7-hydroxy-3-methoxy-1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxyxanthen-9-one

Details

• Internal ID: d0ad11ce-014e-4770-8314-eec7c4d11f28
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones
• IUPAC Name: 7-hydroxy-3-methoxy-1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxyxanthen-9-one
• SMILES (Canonical): COC1=CC2=C(C(=C1)OC3C(C(C(C(O3)COC4C(C(C(CO4)O)O)O)O)O)O)C(=O)C5=C(O2)C=CC(=C5)O
• SMILES (Isomeric): COC1=CC2=C(C(=C1)O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO[C@H]4[C@@H]([C@H]([C@@H](CO4)O)O)O)O)O)O)C(=O)C5=C(O2)C=CC(=C5)O
• InChI: InChI=1S/C25H28O14/c1-34-10-5-14-17(18(28)11-4-9(26)2-3-13(11)37-14)15(6-10)38-25-23(33)21(31)20(30)16(39-25)8-36-24-22(32)19(29)12(27)7-35-24/h2-6,12,16,19-27,29-33H,7-8H2,1H3/t12-,16-,19+,20-,21+,22-,23-,24+,25+/m1/s1
• InChI Key: MWZPGBNWDUPMFG-BNCUQFIESA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₂₈O₁₄
• Molecular Weight: 552.50 g/mol
• Exact Mass: 552.14790556 g/mol
• Topological Polar Surface Area (TPSA): 214.00 Ų
• XlogP: -1.70
• Atomic LogP (AlogP): -1.70
• H-Bond Acceptor: 14
• H-Bond Donor: 7
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5545	55.45%
Caco-2	-	0.9034	90.34%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.6126	61.26%
OATP2B1 inhibitior	-	0.7101	71.01%
OATP1B1 inhibitior	+	0.8705	87.05%
OATP1B3 inhibitior	+	0.9602	96.02%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.5252	52.52%
P-glycoprotein inhibitior	-	0.6689	66.89%
P-glycoprotein substrate	+	0.5824	58.24%
CYP3A4 substrate	+	0.6486	64.86%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8277	82.77%
CYP3A4 inhibition	-	0.9415	94.15%
CYP2C9 inhibition	-	0.9677	96.77%
CYP2C19 inhibition	-	0.9193	91.93%
CYP2D6 inhibition	-	0.8930	89.30%
CYP1A2 inhibition	-	0.8938	89.38%
CYP2C8 inhibition	+	0.5445	54.45%
CYP inhibitory promiscuity	-	0.9267	92.67%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6233	62.33%
Eye corrosion	-	0.9903	99.03%
Eye irritation	-	0.9348	93.48%
Skin irritation	-	0.8295	82.95%
Skin corrosion	-	0.9649	96.49%
Ames mutagenesis	+	0.7500	75.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6561	65.61%
Micronuclear	+	0.5374	53.74%
Hepatotoxicity	-	0.7476	74.76%
skin sensitisation	-	0.9112	91.12%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.9558	95.58%
Acute Oral Toxicity (c)	III	0.7275	72.75%
Estrogen receptor binding	+	0.8370	83.70%
Androgen receptor binding	+	0.6358	63.58%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.6019	60.19%
Aromatase binding	+	0.7026	70.26%
PPAR gamma	+	0.7685	76.85%
Honey bee toxicity	-	0.7823	78.23%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6449	64.49%
Fish aquatic toxicity	+	0.7209	72.09%

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	99.45%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.77%	94.00%
CHEMBL2581	P07339	Cathepsin D	95.47%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.28%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.88%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.05%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.57%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.64%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.44%	94.45%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	91.28%	89.62%
CHEMBL220	P22303	Acetylcholinesterase	89.99%	94.45%
CHEMBL2535	P11166	Glucose transporter	88.38%	98.75%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.90%	95.89%
CHEMBL3401	O75469	Pregnane X receptor	87.07%	94.73%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.45%	99.23%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	85.21%	95.83%
CHEMBL3714130	P46095	G-protein coupled receptor 6	83.62%	97.36%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.02%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.26%	86.33%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.15%	95.89%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.97%	99.15%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.36%	92.94%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.28%	92.62%
CHEMBL3192	Q9BY41	Histone deacetylase 8	80.02%	93.99%

Plants that contains it

• Gentiana lutea

Cross-Links

• PubChem: 163090513
• LOTUS: LTS0268447
• wikiData: Q105173913