(3S)-3-[(E)-2-(1,3-dihydroxy-5-methoxy-9-oxoxanthen-2-yl)ethenyl]-8,10-dihydroxy-5-methoxy-3-methyl-2H-[1,4]dioxino[2,3-c]xanthen-7-one

Details

• Internal ID: d4e01423-a001-4a13-805d-7d38cc089e4c
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones
• IUPAC Name: (3S)-3-[(E)-2-(1,3-dihydroxy-5-methoxy-9-oxoxanthen-2-yl)ethenyl]-8,10-dihydroxy-5-methoxy-3-methyl-2H-[1,4]dioxino[2,3-c]xanthen-7-one
• SMILES (Canonical): CC1(COC2=C3C(=CC(=C2O1)OC)C(=O)C4=C(C=C(C=C4O3)O)O)C=CC5=C(C6=C(C=C5O)OC7=C(C6=O)C=CC=C7OC)O
• SMILES (Isomeric): C[C@@]1(COC2=C3C(=CC(=C2O1)OC)C(=O)C4=C(C=C(C=C4O3)O)O)/C=C/C5=C(C6=C(C=C5O)OC7=C(C6=O)C=CC=C7OC)O
• InChI: InChI=1S/C33H24O12/c1-33(8-7-15-18(35)12-22-25(26(15)37)27(38)16-5-4-6-20(40-2)29(16)43-22)13-42-32-30-17(11-23(41-3)31(32)45-33)28(39)24-19(36)9-14(34)10-21(24)44-30/h4-12,34-37H,13H2,1-3H3/b8-7+/t33-/m0/s1
• InChI Key: WGDMAYIQPVHOTQ-FFVYOMBOSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₂₄O₁₂
• Molecular Weight: 612.50 g/mol
• Exact Mass: 612.12677620 g/mol
• Topological Polar Surface Area (TPSA): 170.00 Ų
• XlogP: 5.70
• Atomic LogP (AlogP): 5.29
• H-Bond Acceptor: 12
• H-Bond Donor: 4
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9203	92.03%
Caco-2	-	0.8174	81.74%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.5655	56.55%
OATP2B1 inhibitior	-	0.5657	56.57%
OATP1B1 inhibitior	+	0.8848	88.48%
OATP1B3 inhibitior	+	0.9352	93.52%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9566	95.66%
P-glycoprotein inhibitior	+	0.8479	84.79%
P-glycoprotein substrate	+	0.5997	59.97%
CYP3A4 substrate	+	0.7180	71.80%
CYP2C9 substrate	-	0.6192	61.92%
CYP2D6 substrate	-	0.8382	83.82%
CYP3A4 inhibition	+	0.5576	55.76%
CYP2C9 inhibition	-	0.8443	84.43%
CYP2C19 inhibition	-	0.7439	74.39%
CYP2D6 inhibition	-	0.7505	75.05%
CYP1A2 inhibition	-	0.5052	50.52%
CYP2C8 inhibition	+	0.8527	85.27%
CYP inhibitory promiscuity	-	0.7101	71.01%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5841	58.41%
Eye corrosion	-	0.9888	98.88%
Eye irritation	-	0.8825	88.25%
Skin irritation	-	0.8156	81.56%
Skin corrosion	-	0.9429	94.29%
Ames mutagenesis	+	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7047	70.47%
Micronuclear	+	0.6000	60.00%
Hepatotoxicity	-	0.5000	50.00%
skin sensitisation	-	0.7932	79.32%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	+	0.4802	48.02%
Acute Oral Toxicity (c)	III	0.6179	61.79%
Estrogen receptor binding	+	0.8607	86.07%
Androgen receptor binding	+	0.8384	83.84%
Thyroid receptor binding	+	0.6358	63.58%
Glucocorticoid receptor binding	+	0.8797	87.97%
Aromatase binding	+	0.6483	64.83%
PPAR gamma	+	0.7010	70.10%
Honey bee toxicity	-	0.6867	68.67%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.6100	61.00%
Fish aquatic toxicity	+	0.9258	92.58%

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	99.37%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	99.06%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	98.00%	89.00%
CHEMBL3192	Q9BY41	Histone deacetylase 8	97.14%	93.99%
CHEMBL1937	Q92769	Histone deacetylase 2	97.10%	94.75%
CHEMBL220	P22303	Acetylcholinesterase	96.99%	94.45%
CHEMBL2581	P07339	Cathepsin D	96.42%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.25%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.92%	94.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.33%	94.45%
CHEMBL2535	P11166	Glucose transporter	89.89%	98.75%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.78%	99.23%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	89.15%	96.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	86.33%	97.14%
CHEMBL3194	P02766	Transthyretin	84.63%	90.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.39%	95.89%
CHEMBL3401	O75469	Pregnane X receptor	83.88%	94.73%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	83.28%	97.33%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.15%	92.62%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	82.30%	100.00%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	82.09%	80.78%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.04%	96.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.45%	92.94%
CHEMBL3492	P49721	Proteasome Macropain subunit	80.78%	90.24%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.36%	95.50%

Plants that contains it

• Mesua ferrea

Cross-Links

• PubChem: 163193743
• LOTUS: LTS0183901
• wikiData: Q105304406