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

Details

• Internal ID: 86937bb4-5ec4-4002-a45f-5e5461f07bfc
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: [(2S,6R)-8-[(1R,4aS,7R,7aS)-7-hydroxy-7-methyl-1-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carbonyl]oxy-2,6-dimethyloctyl] (1S,4aR,7R,7aS)-7-hydroxy-7-methyl-1-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-3-carboxylate
• SMILES (Canonical): CC(CCCC(C)COC(=O)C1=CC2CCC(C2C(O1)OC3C(C(C(C(O3)CO)O)O)O)(C)O)CCOC(=O)C4=COC(C5C4CCC5(C)O)OC6C(C(C(C(O6)CO)O)O)O
• SMILES (Isomeric): C[C@H](CCC[C@H](C)COC(=O)C1=C[C@H]2CC[C@@]([C@H]2[C@@H](O1)O[C@@H]3[C@H]([C@@H]([C@H]([C@@H](O3)CO)O)O)O)(C)O)CCOC(=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(10-13-55-35(51)23-18-57-37(28-22(23)9-12-42(28,4)54)61-39-33(49)31(47)29(45)25(15-43)59-39)6-5-7-20(2)17-56-36(52)24-14-21-8-11-41(3,53)27(21)38(58-24)62-40-34(50)32(48)30(46)26(16-44)60-40/h14,18-22,25-34,37-40,43-50,53-54H,5-13,15-17H2,1-4H3/t19-,20+,21-,22-,25+,26+,27-,28-,29+,30+,31-,32-,33+,34+,37-,38+,39-,40-,41-,42-/m1/s1
• InChI Key: RBFJXCYMNQQEGC-MQOXPCDNSA-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: 0.40
• 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	-	0.8702	87.02%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.8033	80.33%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7771	77.71%
OATP1B3 inhibitior	+	0.8903	89.03%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.5798	57.98%
BSEP inhibitior	+	0.8498	84.98%
P-glycoprotein inhibitior	+	0.7435	74.35%
P-glycoprotein substrate	+	0.5994	59.94%
CYP3A4 substrate	+	0.7241	72.41%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8805	88.05%
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	+	0.6374	63.74%
CYP inhibitory promiscuity	-	0.9671	96.71%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6448	64.48%
Eye corrosion	-	0.9914	99.14%
Eye irritation	-	0.9052	90.52%
Skin irritation	+	0.5261	52.61%
Skin corrosion	-	0.9451	94.51%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7269	72.69%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	-	0.8000	80.00%
skin sensitisation	-	0.9328	93.28%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.6622	66.22%
Acute Oral Toxicity (c)	I	0.5806	58.06%
Estrogen receptor binding	+	0.8284	82.84%
Androgen receptor binding	+	0.7109	71.09%
Thyroid receptor binding	+	0.5202	52.02%
Glucocorticoid receptor binding	+	0.7699	76.99%
Aromatase binding	+	0.6862	68.62%
PPAR gamma	+	0.7829	78.29%
Honey bee toxicity	-	0.7716	77.16%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7150	71.50%
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	98.60%	96.09%
CHEMBL220	P22303	Acetylcholinesterase	96.72%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.58%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.05%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.80%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.63%	94.45%
CHEMBL2581	P07339	Cathepsin D	88.66%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.56%	95.89%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	88.29%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.15%	100.00%
CHEMBL221	P23219	Cyclooxygenase-1	87.53%	90.17%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	87.47%	96.21%
CHEMBL5255	O00206	Toll-like receptor 4	86.24%	92.50%
CHEMBL4227	P25090	Lipoxin A4 receptor	85.86%	100.00%
CHEMBL226	P30542	Adenosine A1 receptor	83.89%	95.93%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.65%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.51%	99.17%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	83.12%	89.05%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.04%	96.00%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	82.71%	96.90%
CHEMBL218	P21554	Cannabinoid CB1 receptor	82.47%	96.61%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.18%	89.00%

Plants that contains it

• Premna odorata

Cross-Links

• PubChem: 163009628
• LOTUS: LTS0043580
• wikiData: Q105233087