[4,5-Dihydroxy-6-(hydroxymethyl)-2-[[6-(methylsulfanylcarbonyloxymethyl)-2-oxo-3,9-dioxatricyclo[5.3.1.04,11]undeca-1(10),5-dien-8-yl]oxy]oxan-3-yl] 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: b178112f-1d66-429a-a2aa-10bb7958448d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: [4,5-dihydroxy-6-(hydroxymethyl)-2-[[6-(methylsulfanylcarbonyloxymethyl)-2-oxo-3,9-dioxatricyclo[5.3.1.04,11]undeca-1(10),5-dien-8-yl]oxy]oxan-3-yl] 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): CSC(=O)OCC1=CC(C2C1C(OC=C2C(=O)OC3C(C(C(OC3OC4C5C6C(C=C5COC(=O)SC)OC(=O)C6=CO4)CO)O)O)OC7C(C(C(C(O7)CO)O)O)O)O
• SMILES (Isomeric): CSC(=O)OCC1=CC(C2C1C(OC=C2C(=O)OC3C(C(C(OC3OC4C5C6C(C=C5COC(=O)SC)OC(=O)C6=CO4)CO)O)O)OC7C(C(C(C(O7)CO)O)O)O)O
• InChI: InChI=1S/C36H44O22S2/c1-59-35(47)51-7-11-3-15(39)21-13(9-49-31(19(11)21)57-33-27(44)25(42)23(40)17(5-37)54-33)30(46)56-28-26(43)24(41)18(6-38)55-34(28)58-32-20-12(8-52-36(48)60-2)4-16-22(20)14(10-50-32)29(45)53-16/h3-4,9-10,15-28,31-34,37-44H,5-8H2,1-2H3
• InChI Key: YUOFAUXZZZPWPA-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₄₄O₂₂S₂
• Molecular Weight: 892.90 g/mol
• Exact Mass: 892.17656537 g/mol
• Topological Polar Surface Area (TPSA): 373.00 Ų
• XlogP: -3.00
• Atomic LogP (AlogP): -2.72
• H-Bond Acceptor: 24
• H-Bond Donor: 8
• Rotatable Bonds: 12

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6321	63.21%
Caco-2	-	0.8804	88.04%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.7312	73.12%
OATP2B1 inhibitior	-	0.7227	72.27%
OATP1B1 inhibitior	+	0.7792	77.92%
OATP1B3 inhibitior	+	0.9311	93.11%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.6548	65.48%
P-glycoprotein inhibitior	+	0.7138	71.38%
P-glycoprotein substrate	-	0.5983	59.83%
CYP3A4 substrate	+	0.6820	68.20%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8664	86.64%
CYP3A4 inhibition	-	0.7458	74.58%
CYP2C9 inhibition	-	0.8042	80.42%
CYP2C19 inhibition	-	0.7137	71.37%
CYP2D6 inhibition	-	0.8835	88.35%
CYP1A2 inhibition	-	0.8184	81.84%
CYP2C8 inhibition	+	0.6067	60.67%
CYP inhibitory promiscuity	-	0.5972	59.72%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5598	55.98%
Eye corrosion	-	0.9836	98.36%
Eye irritation	-	0.9089	90.89%
Skin irritation	-	0.7629	76.29%
Skin corrosion	-	0.9370	93.70%
Ames mutagenesis	-	0.5837	58.37%
Human Ether-a-go-go-Related Gene inhibition	+	0.7535	75.35%
Micronuclear	-	0.5400	54.00%
Hepatotoxicity	-	0.7446	74.46%
skin sensitisation	-	0.8417	84.17%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	+	0.6791	67.91%
Acute Oral Toxicity (c)	III	0.5496	54.96%
Estrogen receptor binding	+	0.7799	77.99%
Androgen receptor binding	+	0.7090	70.90%
Thyroid receptor binding	-	0.4904	49.04%
Glucocorticoid receptor binding	+	0.6208	62.08%
Aromatase binding	+	0.5332	53.32%
PPAR gamma	+	0.7047	70.47%
Honey bee toxicity	-	0.6579	65.79%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.8390	83.90%

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	93.78%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.44%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	91.40%	94.73%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.09%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.03%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.73%	95.56%
CHEMBL3714130	P46095	G-protein coupled receptor 6	87.19%	97.36%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.17%	94.00%
CHEMBL5255	O00206	Toll-like receptor 4	85.35%	92.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.77%	89.00%

Plants that contains it

• Paederia foetida
• Saprosma scortechinii

Cross-Links

• PubChem: 85348405
• LOTUS: LTS0117380
• wikiData: Q105364261