Swertianin 8-glucoside

Details

• Internal ID: 6217b826-90c4-4ce6-8ba3-f0d11e0ad6c2
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones
• IUPAC Name: 2,8-dihydroxy-6-methoxy-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyxanthen-9-one
• SMILES (Canonical): COC1=CC(=C2C(=C1)OC3=C(C2=O)C(=C(C=C3)O)OC4C(C(C(C(O4)CO)O)O)O)O
• SMILES (Isomeric): COC1=CC(=C2C(=C1)OC3=C(C2=O)C(=C(C=C3)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O
• InChI: InChI=1S/C20H20O11/c1-28-7-4-9(23)13-11(5-7)29-10-3-2-8(22)19(14(10)16(13)25)31-20-18(27)17(26)15(24)12(6-21)30-20/h2-5,12,15,17-18,20-24,26-27H,6H2,1H3/t12-,15-,17+,18-,20+/m1/s1
• InChI Key: VIUYJOIABSSSIN-DPZUNCSASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₀O₁₁
• Molecular Weight: 436.40 g/mol
• Exact Mass: 436.10056145 g/mol
• Topological Polar Surface Area (TPSA): 175.00 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): -0.46
• H-Bond Acceptor: 11
• H-Bond Donor: 6
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5647	56.47%
Caco-2	-	0.8890	88.90%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.5367	53.67%
OATP2B1 inhibitior	+	0.5880	58.80%
OATP1B1 inhibitior	+	0.8972	89.72%
OATP1B3 inhibitior	+	0.9769	97.69%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.8521	85.21%
P-glycoprotein inhibitior	-	0.7173	71.73%
P-glycoprotein substrate	-	0.8307	83.07%
CYP3A4 substrate	+	0.5761	57.61%
CYP2C9 substrate	-	0.8485	84.85%
CYP2D6 substrate	-	0.8501	85.01%
CYP3A4 inhibition	-	0.9107	91.07%
CYP2C9 inhibition	-	0.9346	93.46%
CYP2C19 inhibition	-	0.9158	91.58%
CYP2D6 inhibition	-	0.9306	93.06%
CYP1A2 inhibition	-	0.8772	87.72%
CYP2C8 inhibition	+	0.5071	50.71%
CYP inhibitory promiscuity	-	0.8094	80.94%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6881	68.81%
Eye corrosion	-	0.9890	98.90%
Eye irritation	-	0.8687	86.87%
Skin irritation	-	0.8111	81.11%
Skin corrosion	-	0.9624	96.24%
Ames mutagenesis	+	0.8400	84.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4834	48.34%
Micronuclear	+	0.6133	61.33%
Hepatotoxicity	-	0.7448	74.48%
skin sensitisation	-	0.9164	91.64%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	-	0.8156	81.56%
Acute Oral Toxicity (c)	III	0.7058	70.58%
Estrogen receptor binding	+	0.6875	68.75%
Androgen receptor binding	+	0.6726	67.26%
Thyroid receptor binding	-	0.5366	53.66%
Glucocorticoid receptor binding	+	0.6847	68.47%
Aromatase binding	+	0.6153	61.53%
PPAR gamma	+	0.6448	64.48%
Honey bee toxicity	-	0.8401	84.01%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	+	0.6492	64.92%

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	99.28%	91.11%
CHEMBL2581	P07339	Cathepsin D	93.67%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.34%	94.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	93.22%	99.15%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.89%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.48%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.37%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.95%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.63%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	86.77%	94.73%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.65%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.14%	94.45%
CHEMBL4208	P20618	Proteasome component C5	85.62%	90.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.12%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	80.31%	91.49%

Plants that contains it

• Calophyllum apetalum
• Delphinium oliverianum
• Drypetes molunduana
• Euphorbia makinoi
• Gentiana verna
• Gentianella nitida
• Lophozia barbata
• Monnina emarginata
• Polygala fallax
• Pyrus calleryana
• Wettsteinia inversa

Cross-Links

• PubChem: 102506431
• NPASS: NPC70943
• LOTUS: LTS0080254
• wikiData: Q105287041