BIOCHANIN

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Synonyms
UNII U13J6U390T
Source Gaulton A, Kale N, van Westen GJ, Bellis LJ, Bento AP, Davies M, Hersey A, Papadatos G, Forster M, Wege P, Overington JP. A large-scale crop protection bioassay data set. Sci Data. 2015 Jul 7;2:150032. Read more ...

Structure

InChI Key WUADCCWRTIWANL-UHFFFAOYSA-N
Smiles COc1ccc(cc1)C2=COc3cc(O)cc(O)c3C2=O
InChI
InChI=1S/C16H12O5/c1-20-11-4-2-9(3-5-11)12-8-21-14-7-10(17)6-13(18)15(14)16(12)19/h2-8,17-18H,1H3

Physicochemical Descriptors

Property Name Value
Molecular Formula C16H12O5
Molecular Weight 284.26
AlogP 2.37
Hydrogen Bond Acceptor 5.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 2.0
Polar Surface Area 75.99
Molecular species ACID
Aromatic Rings 2.0
Heavy Atoms 21.0
Assay Description Organism Bioactivity Reference
Drug metabolism in Echinochloa crus-galli (barnyard grass) root assessed as transformation to genistein at 400 uM after 14 days measured per gm of dry weight by LC-MS analysis Echinochloa crus-galli 0.12 umol
Drug metabolism in Echinochloa crus-galli (barnyard grass) root assessed as transformation to genistein at 20 uM after 14 days measured per gm of dry weight by LC-MS analysis Echinochloa crus-galli 0.07 umol
Drug metabolism in Geranium molle root assessed as transformation to genistein at 400 uM after 14 days measured per gm of dry weight by LC-MS analysis Geranium molle 0.08 umol
Drug metabolism in Geranium molle root assessed as transformation to genistein at 20 uM after 14 days measured per gm of dry weight by LC-MS analysis Geranium molle 0.05 umol
Drug metabolism in Silene noctiflora root assessed as transformation to genistein at 400 uM after 14 days measured per gm of dry weight by LC-MS analysis Silene noctiflora 0.13 umol
Drug metabolism in Silene noctiflora root assessed as transformation to genistein at 20 uM after 14 days measured per gm of dry weight by LC-MS analysis Silene noctiflora 0.08 umol
Drug metabolism in Echinochloa crus-galli (barnyard grass) shoot assessed as transformation to dihydrobiochanin A at 400 uM after 14 days measured per gm of dry weight by LC-MS analysis Echinochloa crus-galli 0.27 umol
Drug metabolism in Echinochloa crus-galli (barnyard grass) shoot assessed as transformation to dihydrobiochanin A at 20 uM after 14 days measured per gm of dry weight by LC-MS analysis Echinochloa crus-galli 0.0 umol
Drug metabolism in Geranium molle shoot assessed as transformation to dihydrobiochanin A at 400 uM after 14 days measured per gm of dry weight by LC-MS analysis Geranium molle 0.02 umol
Drug metabolism in Geranium molle shoot assessed as transformation to dihydrobiochanin A at 20 uM after 14 days measured per gm of dry weight by LC-MS analysis Geranium molle 0.01 umol
Drug metabolism in Silene noctiflora shoot assessed as transformation to dihydrobiochanin A at 400 uM after 14 days measured per gm of dry weight by LC-MS analysis Silene noctiflora 0.02 umol
Drug metabolism in Silene noctiflora shoot assessed as transformation to dihydrobiochanin A at 20 uM after 14 days measured per gm of dry weight by LC-MS analysis Silene noctiflora 0.0 umol
Drug metabolism in Echinochloa crus-galli (barnyard grass) root assessed as transformation to dihydrobiochanin A at 400 uM after 14 days measured per gm of dry weight by LC-MS analysis Echinochloa crus-galli 0.27 umol
Drug metabolism in Echinochloa crus-galli (barnyard grass) root assessed as transformation to dihydrobiochanin A at 20 uM after 14 days measured per gm of dry weight by LC-MS analysis Echinochloa crus-galli 0.05 umol
Drug metabolism in Geranium molle root assessed as transformation to dihydrobiochanin A at 400 uM after 14 days measured per gm of dry weight by LC-MS analysis Geranium molle 0.31 umol
