(20S)-3beta-[4-O-(2-O-alpha-L-Rhamnopyranosyl-beta-D-glucopyranosyl)-alpha-L-arabinopyranosyloxy]-13,28-epoxy-16alpha-hydroxyoleanane-29-al

Details

• Internal ID: dc0eca8b-4d06-4da0-aeef-cb57eb79cb4e
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (1S,2R,4S,5R,8R,10S,13R,14R,17S,18R,20S)-10-[(2S,3R,4R,5S)-5-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxyoxan-2-yl]oxy-2-hydroxy-4,5,9,9,13,20-hexamethyl-24-oxahexacyclo[15.5.2.01,18.04,17.05,14.08,13]tetracosane-20-carbaldehyde
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(C(OC2OC3COC(C(C3O)O)OC4CCC5(C(C4(C)C)CCC6(C5CCC78C6(CC(C9(C7CC(CC9)(C)C=O)CO8)O)C)C)C)CO)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2O[C@H]3CO[C@H]([C@@H]([C@H]3O)O)O[C@H]4CC[C@@]5([C@H]6CC[C@@]78[C@@H]9C[C@@](CC[C@]9(CO7)[C@@H](C[C@]8([C@@]6(CC[C@H]5C4(C)C)C)C)O)(C)C=O)C)CO)O)O)O)O)O
• InChI: InChI=1S/C47H76O17/c1-22-30(51)33(54)36(57)39(60-22)64-37-34(55)31(52)23(18-48)61-40(37)62-24-19-58-38(35(56)32(24)53)63-29-10-11-43(5)25(41(29,2)3)8-12-44(6)26(43)9-13-47-27-16-42(4,20-49)14-15-46(27,21-59-47)28(50)17-45(44,47)7/h20,22-40,48,50-57H,8-19,21H2,1-7H3/t22-,23+,24-,25-,26+,27+,28+,29-,30-,31+,32-,33+,34-,35+,36+,37+,38-,39-,40-,42-,43-,44+,45-,46+,47-/m0/s1
• InChI Key: MKOLINYFCYHLHC-AIZXFEFNSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₇H₇₆O₁₇
• Molecular Weight: 913.10 g/mol
• Exact Mass: 912.50825095 g/mol
• Topological Polar Surface Area (TPSA): 264.00 Ų
• XlogP: 1.00
• Atomic LogP (AlogP): 0.67
• H-Bond Acceptor: 17
• H-Bond Donor: 9
• Rotatable Bonds: 8

Synonyms

• (20S)-3beta-[4-O-(2-O-alpha-L-Rhamnopyranosyl-beta-D-glucopyranosyl)-alpha-L-arabinopyranosyloxy]-13,28-epoxy-16alpha-hydroxyoleanane-29-al

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6397	63.97%
Caco-2	-	0.8846	88.46%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.7227	72.27%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7901	79.01%
OATP1B3 inhibitior	+	0.9276	92.76%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	+	0.8112	81.12%
P-glycoprotein inhibitior	+	0.7453	74.53%
P-glycoprotein substrate	+	0.5533	55.33%
CYP3A4 substrate	+	0.7452	74.52%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8272	82.72%
CYP3A4 inhibition	-	0.9228	92.28%
CYP2C9 inhibition	-	0.8526	85.26%
CYP2C19 inhibition	-	0.8627	86.27%
CYP2D6 inhibition	-	0.9523	95.23%
CYP1A2 inhibition	-	0.9157	91.57%
CYP2C8 inhibition	+	0.7139	71.39%
CYP inhibitory promiscuity	-	0.9693	96.93%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6545	65.45%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.9069	90.69%
Skin irritation	-	0.6766	67.66%
Skin corrosion	-	0.9455	94.55%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7674	76.74%
Micronuclear	-	0.9000	90.00%
Hepatotoxicity	-	0.8125	81.25%
skin sensitisation	-	0.9229	92.29%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	-	0.8012	80.12%
Acute Oral Toxicity (c)	I	0.6300	63.00%
Estrogen receptor binding	+	0.7814	78.14%
Androgen receptor binding	+	0.7489	74.89%
Thyroid receptor binding	-	0.5506	55.06%
Glucocorticoid receptor binding	+	0.6889	68.89%
Aromatase binding	+	0.6544	65.44%
PPAR gamma	+	0.7824	78.24%
Honey bee toxicity	-	0.5468	54.68%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5145	51.45%
Fish aquatic toxicity	+	0.8764	87.64%

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	96.35%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.32%	96.09%
CHEMBL3714130	P46095	G-protein coupled receptor 6	91.55%	97.36%
CHEMBL226	P30542	Adenosine A1 receptor	91.28%	95.93%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	90.66%	91.24%
CHEMBL2581	P07339	Cathepsin D	89.99%	98.95%
CHEMBL218	P21554	Cannabinoid CB1 receptor	88.08%	96.61%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.03%	100.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	87.74%	95.50%
CHEMBL1937	Q92769	Histone deacetylase 2	86.91%	94.75%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.69%	95.89%
CHEMBL203	P00533	Epidermal growth factor receptor erbB1	86.49%	97.34%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.37%	89.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	86.02%	96.21%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.19%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.82%	95.89%
CHEMBL2534	O15530	3-phosphoinositide dependent protein kinase-1	84.38%	95.36%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.67%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.41%	86.33%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	82.62%	95.71%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.60%	92.94%
CHEMBL2243	O00519	Anandamide amidohydrolase	82.53%	97.53%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	82.21%	91.03%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.98%	94.33%
CHEMBL1163125	O60885	Bromodomain-containing protein 4	81.26%	97.31%
CHEMBL3589	P55263	Adenosine kinase	80.80%	98.05%
CHEMBL5028	O14672	ADAM10	80.58%	97.50%
CHEMBL233	P35372	Mu opioid receptor	80.56%	97.93%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.19%	95.56%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	80.09%	100.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.03%	99.17%

Plants that contains it

• Ardisia crenata
• Ardisia japonica
• Ardisia mamillata
• Myrsine pellucida

Cross-Links

• PubChem: 44419686
• NPASS: NPC158367
• ChEMBL: CHEMBL374093
• LOTUS: LTS0081239
• wikiData: Q105166111