Esculentoside M

Details

• Internal ID: 99a5eee6-ee20-4a55-bbc9-dae61858686b
• 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,12aS,14bR)-10-[(2S,3R,4R,5R)-3,4-dihydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-11-hydroxy-9-(hydroxymethyl)-2,6a,6b,9,12a-pentamethyl-13-oxo-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1H-picene-2,4a-dicarboxylate
• SMILES (Canonical): CC1(CCC2(CCC3(C(=CC(=O)C4C3(CCC5C4(CC(C(C5(C)CO)OC6C(C(C(CO6)OC7C(C(C(C(O7)CO)O)O)O)O)O)O)C)C)C2C1)C)C(=O)OC8C(C(C(C(O8)CO)O)O)O)C(=O)OC
• SMILES (Isomeric): C[C@]1(CC[C@@]2(CC[C@@]3(C(=CC(=O)[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](CO6)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)O)O)O)C)C)[C@H]2C1)C)C(=O)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)C(=O)OC
• InChI: InChI=1S/C48H74O22/c1-43(41(62)64-6)9-11-48(42(63)70-40-35(61)32(58)29(55)25(17-50)67-40)12-10-46(4)20(21(48)14-43)13-22(52)36-44(2)15-23(53)37(45(3,19-51)27(44)7-8-47(36,46)5)69-38-33(59)30(56)26(18-65-38)68-39-34(60)31(57)28(54)24(16-49)66-39/h13,21,23-40,49-51,53-61H,7-12,14-19H2,1-6H3/t21-,23+,24-,25-,26-,27?,28-,29-,30+,31+,32+,33-,34-,35-,36-,37+,38+,39+,40+,43-,44+,45+,46-,47-,48+/m1/s1
• InChI Key: DTFZRJDDQMLMNU-VTLMFQDDSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₈H₇₄O₂₂
• Molecular Weight: 1003.10 g/mol
• Exact Mass: 1002.46717398 g/mol
• Topological Polar Surface Area (TPSA): 359.00 Ų
• XlogP: -2.00
• Atomic LogP (AlogP): -2.95
• H-Bond Acceptor: 22
• H-Bond Donor: 12
• Rotatable Bonds: 10

Synonyms

• 140364-79-0
• 3-(beta-D-Glucopyranosyl(1-4)-beta-D-xylopyranosyl)-28-O-beta-D-glucopyranosyl-11-oxo-30-methyloleanate-12-en-2beta,3beta,23-trihydroxy-28-oic acid
• Olean-12-ene-28,29-dioic acid, 3-((4-O-beta-D-glucopyranosyl-beta-D-xylopyranosyl)oxy)-2,23-dihydroxy-11-oxo-, 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	-	0.8770	87.70%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.8112	81.12%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7431	74.31%
OATP1B3 inhibitior	-	0.2293	22.93%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.5771	57.71%
BSEP inhibitior	+	0.9090	90.90%
P-glycoprotein inhibitior	+	0.7490	74.90%
P-glycoprotein substrate	+	0.5826	58.26%
CYP3A4 substrate	+	0.7391	73.91%
CYP2C9 substrate	-	0.7964	79.64%
CYP2D6 substrate	-	0.8896	88.96%
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	+	0.7156	71.56%
CYP inhibitory promiscuity	-	0.9806	98.06%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5987	59.87%
Eye corrosion	-	0.9894	98.94%
Eye irritation	-	0.9021	90.21%
Skin irritation	-	0.5824	58.24%
Skin corrosion	-	0.9452	94.52%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7870	78.70%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.6250	62.50%
skin sensitisation	-	0.9182	91.82%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	+	0.6531	65.31%
Acute Oral Toxicity (c)	III	0.6557	65.57%
Estrogen receptor binding	+	0.7879	78.79%
Androgen receptor binding	+	0.7621	76.21%
Thyroid receptor binding	+	0.5170	51.70%
Glucocorticoid receptor binding	+	0.7702	77.02%
Aromatase binding	+	0.6175	61.75%
PPAR gamma	+	0.8119	81.19%
Honey bee toxicity	-	0.6855	68.55%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6500	65.00%
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	99.73%	91.11%
CHEMBL3714130	P46095	G-protein coupled receptor 6	97.69%	97.36%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.42%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.34%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.06%	96.09%
CHEMBL2581	P07339	Cathepsin D	92.38%	98.95%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	90.32%	94.78%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	90.06%	91.24%
CHEMBL4040	P28482	MAP kinase ERK2	90.04%	83.82%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.50%	95.56%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	88.45%	91.07%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	88.42%	94.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.05%	99.23%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.65%	95.89%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	84.77%	97.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.93%	94.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	83.81%	95.50%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	83.72%	96.90%
CHEMBL340	P08684	Cytochrome P450 3A4	83.54%	91.19%
CHEMBL5255	O00206	Toll-like receptor 4	83.40%	92.50%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	81.41%	95.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.02%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.42%	100.00%

Plants that contains it

• Phytolacca americana

Cross-Links

• PubChem: 132281
• LOTUS: LTS0129859
• wikiData: Q104401242