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

Details

• Internal ID: c87b5862-7e61-487f-84c7-49057e2f54ab
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: methyl 7-formyl-7-hydroxy-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,7a-dihydro-1H-cyclopenta[c]pyran-4-carboxylate
• SMILES (Canonical): COC(=O)C1=COC(C2C1C=CC2(C=O)O)OC3C(C(C(C(O3)CO)O)O)O
• SMILES (Isomeric): COC(=O)C1=COC(C2C1C=CC2(C=O)O)OC3C(C(C(C(O3)CO)O)O)O
• InChI: InChI=1S/C17H22O11/c1-25-14(23)8-5-26-15(10-7(8)2-3-17(10,24)6-19)28-16-13(22)12(21)11(20)9(4-18)27-16/h2-3,5-7,9-13,15-16,18,20-22,24H,4H2,1H3
• InChI Key: KUPAPVWGAYWLHS-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₂O₁₁
• Molecular Weight: 402.30 g/mol
• Exact Mass: 402.11621151 g/mol
• Topological Polar Surface Area (TPSA): 172.00 Ų
• XlogP: -2.40
• Atomic LogP (AlogP): -3.05
• H-Bond Acceptor: 11
• H-Bond Donor: 5
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5642	56.42%
Caco-2	-	0.8907	89.07%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.7202	72.02%
OATP2B1 inhibitior	-	0.8540	85.40%
OATP1B1 inhibitior	+	0.7719	77.19%
OATP1B3 inhibitior	+	0.9630	96.30%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.9082	90.82%
P-glycoprotein inhibitior	-	0.8301	83.01%
P-glycoprotein substrate	-	0.7309	73.09%
CYP3A4 substrate	+	0.6436	64.36%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8652	86.52%
CYP3A4 inhibition	-	0.9363	93.63%
CYP2C9 inhibition	-	0.8840	88.40%
CYP2C19 inhibition	-	0.8757	87.57%
CYP2D6 inhibition	-	0.9304	93.04%
CYP1A2 inhibition	-	0.9098	90.98%
CYP2C8 inhibition	+	0.5092	50.92%
CYP inhibitory promiscuity	-	0.8337	83.37%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6296	62.96%
Eye corrosion	-	0.9867	98.67%
Eye irritation	-	0.9537	95.37%
Skin irritation	-	0.7551	75.51%
Skin corrosion	-	0.9424	94.24%
Ames mutagenesis	+	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6493	64.93%
Micronuclear	-	0.5741	57.41%
Hepatotoxicity	-	0.7816	78.16%
skin sensitisation	-	0.8677	86.77%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	+	0.6108	61.08%
Acute Oral Toxicity (c)	III	0.4652	46.52%
Estrogen receptor binding	+	0.6384	63.84%
Androgen receptor binding	-	0.5110	51.10%
Thyroid receptor binding	-	0.5423	54.23%
Glucocorticoid receptor binding	+	0.5557	55.57%
Aromatase binding	-	0.5346	53.46%
PPAR gamma	-	0.5728	57.28%
Honey bee toxicity	-	0.8321	83.21%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7300	73.00%
Fish aquatic toxicity	-	0.4915	49.15%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.96%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.10%	91.11%
CHEMBL4208	P20618	Proteasome component C5	91.36%	90.00%
CHEMBL3401	O75469	Pregnane X receptor	90.59%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.88%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	87.43%	96.00%
CHEMBL2581	P07339	Cathepsin D	85.65%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.39%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.28%	89.00%
CHEMBL5028	O14672	ADAM10	82.13%	97.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.38%	99.17%

Plants that contains it

• Aidia canthioides
• Allamanda schottii
• Cordiera sessilis

Cross-Links

• PubChem: 162963050
• LOTUS: LTS0249694
• wikiData: Q105146278