Bavachinin

Details

• Internal ID: 33c3c7c5-a1a4-4212-bd8f-107cb1ab4c1b
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > 6-prenylated flavans > 6-prenylated flavanones
• IUPAC Name: (2S)-2-(4-hydroxyphenyl)-7-methoxy-6-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
• InChI: InChI=1S/C21H22O4/c1-13(2)4-5-15-10-17-18(23)11-20(14-6-8-16(22)9-7-14)25-21(17)12-19(15)24-3/h4,6-10,12,20,22H,5,11H2,1-3H3/t20-/m0/s1
• InChI Key: VOCGSQHKPZSIKB-FQEVSTJZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₂O₄
• Molecular Weight: 338.40 g/mol
• Exact Mass: 338.15180918 g/mol
• Topological Polar Surface Area (TPSA): 55.80 Ų
• XlogP: 4.40
• Atomic LogP (AlogP): 4.62
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

• 19879-30-2
• Bavachinin A
• VL3EV483SZ
• (2S)-2-(4-hydroxyphenyl)-7-methoxy-6-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
• 4'-Hydroxy-7-methoxy-6-(3-methyl-2-butenyl)flavanone
• (2S)-2,3-DIHYDRO-2-(4-HYDROXYPHENYL)-7-METHOXY-6-(3-METHYL-2-BUTEN-1-YL)-4H-1-BENZOPYRAN-4-ONE
• RefChem:29609
• 2-(4-hydroxyphenyl)-7-methoxy-6-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
• 4H-1-Benzopyran-4-one, 2,3-dihydro-2-(4-hydroxyphenyl)-7-methoxy-6-(3-methyl-2-buten-1-yl)-, (2S)-
• MFCD06858307
• (S)-2-(4-Hydroxyphenyl)-7-methoxy-6-(3-methylbut-2-en-1-yl)chroman-4-one
• Bavachinin (Standard)
• BRN 3629340
• UNII-VL3EV483SZ
• Flavanone, 4'-hydroxy-7-methoxy-6-(3-methyl-2-butenyl)-
• 5-18-04-00132 (Beilstein Handbook Reference)
• orb1304583
• SCHEMBL4220751
• CHEMBL1551302
• HY-N0234R
• CHEBI:184255
• EX-A3649
• HY-N0234
• BDBM50084040
• s3878
• AKOS032962310
• Bavachinin, >=95% (LC/MS-ELSD)
• CCG-208380
• CS-3751
• FB74197
• NCGC00163517-01
• AC-31454
• BS-15784
• DA-50947
• NS00097154
• SR-05000002282
• SR-05000002282-2
• Z2037316850
• (2S)-2-(4-hydroxyphenyl)-7-methoxy-6-(3-methylbut-2-enyl)chroman-4-one
• 4H-1-Benzopyran-4-one, 2,3-dihydro-2-(4-hydroxyphenyl)-7-methoxy-6-(3-methyl-2-butenyl)-, (S)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9949	99.49%
Caco-2	+	0.6720	67.20%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.7970	79.70%
OATP2B1 inhibitior	-	0.8581	85.81%
OATP1B1 inhibitior	+	0.8656	86.56%
OATP1B3 inhibitior	+	0.9153	91.53%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.9214	92.14%
P-glycoprotein inhibitior	+	0.7007	70.07%
P-glycoprotein substrate	-	0.6860	68.60%
CYP3A4 substrate	+	0.5662	56.62%
CYP2C9 substrate	-	0.8006	80.06%
CYP2D6 substrate	-	0.7235	72.35%
CYP3A4 inhibition	-	0.6908	69.08%
CYP2C9 inhibition	+	0.7146	71.46%
CYP2C19 inhibition	+	0.9095	90.95%
CYP2D6 inhibition	-	0.7961	79.61%
CYP1A2 inhibition	+	0.6811	68.11%
CYP2C8 inhibition	+	0.4945	49.45%
CYP inhibitory promiscuity	+	0.8742	87.42%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9613	96.13%
Carcinogenicity (trinary)	Non-required	0.6836	68.36%
Eye corrosion	-	0.9905	99.05%
Eye irritation	-	0.6928	69.28%
Skin irritation	-	0.7900	79.00%
Skin corrosion	-	0.9715	97.15%
Ames mutagenesis	-	0.6354	63.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.4432	44.32%
Micronuclear	-	0.5700	57.00%
Hepatotoxicity	+	0.8000	80.00%
skin sensitisation	-	0.8121	81.21%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	+	0.6192	61.92%
Acute Oral Toxicity (c)	III	0.6865	68.65%
Estrogen receptor binding	+	0.8161	81.61%
Androgen receptor binding	+	0.5894	58.94%
Thyroid receptor binding	+	0.6426	64.26%
Glucocorticoid receptor binding	+	0.8631	86.31%
Aromatase binding	+	0.5790	57.90%
PPAR gamma	+	0.9239	92.39%
Honey bee toxicity	-	0.7722	77.22%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.9825	98.25%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	3470 nM	IC50	PMID: 26900660
CHEMBL3180	O00748	Carboxylesterase 2	4310 nM	IC50	PMID: 26900660
CHEMBL235	P37231	Peroxisome proliferator-activated receptor gamma	616.7 nM; 221.4 nM; 169.1 nM	IC50; Ki; Ki	PMID: 25978962; via Super-PRED; via Super-PRED
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	31622.8 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	98.38%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.46%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.58%	96.09%
CHEMBL2581	P07339	Cathepsin D	95.52%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.92%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.27%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.04%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.52%	99.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.55%	95.89%
CHEMBL2535	P11166	Glucose transporter	86.25%	98.75%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.10%	94.45%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.51%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.40%	89.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.05%	90.71%
CHEMBL4208	P20618	Proteasome component C5	82.28%	90.00%
CHEMBL2413	P32246	C-C chemokine receptor type 1	81.42%	89.50%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.08%	94.00%
CHEMBL3194	P02766	Transthyretin	80.65%	90.71%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.28%	92.62%

Plants that contains it

• Cullen corylifolium

Cross-Links

• PubChem: 10337211
• NPASS: NPC169591
• ChEMBL: CHEMBL1551302
• LOTUS: LTS0188048
• wikiData: Q105290095