Drug metabolism in Geranium molle root assessed as transformation to dihydrobiochanin A at 20 uM after 14 days measured per gm of dry weight by LC-MS analysis Geranium molle 0.38 umol
Drug metabolism in Silene noctiflora root assessed as transformation to dihydrobiochanin A at 400 uM after 14 days measured per gm of dry weight by LC-MS analysis Silene noctiflora 0.07 umol
Drug metabolism in Silene noctiflora root assessed as transformation to dihydrobiochanin A at 20 uM after 14 days measured per gm of dry weight by LC-MS analysis Silene noctiflora 0.01 umol
Drug uptake in Echinochloa crus-galli (barnyard grass) shoot at 400 uM after 14 days measured per gm of dry weight by LC-MS analysis Echinochloa crus-galli 0.67 umol
Drug uptake in Echinochloa crus-galli (barnyard grass) shoot at 20 uM after 14 days measured per gm of dry weight by LC-MS analysis Echinochloa crus-galli 0.05 umol
Drug uptake in Geranium molle shoot at 400 uM after 14 days measured per gm of dry weight by LC-MS analysis Geranium molle 1.13 umol
Drug uptake in Silene noctiflora shoot at 400 uM after 14 days measured per gm of dry weight by LC-MS analysis Silene noctiflora 1.11 umol
Drug uptake in Geranium molle shoot at 20 uM after 14 days measured per gm of dry weight by LC-MS analysis Geranium molle 1.0 umol
Drug uptake in Silene noctiflora shoot at 20 uM after 14 days measured per gm of dry weight by LC-MS analysis Silene noctiflora 0.76 umol
Drug uptake in Echinochloa crus-galli (barnyard grass) root at 400 uM after 14 days measured per gm of dry weight by LC-MS analysis Echinochloa crus-galli 2.13 umol
Drug uptake in Echinochloa crus-galli (barnyard grass) root at 20 uM after 14 days measured per gm of dry weight by LC-MS analysis Echinochloa crus-galli 1.75 umol
Drug uptake in Geranium molle root at 400 uM after 14 days measured per gm of dry weight by LC-MS analysis Geranium molle 11.46 umol
Drug uptake in Geranium molle root at 20 uM after 14 days measured per gm of dry weight by LC-MS analysis Geranium molle 9.93 umol
Drug uptake in Silene noctiflora root at 400 uM after 14 days measured per gm of dry weight by LC-MS analysis Silene noctiflora 4.54 umol
Drug recovery in leaf of Lolium perenne (perennial ryegrass) at 50 ng/g by LC-MS analysis Lolium perenne 93.0 %
Drug uptake in Silene noctiflora root at 20 uM after 14 days measured per gm of dry weight by LC-MS analysis Silene noctiflora 4.65 umol
Drug recovery in leaf of Lolium perenne (perennial ryegrass) at 5 ng/g by LC-MS analysis Lolium perenne 93.0 %
Phytotoxicity against Amaranthus caudatus assessed as root growth inhibition at 100 to 400 uM after 2 weeks by agar medium bioassay Amaranthus caudatus None
Phytotoxicity against Lolium perenne (perennial ryegrass) assessed as root growth inhibition at 100 to 400 uM after 2 weeks by agar medium bioassay Lolium perenne None
Phytotoxicity against Echinochloa crus-galli (barnyard grass) assessed as root growth inhibition at 100 to 400 uM after 2 weeks by agar medium bioassay Echinochloa crus-galli None
Phytotoxicity against Geranium molle assessed as root growth inhibition after 2 weeks by agar medium bioassay Geranium molle 400000.0 nM Phytotoxicity against Geranium molle assessed as root growth inhibition after 2 weeks by agar medium bioassay Geranium molle 400.0 uM
Phytotoxicity against Silene noctiflora assessed as root growth inhibition after 2 weeks by agar medium bioassay Silene noctiflora 35800.0 nM Phytotoxicity against Silene noctiflora assessed as root growth inhibition after 2 weeks by agar medium bioassay Silene noctiflora 5.2 uM
Drug metabolism in Echinochloa crus-galli (barnyard grass) shoot assessed as transformation to sissotrin at 400 uM after 14 days measured per gm of dry weight by LC-MS analysis Echinochloa crus-galli 0.0 umol
