Flavanone

Details

• Internal ID: 8289086d-9e3a-4211-a730-0b4a618e9f66
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > Flavanones
• IUPAC Name: 2-phenyl-2,3-dihydrochromen-4-one
• SMILES (Canonical): C1C(OC2=CC=CC=C2C1=O)C3=CC=CC=C3
• SMILES (Isomeric): C1C(OC2=CC=CC=C2C1=O)C3=CC=CC=C3
• InChI: InChI=1S/C15H12O2/c16-13-10-15(11-6-2-1-3-7-11)17-14-9-5-4-8-12(13)14/h1-9,15H,10H2
• InChI Key: ZONYXWQDUYMKFB-UHFFFAOYSA-N
• Popularity: 6,203 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₂O₂
• Molecular Weight: 224.25 g/mol
• Exact Mass: 224.083729621 g/mol
• Topological Polar Surface Area (TPSA): 26.30 Ų
• XlogP: 3.20
• Atomic LogP (AlogP): 3.39
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 1

Synonyms

• 487-26-3
• 2-Phenylchroman-4-one
• 2,3-Dihydroflavone
• 4-Flavanone
• 2-Phenyl-4-chromanone
• 2,3-Dihydro-2-phenyl-4H-1-benzopyran-4-one
• NSC-50393
• 2,3-Dihydro-2-phenyl-4H-benzopyran-4-one
• 4H-1-Benzopyran-4-one, 2,3-dihydro-2-phenyl-
• 2-Phenylchromanone
• 2-Phenyl-2,3-dihydro-4H-chromen-4-one
• 2-phenyl-2,3-dihydrochromen-4-one
• EINECS 207-654-8
• NSC 50393
• BRN 0183227
• UNII-WX22P730FB
• MLS002667384
• CHEBI:5070
• CHEMBL274318
• WX22P730FB
• NSC50393
• Propafenone IMpurity H (EP/BP/USP)
• 5-17-10-00480 (Beilstein Handbook Reference)
• FLAVANONE (3,3-D2)
• SMR001306759
• 2-Phenyl-chroman-4-one
• (2RS)-2-Phenyl-2,3-dihydro-4H-1-benzopyran-4-one
• 2-phenyl-3,4-dihydro-2H-1-benzopyran-4-one
• flavan-4-one
• Flavanone, 98%
• MFCD00006841
• (+/-)-flavanone
• 2-phenyl-2
• DL-FLAVANONE
• Spectrum_000081
• SpecPlus_000724
• Spectrum2_000205
• Spectrum3_000174
• Spectrum4_001646
• Spectrum5_000491
• Flavone, 2,3-dihydro-
• D0B4VE
• D0L3CJ
• Oprea1_401736
• SCHEMBL19745
• BSPBio_001667
• GTPL408
• KBioGR_002111
• KBioSS_000501
• SPECTRUM200343
• MLS002207195
• DivK1c_006820
• SPBio_000189
• MEGxp0_001684
• DTXSID9022318
• FLAVANONE, (+/-)-
• ACon1_002246
• KBio1_001764
• KBio2_000501
• KBio2_003069
• KBio2_005637
• KBio3_001167
• ZONYXWQDUYMKFB-UHFFFAOYSA-
• HY-N7128
• BBL027613
• BDBM50051358
• CCG-21177
• s3679
• STL373060
• AKOS000120276
• AKOS016040110
• AM10046
• CS-T-54718
• NCGC00095802-01
• NCGC00095802-02
• NCGC00095802-03
• NCGC00095802-05
• AS-48159
• LS-68930
• NCI60_004213
• 2-Phenyl-2,3-dihydro-4H-chromen-4-one #
• CS-0030762
• EU-0012871
• F0255
• FT-0618436
• FT-0668547
• 4H-1-Benzopyran-4-one,3-dihydro-2-phenyl-
• EN300-17915
• C00766
• F19539
• L000786
• SR-01000500943
• F4C11F5A-DFFA-4E0E-BCC9-2FD60204B2DD
• SR-01000500943-1
• BRD-A07824748-001-02-6
• BRD-A07824748-001-03-4
• Q27077305
• Z57085783
• PROPAFENONE HYDROCHLORIDE IMPURITY H [EP IMPURITY]
• InChI=1/C15H12O2/c16-13-10-15(11-6-2-1-3-7-11)17-14-9-5-4-8-12(13)14/h1-9,15H,10H2

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.7343	73.43%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.6976	69.76%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9413	94.13%
OATP1B3 inhibitior	+	0.9874	98.74%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.6423	64.23%
P-glycoprotein inhibitior	-	0.9384	93.84%
P-glycoprotein substrate	-	0.9739	97.39%
CYP3A4 substrate	-	0.6426	64.26%
CYP2C9 substrate	-	0.8256	82.56%
CYP2D6 substrate	+	0.3744	37.44%
CYP3A4 inhibition	-	0.8210	82.10%
CYP2C9 inhibition	+	0.8448	84.48%
CYP2C19 inhibition	+	0.9606	96.06%
CYP2D6 inhibition	-	0.9302	93.02%
CYP1A2 inhibition	+	0.9501	95.01%
CYP2C8 inhibition	-	0.8856	88.56%
CYP inhibitory promiscuity	+	0.5690	56.90%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9413	94.13%
Carcinogenicity (trinary)	Non-required	0.4729	47.29%
Eye corrosion	-	0.9605	96.05%
Eye irritation	+	0.7873	78.73%
Skin irritation	+	0.6256	62.56%
Skin corrosion	-	0.9877	98.77%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5148	51.48%
Micronuclear	+	0.6059	60.59%
Hepatotoxicity	+	0.5500	55.00%
skin sensitisation	-	0.5468	54.68%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	-	0.7375	73.75%
Nephrotoxicity	+	0.7451	74.51%
Acute Oral Toxicity (c)	III	0.6555	65.55%
Estrogen receptor binding	-	0.4947	49.47%
Androgen receptor binding	-	0.6886	68.86%
Thyroid receptor binding	-	0.6158	61.58%
Glucocorticoid receptor binding	-	0.7918	79.18%
Aromatase binding	+	0.7397	73.97%
PPAR gamma	+	0.6882	68.82%
Honey bee toxicity	-	0.8381	83.81%
Biodegradation	-	0.5250	52.50%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.7239	72.39%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1871	P10275	Androgen Receptor	20000 nM	IC50	PMID: 19592245
CHEMBL1978	P11511	Cytochrome P450 19A1	28000 nM; 28500 nM; 8000 nM; 8000 nM	IC50; IC50; IC50; IC50	PMID: 18042388; PMID: 11909717; PMID: 24345481; PMID: 26301554
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	39810.7 nM	Potency	via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	35481.3 nM	Potency	via CMAUP
CHEMBL2039	P27338	Monoamine oxidase B	2870 nM	IC50	PMID: 20045650

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.68%	95.56%
CHEMBL2581	P07339	Cathepsin D	92.77%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.53%	91.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.38%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.49%	97.09%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	82.88%	83.00%
CHEMBL6007	O75762	Transient receptor potential cation channel subfamily A member 1	82.21%	92.17%
CHEMBL5805	Q9NR97	Toll-like receptor 8	81.65%	96.25%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.80%	86.33%

Plants that contains it

• Betula pubescens
• Calamus draco
• Chrysanthemum morifolium
• Perityle vaseyi
• Sophora flavescens

Cross-Links

• PubChem: 10251
• NPASS: NPC314329
• ChEMBL: CHEMBL274318
• LOTUS: LTS0238805
• wikiData: Q27077305