Norswertianolin

Details

• Internal ID: af0f394c-f383-4f7a-bc56-9cd4de389141
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones
• IUPAC Name: 1,3,5-trihydroxy-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyxanthen-9-one
• SMILES (Canonical): C1=CC(=C2C(=C1O)OC3=CC(=CC(=C3C2=O)O)O)OC4C(C(C(C(O4)CO)O)O)O
• SMILES (Isomeric): C1=CC(=C2C(=C1O)OC3=CC(=CC(=C3C2=O)O)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O
• InChI: InChI=1S/C19H18O11/c20-5-11-14(24)16(26)17(27)19(30-11)29-9-2-1-7(22)18-13(9)15(25)12-8(23)3-6(21)4-10(12)28-18/h1-4,11,14,16-17,19-24,26-27H,5H2/t11-,14-,16+,17-,19-/m1/s1
• InChI Key: MYWLBRTZOYHDOU-FJMCMGCSSA-N
• Popularity: 8 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₁₈O₁₁
• Molecular Weight: 422.30 g/mol
• Exact Mass: 422.08491139 g/mol
• Topological Polar Surface Area (TPSA): 186.00 Ų
• XlogP: 0.30
• Atomic LogP (AlogP): -0.76
• H-Bond Acceptor: 11
• H-Bond Donor: 7
• Rotatable Bonds: 3

Synonyms

• 54954-12-0
• 8-(beta-D-Glucopyranosyloxy)-1,3,5-trihydroxy-9H-xanthen-9-one
• CHEBI:7638
• bellidin-8-O-beta-D-glucopyranoside
• 1,3,5-trihydroxy-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyxanthen-9-one
• 9H-Xanthen-9-one, 8-(beta-D-glucopyranosyloxy)-1,3,5-trihydroxy-
• 4,6,8-trihydroxy-9-oxo-9H-xanthen-1-yl beta-D-glucopyranoside
• 1,3,5-Trihydroxy-8-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-9H-xanthen-9-one
• CCRIS 5473
• 3,5,8-Trihydroxyxanthone-1-O-glucoside
• 8FEU38L6GD
• CHEMBL512072
• SCHEMBL23782036
• 8-O-Glucosyldesmethylbellidifolin
• DTXSID70203480
• Demethylbellidifolin-8-O-glucoside
• HY-N6617
• AKOS040758190
• MS-27410
• CS-0034378
• E88785
• 1,3,5,8-Tetrahydroxyxanthen-9-one 8-glucoside
• 3-O-Demethylbellidifolin 8-O-beta-D-glucopyranoside
• 1,3,5-Trihydroxyxanthone 8-O-beta-D-glucopyranoside
• Q27089366
• 1,3,5-trihydroxy-8-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-9H-xanthen-9-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6367	63.67%
Caco-2	-	0.9120	91.20%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.5792	57.92%
OATP2B1 inhibitior	+	0.5919	59.19%
OATP1B1 inhibitior	+	0.9062	90.62%
OATP1B3 inhibitior	+	0.9527	95.27%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.7193	71.93%
P-glycoprotein inhibitior	-	0.8011	80.11%
P-glycoprotein substrate	-	0.8235	82.35%
CYP3A4 substrate	+	0.5634	56.34%
CYP2C9 substrate	-	0.6762	67.62%
CYP2D6 substrate	-	0.8575	85.75%
CYP3A4 inhibition	-	0.9271	92.71%
CYP2C9 inhibition	-	0.9542	95.42%
CYP2C19 inhibition	-	0.9292	92.92%
CYP2D6 inhibition	-	0.9339	93.39%
CYP1A2 inhibition	-	0.9202	92.02%
CYP2C8 inhibition	+	0.6516	65.16%
CYP inhibitory promiscuity	-	0.8566	85.66%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6617	66.17%
Eye corrosion	-	0.9925	99.25%
Eye irritation	-	0.8315	83.15%
Skin irritation	-	0.8079	80.79%
Skin corrosion	-	0.9743	97.43%
Ames mutagenesis	+	0.9400	94.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4258	42.58%
Micronuclear	+	0.5633	56.33%
Hepatotoxicity	-	0.6875	68.75%
skin sensitisation	-	0.9024	90.24%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	-	0.5500	55.00%
Nephrotoxicity	-	0.6439	64.39%
Acute Oral Toxicity (c)	III	0.4845	48.45%
Estrogen receptor binding	+	0.7227	72.27%
Androgen receptor binding	+	0.6685	66.85%
Thyroid receptor binding	-	0.5087	50.87%
Glucocorticoid receptor binding	+	0.6724	67.24%
Aromatase binding	+	0.5996	59.96%
PPAR gamma	+	0.6825	68.25%
Honey bee toxicity	-	0.7806	78.06%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6399	63.99%
Fish aquatic toxicity	+	0.7264	72.64%

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	98.75%	91.11%
CHEMBL3194	P02766	Transthyretin	95.94%	90.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.77%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.95%	94.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.79%	99.17%
CHEMBL2581	P07339	Cathepsin D	89.17%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.09%	95.56%
CHEMBL1951	P21397	Monoamine oxidase A	88.02%	91.49%
CHEMBL3401	O75469	Pregnane X receptor	87.20%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.18%	86.33%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	86.44%	96.21%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.25%	94.45%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	83.58%	95.78%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.37%	99.15%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.15%	86.92%
CHEMBL4208	P20618	Proteasome component C5	80.32%	90.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.20%	95.89%

Plants that contains it

• Gentianella amarella
• Gentianella campestris
• Gentianella nitida
• Swertia macrosperma

Cross-Links

• PubChem: 5281659
• LOTUS: LTS0090690
• wikiData: Q27089366