 inhibition	-	0.9078	90.78%
CYP2C8 inhibition	+	0.7341	73.41%
CYP inhibitory promiscuity	-	0.9806	98.06%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5987	59.87%
Eye corrosion	-	0.9894	98.94%
Eye irritation	-	0.9004	90.04%
Skin irritation	-	0.5824	58.24%
Skin corrosion	-	0.9452	94.52%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7649	76.49%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.8125	81.25%
skin sensitisation	-	0.9182	91.82%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	+	0.7033	70.33%
Acute Oral Toxicity (c)	III	0.6557	65.57%
Estrogen receptor binding	+	0.7901	79.01%
Androgen receptor binding	+	0.7556	75.56%
Thyroid receptor binding	+	0.5323	53.23%
Glucocorticoid receptor binding	+	0.7549	75.49%
Aromatase binding	+	0.6136	61.36%
PPAR gamma	+	0.8024	80.24%
Honey bee toxicity	-	0.6876	68.76%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.8974	89.74%

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	99.55%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.37%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.21%	96.09%
CHEMBL3714130	P46095	G-protein coupled receptor 6	96.18%	97.36%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.47%	97.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	91.16%	96.77%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	90.44%	94.33%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	88.26%	95.50%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	88.25%	91.24%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	86.76%	91.07%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.63%	95.56%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	86.36%	95.17%
CHEMBL5255	O00206	Toll-like receptor 4	85.45%	92.50%
CHEMBL4040	P28482	MAP kinase ERK2	85.38%	83.82%
CHEMBL2916	O14746	Telomerase reverse transcriptase	83.97%	90.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.69%	95.89%
CHEMBL340	P08684	Cytochrome P450 3A4	82.50%	91.19%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	82.43%	96.90%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	82.29%	96.21%
CHEMBL2581	P07339	Cathepsin D	82.00%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.43%	100.00%
CHEMBL218	P21554	Cannabinoid CB1 receptor	80.58%	96.61%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.47%	94.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.26%	97.25%

Plants that contains it

• Phytolacca acinosa

Cross-Links

• PubChem: 197456
• LOTUS: LTS0065955
• wikiData: Q105313556