3-O-[beta-D-xylopyranosyl(1->2)-alpha-L-arabinopyranosyl(1->6)-[beta-D-glucopyranosyl(1->2)]-beta-D-glucopyranoside echinocystic acid

Details

• Internal ID: 493b9ec7-7f3d-492b-8440-8c038549e974
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: (4aR,5R,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2R,3R,4S,5S,6R)-6-[[(2S,3R,4S,5S)-4,5-dihydroxy-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxymethyl]-4,5-dihydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
• SMILES (Canonical): CC1(CCC2(C(C1)C3=CCC4C5(CCC(C(C5CCC4(C3(CC2O)C)C)(C)C)OC6C(C(C(C(O6)COC7C(C(C(CO7)O)O)OC8C(C(C(CO8)O)O)O)O)O)OC9C(C(C(C(O9)CO)O)O)O)C)C(=O)O)C
• SMILES (Isomeric): C[C@]12CC[C@@H](C([C@@H]1CC[C@@]3([C@@H]2CC=C4[C@]3(C[C@H]([C@@]5([C@H]4CC(CC5)(C)C)C(=O)O)O)C)C)(C)C)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO[C@H]7[C@@H]([C@H]([C@H](CO7)O)O)O[C@H]8[C@@H]([C@H]([C@@H](CO8)O)O)O)O)O)O[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)CO)O)O)O
• InChI: InChI=1S/C52H84O22/c1-47(2)14-15-52(46(65)66)23(16-47)22-8-9-29-49(5)12-11-31(48(3,4)28(49)10-13-50(29,6)51(22,7)17-30(52)56)72-45-41(74-43-39(64)36(61)34(59)26(18-53)70-43)37(62)35(60)27(71-45)21-69-44-40(33(58)25(55)20-68-44)73-42-38(63)32(57)24(54)19-67-42/h8,23-45,53-64H,9-21H2,1-7H3,(H,65,66)/t23-,24+,25-,26+,27+,28-,29+,30+,31-,32-,33-,34+,35+,36-,37-,38+,39+,40+,41+,42-,43-,44-,45-,49-,50+,51+,52+/m0/s1
• InChI Key: AZFFBGWLLZUTDW-SITIIBQWSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₂H₈₄O₂₂
• Molecular Weight: 1061.20 g/mol
• Exact Mass: 1060.54542430 g/mol
• Topological Polar Surface Area (TPSA): 354.00 Ų
• XlogP: 0.10
• Atomic LogP (AlogP): -1.22
• H-Bond Acceptor: 21
• H-Bond Donor: 13
• Rotatable Bonds: 11

Synonyms

• CHEMBL1765591
• Q27136283
• 16alpha-Hydroxy-3beta-[6-O-[2-O-(beta-D-xylopyranosyl)-alpha-L-arabinopyranosyl]-2-O-(beta-D-glucopyranosyl)-beta-D-glucopyranosyloxy]olean-12-en-28-oic acid
• 3-O-[beta-D-xylopyranosyl(1->2)-alpha-L-arabinopyranosyl(1->6)-[beta-D-glucopyranosyl(1->2)]-beta-D-glucopyranoside echinocystic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7891	78.91%
Caco-2	-	0.8873	88.73%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.8567	85.67%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.6889	68.89%
OATP1B3 inhibitior	-	0.5700	57.00%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6276	62.76%
BSEP inhibitior	+	0.7698	76.98%
P-glycoprotein inhibitior	+	0.7472	74.72%
P-glycoprotein substrate	-	0.6266	62.66%
CYP3A4 substrate	+	0.7332	73.32%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8798	87.98%
CYP3A4 inhibition	-	0.9300	93.00%
CYP2C9 inhibition	-	0.8838	88.38%
CYP2C19 inhibition	-	0.9101	91.01%
CYP2D6 inhibition	-	0.9422	94.22%
CYP1A2 inhibition	-	0.8933	89.33%
CYP2C8 inhibition	+	0.7016	70.16%
CYP inhibitory promiscuity	-	0.9668	96.68%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6254	62.54%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.9025	90.25%
Skin irritation	-	0.6103	61.03%
Skin corrosion	-	0.9480	94.80%
Ames mutagenesis	-	0.6770	67.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7210	72.10%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.9000	90.00%
skin sensitisation	-	0.8917	89.17%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	-	0.7625	76.25%
Nephrotoxicity	-	0.8855	88.55%
Acute Oral Toxicity (c)	III	0.7945	79.45%
Estrogen receptor binding	+	0.8008	80.08%
Androgen receptor binding	+	0.7359	73.59%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.7042	70.42%
Aromatase binding	+	0.6182	61.82%
PPAR gamma	+	0.7891	78.91%
Honey bee toxicity	-	0.6977	69.77%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5905	59.05%
Fish aquatic toxicity	+	0.9411	94.11%

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	97.40%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.96%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.54%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.11%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.55%	95.56%
CHEMBL3714130	P46095	G-protein coupled receptor 6	86.34%	97.36%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.47%	86.33%
CHEMBL5028	O14672	ADAM10	85.40%	97.50%
CHEMBL5255	O00206	Toll-like receptor 4	85.37%	92.50%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	84.41%	95.50%
CHEMBL226	P30542	Adenosine A1 receptor	83.65%	95.93%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.59%	100.00%
CHEMBL221	P23219	Cyclooxygenase-1	82.74%	90.17%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.46%	92.62%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.40%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.81%	94.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	80.79%	96.77%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.77%	95.89%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	80.37%	96.21%
CHEMBL340	P08684	Cytochrome P450 3A4	80.07%	91.19%

Plants that contains it

• Albizia inundata
• Pithecellobium dulce
• Senecio subrubriflorus

Cross-Links

• PubChem: 54581282
• NPASS: NPC51465
• LOTUS: LTS0089516
• wikiData: Q104922360