(5Z)-4-bromo-5-(chloromethylidene)-3-[(1R)-1-hydroxybutyl]furan-2-one

Details

• Internal ID: 32862458-9115-4d50-8138-3e055cd093eb
• Taxonomy: Organoheterocyclic compounds > Dihydrofurans > Furanones > Butenolides
• IUPAC Name: (5Z)-4-bromo-5-(chloromethylidene)-3-[(1R)-1-hydroxybutyl]furan-2-one
• SMILES (Canonical): CCCC(C1=C(C(=CCl)OC1=O)Br)O
• SMILES (Isomeric): CCC[C@H](C1=C(/C(=C/Cl)/OC1=O)Br)O
• InChI: InChI=1S/C9H10BrClO3/c1-2-3-5(12)7-8(10)6(4-11)14-9(7)13/h4-5,12H,2-3H2,1H3/b6-4-/t5-/m1/s1
• InChI Key: VXUYDUOMEUFAII-WEWOIACBSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₉H₁₀BrClO₃
• Molecular Weight: 281.53 g/mol
• Exact Mass: 279.95018 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 2.43
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• BDBM50478849

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9961	99.61%
Caco-2	+	0.7998	79.98%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6135	61.35%
OATP2B1 inhibitior	-	0.8519	85.19%
OATP1B1 inhibitior	+	0.9139	91.39%
OATP1B3 inhibitior	+	0.9439	94.39%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.7820	78.20%
BSEP inhibitior	-	0.8663	86.63%
P-glycoprotein inhibitior	-	0.9493	94.93%
P-glycoprotein substrate	-	0.9425	94.25%
CYP3A4 substrate	-	0.5523	55.23%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8472	84.72%
CYP3A4 inhibition	-	0.7712	77.12%
CYP2C9 inhibition	-	0.7459	74.59%
CYP2C19 inhibition	-	0.6901	69.01%
CYP2D6 inhibition	-	0.8960	89.60%
CYP1A2 inhibition	-	0.8367	83.67%
CYP2C8 inhibition	-	0.9279	92.79%
CYP inhibitory promiscuity	-	0.7748	77.48%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8189	81.89%
Carcinogenicity (trinary)	Danger	0.5101	51.01%
Eye corrosion	-	0.9356	93.56%
Eye irritation	+	0.6505	65.05%
Skin irritation	-	0.5949	59.49%
Skin corrosion	-	0.7912	79.12%
Ames mutagenesis	-	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6529	65.29%
Micronuclear	-	0.8652	86.52%
Hepatotoxicity	+	0.5875	58.75%
skin sensitisation	-	0.7072	70.72%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.5667	56.67%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	+	0.6662	66.62%
Acute Oral Toxicity (c)	III	0.6176	61.76%
Estrogen receptor binding	+	0.8113	81.13%
Androgen receptor binding	-	0.6659	66.59%
Thyroid receptor binding	+	0.5221	52.21%
Glucocorticoid receptor binding	+	0.5371	53.71%
Aromatase binding	-	0.7717	77.17%
PPAR gamma	+	0.6014	60.14%
Honey bee toxicity	-	0.8775	87.75%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.8950	89.50%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	93.46%	98.95%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	92.38%	89.34%
CHEMBL3401	O75469	Pregnane X receptor	91.53%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.18%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.80%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.69%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.23%	97.25%
CHEMBL1907	P15144	Aminopeptidase N	82.24%	93.31%
CHEMBL218	P21554	Cannabinoid CB1 receptor	81.43%	96.61%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.42%	94.45%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.65%	93.56%
CHEMBL221	P23219	Cyclooxygenase-1	80.51%	90.17%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 44583901
• LOTUS: LTS0091359
• wikiData: Q105298780