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

Details

• Internal ID: 41a73f5d-cc99-4473-be66-0de12ba0b96a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: methyl 5-hydroxy-7-(methylsulfanylcarbonyloxymethyl)-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
• SMILES (Canonical): COC(=O)C1=COC(C2C1C(C=C2COC(=O)SC)O)OC3C(C(C(C(O3)CO)O)O)O
• SMILES (Isomeric): COC(=O)C1=COC(C2C1C(C=C2COC(=O)SC)O)OC3C(C(C(C(O3)CO)O)O)O
• InChI: InChI=1S/C19H26O12S/c1-27-16(25)8-6-28-17(31-18-15(24)14(23)13(22)10(4-20)30-18)11-7(3-9(21)12(8)11)5-29-19(26)32-2/h3,6,9-15,17-18,20-24H,4-5H2,1-2H3
• InChI Key: JNDNZIPLLDTLQK-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₆O₁₂S
• Molecular Weight: 478.50 g/mol
• Exact Mass: 478.11449743 g/mol
• Topological Polar Surface Area (TPSA): 207.00 Ų
• XlogP: -1.90
• Atomic LogP (AlogP): -1.75
• H-Bond Acceptor: 13
• H-Bond Donor: 5
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5183	51.83%
Caco-2	-	0.8546	85.46%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.6642	66.42%
OATP2B1 inhibitior	-	0.8622	86.22%
OATP1B1 inhibitior	+	0.7938	79.38%
OATP1B3 inhibitior	+	0.9391	93.91%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.8406	84.06%
P-glycoprotein inhibitior	-	0.7541	75.41%
P-glycoprotein substrate	-	0.7274	72.74%
CYP3A4 substrate	+	0.6352	63.52%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8617	86.17%
CYP3A4 inhibition	-	0.7989	79.89%
CYP2C9 inhibition	-	0.8246	82.46%
CYP2C19 inhibition	-	0.7321	73.21%
CYP2D6 inhibition	-	0.8907	89.07%
CYP1A2 inhibition	-	0.8366	83.66%
CYP2C8 inhibition	+	0.5000	50.00%
CYP inhibitory promiscuity	-	0.6584	65.84%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6533	65.33%
Eye corrosion	-	0.9852	98.52%
Eye irritation	-	0.9480	94.80%
Skin irritation	-	0.7806	78.06%
Skin corrosion	-	0.9403	94.03%
Ames mutagenesis	-	0.5537	55.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.3936	39.36%
Micronuclear	-	0.5400	54.00%
Hepatotoxicity	-	0.7625	76.25%
skin sensitisation	-	0.8473	84.73%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	+	0.8767	87.67%
Acute Oral Toxicity (c)	III	0.5265	52.65%
Estrogen receptor binding	+	0.7662	76.62%
Androgen receptor binding	+	0.5335	53.35%
Thyroid receptor binding	-	0.5216	52.16%
Glucocorticoid receptor binding	-	0.5718	57.18%
Aromatase binding	+	0.5414	54.14%
PPAR gamma	-	0.5215	52.15%
Honey bee toxicity	-	0.6937	69.37%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.7200	72.00%
Fish aquatic toxicity	+	0.7878	78.78%

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	96.31%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.43%	99.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.37%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	90.02%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.06%	86.33%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.27%	94.33%

Plants that contains it

• Paederia foetida
• Saprosma scortechinii

Cross-Links

• PubChem: 20203908
• LOTUS: LTS0267258
• wikiData: Q105131841