Flavokawain A

Details

• Internal ID: 9c9591c1-44a2-4041-9466-3b454bd31cf4
• Taxonomy: Phenylpropanoids and polyketides > Linear 1,3-diarylpropanoids > Chalcones and dihydrochalcones > 2-Hydroxychalcones
• IUPAC Name: (E)-1-(2-hydroxy-4,6-dimethoxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one
• SMILES (Canonical): COC1=CC=C(C=C1)C=CC(=O)C2=C(C=C(C=C2OC)OC)O
• SMILES (Isomeric): COC1=CC=C(C=C1)/C=C/C(=O)C2=C(C=C(C=C2OC)OC)O
• InChI: InChI=1S/C18H18O5/c1-21-13-7-4-12(5-8-13)6-9-15(19)18-16(20)10-14(22-2)11-17(18)23-3/h4-11,20H,1-3H3/b9-6+
• InChI Key: CGIBCVBDFUTMPT-RMKNXTFCSA-N
• Popularity: 57 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₁₈O₅
• Molecular Weight: 314.30 g/mol
• Exact Mass: 314.11542367 g/mol
• Topological Polar Surface Area (TPSA): 65.00 Ų
• XlogP: 3.80
• Atomic LogP (AlogP): 3.31
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 6

Synonyms

• 3420-72-2
• 2'-Hydroxy-4,4',6'-trimethoxychalcone
• Flavokavain A
• 37951-13-6
• flavokavin A
• 1-(2-hydroxy-4,6-dimethoxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one
• (E)-1-(2-hydroxy-4,6-dimethoxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one
• FLAVOKAVAIN A(P)
• 64680-84-8
• 4-Methoxyflavokawain B
• 8OM2XZ2ZM3
• MLS002608040
• (2E)-1-(2-hydroxy-4,6-dimethoxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one
• (2E)-1-(2-Hydroxy-4,6-dimethoxyphenyl)-3-(4-methoxyphenyl)-2-propen-1-one
• 2-Propen-1-one, 1-(2-hydroxy-4,6-dimethoxyphenyl)-3-(4-methoxyphenyl)-, (2E)-
• UNII-8OM2XZ2ZM3
• CHEMBL243829
• SCHEMBL2289181
• SCHEMBL2289188
• CGIBCVBDFUTMPT-RMKNXTFCSA-N
• CHEBI:157725
• DTXSID601317535
• HY-N2420
• NSC37445
• BDBM50360495
• MFCD00017174
• NSC-37445
• s5600
• (E)-1-(2-hydroxy-4,6-dimethoxy-phenyl)-3-(4-methoxyphenyl)prop-2-en-1-one
• AKOS015915333
• CCG-267628
• AS-72376
• SMR001490973
• 2/'-Hydroxy-4,4/',6/'-trimethoxychalcone
• CS-0022627
• 2'-Hydroxy-4,4',6'-trimethoxychalcone, 98%
• A875070
• J-019499
• Q5458164
• 2-Propen-1-one, 1-(2-hydroxy-4,6-dimethoxyphenyl)-3-(4-methoxyphenyl)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9957	99.57%
Caco-2	+	0.9143	91.43%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.8810	88.10%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9507	95.07%
OATP1B3 inhibitior	+	0.9737	97.37%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.7127	71.27%
P-glycoprotein inhibitior	+	0.7791	77.91%
P-glycoprotein substrate	-	0.9285	92.85%
CYP3A4 substrate	-	0.5462	54.62%
CYP2C9 substrate	-	0.8053	80.53%
CYP2D6 substrate	-	0.8356	83.56%
CYP3A4 inhibition	+	0.5188	51.88%
CYP2C9 inhibition	-	0.9654	96.54%
CYP2C19 inhibition	+	0.6722	67.22%
CYP2D6 inhibition	-	0.9232	92.32%
CYP1A2 inhibition	+	0.8002	80.02%
CYP2C8 inhibition	+	0.7453	74.53%
CYP inhibitory promiscuity	+	0.7229	72.29%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.6960	69.60%
Carcinogenicity (trinary)	Non-required	0.6246	62.46%
Eye corrosion	-	0.9722	97.22%
Eye irritation	+	0.7128	71.28%
Skin irritation	-	0.7639	76.39%
Skin corrosion	-	0.9911	99.11%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4849	48.49%
Micronuclear	+	0.5533	55.33%
Hepatotoxicity	-	0.5217	52.17%
skin sensitisation	-	0.9202	92.02%
Respiratory toxicity	-	0.8444	84.44%
Reproductive toxicity	+	0.5444	54.44%
Mitochondrial toxicity	-	0.8000	80.00%
Nephrotoxicity	+	0.4696	46.96%
Acute Oral Toxicity (c)	III	0.5556	55.56%
Estrogen receptor binding	+	0.9322	93.22%
Androgen receptor binding	+	0.8108	81.08%
Thyroid receptor binding	+	0.7251	72.51%
Glucocorticoid receptor binding	+	0.7553	75.53%
Aromatase binding	+	0.8752	87.52%
PPAR gamma	+	0.8949	89.49%
Honey bee toxicity	-	0.9397	93.97%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9897	98.97%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL5393	Q9UNQ0	ATP-binding cassette sub-family G member 2	3000 nM; 5830 nM	IC50; IC50	PMID: 22112540; PMID: 22112540

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.89%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.77%	95.56%
CHEMBL4208	P20618	Proteasome component C5	94.07%	90.00%
CHEMBL3194	P02766	Transthyretin	93.68%	90.71%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.67%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.35%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	92.48%	96.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.18%	99.17%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	87.74%	99.15%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	87.26%	95.50%
CHEMBL2535	P11166	Glucose transporter	84.89%	98.75%
CHEMBL1929	P47989	Xanthine dehydrogenase	83.78%	96.12%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	83.63%	91.07%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.32%	89.00%
CHEMBL3192	Q9BY41	Histone deacetylase 8	80.07%	93.99%

Plants that contains it

• Boesenbergia rotunda
• Dahlia tenuicaulis
• Gamochaeta malvinensis
• Goniothalamus gardneri
• Kaempferia angustifolia
• Piper methysticum
• Pseudognaphalium affine
• Vitex quinata

Cross-Links

• PubChem: 5355469
• NPASS: NPC242294
• ChEMBL: CHEMBL243829
• LOTUS: LTS0165257
• wikiData: Q5458164