methyl 4a-hydroxy-5-(8-hydroxy-2,6-dimethylocta-2,6-dienoyl)oxy-7-methyl-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5,6,7,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylate

Details

• Internal ID: 66300dcc-f1e6-4319-a1db-105a73bed56d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: methyl 4a-hydroxy-5-(8-hydroxy-2,6-dimethylocta-2,6-dienoyl)oxy-7-methyl-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5,6,7,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylate
• SMILES (Canonical): CC1CC(C2(C1C(OC=C2C(=O)OC)OC3C(C(C(C(O3)CO)O)O)O)O)OC(=O)C(=CCCC(=CCO)C)C
• SMILES (Isomeric): CC1CC(C2(C1C(OC=C2C(=O)OC)OC3C(C(C(C(O3)CO)O)O)O)O)OC(=O)C(=CCCC(=CCO)C)C
• InChI: InChI=1S/C27H40O13/c1-13(8-9-28)6-5-7-14(2)23(33)39-18-10-15(3)19-25(37-12-16(24(34)36-4)27(18,19)35)40-26-22(32)21(31)20(30)17(11-29)38-26/h7-8,12,15,17-22,25-26,28-32,35H,5-6,9-11H2,1-4H3
• InChI Key: SERNEFQQZDUGDV-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₄₀O₁₃
• Molecular Weight: 572.60 g/mol
• Exact Mass: 572.24689133 g/mol
• Topological Polar Surface Area (TPSA): 202.00 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): -0.82
• H-Bond Acceptor: 13
• H-Bond Donor: 6
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6215	62.15%
Caco-2	-	0.8480	84.80%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.8076	80.76%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7745	77.45%
OATP1B3 inhibitior	+	0.8910	89.10%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.6271	62.71%
BSEP inhibitior	+	0.8095	80.95%
P-glycoprotein inhibitior	+	0.6224	62.24%
P-glycoprotein substrate	-	0.5308	53.08%
CYP3A4 substrate	+	0.7014	70.14%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8824	88.24%
CYP3A4 inhibition	-	0.9528	95.28%
CYP2C9 inhibition	-	0.9202	92.02%
CYP2C19 inhibition	-	0.9186	91.86%
CYP2D6 inhibition	-	0.9548	95.48%
CYP1A2 inhibition	-	0.9014	90.14%
CYP2C8 inhibition	+	0.6312	63.12%
CYP inhibitory promiscuity	-	0.9505	95.05%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6483	64.83%
Eye corrosion	-	0.9902	99.02%
Eye irritation	-	0.9402	94.02%
Skin irritation	-	0.5926	59.26%
Skin corrosion	-	0.9462	94.62%
Ames mutagenesis	-	0.6024	60.24%
Human Ether-a-go-go-Related Gene inhibition	+	0.6992	69.92%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	-	0.7184	71.84%
skin sensitisation	-	0.9275	92.75%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.6687	66.87%
Acute Oral Toxicity (c)	I	0.5378	53.78%
Estrogen receptor binding	+	0.7068	70.68%
Androgen receptor binding	+	0.5987	59.87%
Thyroid receptor binding	-	0.5457	54.57%
Glucocorticoid receptor binding	+	0.6328	63.28%
Aromatase binding	+	0.6470	64.70%
PPAR gamma	+	0.6468	64.68%
Honey bee toxicity	-	0.7334	73.34%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9303	93.03%

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	99.06%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.78%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.08%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.03%	97.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	88.14%	96.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.93%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.09%	86.33%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	86.78%	91.24%
CHEMBL3401	O75469	Pregnane X receptor	86.71%	94.73%
CHEMBL5255	O00206	Toll-like receptor 4	86.21%	92.50%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.64%	100.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.14%	92.94%
CHEMBL2581	P07339	Cathepsin D	82.68%	98.95%
CHEMBL4208	P20618	Proteasome component C5	82.67%	90.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.75%	100.00%
CHEMBL218	P21554	Cannabinoid CB1 receptor	81.42%	96.61%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	81.37%	96.90%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	80.69%	92.88%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	80.48%	94.80%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.26%	94.33%
CHEMBL3437	Q16853	Amine oxidase, copper containing	80.13%	94.00%

Plants that contains it

• Penstemon cyathophorus
• Rauvolfia biauriculata
• Rauvolfia sellowii

Cross-Links

• PubChem: 162988114
• LOTUS: LTS0053630
• wikiData: Q104960906