2-(Hexopyranosyloxy)-1a-(hydroxymethyl)-1a,1b,2,5a,6,6a-hexahydrooxireno[2',3':4,5]cyclopenta[1,2-c]pyran-6-yl 3,4-dihydroxybenzoate

Details

• Internal ID: f857b218-8363-4c1b-a726-7ce6d9507e40
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
• IUPAC Name: [2-(hydroxymethyl)-10-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,9-dioxatricyclo[4.4.0.02,4]dec-7-en-5-yl] 3,4-dihydroxybenzoate
• SMILES (Canonical): C1=COC(C2C1C(C3C2(O3)CO)OC(=O)C4=CC(=C(C=C4)O)O)OC5C(C(C(C(O5)CO)O)O)O
• SMILES (Isomeric): C1=COC(C2C1C(C3C2(O3)CO)OC(=O)C4=CC(=C(C=C4)O)O)OC5C(C(C(C(O5)CO)O)O)O
• InChI: InChI=1S/C22H26O13/c23-6-12-14(27)15(28)16(29)21(32-12)34-20-13-9(3-4-31-20)17(18-22(13,7-24)35-18)33-19(30)8-1-2-10(25)11(26)5-8/h1-5,9,12-18,20-21,23-29H,6-7H2
• InChI Key: DBUOUVZMYWYRRI-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₆O₁₃
• Molecular Weight: 498.40 g/mol
• Exact Mass: 498.13734088 g/mol
• Topological Polar Surface Area (TPSA): 208.00 Ų
• XlogP: -1.70
• Atomic LogP (AlogP): -2.31
• H-Bond Acceptor: 13
• H-Bond Donor: 7
• Rotatable Bonds: 6

Synonyms

• [1a-(hydroxymethyl)-2-[3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-2,5a,6,6a-tetrahydro-1bH-oxireno[[?]:[?]]cyclopenta[[?]]pyran-6-yl] 3,4-dihydroxybenzoate
• 2-(Hexopyranosyloxy)-1a-(hydroxymethyl)-1a,1b,2,5a,6,6a-hexahydrooxireno[2',3':4,5]cyclopenta[1,2-c]pyran-6-yl 3,4-dihydroxybenzoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6226	62.26%
Caco-2	-	0.9309	93.09%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.5735	57.35%
OATP2B1 inhibitior	-	0.8526	85.26%
OATP1B1 inhibitior	+	0.8015	80.15%
OATP1B3 inhibitior	+	0.9546	95.46%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.8094	80.94%
P-glycoprotein inhibitior	-	0.6949	69.49%
P-glycoprotein substrate	-	0.7126	71.26%
CYP3A4 substrate	+	0.6559	65.59%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8524	85.24%
CYP3A4 inhibition	-	0.9007	90.07%
CYP2C9 inhibition	-	0.8754	87.54%
CYP2C19 inhibition	-	0.7104	71.04%
CYP2D6 inhibition	-	0.8588	85.88%
CYP1A2 inhibition	-	0.8529	85.29%
CYP2C8 inhibition	+	0.6158	61.58%
CYP inhibitory promiscuity	-	0.7400	74.00%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5794	57.94%
Eye corrosion	-	0.9889	98.89%
Eye irritation	-	0.9327	93.27%
Skin irritation	-	0.7722	77.22%
Skin corrosion	-	0.9454	94.54%
Ames mutagenesis	-	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5598	55.98%
Micronuclear	+	0.5233	52.33%
Hepatotoxicity	-	0.7500	75.00%
skin sensitisation	-	0.7644	76.44%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.6065	60.65%
Acute Oral Toxicity (c)	III	0.4480	44.80%
Estrogen receptor binding	+	0.6976	69.76%
Androgen receptor binding	+	0.5213	52.13%
Thyroid receptor binding	+	0.5969	59.69%
Glucocorticoid receptor binding	-	0.4806	48.06%
Aromatase binding	+	0.6610	66.10%
PPAR gamma	+	0.7112	71.12%
Honey bee toxicity	-	0.7465	74.65%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.6250	62.50%
Fish aquatic toxicity	+	0.8031	80.31%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.52%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.42%	91.49%
CHEMBL3194	P02766	Transthyretin	90.70%	90.71%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	90.68%	96.21%
CHEMBL4208	P20618	Proteasome component C5	90.43%	90.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.34%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.48%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.29%	94.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.13%	99.17%
CHEMBL2581	P07339	Cathepsin D	86.81%	98.95%
CHEMBL218	P21554	Cannabinoid CB1 receptor	86.27%	96.61%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	85.91%	95.83%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.63%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.45%	96.09%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	83.65%	86.92%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	83.54%	80.78%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	83.38%	96.95%
CHEMBL211	P08172	Muscarinic acetylcholine receptor M2	82.97%	94.97%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.24%	95.89%
CHEMBL5255	O00206	Toll-like receptor 4	81.77%	92.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.67%	97.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.12%	92.94%
CHEMBL3401	O75469	Pregnane X receptor	80.76%	94.73%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	80.06%	94.23%

Plants that contains it

• Veronica anagallis-aquatica
• Veronica austriaca
• Veronica besseya
• Veronica cymbalaria
• Veronica filiformis
• Veronica fuhsii
• Veronica lavaudiana
• Veronica liwanensis
• Veronica longifolia
• Veronica officinalis
• Veronica persica
• Veronica thomsonii
• Veronica turrilliana

Cross-Links

• PubChem: 495172
• LOTUS: LTS0031864
• wikiData: Q104974872