Drug metabolism in Echinochloa crus-galli (barnyard grass) shoot assessed as transformation to sissotrin at 20 uM after 14 days measured per gm of dry weight by LC-MS analysis Echinochloa crus-galli 0.0 umol
Drug metabolism in Geranium molle shoot assessed as transformation to sissotrin at 400 uM after 14 days measured per gm of dry weight by LC-MS analysis Geranium molle 2.41 umol
Drug metabolism in Geranium molle shoot assessed as transformation to sissotrin at 20 uM after 14 days measured per gm of dry weight by LC-MS analysis Geranium molle 1.5 umol
Drug metabolism in Silene noctiflora shoot assessed as transformation to sissotrin at 400 uM after 14 days measured per gm of dry weight by LC-MS analysis Silene noctiflora 4.34 umol
Drug metabolism in Silene noctiflora shoot assessed as transformation to sissotrin at 20 uM after 14 days measured per gm of dry weight by LC-MS analysis Silene noctiflora 2.36 umol
Drug metabolism in Echinochloa crus-galli (barnyard grass) root assessed as transformation to sissotrin at 400 uM after 14 days measured per gm of dry weight by LC-MS analysis Echinochloa crus-galli 1.0 umol
Drug metabolism in Echinochloa crus-galli (barnyard grass) root assessed as transformation to sissotrin at 20 uM after 14 days measured per gm of dry weight by LC-MS analysis Echinochloa crus-galli 0.48 umol
Drug metabolism in Geranium molle root assessed as transformation to sissotrin at 400 uM after 14 days measured per gm of dry weight by LC-MS analysis Geranium molle 123.61 umol
Drug metabolism in Silene noctiflora root assessed as transformation to sissotrin at 400 uM after 14 days measured per gm of dry weight by LC-MS analysis Silene noctiflora 2.99 umol
Drug metabolism in Geranium molle root assessed as transformation to sissotrin at 20 uM after 14 days measured per gm of dry weight by LC-MS analysis Geranium molle 36.06 umol
Drug metabolism in Silene noctiflora root assessed as transformation to sissotrin at 20 uM after 14 days measured per gm of dry weight by LC-MS analysis Silene noctiflora 1.72 umol
Drug metabolism in Geranium molle shoot assessed as transformation to p-coumaric acid at 400 uM after 14 days measured per gm of dry weight by LC-MS analysis Geranium molle 0.03 umol
Drug metabolism in Silene noctiflora shoot assessed as transformation to p-coumaric acid at 400 uM after 14 days measured per gm of dry weight by LC-MS analysis Silene noctiflora 0.01 umol
Drug metabolism in Echinochloa crus-galli (barnyard grass) root assessed as transformation to p-coumaric acid at 400 uM after 14 days measured per gm of dry weight by LC-MS analysis Echinochloa crus-galli 0.11 umol
Drug metabolism in Echinochloa crus-galli (barnyard grass) root assessed as transformation to p-coumaric acid at 20 uM after 14 days measured per gm of dry weight by LC-MS analysis Echinochloa crus-galli 0.15 umol
Drug metabolism in Geranium molle root assessed as transformation to p-coumaric acid at 400 uM after 14 days measured per gm of dry weight by LC-MS analysis Geranium molle 0.05 umol
Drug metabolism in Geranium molle root assessed as transformation to p-coumaric acid at 20 uM after 14 days measured per gm of dry weight by LC-MS analysis Geranium molle 0.06 umol
Drug metabolism in Echinochloa crus-galli (barnyard grass) shoot assessed as transformation to pratensein at 400 uM after 14 days measured per gm of dry weight by LC-MS analysis Echinochloa crus-galli 0.24 umol
Drug metabolism in Echinochloa crus-galli (barnyard grass) shoot assessed as transformation to pratensein at 20 uM after 14 days measured per gm of dry weight by LC-MS analysis Echinochloa crus-galli 0.47 umol
Drug metabolism in Geranium molle shoot assessed as transformation to pratensein at 400 uM after 14 days measured per gm of dry weight by LC-MS analysis Geranium molle 0.05 umol
