1,8-Dihydroxy-3-methyl-6-(3-methylbut-2-enoxy)xanthen-9-one

Details

• Internal ID: 3ebf9d94-b0b9-4be8-823e-ad5dad83514b
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones
• IUPAC Name: 1,8-dihydroxy-3-methyl-6-(3-methylbut-2-enoxy)xanthen-9-one
• SMILES (Canonical): CC1=CC(=C2C(=C1)OC3=CC(=CC(=C3C2=O)O)OCC=C(C)C)O
• SMILES (Isomeric): CC1=CC(=C2C(=C1)OC3=CC(=CC(=C3C2=O)O)OCC=C(C)C)O
• InChI: InChI=1S/C19H18O5/c1-10(2)4-5-23-12-8-14(21)18-16(9-12)24-15-7-11(3)6-13(20)17(15)19(18)22/h4,6-9,20-21H,5H2,1-3H3
• InChI Key: YCHMIHRTWFOENV-UHFFFAOYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₁₈O₅
• Molecular Weight: 326.30 g/mol
• Exact Mass: 326.11542367 g/mol
• Topological Polar Surface Area (TPSA): 76.00 Ų
• XlogP: 4.60
• Atomic LogP (AlogP): 4.01
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9917	99.17%
Caco-2	+	0.7458	74.58%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.8056	80.56%
OATP2B1 inhibitior	-	0.5679	56.79%
OATP1B1 inhibitior	+	0.9214	92.14%
OATP1B3 inhibitior	+	0.9014	90.14%
MATE1 inhibitior	-	0.6800	68.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	+	0.6483	64.83%
P-glycoprotein inhibitior	-	0.5090	50.90%
P-glycoprotein substrate	-	0.9170	91.70%
CYP3A4 substrate	+	0.5337	53.37%
CYP2C9 substrate	-	0.6279	62.79%
CYP2D6 substrate	-	0.8428	84.28%
CYP3A4 inhibition	-	0.6085	60.85%
CYP2C9 inhibition	+	0.6674	66.74%
CYP2C19 inhibition	+	0.8738	87.38%
CYP2D6 inhibition	-	0.5950	59.50%
CYP1A2 inhibition	+	0.9378	93.78%
CYP2C8 inhibition	-	0.6544	65.44%
CYP inhibitory promiscuity	+	0.8657	86.57%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9413	94.13%
Carcinogenicity (trinary)	Non-required	0.6915	69.15%
Eye corrosion	-	0.9878	98.78%
Eye irritation	+	0.6624	66.24%
Skin irritation	-	0.7787	77.87%
Skin corrosion	-	0.9751	97.51%
Ames mutagenesis	+	0.6336	63.36%
Human Ether-a-go-go-Related Gene inhibition	-	0.4788	47.88%
Micronuclear	-	0.5600	56.00%
Hepatotoxicity	+	0.6033	60.33%
skin sensitisation	-	0.7435	74.35%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	+	0.5244	52.44%
Acute Oral Toxicity (c)	III	0.7786	77.86%
Estrogen receptor binding	+	0.8984	89.84%
Androgen receptor binding	+	0.7835	78.35%
Thyroid receptor binding	-	0.4919	49.19%
Glucocorticoid receptor binding	+	0.8825	88.25%
Aromatase binding	+	0.7953	79.53%
PPAR gamma	+	0.8996	89.96%
Honey bee toxicity	-	0.8602	86.02%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	+	0.9858	98.58%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3401	O75469	Pregnane X receptor	96.33%	94.73%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.13%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	94.47%	91.49%
CHEMBL2581	P07339	Cathepsin D	93.14%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.96%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.84%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.48%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.25%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.85%	86.33%
CHEMBL4208	P20618	Proteasome component C5	87.42%	90.00%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	85.93%	94.80%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.19%	99.15%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	83.33%	93.65%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.63%	99.23%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.46%	96.95%

Plants that contains it

• Endodesmia calophylloides

Cross-Links

• PubChem: 10496349
• LOTUS: LTS0247696
• wikiData: Q105346266