Methyl 1-[3,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-2-yl]oxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate

Details

• Internal ID: 06327ac9-0c91-4bd4-b0d4-ad12f1c06f2f
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: methyl 1-[3,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-2-yl]oxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate
• InChI: InChI=1S/C18H28O9/c1-8-4-5-9-10(16(22)24-3)7-25-17(12(8)9)27-18-14(21)13(20)15(23-2)11(6-19)26-18/h7-9,11-15,17-21H,4-6H2,1-3H3
• InChI Key: LPIDMXWDHVGLDO-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₈O₉
• Molecular Weight: 388.40 g/mol
• Exact Mass: 388.17333247 g/mol
• Topological Polar Surface Area (TPSA): 124.00 Ų
• XlogP: -0.10
• Atomic LogP (AlogP): -0.47
• H-Bond Acceptor: 9
• H-Bond Donor: 3
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7893	78.93%
Caco-2	-	0.7343	73.43%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.7155	71.55%
OATP2B1 inhibitior	-	0.8611	86.11%
OATP1B1 inhibitior	+	0.7930	79.30%
OATP1B3 inhibitior	+	0.9104	91.04%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.8661	86.61%
P-glycoprotein inhibitior	-	0.8497	84.97%
P-glycoprotein substrate	-	0.7259	72.59%
CYP3A4 substrate	+	0.6105	61.05%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8688	86.88%
CYP3A4 inhibition	-	0.9137	91.37%
CYP2C9 inhibition	-	0.8919	89.19%
CYP2C19 inhibition	-	0.8756	87.56%
CYP2D6 inhibition	-	0.9073	90.73%
CYP1A2 inhibition	-	0.7146	71.46%
CYP2C8 inhibition	-	0.6455	64.55%
CYP inhibitory promiscuity	-	0.8341	83.41%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6430	64.30%
Eye corrosion	-	0.9887	98.87%
Eye irritation	-	0.9788	97.88%
Skin irritation	-	0.6357	63.57%
Skin corrosion	-	0.9478	94.78%
Ames mutagenesis	-	0.6024	60.24%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	-	0.6500	65.00%
skin sensitisation	-	0.8883	88.83%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.6270	62.70%
Acute Oral Toxicity (c)	III	0.5021	50.21%
Estrogen receptor binding	+	0.5464	54.64%
Androgen receptor binding	+	0.5422	54.22%
Thyroid receptor binding	-	0.5359	53.59%
Glucocorticoid receptor binding	-	0.6446	64.46%
Aromatase binding	-	0.6036	60.36%
PPAR gamma	-	0.6843	68.43%
Honey bee toxicity	-	0.8842	88.42%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.7500	75.00%
Fish aquatic toxicity	+	0.7128	71.28%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	99.43%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.85%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.70%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.22%	97.09%
CHEMBL2581	P07339	Cathepsin D	90.11%	98.95%
CHEMBL5255	O00206	Toll-like receptor 4	89.50%	92.50%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	87.09%	94.80%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.28%	85.14%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.40%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	82.19%	94.73%
CHEMBL218	P21554	Cannabinoid CB1 receptor	82.03%	96.61%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.46%	89.00%
CHEMBL4208	P20618	Proteasome component C5	81.28%	90.00%
CHEMBL5028	O14672	ADAM10	80.00%	97.50%

Plants that contains it

• Nepeta grandiflora

Cross-Links

• PubChem: 163010302
• LOTUS: LTS0221401
• wikiData: Q105155192