4-Phenyl-1H,3H-naphtho[1,8-cd]pyran-1,3-dione

Details

• Internal ID: 45301c48-4cf6-469b-9fd5-131b38f3854a
• Taxonomy: Benzenoids > Naphthalenes > Phenylnaphthalenes
• IUPAC Name: 6-phenyl-3-oxatricyclo[7.3.1.05,13]trideca-1(12),5,7,9(13),10-pentaene-2,4-dione
• SMILES (Canonical): C1=CC=C(C=C1)C2=C3C4=C(C=CC=C4C(=O)OC3=O)C=C2
• SMILES (Isomeric): C1=CC=C(C=C1)C2=C3C4=C(C=CC=C4C(=O)OC3=O)C=C2
• InChI: InChI=1S/C18H10O3/c19-17-14-8-4-7-12-9-10-13(11-5-2-1-3-6-11)16(15(12)14)18(20)21-17/h1-10H
• InChI Key: ISOSGRNBACDIEA-UHFFFAOYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₁₀O₃
• Molecular Weight: 274.30 g/mol
• Exact Mass: 274.062994177 g/mol
• Topological Polar Surface Area (TPSA): 43.40 Ų
• XlogP: 4.20
• Atomic LogP (AlogP): 3.82
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 1

Synonyms

• CHEMBL3593482
• DTXSID101255015
• 6-phenyl-3-oxatricyclo[7.3.1.0^{5,13}]trideca-1(13),5,7,9,11-pentaene-2,4-dione
• 56252-04-1

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9938	99.38%
Caco-2	+	0.6333	63.33%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.6483	64.83%
OATP2B1 inhibitior	-	0.8673	86.73%
OATP1B1 inhibitior	+	0.9318	93.18%
OATP1B3 inhibitior	+	0.9835	98.35%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	+	0.7477	74.77%
P-glycoprotein inhibitior	-	0.7771	77.71%
P-glycoprotein substrate	-	0.9559	95.59%
CYP3A4 substrate	-	0.6300	63.00%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7928	79.28%
CYP3A4 inhibition	-	0.9351	93.51%
CYP2C9 inhibition	+	0.5768	57.68%
CYP2C19 inhibition	-	0.6125	61.25%
CYP2D6 inhibition	-	0.9252	92.52%
CYP1A2 inhibition	+	0.6737	67.37%
CYP2C8 inhibition	-	0.5824	58.24%
CYP inhibitory promiscuity	-	0.8902	89.02%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9713	97.13%
Carcinogenicity (trinary)	Non-required	0.6830	68.30%
Eye corrosion	-	0.8973	89.73%
Eye irritation	+	0.8767	87.67%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.9520	95.20%
Ames mutagenesis	+	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7581	75.81%
Micronuclear	+	0.5642	56.42%
Hepatotoxicity	+	0.7301	73.01%
skin sensitisation	-	0.8328	83.28%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.5111	51.11%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	+	0.8237	82.37%
Acute Oral Toxicity (c)	III	0.3373	33.73%
Estrogen receptor binding	+	0.7734	77.34%
Androgen receptor binding	+	0.8849	88.49%
Thyroid receptor binding	+	0.5188	51.88%
Glucocorticoid receptor binding	+	0.7243	72.43%
Aromatase binding	+	0.7448	74.48%
PPAR gamma	+	0.6476	64.76%
Honey bee toxicity	-	0.8847	88.47%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.7000	70.00%
Fish aquatic toxicity	+	0.9644	96.44%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	96.52%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.61%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.61%	86.33%
CHEMBL1907	P15144	Aminopeptidase N	91.09%	93.31%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.21%	99.23%
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	90.17%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.44%	91.11%
CHEMBL262	P49841	Glycogen synthase kinase-3 beta	89.35%	95.72%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	85.55%	96.67%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	85.17%	83.00%
CHEMBL1951	P21397	Monoamine oxidase A	85.02%	91.49%
CHEMBL2083	P15090	Fatty acid binding protein adipocyte	84.63%	95.71%
CHEMBL5805	Q9NR97	Toll-like receptor 8	81.90%	96.25%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.08%	94.00%

Plants that contains it

• Wachendorfia thyrsiflora

Cross-Links

• PubChem: 11818168
• LOTUS: LTS0068671
• wikiData: Q105119680