[3,4,5-Trihydroxy-6-[[6-(methylsulfanylcarbonyloxymethyl)-2-oxo-3,9-dioxatricyclo[5.3.1.04,11]undeca-1(10),5-dien-8-yl]oxy]oxan-2-yl]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: f13e4123-8be4-4ae5-8943-0fa8949ded00
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: [3,4,5-trihydroxy-6-[[6-(methylsulfanylcarbonyloxymethyl)-2-oxo-3,9-dioxatricyclo[5.3.1.04,11]undeca-1(10),5-dien-8-yl]oxy]oxan-2-yl]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): CSC(=O)OCC1=CC(C2C1C(OC=C2C(=O)OCC3C(C(C(C(O3)OC4C5C6C(C=C5COC(=O)SC)OC(=O)C6=CO4)O)O)O)OC7C(C(C(C(O7)CO)O)O)O)O
• SMILES (Isomeric): CSC(=O)OCC1=CC(C2C1C(OC=C2C(=O)OCC3C(C(C(C(O3)OC4C5C6C(C=C5COC(=O)SC)OC(=O)C6=CO4)O)O)O)OC7C(C(C(C(O7)CO)O)O)O)O
• InChI: InChI=1S/C36H44O22S2/c1-59-35(47)52-6-11-3-15(38)21-13(8-50-31(19(11)21)57-33-27(43)25(41)23(39)17(5-37)55-33)29(45)49-10-18-24(40)26(42)28(44)34(56-18)58-32-20-12(7-53-36(48)60-2)4-16-22(20)14(9-51-32)30(46)54-16/h3-4,8-9,15-28,31-34,37-44H,5-7,10H2,1-2H3
• InChI Key: ZYXYLRAAHSMUQG-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: -3.50
• 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	-	0.8777	87.77%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.7312	73.12%
OATP2B1 inhibitior	-	0.7247	72.47%
OATP1B1 inhibitior	+	0.7811	78.11%
OATP1B3 inhibitior	+	0.9311	93.11%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.8803	88.03%
P-glycoprotein inhibitior	+	0.7252	72.52%
P-glycoprotein substrate	-	0.6192	61.92%
CYP3A4 substrate	+	0.6773	67.73%
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	+	0.5797	57.97%
CYP inhibitory promiscuity	-	0.5972	59.72%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5598	55.98%
Eye corrosion	-	0.9836	98.36%
Eye irritation	-	0.9078	90.78%
Skin irritation	-	0.7629	76.29%
Skin corrosion	-	0.9370	93.70%
Ames mutagenesis	-	0.6037	60.37%
Human Ether-a-go-go-Related Gene inhibition	+	0.7168	71.68%
Micronuclear	-	0.5400	54.00%
Hepatotoxicity	-	0.7696	76.96%
skin sensitisation	-	0.8417	84.17%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	+	0.7388	73.88%
Acute Oral Toxicity (c)	III	0.5496	54.96%
Estrogen receptor binding	+	0.7912	79.12%
Androgen receptor binding	+	0.6918	69.18%
Thyroid receptor binding	-	0.4904	49.04%
Glucocorticoid receptor binding	+	0.6903	69.03%
Aromatase binding	+	0.5743	57.43%
PPAR gamma	+	0.7527	75.27%
Honey bee toxicity	-	0.6767	67.67%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
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	93.48%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.55%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	90.97%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.59%	99.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.38%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.79%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.21%	95.56%
CHEMBL5255	O00206	Toll-like receptor 4	84.02%	92.50%
CHEMBL3714130	P46095	G-protein coupled receptor 6	83.19%	97.36%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.49%	94.00%

Plants that contains it

• Paederia foetida

Cross-Links

• PubChem: 74029688
• LOTUS: LTS0064531
• wikiData: Q105386532