Methyl 1-[6-(acetyloxymethyl)-4,5-dihydroxy-3-(3-hydroxybenzoyl)oxyoxan-2-yl]oxy-6-hydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate

Details

• Internal ID: d984054a-cccf-4236-9308-7c59a476024e
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: methyl 1-[6-(acetyloxymethyl)-4,5-dihydroxy-3-(3-hydroxybenzoyl)oxyoxan-2-yl]oxy-6-hydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate
• SMILES (Canonical): CC1C(CC2C1C(OC=C2C(=O)OC)OC3C(C(C(C(O3)COC(=O)C)O)O)OC(=O)C4=CC(=CC=C4)O)O
• SMILES (Isomeric): CC1C(CC2C1C(OC=C2C(=O)OC)OC3C(C(C(C(O3)COC(=O)C)O)O)OC(=O)C4=CC(=CC=C4)O)O
• InChI: InChI=1S/C26H32O13/c1-11-17(29)8-15-16(24(33)34-3)9-36-25(19(11)15)39-26-22(38-23(32)13-5-4-6-14(28)7-13)21(31)20(30)18(37-26)10-35-12(2)27/h4-7,9,11,15,17-22,25-26,28-31H,8,10H2,1-3H3
• InChI Key: QZOWXVWZQQHCEK-UHFFFAOYSA-N
• Popularity: 0 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): 188.00 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): -0.01
• H-Bond Acceptor: 13
• H-Bond Donor: 4
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9135	91.35%
Caco-2	-	0.8531	85.31%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.6423	64.23%
OATP2B1 inhibitior	-	0.8648	86.48%
OATP1B1 inhibitior	-	0.3518	35.18%
OATP1B3 inhibitior	+	0.9021	90.21%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.6269	62.69%
P-glycoprotein inhibitior	-	0.4382	43.82%
P-glycoprotein substrate	+	0.5933	59.33%
CYP3A4 substrate	+	0.7008	70.08%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8745	87.45%
CYP3A4 inhibition	-	0.8677	86.77%
CYP2C9 inhibition	-	0.8111	81.11%
CYP2C19 inhibition	-	0.8379	83.79%
CYP2D6 inhibition	-	0.8785	87.85%
CYP1A2 inhibition	-	0.7090	70.90%
CYP2C8 inhibition	+	0.7390	73.90%
CYP inhibitory promiscuity	-	0.8412	84.12%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6219	62.19%
Eye corrosion	-	0.9903	99.03%
Eye irritation	-	0.9345	93.45%
Skin irritation	-	0.7357	73.57%
Skin corrosion	-	0.9494	94.94%
Ames mutagenesis	+	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4552	45.52%
Micronuclear	-	0.5241	52.41%
Hepatotoxicity	-	0.7015	70.15%
skin sensitisation	-	0.8420	84.20%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	-	0.8605	86.05%
Acute Oral Toxicity (c)	III	0.4368	43.68%
Estrogen receptor binding	+	0.7940	79.40%
Androgen receptor binding	+	0.5228	52.28%
Thyroid receptor binding	+	0.5361	53.61%
Glucocorticoid receptor binding	+	0.6740	67.40%
Aromatase binding	-	0.5161	51.61%
PPAR gamma	+	0.5919	59.19%
Honey bee toxicity	-	0.7864	78.64%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.9399	93.99%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	98.25%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.79%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.64%	96.09%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	96.00%	97.21%
CHEMBL3401	O75469	Pregnane X receptor	95.61%	94.73%
CHEMBL2581	P07339	Cathepsin D	94.78%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.67%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.05%	97.09%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	92.82%	96.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.71%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.27%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.90%	99.17%
CHEMBL4208	P20618	Proteasome component C5	91.35%	90.00%
CHEMBL2535	P11166	Glucose transporter	87.70%	98.75%
CHEMBL340	P08684	Cytochrome P450 3A4	86.79%	91.19%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	85.99%	95.83%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.78%	99.23%
CHEMBL2782	P35610	Acyl coenzyme A:cholesterol acyltransferase 1	83.29%	91.65%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.65%	95.89%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.61%	97.25%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.76%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.16%	94.00%

Plants that contains it

• Gentiana verna

Cross-Links

• PubChem: 14487128
• LOTUS: LTS0215487
• wikiData: Q105232253