alpha-Naphthoflavone

Details

• Internal ID: fe776818-431c-4431-adff-f0c85bf83986
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavones
• IUPAC Name: 2-phenylbenzo[h]chromen-4-one
• SMILES (Canonical): C1=CC=C(C=C1)C2=CC(=O)C3=C(O2)C4=CC=CC=C4C=C3
• SMILES (Isomeric): C1=CC=C(C=C1)C2=CC(=O)C3=C(O2)C4=CC=CC=C4C=C3
• InChI: InChI=1S/C19H12O2/c20-17-12-18(14-7-2-1-3-8-14)21-19-15-9-5-4-6-13(15)10-11-16(17)19/h1-12H
• InChI Key: VFMMPHCGEFXGIP-UHFFFAOYSA-N
• Popularity: 1,347 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₁₂O₂
• Molecular Weight: 272.30 g/mol
• Exact Mass: 272.083729621 g/mol
• Topological Polar Surface Area (TPSA): 26.30 Ų
• XlogP: 4.80
• Atomic LogP (AlogP): 4.61
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 1

Synonyms

• 7,8-Benzoflavone
• 604-59-1
• alpha-Naphthylflavone
• 2-phenylbenzo[h]chromen-4-one
• Benzo(h)flavone
• 2-Phenyl-4H-naphtho(1,2-b)pyran-4-one
• 7,8-BF
• 2-Phenylbenzo(h)chromen-4-one
• FML65D8PY5
• DTXSID2040650
• NSC-407011
• benzo[h]flavone
• CCRIS-3607
• CHEBI:76995
• RefChem:111352
• DTXCID0020650
• 210-071-1
• 2-Phenyl-4H-benzo[h]chromen-4-one
• 4H-Naphtho[1,2-b]pyran-4-one, 2-phenyl-
• .alpha.-Naphthoflavone
• 2-Phenyl-benzo[h]chromen-4-one
• MFCD00004985
• .alpha.-Naphthylflavone
• A-NAPHTHYLFLAVONE
• 4H-NAPHTHO(1,2-b)PYRAN-4-ONE, 2-PHENYL-
• MLS003171601
• CHEMBL283196
• BHF
• 2-PHENYL-4H-BENZO(H)CHROMEN-4-ONE
• CCRIS 3607
• EINECS 210-071-1
• NSC 407011
• BRN 0210862
• Naphthoflavon
• a-naphthoflavone
• alpha -Naphthoflavone
• UNII-FML65D8PY5
• Oprea1_054595
• Oprea1_802803
• 4H-Naphtho[1, 2-phenyl-
• 5-17-10-00726 (Beilstein Handbook Reference)
• BENZOFLAVONE, 7,8-
• BIDD:ER0569
• SCHEMBL121594
• orb1304733
• SCHEMBL29351090
• HMS3740O15
• TNP00080
• BDBM50014323
• NSC407011
• 2-phenyl-4-benzo[h][1]benzopyranone
• AKOS000505579
• CCG-267182
• CS-W014028
• DB07453
• EBC-459081
• FB09432
• PS-7270
• 2-Phenyl-4H-benzo[h]chromen-4-one #
• NCGC00017210-01
• NCGC00017210-02
• NCGC00142408-01
• DA-60547
• SMR000112233
• ST055359
• SY012881
• HY-125833
• B0056
• NS00043017
• S5158
• 7,8-BENZOFLAVONE; ALPHA-NAPHTHOFLAVONE
• EN300-122288
• F16466
• A832737
• AR-683/40897030
• Q4734915

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.6137	61.37%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.5940	59.40%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9555	95.55%
OATP1B3 inhibitior	+	0.9907	99.07%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	+	0.7697	76.97%
P-glycoprotein inhibitior	-	0.5941	59.41%
P-glycoprotein substrate	-	0.9328	93.28%
CYP3A4 substrate	-	0.5672	56.72%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7979	79.79%
CYP3A4 inhibition	+	0.6321	63.21%
CYP2C9 inhibition	-	0.5201	52.01%
CYP2C19 inhibition	+	0.8993	89.93%
CYP2D6 inhibition	-	0.9372	93.72%
CYP1A2 inhibition	+	0.9644	96.44%
CYP2C8 inhibition	-	0.6604	66.04%
CYP inhibitory promiscuity	+	0.5396	53.96%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9213	92.13%
Carcinogenicity (trinary)	Warning	0.4507	45.07%
Eye corrosion	-	0.9343	93.43%
Eye irritation	+	0.8793	87.93%
Skin irritation	+	0.7329	73.29%
Skin corrosion	-	0.9859	98.59%
Ames mutagenesis	+	0.7600	76.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6844	68.44%
Micronuclear	+	0.6959	69.59%
Hepatotoxicity	+	0.5750	57.50%
skin sensitisation	-	0.7363	73.63%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.5667	56.67%
Mitochondrial toxicity	-	0.8375	83.75%
Nephrotoxicity	-	0.6658	66.58%
Acute Oral Toxicity (c)	III	0.5110	51.10%
Estrogen receptor binding	+	0.9333	93.33%
Androgen receptor binding	+	0.9741	97.41%
Thyroid receptor binding	+	0.7137	71.37%
Glucocorticoid receptor binding	+	0.8846	88.46%
Aromatase binding	+	0.9365	93.65%
PPAR gamma	+	0.8602	86.02%
Honey bee toxicity	-	0.8918	89.18%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.6500	65.00%
Fish aquatic toxicity	+	0.7260	72.60%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1978	P11511	Cytochrome P450 19A1	70 nM	IC50	via Super-PRED
CHEMBL2231	P04798	Cytochrome P450 1A1	10 nM	IC50	via Super-PRED
CHEMBL3356	P05177	Cytochrome P450 1A2	20 nM	Ki	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.64%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.55%	95.56%
CHEMBL3959	P16083	Quinone reductase 2	92.02%	89.49%
CHEMBL2581	P07339	Cathepsin D	91.71%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.85%	86.33%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	87.51%	92.08%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.84%	99.23%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.92%	94.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	84.49%	95.50%
CHEMBL5284	Q96RR4	CaM-kinase kinase beta	84.38%	89.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.38%	89.00%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	81.48%	85.94%
CHEMBL3401	O75469	Pregnane X receptor	80.14%	94.73%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 11790
• LOTUS: LTS0046466
• wikiData: Q4734915