Pratol

Details

• Internal ID: 921f80a9-0e26-4a3d-85c7-841b186ee19b
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > O-methylated flavonoids > 4-O-methylated flavonoids
• IUPAC Name: 7-hydroxy-2-(4-methoxyphenyl)chromen-4-one
• SMILES (Canonical): COC1=CC=C(C=C1)C2=CC(=O)C3=C(O2)C=C(C=C3)O
• SMILES (Isomeric): COC1=CC=C(C=C1)C2=CC(=O)C3=C(O2)C=C(C=C3)O
• InChI: InChI=1S/C16H12O4/c1-19-12-5-2-10(3-6-12)15-9-14(18)13-7-4-11(17)8-16(13)20-15/h2-9,17H,1H3
• InChI Key: SQVXWIUVAILQRH-UHFFFAOYSA-N
• Popularity: 56 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₂O₄
• Molecular Weight: 268.26 g/mol
• Exact Mass: 268.07355886 g/mol
• Topological Polar Surface Area (TPSA): 55.80 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 3.17
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• 487-24-1
• 7-Hydroxy-4'-methoxyflavone
• 7-Hydroxy-2-(4-methoxyphenyl)-4H-chromen-4-one
• 7-hydroxy-2-(4-methoxyphenyl)chromen-4-one
• 7-Hydroxy-4-methoxyflavone
• C.I. 75570
• EINECS 207-653-2
• 4H-1-Benzopyran-4-one, 7-hydroxy-2-(4-methoxyphenyl)-
• Flavone, 7-hydroxy-4'-methoxy-
• NSC 123414
• NSC-123414
• BRN 0237239
• UNII-KU5R959MO7
• MLS002707301
• KU5R959MO7
• 7-Hydroxy-2-(4-methoxyphenyl)-4-benzopyrone
• NSC123414
• 7-Hydroxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one
• 487-17-2
• 5-18-04-00083 (Beilstein Handbook Reference)
• 4hl5
• 7-Hydroxy-flavone, 5h
• 4'-methoxy-7-hydroxyflavone
• Oprea1_854602
• CHEMBL16751
• SCHEMBL534596
• BDBM85573
• DTXSID20197587
• TNP00065
• MFCD00016937
• AKOS004110700
• CCG-208438
• NCGC00017200-01
• NCGC00017200-02
• NCGC00017200-03
• NCGC00142412-01
• NCGC00142412-02
• LS-39700
• SMR001488172
• CS-0148969
• FT-0730316
• Flavone, 7-hydroxy-4'-methoxy- (7CI,8CI)
• EN300-179336
• AN-829/40761415
• SR-05000002252
• 7-Hydroxy-2-(4-methoxyphenyl)-4H-chromen-4-one #
• SR-05000002252-2
• BRD-K35651673-001-05-9
• Q15424797
• Z1846974262
• 15W

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9919	99.19%
Caco-2	-	0.5265	52.65%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7440	74.40%
OATP2B1 inhibitior	-	0.7152	71.52%
OATP1B1 inhibitior	+	0.8942	89.42%
OATP1B3 inhibitior	+	0.9971	99.71%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.7176	71.76%
P-glycoprotein inhibitior	-	0.5906	59.06%
P-glycoprotein substrate	-	0.8129	81.29%
CYP3A4 substrate	+	0.5486	54.86%
CYP2C9 substrate	-	0.8382	83.82%
CYP2D6 substrate	-	0.7720	77.20%
CYP3A4 inhibition	+	0.7960	79.60%
CYP2C9 inhibition	+	0.8948	89.48%
CYP2C19 inhibition	+	0.8994	89.94%
CYP2D6 inhibition	-	0.9230	92.30%
CYP1A2 inhibition	+	0.9443	94.43%
CYP2C8 inhibition	+	0.7082	70.82%
CYP inhibitory promiscuity	+	0.6221	62.21%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9113	91.13%
Carcinogenicity (trinary)	Non-required	0.4512	45.12%
Eye corrosion	-	0.9407	94.07%
Eye irritation	+	0.8458	84.58%
Skin irritation	-	0.6036	60.36%
Skin corrosion	-	0.9855	98.55%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6295	62.95%
Micronuclear	+	0.8500	85.00%
Hepatotoxicity	-	0.6675	66.75%
skin sensitisation	-	0.9737	97.37%
Respiratory toxicity	-	0.6111	61.11%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.7062	70.62%
Acute Oral Toxicity (c)	III	0.8852	88.52%
Estrogen receptor binding	+	0.9432	94.32%
Androgen receptor binding	+	0.9676	96.76%
Thyroid receptor binding	+	0.7259	72.59%
Glucocorticoid receptor binding	+	0.9308	93.08%
Aromatase binding	+	0.9403	94.03%
PPAR gamma	+	0.8658	86.58%
Honey bee toxicity	-	0.8776	87.76%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.7657	76.57%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4096	P04637	Cellular tumor antigen p53	15848.9 nM; 12589.3 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL3622	P33261	Cytochrome P450 2C19	3162.3 nM	Potency	via CMAUP
CHEMBL3397	P11712	Cytochrome P450 2C9	3981.1 nM	Potency	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	7943.3 nM; 7943.3 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL6164	O95271	Tankyrase-1	560 nM; 560 nM; 562.34 nM	IC50; IC50; IC50	via Super-PRED; PMID: 23574272; PMID: 23574272
CHEMBL6154	Q9H2K2	Tankyrase-2	450 nM; 450 nM; 457.09 nM	IC50; IC50; IC50	via Super-PRED; PMID: 23574272; PMID: 23574272

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.68%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.83%	85.14%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.71%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.94%	95.56%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	94.45%	83.57%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	94.17%	99.15%
CHEMBL242	Q92731	Estrogen receptor beta	93.53%	98.35%
CHEMBL2581	P07339	Cathepsin D	93.30%	98.95%
CHEMBL1907	P15144	Aminopeptidase N	92.70%	93.31%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.52%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.84%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.66%	94.45%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	84.12%	95.53%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.29%	99.17%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.25%	86.92%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.63%	99.23%
CHEMBL3192	Q9BY41	Histone deacetylase 8	80.06%	93.99%

Plants that contains it

• Caragana microphylla
• Cicer arietinum
• Fordia cauliflora
• Hedysarum polybotrys
• Oxytropis trichophysa
• Trifolium pratense

Cross-Links

• PubChem: 5320693
• NPASS: NPC266597
• ChEMBL: CHEMBL16751
• LOTUS: LTS0048623
• wikiData: Q15424797