Drug metabolism in Geranium molle shoot assessed as transformation to pratensein at 20 uM after 14 days measured per gm of dry weight by LC-MS analysis Geranium molle 0.02 umol
Drug metabolism in Silene noctiflora shoot assessed as transformation to pratensein at 400 uM after 14 days measured per gm of dry weight by LC-MS analysis Silene noctiflora 0.06 umol
Drug metabolism in Silene noctiflora shoot assessed as transformation to pratensein at 20 uM after 14 days measured per gm of dry weight by LC-MS analysis Silene noctiflora 0.1 umol
Drug metabolism in Echinochloa crus-galli (barnyard grass) root assessed as transformation to pratensein at 400 uM after 14 days measured per gm of dry weight by LC-MS analysis Echinochloa crus-galli 0.35 umol
Drug metabolism in Echinochloa crus-galli (barnyard grass) root assessed as transformation to pratensein at 20 uM after 14 days measured per gm of dry weight by LC-MS analysis Echinochloa crus-galli 0.38 umol
Drug metabolism in Geranium molle root assessed as transformation to pratensein at 400 uM after 14 days measured per gm of dry weight by LC-MS analysis Geranium molle 0.32 umol
Drug metabolism in Geranium molle root assessed as transformation to pratensein at 20 uM after 14 days measured per gm of dry weight by LC-MS analysis Geranium molle 0.66 umol
Drug metabolism in Silene noctiflora root assessed as transformation to pratensein at 400 uM after 14 days measured per gm of dry weight by LC-MS analysis Silene noctiflora 0.11 umol
Drug metabolism in Echinochloa crus-galli (barnyard grass) shoot assessed as transformation to genistein at 400 uM after 14 days measured per gm of dry weight by LC-MS analysis Echinochloa crus-galli 0.2 umol
Drug metabolism in Echinochloa crus-galli (barnyard grass) shoot assessed as transformation to genistein at 20 uM after 14 days measured per gm of dry weight by LC-MS analysis Echinochloa crus-galli 0.28 umol
Drug metabolism in Geranium molle shoot assessed as transformation to genistein at 400 uM after 14 days measured per gm of dry weight by LC-MS analysis Geranium molle 0.12 umol
Drug metabolism in Geranium molle shoot assessed as transformation to genistein at 20 uM after 14 days measured per gm of dry weight by LC-MS analysis Geranium molle 0.09 umol
Drug metabolism in Silene noctiflora shoot assessed as transformation to genistein at 400 uM after 14 days measured per gm of dry weight by LC-MS analysis Silene noctiflora 0.15 umol
Drug metabolism in Silene noctiflora shoot assessed as transformation to genistein at 20 uM after 14 days measured per gm of dry weight by LC-MS analysis Silene noctiflora 0.24 umol
Apparent volume of distribution in Rattus norvegicus Sprague-Dawley (rat) at 5 mg/kg, iv Rattus norvegicus 10.56 L/Kg
Total clearance in Rattus norvegicus Sprague-Dawley (rat) at 5 mg/kg, iv Rattus norvegicus 261.67 mL.min-1.kg-1
Apparent elimination half life in Rattus norvegicus Sprague-Dawley (rat) at 50 mg/kg, po Rattus norvegicus 13.73 hr
Apparent elimination half life in Rattus norvegicus Sprague-Dawley (rat) at 5 mg/kg, iv Rattus norvegicus 1.0 hr
Tmax in Rattus norvegicus Sprague-Dawley (rat) at 50 mg/kg, po Rattus norvegicus 0.42 hr
Cmax in Rattus norvegicus Sprague-Dawley (rat) at 5 mg/kg, iv Rattus norvegicus 1.11 ug.mL-1
AUC (0 to t) in Rattus norvegicus Sprague-Dawley (rat) at 5 mg/kg, iv Rattus norvegicus 480.8 hr.ng/ml
Cmax in Rattus norvegicus Sprague-Dawley (rat) at 50 mg/kg, po Rattus norvegicus 0.0335 ug.mL-1
AUC (0 to t) in Rattus norvegicus Sprague-Dawley (rat) at 50 mg/kg, po Rattus norvegicus 220.29 hr.ng/ml

Cross References

Resources Reference
ChEMBL CHEMBL131921
FDA SRS U13J6U390T
PDB QSO
PubChem 5280373
SureChEMBL SCHEMBL61258
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