[(2R,7R)-8-[(1S,4aS,7S,7aS)-7-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carbonyl]oxy-2,7-dimethyloctyl] (1S,4aS,7S,7aS)-7-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylate

Details

• Internal ID: b8a4137e-0f17-4f51-8c38-e2b0ed21ef48
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: [(2R,7R)-8-[(1S,4aS,7S,7aS)-7-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carbonyl]oxy-2,7-dimethyloctyl] (1S,4aS,7S,7aS)-7-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylate
• SMILES (Canonical): CC(CCCCC(C)COC(=O)C1=COC(C2C1CCC2(C)O)OC3C(C(C(C(O3)CO)O)O)O)COC(=O)C4=COC(C5C4CCC5(C)O)OC6C(C(C(C(O6)CO)O)O)O
• SMILES (Isomeric): C[C@H](CCCC[C@@H](C)COC(=O)C1=CO[C@H]([C@H]2[C@@H]1CC[C@]2(C)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)COC(=O)C4=CO[C@H]([C@H]5[C@@H]4CC[C@]5(C)O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O
• InChI: InChI=1S/C42H66O20/c1-19(15-55-35(51)23-17-57-37(27-21(23)9-11-41(27,3)53)61-39-33(49)31(47)29(45)25(13-43)59-39)7-5-6-8-20(2)16-56-36(52)24-18-58-38(28-22(24)10-12-42(28,4)54)62-40-34(50)32(48)30(46)26(14-44)60-40/h17-22,25-34,37-40,43-50,53-54H,5-16H2,1-4H3/t19-,20-,21-,22-,25-,26-,27-,28-,29-,30-,31+,32+,33-,34-,37+,38+,39+,40+,41+,42+/m1/s1
• InChI Key: FLSSLHNUZDULJM-QHIBPMJRSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₂H₆₆O₂₀
• Molecular Weight: 891.00 g/mol
• Exact Mass: 890.41474449 g/mol
• Topological Polar Surface Area (TPSA): 310.00 Ų
• XlogP: -0.10
• Atomic LogP (AlogP): -1.43
• H-Bond Acceptor: 20
• H-Bond Donor: 10
• Rotatable Bonds: 17

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6790	67.90%
Caco-2	-	0.8658	86.58%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.8033	80.33%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7818	78.18%
OATP1B3 inhibitior	+	0.8903	89.03%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.5798	57.98%
BSEP inhibitior	+	0.7644	76.44%
P-glycoprotein inhibitior	+	0.7430	74.30%
P-glycoprotein substrate	-	0.6686	66.86%
CYP3A4 substrate	+	0.6932	69.32%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8720	87.20%
CYP3A4 inhibition	-	0.8984	89.84%
CYP2C9 inhibition	-	0.9204	92.04%
CYP2C19 inhibition	-	0.9387	93.87%
CYP2D6 inhibition	-	0.9545	95.45%
CYP1A2 inhibition	-	0.9218	92.18%
CYP2C8 inhibition	-	0.5844	58.44%
CYP inhibitory promiscuity	-	0.9671	96.71%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6448	64.48%
Eye corrosion	-	0.9914	99.14%
Eye irritation	-	0.9024	90.24%
Skin irritation	+	0.5261	52.61%
Skin corrosion	-	0.9451	94.51%
Ames mutagenesis	-	0.7500	75.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7228	72.28%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	-	0.7875	78.75%
skin sensitisation	-	0.9328	93.28%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	+	0.4618	46.18%
Acute Oral Toxicity (c)	I	0.5806	58.06%
Estrogen receptor binding	+	0.8091	80.91%
Androgen receptor binding	+	0.7461	74.61%
Thyroid receptor binding	+	0.5506	55.06%
Glucocorticoid receptor binding	+	0.7431	74.31%
Aromatase binding	+	0.6552	65.52%
PPAR gamma	+	0.7788	77.88%
Honey bee toxicity	-	0.8438	84.38%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.7250	72.50%
Fish aquatic toxicity	+	0.9442	94.42%

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	98.80%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.16%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.06%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.22%	97.09%
CHEMBL2581	P07339	Cathepsin D	90.80%	98.95%
CHEMBL5255	O00206	Toll-like receptor 4	90.45%	92.50%
CHEMBL4227	P25090	Lipoxin A4 receptor	88.32%	100.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	88.14%	95.89%
CHEMBL218	P21554	Cannabinoid CB1 receptor	87.85%	96.61%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.36%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.28%	94.45%
CHEMBL2996	Q05655	Protein kinase C delta	87.04%	97.79%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.16%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.42%	89.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	83.72%	96.21%
CHEMBL220	P22303	Acetylcholinesterase	82.33%	94.45%
CHEMBL226	P30542	Adenosine A1 receptor	82.30%	95.93%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.27%	96.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.86%	99.17%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	80.64%	91.24%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.44%	93.56%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.44%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.18%	86.33%
CHEMBL2514	O95665	Neurotensin receptor 2	80.15%	100.00%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	80.12%	89.05%

Plants that contains it

• Premna odorata

Cross-Links

• PubChem: 163104001
• LOTUS: LTS0275092
• wikiData: Q104997472