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

Details

• Internal ID: eb6980a0-2d50-4230-9463-ad5d4cd83639
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: methyl 7-acetyloxy-5-hydroxy-7-methyl-1-[3,4,5-trihydroxy-6-[[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylate
• SMILES (Canonical): CC(=O)OC1(CC(C2C1C(OC=C2C(=O)OC)OC3C(C(C(C(O3)COC4C(C(C(C(O4)CO)O)O)O)O)O)O)O)C
• SMILES (Isomeric): CC(=O)OC1(CC(C2C1C(OC=C2C(=O)OC)OC3C(C(C(C(O3)COC4C(C(C(C(O4)CO)O)O)O)O)O)O)O)C
• InChI: InChI=1S/C25H38O17/c1-8(27)42-25(2)4-10(28)13-9(21(35)36-3)6-37-22(14(13)25)41-24-20(34)18(32)16(30)12(40-24)7-38-23-19(33)17(31)15(29)11(5-26)39-23/h6,10-20,22-24,26,28-34H,4-5,7H2,1-3H3
• InChI Key: ZQEDPNMGPBEOEA-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₈O₁₇
• Molecular Weight: 610.60 g/mol
• Exact Mass: 610.21089974 g/mol
• Topological Polar Surface Area (TPSA): 261.00 Ų
• XlogP: -4.20
• Atomic LogP (AlogP): -4.64
• H-Bond Acceptor: 17
• H-Bond Donor: 8
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5481	54.81%
Caco-2	-	0.8817	88.17%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.6058	60.58%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7673	76.73%
OATP1B3 inhibitior	+	0.9314	93.14%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.8006	80.06%
P-glycoprotein inhibitior	-	0.5175	51.75%
P-glycoprotein substrate	-	0.5937	59.37%
CYP3A4 substrate	+	0.6725	67.25%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8839	88.39%
CYP3A4 inhibition	-	0.9060	90.60%
CYP2C9 inhibition	-	0.8998	89.98%
CYP2C19 inhibition	-	0.9085	90.85%
CYP2D6 inhibition	-	0.9427	94.27%
CYP1A2 inhibition	-	0.9168	91.68%
CYP2C8 inhibition	+	0.4673	46.73%
CYP inhibitory promiscuity	-	0.9228	92.28%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5869	58.69%
Eye corrosion	-	0.9890	98.90%
Eye irritation	-	0.9345	93.45%
Skin irritation	-	0.6962	69.62%
Skin corrosion	-	0.9418	94.18%
Ames mutagenesis	-	0.5637	56.37%
Human Ether-a-go-go-Related Gene inhibition	+	0.6734	67.34%
Micronuclear	-	0.6900	69.00%
Hepatotoxicity	-	0.7995	79.95%
skin sensitisation	-	0.8657	86.57%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	+	0.7679	76.79%
Acute Oral Toxicity (c)	III	0.5219	52.19%
Estrogen receptor binding	+	0.7171	71.71%
Androgen receptor binding	+	0.5811	58.11%
Thyroid receptor binding	-	0.5655	56.55%
Glucocorticoid receptor binding	+	0.5879	58.79%
Aromatase binding	+	0.5768	57.68%
PPAR gamma	+	0.5790	57.90%
Honey bee toxicity	-	0.7474	74.74%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.7500	75.00%
Fish aquatic toxicity	-	0.3854	38.54%

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	98.84%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.83%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.62%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.87%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.63%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	89.37%	94.73%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	86.03%	96.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.77%	97.09%
CHEMBL4208	P20618	Proteasome component C5	84.74%	90.00%
CHEMBL5255	O00206	Toll-like receptor 4	84.50%	92.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.82%	89.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	83.73%	95.50%
CHEMBL221	P23219	Cyclooxygenase-1	82.68%	90.17%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.19%	96.00%
CHEMBL5028	O14672	ADAM10	82.17%	97.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.06%	95.89%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.19%	95.83%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	80.62%	96.90%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.53%	94.33%

Plants that contains it

• Phlomoides rotata

Cross-Links

• PubChem: 162930371
• LOTUS: LTS0110079
• wikiData: Q105381410