Methyl 7-(hydroxymethyl)-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,7,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate

Details

• Internal ID: fed753e4-96ce-4790-961f-d7763ba78c25
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: methyl 7-(hydroxymethyl)-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,7,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
• SMILES (Canonical): COC(=O)C1=COC(C2C1C=CC2CO)OC3C(C(C(C(O3)CO)O)O)O
• SMILES (Isomeric): COC(=O)C1=COC(C2C1C=CC2CO)OC3C(C(C(C(O3)CO)O)O)O
• InChI: InChI=1S/C17H24O10/c1-24-15(23)9-6-25-16(11-7(4-18)2-3-8(9)11)27-17-14(22)13(21)12(20)10(5-19)26-17/h2-3,6-8,10-14,16-22H,4-5H2,1H3
• InChI Key: SPCURNZYGRLEBA-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₄O₁₀
• Molecular Weight: 388.40 g/mol
• Exact Mass: 388.13694696 g/mol
• Topological Polar Surface Area (TPSA): 155.00 Ų
• XlogP: -1.70
• Atomic LogP (AlogP): -2.37
• H-Bond Acceptor: 10
• 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	-	0.5197	51.97%
Caco-2	-	0.8736	87.36%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.6687	66.87%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7598	75.98%
OATP1B3 inhibitior	+	0.9687	96.87%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9495	94.95%
P-glycoprotein inhibitior	-	0.8949	89.49%
P-glycoprotein substrate	-	0.8647	86.47%
CYP3A4 substrate	+	0.5727	57.27%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8633	86.33%
CYP3A4 inhibition	-	0.9584	95.84%
CYP2C9 inhibition	-	0.9103	91.03%
CYP2C19 inhibition	-	0.8324	83.24%
CYP2D6 inhibition	-	0.9035	90.35%
CYP1A2 inhibition	-	0.8940	89.40%
CYP2C8 inhibition	-	0.5714	57.14%
CYP inhibitory promiscuity	-	0.7100	71.00%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6732	67.32%
Eye corrosion	-	0.9865	98.65%
Eye irritation	-	0.9741	97.41%
Skin irritation	-	0.8055	80.55%
Skin corrosion	-	0.9549	95.49%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7026	70.26%
Micronuclear	-	0.7241	72.41%
Hepatotoxicity	-	0.7726	77.26%
skin sensitisation	-	0.8843	88.43%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	+	0.6550	65.50%
Acute Oral Toxicity (c)	III	0.4889	48.89%
Estrogen receptor binding	-	0.4863	48.63%
Androgen receptor binding	-	0.5345	53.45%
Thyroid receptor binding	-	0.5919	59.19%
Glucocorticoid receptor binding	-	0.6350	63.50%
Aromatase binding	-	0.5090	50.90%
PPAR gamma	-	0.5224	52.24%
Honey bee toxicity	-	0.9000	90.00%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.7800	78.00%
Fish aquatic toxicity	-	0.6246	62.46%

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	97.02%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.40%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	92.29%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.58%	99.17%
CHEMBL2581	P07339	Cathepsin D	86.86%	98.95%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.30%	96.00%
CHEMBL221	P23219	Cyclooxygenase-1	85.45%	90.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.40%	86.33%
CHEMBL4208	P20618	Proteasome component C5	81.87%	90.00%

Plants that contains it

• Feretia apodanthera
• Gardenia jasminoides

Cross-Links

• PubChem: 72821258
• LOTUS: LTS0263698
• wikiData: Q105257362