Bonducellin

Details

• Internal ID: 4941a3b1-61ce-43f7-92b1-211fe41e89fd
• Taxonomy: Phenylpropanoids and polyketides > Homoisoflavonoids
• IUPAC Name: (3E)-7-hydroxy-3-[(4-methoxyphenyl)methylidene]chromen-4-one
• SMILES (Canonical): COC1=CC=C(C=C1)C=C2COC3=C(C2=O)C=CC(=C3)O
• SMILES (Isomeric): COC1=CC=C(C=C1)/C=C/2\COC3=C(C2=O)C=CC(=C3)O
• InChI: InChI=1S/C17H14O4/c1-20-14-5-2-11(3-6-14)8-12-10-21-16-9-13(18)4-7-15(16)17(12)19/h2-9,18H,10H2,1H3/b12-8+
• InChI Key: DLQSYZMPSWHYMW-XYOKQWHBSA-N
• Popularity: 10 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₄O₄
• Molecular Weight: 282.29 g/mol
• Exact Mass: 282.08920892 g/mol
• Topological Polar Surface Area (TPSA): 55.80 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 3.06
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• 83162-84-9
• ISOBONDUCELLIN
• (3E)-7-hydroxy-3-[(4-methoxyphenyl)methylidene]chromen-4-one
• 610778-85-3
• CHEMBL450675
• BDBM50443669
• AKOS040762678
• (e)-7-hydroxy-3-(4'-methoxybenzylidene) chroman-4-one
• (3E)-7-hydroxy-3-[(4-methoxyphenyl)methylene]chroman-4-one
• 2,3-dihydro-7-hydroxy-3-[(4-methoxyphenyl)methylene]-4H-1-benzopyran-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9943	99.43%
Caco-2	+	0.8942	89.42%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7951	79.51%
OATP2B1 inhibitior	-	0.8615	86.15%
OATP1B1 inhibitior	+	0.9347	93.47%
OATP1B3 inhibitior	+	0.9909	99.09%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.6453	64.53%
P-glycoprotein inhibitior	-	0.7661	76.61%
P-glycoprotein substrate	-	0.9129	91.29%
CYP3A4 substrate	+	0.5458	54.58%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7502	75.02%
CYP3A4 inhibition	+	0.5731	57.31%
CYP2C9 inhibition	+	0.6633	66.33%
CYP2C19 inhibition	+	0.9548	95.48%
CYP2D6 inhibition	-	0.8007	80.07%
CYP1A2 inhibition	+	0.9688	96.88%
CYP2C8 inhibition	-	0.8062	80.62%
CYP inhibitory promiscuity	+	0.8932	89.32%
UGT catelyzed	+	1.0000	100.00%
Carcinogenicity (binary)	-	0.9313	93.13%
Carcinogenicity (trinary)	Non-required	0.6628	66.28%
Eye corrosion	-	0.9777	97.77%
Eye irritation	+	0.9395	93.95%
Skin irritation	-	0.6912	69.12%
Skin corrosion	-	0.9811	98.11%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6023	60.23%
Micronuclear	+	0.8159	81.59%
Hepatotoxicity	-	0.5016	50.16%
skin sensitisation	-	0.8251	82.51%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	-	0.6375	63.75%
Nephrotoxicity	+	0.5537	55.37%
Acute Oral Toxicity (c)	III	0.5300	53.00%
Estrogen receptor binding	+	0.9038	90.38%
Androgen receptor binding	+	0.9422	94.22%
Thyroid receptor binding	+	0.6274	62.74%
Glucocorticoid receptor binding	+	0.8456	84.56%
Aromatase binding	+	0.8756	87.56%
PPAR gamma	+	0.7628	76.28%
Honey bee toxicity	-	0.8766	87.66%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9554	95.54%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2039	P27338	Monoamine oxidase B	1060 nM	IC50	PMID: 24128814

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.47%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	97.97%	95.56%
CHEMBL2581	P07339	Cathepsin D	93.46%	98.95%
CHEMBL4208	P20618	Proteasome component C5	92.79%	90.00%
CHEMBL1929	P47989	Xanthine dehydrogenase	91.07%	96.12%
CHEMBL1951	P21397	Monoamine oxidase A	90.73%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.34%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.14%	96.09%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	89.95%	83.57%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.03%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.89%	97.09%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	88.37%	95.89%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.61%	95.89%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.33%	99.17%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.33%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.96%	99.23%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	81.90%	82.67%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	81.46%	93.40%
CHEMBL2535	P11166	Glucose transporter	81.44%	98.75%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.11%	99.15%
CHEMBL226	P30542	Adenosine A1 receptor	80.48%	95.93%
CHEMBL3194	P02766	Transthyretin	80.10%	90.71%

Plants that contains it

• Aeschynanthus pulcher
• Andrographis lineata
• Baccharis patagonica
• Betula papyrifera
• Biancaea sappan
• Boronia alata
• Caesalpinia pulcherrima
• Cinnamomum philippinense
• Coronilla cretica
• Cryptochilus siamensis
• Cyperus capitatus
• Delphinium tricorne
• Dendrolirium tomentosum
• Ephedra altissima
• Erica cinerea
• Eucalyptus froggattii
• Gymnosporia emarginata
• Haemanthus albiflos
• Helleborus viridis
• Hordeum bulbosum
• Hoya australis
• Iris sibirica
• Isolona pilosa
• Jatropha gossypiifolia
• Lepidaploa aurea
• Litsea nitida
• Lobelia langeana
• Magnolia henryi
• Microdesmis keayana
• Micromelum minutum
• Peltophorum dubium
• Pistacia mexicana
• Prunus pseudocerasus
• Salvia miniata
• Sibiraea angustata
• Stuhlmannia moavi
• Tamarix dioica
• Thalictrum speciosissimum
• Tripterygium wilfordii
• Valeriana officinalis
• Xanthium spinosum subsp. spinosum

Cross-Links

• PubChem: 14079439
• NPASS: NPC188947
• ChEMBL: CHEMBL450675
• LOTUS: LTS0198403
• wikiData: Q105342374