[6-[2-(3,4-dihydroxyphenyl)ethoxy]-3-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-5-hydroxy-4-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl]methyl 7-hydroxy-7-methyl-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylate

Details

• Internal ID: 6fab7a36-c9e8-403a-9030-ace161479714
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: [6-[2-(3,4-dihydroxyphenyl)ethoxy]-3-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-5-hydroxy-4-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl]methyl 7-hydroxy-7-methyl-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(OC(C2OC(=O)C=CC3=CC(=C(C=C3)O)O)COC(=O)C4=COC(C5C4CCC5(C)O)OC6C(C(C(C(O6)CO)O)O)O)OCCC7=CC(=C(C=C7)O)O)O)O)O)O
• SMILES (Isomeric): CC1C(C(C(C(O1)OC2C(C(OC(C2OC(=O)C=CC3=CC(=C(C=C3)O)O)COC(=O)C4=COC(C5C4CCC5(C)O)OC6C(C(C(C(O6)CO)O)O)O)OCCC7=CC(=C(C=C7)O)O)O)O)O)O
• InChI: InChI=1S/C45H58O24/c1-18-31(52)33(54)35(56)43(64-18)68-39-37(58)42(61-12-10-20-4-7-24(48)26(50)14-20)66-28(38(39)67-29(51)8-5-19-3-6-23(47)25(49)13-19)17-62-40(59)22-16-63-41(30-21(22)9-11-45(30,2)60)69-44-36(57)34(55)32(53)27(15-46)65-44/h3-8,13-14,16,18,21,27-28,30-39,41-44,46-50,52-58,60H,9-12,15,17H2,1-2H3
• InChI Key: LPZNWBWAJWXXLI-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₅H₅₈O₂₄
• Molecular Weight: 982.90 g/mol
• Exact Mass: 982.33180271 g/mol
• Topological Polar Surface Area (TPSA): 380.00 Ų
• XlogP: -1.70
• Atomic LogP (AlogP): -2.63
• H-Bond Acceptor: 24
• H-Bond Donor: 13
• Rotatable Bonds: 15

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7562	75.62%
Caco-2	-	0.8752	87.52%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.6892	68.92%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7913	79.13%
OATP1B3 inhibitior	+	0.9176	91.76%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.7879	78.79%
BSEP inhibitior	+	0.8835	88.35%
P-glycoprotein inhibitior	+	0.7258	72.58%
P-glycoprotein substrate	+	0.6574	65.74%
CYP3A4 substrate	+	0.7378	73.78%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8747	87.47%
CYP3A4 inhibition	-	0.8835	88.35%
CYP2C9 inhibition	-	0.7993	79.93%
CYP2C19 inhibition	-	0.8464	84.64%
CYP2D6 inhibition	-	0.8966	89.66%
CYP1A2 inhibition	-	0.7150	71.50%
CYP2C8 inhibition	+	0.8433	84.33%
CYP inhibitory promiscuity	-	0.8654	86.54%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6405	64.05%
Eye corrosion	-	0.9909	99.09%
Eye irritation	-	0.9031	90.31%
Skin irritation	-	0.7072	70.72%
Skin corrosion	-	0.9315	93.15%
Ames mutagenesis	-	0.7270	72.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7447	74.47%
Micronuclear	-	0.6900	69.00%
Hepatotoxicity	-	0.9250	92.50%
skin sensitisation	-	0.8713	87.13%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	-	0.9398	93.98%
Acute Oral Toxicity (c)	I	0.4432	44.32%
Estrogen receptor binding	+	0.8059	80.59%
Androgen receptor binding	+	0.5448	54.48%
Thyroid receptor binding	+	0.5974	59.74%
Glucocorticoid receptor binding	+	0.6529	65.29%
Aromatase binding	+	0.5309	53.09%
PPAR gamma	+	0.7866	78.66%
Honey bee toxicity	-	0.6455	64.55%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9725	97.25%

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	99.78%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	98.49%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.92%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	97.53%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.53%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.86%	97.09%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	93.71%	86.92%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	92.00%	96.00%
CHEMBL218	P21554	Cannabinoid CB1 receptor	91.17%	96.61%
CHEMBL4208	P20618	Proteasome component C5	91.10%	90.00%
CHEMBL226	P30542	Adenosine A1 receptor	91.00%	95.93%
CHEMBL3194	P02766	Transthyretin	90.77%	90.71%
CHEMBL2581	P07339	Cathepsin D	89.82%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.36%	95.89%
CHEMBL5255	O00206	Toll-like receptor 4	89.17%	92.50%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	88.66%	95.89%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.81%	92.94%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.70%	94.45%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	87.42%	94.62%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.11%	99.17%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	85.59%	80.78%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.54%	96.95%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	85.05%	94.80%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	84.39%	95.83%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.09%	100.00%
CHEMBL3401	O75469	Pregnane X receptor	82.15%	94.73%

Plants that contains it

• Premna corymbosa

Cross-Links

• PubChem: 163060190
• LOTUS: LTS0271687
• wikiData: Q105155436