2-hydroxy-1,6-dimethoxy-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyxanthen-9-one

Details

• Internal ID: f90cd4fd-149b-4bbb-8d8d-96e6dc3668fc
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones
• IUPAC Name: 2-hydroxy-1,6-dimethoxy-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyxanthen-9-one
• InChI: InChI=1S/C21H22O11/c1-28-8-5-11-14(17(25)15-10(30-11)4-3-9(23)20(15)29-2)12(6-8)31-21-19(27)18(26)16(24)13(7-22)32-21/h3-6,13,16,18-19,21-24,26-27H,7H2,1-2H3/t13-,16-,18+,19-,21-/m1/s1
• InChI Key: CLLIMVPNWOBNEF-GUTCHGCDSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₂O₁₁
• Molecular Weight: 450.40 g/mol
• Exact Mass: 450.11621151 g/mol
• Topological Polar Surface Area (TPSA): 164.00 Ų
• XlogP: 0.40
• Atomic LogP (AlogP): -0.15
• H-Bond Acceptor: 11
• H-Bond Donor: 5
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5891	58.91%
Caco-2	-	0.8256	82.56%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.5382	53.82%
OATP2B1 inhibitior	-	0.5615	56.15%
OATP1B1 inhibitior	+	0.9098	90.98%
OATP1B3 inhibitior	+	0.9702	97.02%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.6253	62.53%
P-glycoprotein inhibitior	-	0.6548	65.48%
P-glycoprotein substrate	-	0.8407	84.07%
CYP3A4 substrate	+	0.5665	56.65%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8324	83.24%
CYP3A4 inhibition	-	0.8887	88.87%
CYP2C9 inhibition	-	0.9431	94.31%
CYP2C19 inhibition	-	0.9262	92.62%
CYP2D6 inhibition	-	0.9179	91.79%
CYP1A2 inhibition	-	0.8804	88.04%
CYP2C8 inhibition	-	0.5680	56.80%
CYP inhibitory promiscuity	-	0.8059	80.59%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7283	72.83%
Eye corrosion	-	0.9891	98.91%
Eye irritation	-	0.9054	90.54%
Skin irritation	-	0.8272	82.72%
Skin corrosion	-	0.9636	96.36%
Ames mutagenesis	+	0.8000	80.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	+	0.6133	61.33%
Hepatotoxicity	-	0.7250	72.50%
skin sensitisation	-	0.9214	92.14%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	-	0.6000	60.00%
Nephrotoxicity	-	0.8463	84.63%
Acute Oral Toxicity (c)	III	0.7037	70.37%
Estrogen receptor binding	+	0.7657	76.57%
Androgen receptor binding	+	0.5794	57.94%
Thyroid receptor binding	+	0.5143	51.43%
Glucocorticoid receptor binding	+	0.7685	76.85%
Aromatase binding	+	0.6884	68.84%
PPAR gamma	+	0.6786	67.86%
Honey bee toxicity	-	0.8303	83.03%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.6994	69.94%

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	99.43%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.62%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.49%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	93.24%	99.15%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.93%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.01%	89.00%
CHEMBL2581	P07339	Cathepsin D	90.46%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	86.46%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.06%	99.17%
CHEMBL4208	P20618	Proteasome component C5	85.64%	90.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.48%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.85%	97.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.52%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.17%	86.33%

Plants that contains it

• Gentiana acaulis
• Gentianopsis paludosa

Cross-Links

• PubChem: 14828374
• LOTUS: LTS0163673
• wikiData: Q104963595