Flavokawain B

Details

• Internal ID: ef3479ca-3be9-48c1-9b36-d6f8d493449f
• Taxonomy: Phenylpropanoids and polyketides > Linear 1,3-diarylpropanoids > Chalcones and dihydrochalcones > 2-Hydroxychalcones
• IUPAC Name: (E)-1-(2-hydroxy-4,6-dimethoxyphenyl)-3-phenylprop-2-en-1-one
• SMILES (Canonical): COC1=CC(=C(C(=C1)OC)C(=O)C=CC2=CC=CC=C2)O
• SMILES (Isomeric): COC1=CC(=C(C(=C1)OC)C(=O)/C=C/C2=CC=CC=C2)O
• InChI: InChI=1S/C17H16O4/c1-20-13-10-15(19)17(16(11-13)21-2)14(18)9-8-12-6-4-3-5-7-12/h3-11,19H,1-2H3/b9-8+
• InChI Key: QKQLSQLKXBHUSO-CMDGGOBGSA-N
• Popularity: 86 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₆O₄
• Molecular Weight: 284.31 g/mol
• Exact Mass: 284.10485899 g/mol
• Topological Polar Surface Area (TPSA): 55.80 Ų
• XlogP: 3.80
• Atomic LogP (AlogP): 3.31
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

• 1775-97-9
• Flavokavain B
• (E)-1-(2-hydroxy-4,6-dimethoxyphenyl)-3-phenylprop-2-en-1-one
• Flavokavin B
• Flavokawin B
• 4',6'-Dimethoxy-2'-hydroxychalcone
• 2'-Hydroxy-4',6'-dimethoxychalcone
• CHEBI:65899
• R9WC6SM4UQ
• 2-Propen-1-one, 1-(2-hydroxy-4,6-dimethoxyphenyl)-3-phenyl-, (2E)-
• PERSICOCHALCONE
• UNII-R9WC6SM4UQ
• NSC-51351
• (E)-2'-Hydroxy-4',6'-dimethoxychalcone
• MLS000737282
• (2E)-1-(2-hydroxy-4,6-dimethoxyphenyl)-3-phenylprop-2-en-1-one
• CHALCONE,2-HYDROXY-4,6-DIMETHYL
• 2-Propen-1-one, 1-(2-hydroxy-4,6-dimethoxyphenyl)-3-phenyl-, (E)-
• 1-(2-hydroxy-4,6-dimethoxyphenyl)-3-phenyl-2-propen-1-one
• (2E)-1-(2-HYDROXY-4,6-DIMETHOXYPHENYL)-3-PHENYL-2-PROPEN-1-ONE
• Spectrum5_000188
• CHALCONE,6-DIMETHYL
• BSPBio_001873
• SPECTRUM201610
• CHEMBL104255
• MEGxp0_001270
• SCHEMBL1675987
• CHEBI:92523
• QKQLSQLKXBHUSO-CMDGGOBGSA-N
• DTXSID601028794
• HMS2267O16
• HY-N2132
• NSC51351
• BDBM50491168
• CCG-38384
• LMPK12120246
• MFCD00075877
• s9412
• AKOS027383422
• NCGC00095512-01
• NCGC00095512-02
• AC-34272
• Chalcone, 2'-hydroxy-4',6'-dimethoxy-
• SMR000528248
• CS-0018683
• 4\',6\'-DIMETHOXY-2\'-HYDROXYCHALCONE
• A812279
• SR-01000777225
• J-011297
• Q5458167
• SR-01000777225-3
• BRD-K30296925-001-02-1
• 1175-97-9
• 76554-24-0

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9961	99.61%
Caco-2	+	0.8149	81.49%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.8978	89.78%
OATP2B1 inhibitior	-	0.8619	86.19%
OATP1B1 inhibitior	+	0.9414	94.14%
OATP1B3 inhibitior	+	0.9897	98.97%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.6525	65.25%
P-glycoprotein inhibitior	+	0.6923	69.23%
P-glycoprotein substrate	-	0.9362	93.62%
CYP3A4 substrate	-	0.5728	57.28%
CYP2C9 substrate	-	0.8053	80.53%
CYP2D6 substrate	-	0.8356	83.56%
CYP3A4 inhibition	+	0.5000	50.00%
CYP2C9 inhibition	-	0.9037	90.37%
CYP2C19 inhibition	+	0.8684	86.84%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	+	0.8968	89.68%
CYP2C8 inhibition	+	0.8546	85.46%
CYP inhibitory promiscuity	+	0.7605	76.05%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.6960	69.60%
Carcinogenicity (trinary)	Non-required	0.6565	65.65%
Eye corrosion	-	0.9569	95.69%
Eye irritation	+	0.8552	85.52%
Skin irritation	-	0.6490	64.90%
Skin corrosion	-	0.9851	98.51%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4851	48.51%
Micronuclear	+	0.6233	62.33%
Hepatotoxicity	+	0.6908	69.08%
skin sensitisation	-	0.8735	87.35%
Respiratory toxicity	-	0.8111	81.11%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	-	0.7750	77.50%
Nephrotoxicity	-	0.5839	58.39%
Acute Oral Toxicity (c)	III	0.6034	60.34%
Estrogen receptor binding	+	0.9147	91.47%
Androgen receptor binding	+	0.8212	82.12%
Thyroid receptor binding	+	0.6125	61.25%
Glucocorticoid receptor binding	+	0.6591	65.91%
Aromatase binding	+	0.8153	81.53%
PPAR gamma	+	0.8322	83.22%
Honey bee toxicity	-	0.9294	92.94%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5355	53.55%
Fish aquatic toxicity	+	0.9891	98.91%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4096	P04637	Cellular tumor antigen p53	31622.8 nM	Potency	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	15848.9 nM; 15848.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	25118.9 nM	Potency	via CMAUP
CHEMBL1293299	Q03164	Histone-lysine N-methyltransferase MLL	17782.8 nM	Potency	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	14125.4 nM; 10000 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL3797	Q13315	Serine-protein kinase ATM	28183.8 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.97%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.95%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.84%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	92.78%	96.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.60%	96.09%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	92.20%	95.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.61%	99.17%
CHEMBL3194	P02766	Transthyretin	89.51%	90.71%
CHEMBL4208	P20618	Proteasome component C5	89.36%	90.00%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	87.74%	94.08%
CHEMBL2535	P11166	Glucose transporter	86.29%	98.75%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.95%	99.15%
CHEMBL3192	Q9BY41	Histone deacetylase 8	84.84%	93.99%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	84.46%	91.71%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.93%	91.07%
CHEMBL2581	P07339	Cathepsin D	80.92%	98.95%

Plants that contains it

• Aconitum variegatum
• Alpinia mutica
• Alpinia pricei
• Alpinia zerumbet
• Aniba riparia
• Artocarpus altilis
• Carthamus arborescens
• Cedrelopsis grevei
• Cephalotaxus fortunei
• Hemionitis pteridioides
• Kaempferia parviflora
• Litsea pedunculata
• Ostrya carpinifolia
• Persicaria ferruginea
• Persicaria senegalensis
• Piper dilatatum
• Piper methysticum
• Piper rusbyi
• Pteris cretica subsp. cretica
• Renealmia nicolaioides
• Stephania dielsiana
• Uvaria angolensis
• Uvaria mocoli
• Vangueria agrestis

Cross-Links

• PubChem: 5356121
• NPASS: NPC188646
• ChEMBL: CHEMBL104255
• LOTUS: LTS0134402
• wikiData: Q5458167