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

Details

• Internal ID: 167a5147-73c7-460c-bf3b-4dd360fb12e4
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: methyl 1-[5-acetyloxy-4-hydroxy-3-(3-hydroxybenzoyl)oxy-6-(hydroxymethyl)oxan-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)CO)OC(=O)C)O)OC(=O)C4=CC(=CC=C4)O)O
• SMILES (Isomeric): CC1C(CC2C1C(OC=C2C(=O)OC)OC3C(C(C(C(O3)CO)OC(=O)C)O)OC(=O)C4=CC(=CC=C4)O)O
• InChI: InChI=1S/C26H32O13/c1-11-17(30)8-15-16(24(33)34-3)10-35-25(19(11)15)39-26-22(38-23(32)13-5-4-6-14(29)7-13)20(31)21(36-12(2)28)18(9-27)37-26/h4-7,10-11,15,17-22,25-27,29-31H,8-9H2,1-3H3
• InChI Key: LXDIJQSXQCZMRW-UHFFFAOYSA-N
• Popularity: 1 reference 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	+	0.9390	93.90%
Caco-2	-	0.8599	85.99%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.6204	62.04%
OATP2B1 inhibitior	-	0.8641	86.41%
OATP1B1 inhibitior	-	0.3526	35.26%
OATP1B3 inhibitior	+	0.8912	89.12%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.6665	66.65%
P-glycoprotein inhibitior	-	0.4318	43.18%
P-glycoprotein substrate	+	0.6245	62.45%
CYP3A4 substrate	+	0.7015	70.15%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8733	87.33%
CYP3A4 inhibition	-	0.7052	70.52%
CYP2C9 inhibition	-	0.8178	81.78%
CYP2C19 inhibition	-	0.8269	82.69%
CYP2D6 inhibition	-	0.8703	87.03%
CYP1A2 inhibition	-	0.7307	73.07%
CYP2C8 inhibition	+	0.6993	69.93%
CYP inhibitory promiscuity	-	0.6807	68.07%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5699	56.99%
Eye corrosion	-	0.9898	98.98%
Eye irritation	-	0.9386	93.86%
Skin irritation	-	0.7161	71.61%
Skin corrosion	-	0.9532	95.32%
Ames mutagenesis	+	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6578	65.78%
Micronuclear	-	0.5700	57.00%
Hepatotoxicity	-	0.5442	54.42%
skin sensitisation	-	0.8328	83.28%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	-	0.6866	68.66%
Acute Oral Toxicity (c)	I	0.3948	39.48%
Estrogen receptor binding	+	0.8066	80.66%
Androgen receptor binding	+	0.5725	57.25%
Thyroid receptor binding	+	0.5188	51.88%
Glucocorticoid receptor binding	+	0.6473	64.73%
Aromatase binding	-	0.5111	51.11%
PPAR gamma	+	0.6011	60.11%
Honey bee toxicity	-	0.7744	77.44%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.7400	74.00%
Fish aquatic toxicity	+	0.8654	86.54%

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	98.20%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.55%	96.09%
CHEMBL2581	P07339	Cathepsin D	95.78%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	95.46%	94.73%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.26%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.04%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.55%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.13%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.34%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	91.17%	91.49%
CHEMBL4208	P20618	Proteasome component C5	90.76%	90.00%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	89.76%	95.83%
CHEMBL340	P08684	Cytochrome P450 3A4	87.30%	91.19%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	87.26%	96.95%
CHEMBL2996	Q05655	Protein kinase C delta	86.57%	97.79%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.66%	94.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.18%	95.89%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.56%	95.89%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.33%	86.92%
CHEMBL2535	P11166	Glucose transporter	82.16%	98.75%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.08%	91.07%
CHEMBL2782	P35610	Acyl coenzyme A:cholesterol acyltransferase 1	81.79%	91.65%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	81.65%	89.67%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	81.40%	97.21%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.32%	99.23%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	80.30%	81.11%

Plants that contains it

• Gentiana verna

Cross-Links

• PubChem: 14487126
• LOTUS: LTS0252862
• wikiData: Q105158793