1,5-dihydroxy-3-methoxy-8-[(2S,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: 2f9398c7-2105-4322-ada2-b0b07b5e4ac4
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones
• IUPAC Name: 1,5-dihydroxy-3-methoxy-8-[(2S,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=CC(=C2C(=C1)OC3=C(C=CC(=C3C2=O)OC4C(C(C(C(O4)COC5C(C(C(CO5)O)O)O)O)O)O)O)O
• SMILES (Isomeric): COC1=CC(=C2C(=C1)OC3=C(C=CC(=C3C2=O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO[C@H]5[C@@H]([C@H]([C@@H](CO5)O)O)O)O)O)O)O)O
• InChI: InChI=1S/C25H28O15/c1-35-8-4-10(27)15-13(5-8)38-23-9(26)2-3-12(16(23)19(15)31)39-25-22(34)20(32)18(30)14(40-25)7-37-24-21(33)17(29)11(28)6-36-24/h2-5,11,14,17-18,20-22,24-30,32-34H,6-7H2,1H3/t11-,14-,17+,18-,20+,21-,22-,24+,25-/m1/s1
• InChI Key: WXFWOAZVJQTYOI-MUFLDDDDSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₂₈O₁₅
• Molecular Weight: 568.50 g/mol
• Exact Mass: 568.14282018 g/mol
• Topological Polar Surface Area (TPSA): 234.00 Ų
• XlogP: -1.50
• Atomic LogP (AlogP): -1.99
• H-Bond Acceptor: 15
• H-Bond Donor: 8
• 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	-	0.9089	90.89%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.6126	61.26%
OATP2B1 inhibitior	-	0.5755	57.55%
OATP1B1 inhibitior	+	0.8996	89.96%
OATP1B3 inhibitior	+	0.9602	96.02%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.7193	71.93%
P-glycoprotein inhibitior	-	0.6319	63.19%
P-glycoprotein substrate	-	0.5064	50.64%
CYP3A4 substrate	+	0.6372	63.72%
CYP2C9 substrate	-	0.8664	86.64%
CYP2D6 substrate	-	0.8478	84.78%
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	+	0.5941	59.41%
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	-	0.9238	92.38%
Skin irritation	-	0.8295	82.95%
Skin corrosion	-	0.9649	96.49%
Ames mutagenesis	+	0.8300	83.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4127	41.27%
Micronuclear	+	0.5374	53.74%
Hepatotoxicity	-	0.8226	82.26%
skin sensitisation	-	0.9112	91.12%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.9117	91.17%
Acute Oral Toxicity (c)	III	0.7275	72.75%
Estrogen receptor binding	+	0.7898	78.98%
Androgen receptor binding	+	0.6190	61.90%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.5583	55.83%
Aromatase binding	+	0.6460	64.60%
PPAR gamma	+	0.7649	76.49%
Honey bee toxicity	-	0.8158	81.58%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6849	68.49%
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	99.39%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.06%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.08%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.08%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.88%	96.09%
CHEMBL2581	P07339	Cathepsin D	92.39%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.05%	97.09%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.65%	99.15%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.43%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.72%	85.14%
CHEMBL4208	P20618	Proteasome component C5	89.26%	90.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.01%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	88.76%	91.49%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	88.60%	89.62%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.30%	99.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.16%	95.89%
CHEMBL3401	O75469	Pregnane X receptor	85.74%	94.73%
CHEMBL3194	P02766	Transthyretin	84.57%	90.71%
CHEMBL4040	P28482	MAP kinase ERK2	84.40%	83.82%
CHEMBL2535	P11166	Glucose transporter	84.17%	98.75%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	81.85%	86.92%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.41%	99.23%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.24%	95.83%

Plants that contains it

• Swertia japonica

Cross-Links

• PubChem: 14524491
• NPASS: NPC180890
• LOTUS: LTS0039659
• wikiData: Q105314576