Flavone

Details

• Internal ID: db559728-6506-4b81-a5a7-044f4e512c89
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavones
• IUPAC Name: 2-phenylchromen-4-one
• SMILES (Canonical): C1=CC=C(C=C1)C2=CC(=O)C3=CC=CC=C3O2
• SMILES (Isomeric): C1=CC=C(C=C1)C2=CC(=O)C3=CC=CC=C3O2
• InChI: InChI=1S/C15H10O2/c16-13-10-15(11-6-2-1-3-7-11)17-14-9-5-4-8-12(13)14/h1-10H
• InChI Key: VHBFFQKBGNRLFZ-UHFFFAOYSA-N
• Popularity: 13,141 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₀O₂
• Molecular Weight: 222.24 g/mol
• Exact Mass: 222.068079557 g/mol
• Topological Polar Surface Area (TPSA): 26.30 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 3.46
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 1

Synonyms

• 525-82-6
• 2-Phenyl-4H-chromen-4-one
• 2-Phenylchromone
• 2-Phenyl-4-chromone
• Asmacoril
• 2-phenylchromen-4-one
• Chromocor
• Cromaril
• 2-Phenyl-4H-1-benzopyran-4-one
• 2-Phenyl-4-benzopyron
• 4H-1-Benzopyran-4-one, 2-phenyl-
• 2-Phenyl-chromen-4-one
• Phenylchromone
• Cromarile
• 2-Phenyl-gamma-benzopyrone
• 2-Phenylbenzopyran-4-one
• 2-Phenyl-4H-benzopyran-4-one
• Flavon
• 2-Phenyl-.gamma.-benzopyrone
• NSC 19028
• NSC-19028
• 2-Phenyl-4H-chromen-4-on
• Flavone (VAN)
• CCRIS 4288
• NSC19028
• EINECS 208-383-8
• 2-phenyl-1,4-benzopyrone
• BRN 0157598
• UNII-S2V45N7G3B
• 2-phenyl-1-benzopyran-4-one
• MLS002638647
• CHEMBL275638
• S2V45N7G3B
• DTXSID2022048
• CHEBI:42491
• NCGC00090962-05
• 5-17-10-00552 (Beilstein Handbook Reference)
• DTXCID602048
• CAS-525-82-6
• FLN
• SMR000112315
• MFCD00006825
• 54849-74-0
• Flavone, Flavone
• 4hki
• 2-phenyl-4H-chromone
• FLAVONE [MI]
• Maybridge3_005286
• bmse000945
• D08RVN
• D0S0RK
• CBiol_000263
• SCHEMBL18879
• GTPL409
• MLS002177804
• MLS002473400
• 2-Phenylbenzo[b]pyran-4-one
• BIDD:ER0515
• MEGxp0_001685
• 2-Phenyl-4H-chromen-4-one #
• ACon1_000055
• HMS1446A06
• HMS2269O06
• HMS3604K19
• 4h-1-benzopyran-4-one,2-phenyl-
• HY-N2424
• Tox21_202987
• Tox21_400059
• BDBM50028962
• ICCB2_000263
• LMPK12110097
• s3967
• STK164205
• AKOS000603572
• CCG-214679
• DB07776
• IDI1_016673
• NCGC00090962-01
• NCGC00090962-02
• NCGC00090962-03
• NCGC00090962-04
• NCGC00090962-06
• NCGC00168837-01
• NCGC00260532-01
• AC-35144
• AS-58464
• LS-39844
• CS-0022637
• F0015
• FT-0603450
• C10043
• F-2700
• A829155
• EN300-18246169
• L001213
• CU-00000000060-1
• Q2742033
• BRD-K86741145-001-01-5
• 6CC153EB-39A6-42FC-BE96-C8BF1D585E27
• 11091-19-3
• 66585-04-4
• InChI=1/C15H10O2/c16-13-10-15(11-6-2-1-3-7-11)17-14-9-5-4-8-12(13)14/h1-10

