Operculinoside B

Details

• Internal ID: 6512a640-e945-430e-b1d5-6b3715d515fa
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: (2R,3R,4S,5S,6R)-2-[[(2S,5S)-5-[(3S,5R,8R,9R,10R,13R,14R,16R,17R)-3-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-16-hydroxy-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-5-methyl-2-propan-2-yloxolan-2-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): CC(C)C1(CCC(O1)(C)C2C3CCC4C5(CCC(C(C5CCC4(C3(CC2O)C)C)(C)C)OC6C(C(C(C(O6)CO)O)O)OC7C(C(C(C(O7)CO)O)O)O)C)COC8C(C(C(C(O8)CO)O)O)O
• SMILES (Isomeric): CC(C)[C@@]1(CC[C@@](O1)(C)[C@@H]2[C@H]3CC[C@@H]4[C@]5(CC[C@@H](C([C@@H]5CC[C@]4([C@@]3(C[C@H]2O)C)C)(C)C)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)C)CO[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O
• InChI: InChI=1S/C49H84O19/c1-22(2)49(21-62-41-38(60)35(57)32(54)25(18-50)63-41)16-15-48(8,68-49)31-23-9-10-29-45(5)13-12-30(44(3,4)28(45)11-14-46(29,6)47(23,7)17-24(31)53)66-43-40(37(59)34(56)27(20-52)65-43)67-42-39(61)36(58)33(55)26(19-51)64-42/h22-43,50-61H,9-21H2,1-8H3/t23-,24-,25-,26-,27-,28+,29-,30+,31-,32-,33-,34-,35+,36+,37+,38-,39-,40-,41-,42+,43+,45+,46-,47-,48+,49-/m1/s1
• InChI Key: OISDMADOIFBDNZ-XIWGVEJXSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₉H₈₄O₁₉
• Molecular Weight: 977.20 g/mol
• Exact Mass: 976.56068045 g/mol
• Topological Polar Surface Area (TPSA): 307.00 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): -0.57
• H-Bond Acceptor: 19
• H-Bond Donor: 12
• Rotatable Bonds: 12

Synonyms

• RefChem:168339
• (2R,3R,4S,5S,6R)-2-(((2S,5S)-5-((3S,5R,8R,9R,10R,13R,14R,16R,17R)-3-((2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxyoxan-2-yl)oxy-16-hydroxy-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta(a)phenanthren-17-yl)-5-methyl-2-propan-2-yloxolan-2-yl)methoxy)-6-(hydroxymethyl)oxane-3,4,5-triol
• (2R,3R,4S,5S,6R)-2-[[(2S,5S)-5-[(3S,5R,8R,9R,10R,13R,14R,16R,17R)-3-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-16-hydroxy-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-5-methyl-2-propan-2-yloxolan-2-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• CHEBI:69310
• CHEMBL1910786
• Q27137651

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6445	64.45%
Caco-2	-	0.8872	88.72%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.7384	73.84%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8489	84.89%
OATP1B3 inhibitior	+	0.9365	93.65%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	+	0.6535	65.35%
P-glycoprotein inhibitior	+	0.7527	75.27%
P-glycoprotein substrate	-	0.6283	62.83%
CYP3A4 substrate	+	0.7419	74.19%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8278	82.78%
CYP3A4 inhibition	-	0.9134	91.34%
CYP2C9 inhibition	-	0.8836	88.36%
CYP2C19 inhibition	-	0.8938	89.38%
CYP2D6 inhibition	-	0.9488	94.88%
CYP1A2 inhibition	-	0.9271	92.71%
CYP2C8 inhibition	+	0.6484	64.84%
CYP inhibitory promiscuity	-	0.9430	94.30%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6251	62.51%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.9021	90.21%
Skin irritation	-	0.7136	71.36%
Skin corrosion	-	0.9502	95.02%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8070	80.70%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	-	0.8031	80.31%
skin sensitisation	-	0.9311	93.11%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	-	0.7927	79.27%
Acute Oral Toxicity (c)	I	0.7469	74.69%
Estrogen receptor binding	+	0.7750	77.50%
Androgen receptor binding	+	0.7593	75.93%
Thyroid receptor binding	-	0.5384	53.84%
Glucocorticoid receptor binding	+	0.6750	67.50%
Aromatase binding	+	0.6463	64.63%
PPAR gamma	+	0.7565	75.65%
Honey bee toxicity	-	0.5818	58.18%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.8453	84.53%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.54%	96.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	97.27%	96.61%
CHEMBL226	P30542	Adenosine A1 receptor	93.81%	95.93%
CHEMBL4302	P08183	P-glycoprotein 1	91.69%	92.98%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	90.78%	92.86%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.64%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.13%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.13%	95.89%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	89.76%	96.21%
CHEMBL2581	P07339	Cathepsin D	89.29%	98.95%
CHEMBL2815	P04629	Nerve growth factor receptor Trk-A	89.06%	87.16%
CHEMBL220	P22303	Acetylcholinesterase	88.88%	94.45%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	88.75%	96.38%
CHEMBL1937	Q92769	Histone deacetylase 2	88.73%	94.75%
CHEMBL237	P41145	Kappa opioid receptor	88.41%	98.10%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.85%	100.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	87.12%	97.14%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.90%	97.25%
CHEMBL2996	Q05655	Protein kinase C delta	86.84%	97.79%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	86.26%	95.58%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	86.02%	82.50%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	85.97%	95.50%
CHEMBL3714130	P46095	G-protein coupled receptor 6	85.96%	97.36%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	85.10%	91.24%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.81%	92.62%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	84.73%	82.69%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	84.59%	95.71%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.57%	95.89%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	83.42%	89.05%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.37%	94.45%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	83.33%	95.83%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	83.20%	100.00%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	82.45%	100.00%
CHEMBL1974	P36888	Tyrosine-protein kinase receptor FLT3	81.95%	91.83%
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	81.59%	96.09%
CHEMBL2534	O15530	3-phosphoinositide dependent protein kinase-1	81.34%	95.36%
CHEMBL5255	O00206	Toll-like receptor 4	80.78%	92.50%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.49%	94.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.23%	93.04%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	80.00%	92.88%

Plants that contains it

• Operculina turpethum

Cross-Links

• PubChem: 54671548
• NPASS: NPC304011
• LOTUS: LTS0070889
• wikiData: Q27137651