6-Hydroxy-5-methoxy-7-phenyl-3h-benzo[de]isochromen-1-one

Details

• Internal ID: 33f31df4-8e12-4195-8979-27d8c3806a41
• Taxonomy: Benzenoids > Naphthalenes > Naphthols and derivatives
• IUPAC Name: 8-hydroxy-7-methoxy-10-phenyl-3-oxatricyclo[7.3.1.05,13]trideca-1(13),5,7,9,11-pentaen-2-one
• SMILES (Canonical): COC1=C(C2=C(C=CC3=C2C(=C1)COC3=O)C4=CC=CC=C4)O
• SMILES (Isomeric): COC1=C(C2=C(C=CC3=C2C(=C1)COC3=O)C4=CC=CC=C4)O
• InChI: InChI=1S/C19H14O4/c1-22-15-9-12-10-23-19(21)14-8-7-13(11-5-3-2-4-6-11)17(16(12)14)18(15)20/h2-9,20H,10H2,1H3
• InChI Key: SXWREBCNSRFADJ-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₁₄O₄
• Molecular Weight: 306.30 g/mol
• Exact Mass: 306.08920892 g/mol
• Topological Polar Surface Area (TPSA): 55.80 Ų
• XlogP: 3.80
• Atomic LogP (AlogP): 3.89
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• 8-Hydroxy-7-methoxy-10-phenyl-3-oxatricyclo[7.3.1.05,13]trideca-1(13),5,7,9,11-pentaen-2-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9812	98.12%
Caco-2	+	0.8475	84.75%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.8373	83.73%
OATP2B1 inhibitior	-	0.8604	86.04%
OATP1B1 inhibitior	+	0.9317	93.17%
OATP1B3 inhibitior	+	0.9651	96.51%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.8598	85.98%
P-glycoprotein inhibitior	-	0.5656	56.56%
P-glycoprotein substrate	-	0.7218	72.18%
CYP3A4 substrate	+	0.5341	53.41%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7574	75.74%
CYP3A4 inhibition	-	0.7152	71.52%
CYP2C9 inhibition	+	0.8594	85.94%
CYP2C19 inhibition	-	0.5091	50.91%
CYP2D6 inhibition	-	0.9087	90.87%
CYP1A2 inhibition	+	0.5464	54.64%
CYP2C8 inhibition	-	0.5994	59.94%
CYP inhibitory promiscuity	+	0.5299	52.99%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9710	97.10%
Carcinogenicity (trinary)	Non-required	0.5658	56.58%
Eye corrosion	-	0.9704	97.04%
Eye irritation	+	0.7080	70.80%
Skin irritation	-	0.6678	66.78%
Skin corrosion	-	0.9779	97.79%
Ames mutagenesis	+	0.5582	55.82%
Human Ether-a-go-go-Related Gene inhibition	-	0.6846	68.46%
Micronuclear	+	0.7933	79.33%
Hepatotoxicity	+	0.6625	66.25%
skin sensitisation	-	0.9481	94.81%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	-	0.5689	56.89%
Acute Oral Toxicity (c)	III	0.7652	76.52%
Estrogen receptor binding	+	0.9272	92.72%
Androgen receptor binding	+	0.8380	83.80%
Thyroid receptor binding	-	0.5062	50.62%
Glucocorticoid receptor binding	+	0.8436	84.36%
Aromatase binding	+	0.6692	66.92%
PPAR gamma	+	0.6459	64.59%
Honey bee toxicity	-	0.8836	88.36%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5551	55.51%
Fish aquatic toxicity	+	0.9155	91.55%

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	98.13%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.30%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.04%	86.33%
CHEMBL2002	P12268	Inosine-5'-monophosphate dehydrogenase 2	96.82%	98.21%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.45%	95.56%
CHEMBL1951	P21397	Monoamine oxidase A	95.61%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.16%	96.09%
CHEMBL3192	Q9BY41	Histone deacetylase 8	88.25%	93.99%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.97%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.16%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.83%	99.17%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.74%	85.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.29%	99.23%
CHEMBL1907	P15144	Aminopeptidase N	80.96%	93.31%

Plants that contains it

• Xiphidium caeruleum

Cross-Links

• PubChem: 23244116
• LOTUS: LTS0231666
• wikiData: Q105263380