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.7413	74.13%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	+	0.7714	77.14%
Subcellular localzation	Mitochondria	0.5940	59.40%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9548	95.48%
OATP1B3 inhibitior	+	0.9907	99.07%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.4722	47.22%
P-glycoprotein inhibitior	-	0.7353	73.53%
P-glycoprotein substrate	-	0.9629	96.29%
CYP3A4 substrate	-	0.6034	60.34%
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	-	0.7240	72.40%
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	+	0.9299	92.99%
Skin irritation	+	0.7329	73.29%
Skin corrosion	-	0.9859	98.59%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7082	70.82%
Micronuclear	+	0.6959	69.59%
Hepatotoxicity	+	0.6625	66.25%
skin sensitisation	-	0.7363	73.63%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.5667	56.67%
Mitochondrial toxicity	-	0.8375	83.75%
Nephrotoxicity	-	0.5791	57.91%
Acute Oral Toxicity (c)	III	0.5110	51.10%
Estrogen receptor binding	+	0.8906	89.06%
Androgen receptor binding	+	0.8695	86.95%
Thyroid receptor binding	+	0.6251	62.51%
Glucocorticoid receptor binding	+	0.8581	85.81%
Aromatase binding	+	0.9532	95.32%
PPAR gamma	+	0.8530	85.30%
Honey bee toxicity	-	0.8435	84.35%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.6700	67.00%
Fish aquatic toxicity	+	0.7260	72.60%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	8912.5 nM	Potency	via CMAUP
CHEMBL256	P0DMS8	Adenosine A3 receptor	16900 nM; 16900 nM	Ki; Ki	PMID: 8691424; PMID: 8576921
CHEMBL1871	P10275	Androgen Receptor	5900 nM; 5900 nM	IC50; IC50	PMID: 19592245; PMID: 19592245
CHEMBL5393	Q9UNQ0	ATP-binding cassette sub-family G member 2	17000 nM; 26000 nM	IC50; IC50	PMID: 21354800; PMID: 21354800
CHEMBL261	P00915	Carbonic anhydrase I	1880 nM; 1890 nM	Ki; Ki	PMID: 22487176; PMID: 22487176
CHEMBL205	P00918	Carbonic anhydrase II	8710 nM; 8800 nM	Ki; Ki	PMID: 22487176; PMID: 22487176
CHEMBL3594	Q16790	Carbonic anhydrase IX	4130 nM; 4220 nM	Ki; Ki	PMID: 22487176; PMID: 22487176
CHEMBL3242	O43570	Carbonic anhydrase XII	7220 nM; 7330 nM	Ki; Ki	PMID: 22487176; PMID: 22487176
CHEMBL4096	P04637	Cellular tumor antigen p53	5 nM; 5 nM	Potency; Potency	via CMAUP; via Super-PRED
CHEMBL1978	P11511	Cytochrome P450 19A1	10000 nM; 8000 nM; 8 nM	IC50; IC50; IC50	PMID: 24345481; PMID: 26301554; via Super-PRED
CHEMBL4878	Q16678	Cytochrome P450 1B1	600 nM	IC50	via Super-PRED
CHEMBL340	P08684	Cytochrome P450 3A4	12589.3 nM; 12589.3 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL284	P27487	Dipeptidyl peptidase IV	170 nM	IC50	via Super-PRED
CHEMBL1293277	O15118	Niemann-Pick C1 protein	5623.4 nM	Potency	via CMAUP
CHEMBL3105	P09874	Poly [ADP-ribose] polymerase-1	1380.38 nM; 1400 nM	IC50; IC50	PMID: 23574272; PMID: 23574272
CHEMBL1293294	P51151	Ras-related protein Rab-9A	3162.3 nM	Potency	via CMAUP
CHEMBL1293232	Q16637	Survival motor neuron protein	14125.4 nM	Potency	via CMAUP
CHEMBL6164	O95271	Tankyrase-1	323.59 nM; 320 nM; 320 nM; 323.59 nM	IC50; IC50; IC50; IC50	PMID: 23574272; PMID: 23574272; via Super-PRED; PMID: 24116873
CHEMBL6154	Q9H2K2	Tankyrase-2	147.91 nM; 140 nM; 140 nM	IC50; IC50; IC50	PMID: 23574272; PMID: 23574272; via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.24%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.32%	95.56%
CHEMBL2581	P07339	Cathepsin D	92.95%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.46%	89.00%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	87.92%	94.23%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.99%	85.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.81%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.82%	86.33%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	84.46%	94.62%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	84.44%	92.08%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	82.43%	96.37%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.64%	95.50%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.68%	94.00%

Plants that contains it

• Anaphalis lactea
• Anthocleista grandiflora
• Artemisia monosperma
• Asphodeline damascena
• Asplenium normale
• Brucea javanica
• Carpobrotus edulis
• Castanea crenata
• Centrolobium tomentosum
• Ceratophyllum submersum
• Chamaemelum nobile
• Chrysanthemum morifolium
• Commelina communis
• Conchocarpus heterophyllus
• Coriandrum sativum
• Dracocephalum kotschyi
• Grindelia hirsutula
• Grona styracifolia
• Helleborus orientalis
• Hypoestes serpens
• Lespedeza homoloba
• Lippia carviodora
• Lolium perenne
• Myrica nana
• Oroxylum indicum
• Phoenix dactylifera
• Picradeniopsis multiflora
• Primula denticulata
• Primula farinosa
• Primula veris
• Psilostrophe cooperi
• Sideritis tragoriganum
• Solanum jamaicense
• Swertia hickinii
• Tilia tomentosa
• Trifolium alexandrinum

Cross-Links

• PubChem: 10680
• NPASS: NPC32298
• ChEMBL: CHEMBL275638
• LOTUS: LTS0083403
• wikiData: Q2742033