methyl 1-[6-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-7-hydroxy-7-methyl-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylate

Details

• Internal ID: c9cd6cd5-4141-44fe-a44f-79662e1cbd1f
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: methyl 1-[6-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-7-hydroxy-7-methyl-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylate
• InChI: InChI=1S/C26H32O13/c1-26(34)8-7-13-14(23(33)35-2)10-37-24(19(13)26)39-25-22(32)21(31)20(30)17(38-25)11-36-18(29)6-4-12-3-5-15(27)16(28)9-12/h3-6,9-10,13,17,19-22,24-25,27-28,30-32,34H,7-8,11H2,1-2H3
• InChI Key: IMGCLEIFKMJSCC-UHFFFAOYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₂O₁₃
• Molecular Weight: 552.50 g/mol
• Exact Mass: 552.18429107 g/mol
• Topological Polar Surface Area (TPSA): 202.00 Ų
• XlogP: -0.20
• Atomic LogP (AlogP): -0.33
• H-Bond Acceptor: 13
• H-Bond Donor: 6
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8572	85.72%
Caco-2	-	0.8857	88.57%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.6532	65.32%
OATP2B1 inhibitior	-	0.8619	86.19%
OATP1B1 inhibitior	+	0.8056	80.56%
OATP1B3 inhibitior	+	0.9223	92.23%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8819	88.19%
BSEP inhibitior	-	0.5920	59.20%
P-glycoprotein inhibitior	-	0.5314	53.14%
P-glycoprotein substrate	-	0.5892	58.92%
CYP3A4 substrate	+	0.7068	70.68%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8755	87.55%
CYP3A4 inhibition	-	0.8646	86.46%
CYP2C9 inhibition	-	0.7776	77.76%
CYP2C19 inhibition	-	0.8429	84.29%
CYP2D6 inhibition	-	0.8751	87.51%
CYP1A2 inhibition	-	0.6847	68.47%
CYP2C8 inhibition	+	0.8134	81.34%
CYP inhibitory promiscuity	-	0.8512	85.12%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6364	63.64%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.9325	93.25%
Skin irritation	-	0.6832	68.32%
Skin corrosion	-	0.9269	92.69%
Ames mutagenesis	-	0.6570	65.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.4066	40.66%
Micronuclear	-	0.7000	70.00%
Hepatotoxicity	-	0.7351	73.51%
skin sensitisation	-	0.8572	85.72%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.9889	98.89%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	-	0.7938	79.38%
Acute Oral Toxicity (c)	I	0.4989	49.89%
Estrogen receptor binding	+	0.8292	82.92%
Androgen receptor binding	+	0.6578	65.78%
Thyroid receptor binding	+	0.5326	53.26%
Glucocorticoid receptor binding	+	0.7109	71.09%
Aromatase binding	+	0.5499	54.99%
PPAR gamma	+	0.6979	69.79%
Honey bee toxicity	-	0.7884	78.84%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.9552	95.52%

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%
CHEMBL1951	P21397	Monoamine oxidase A	98.49%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.49%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.07%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.24%	89.00%
CHEMBL4208	P20618	Proteasome component C5	92.51%	90.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.49%	97.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	92.21%	96.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.65%	95.89%
CHEMBL5255	O00206	Toll-like receptor 4	87.66%	92.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.96%	100.00%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	84.49%	95.83%
CHEMBL226	P30542	Adenosine A1 receptor	84.41%	95.93%
CHEMBL221	P23219	Cyclooxygenase-1	83.62%	90.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.62%	94.45%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.67%	100.00%
CHEMBL5028	O14672	ADAM10	82.23%	97.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.11%	95.56%
CHEMBL218	P21554	Cannabinoid CB1 receptor	81.79%	96.61%
CHEMBL3401	O75469	Pregnane X receptor	80.91%	94.73%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.75%	92.62%
CHEMBL2581	P07339	Cathepsin D	80.52%	98.95%
CHEMBL3194	P02766	Transthyretin	80.13%	90.71%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.11%	92.94%

Plants that contains it

• Veronica officinalis

Cross-Links

• PubChem: 73798876
• LOTUS: LTS0141013
• wikiData: Q104388621