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Compound Detail

CHEMBL214321

CHRYSOERIOL
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COc1cc(-c2cc(=O)c3c(O)cc(O)cc3o2)ccc1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL214321
Name CHRYSOERIOL
Phase Preclinical
Structure Type MOL
InChI Key SCZVLDHREVKTSH-UHFFFAOYSA-N
10
Targets
19
Activities
1
Assay Types
8
PK Parameters
20
Publications
0
Known Names

Molecular Properties

300.3
MW (Da)
2.59
ALogP
6
HBA
3
HBD
100.1
PSA (Ų)
0.67
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C16H12O6
MW 300.27
Aromatic Rings 3
Heavy Atoms 22
NP-Likeness 1.37

Activity Summary

IC50 19 meas. best 7.71

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Cytochrome P450 1B1
CHEMBL4878
 IC50 7.71 7.705 19.7 2
Cytochrome P450 1A1
CHEMBL2231
 IC50 7.02 7.02 94.7 2
RAW264.7
CHEMBL612557
 IC50 6.62 5.66 240.0 3
Neutrophil
CHEMBL613710
 IC50 6.4 5.5425 400.0 4
Cytochrome P450 1A2
CHEMBL3356
 IC50 5.95 5.95 1118.0 1
Monocyte
CHEMBL614076
 IC50 5.58 5.12 2600.0 2
Multidrug resistance-associated protein 1
CHEMBL3004
 IC50 5.52 5.52 3000.0 1
Xanthine dehydrogenase/oxidase
CHEMBL3649
 IC50 4.85 4.85 14000.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 4.57 4.57 27140.0 1
ADMET
CHEMBL612558
 IC50 4.44 4.44 36000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 2090.0 ng.hr.mL-1 Rattus norvegicus
AUC 2280.0 ng.hr.mL-1 Rattus norvegicus
CL 49.0 mL.min-1.kg-1 Rattus norvegicus
Cmax 6860.49 nM Rattus norvegicus
MRT 1.24 hr Rattus norvegicus
MRT 1.76 hr Rattus norvegicus
T1/2 1.57 hr Rattus norvegicus
Vd 6.34 L.kg-1 Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Cytochrome P450 1B1 IC50 = 19.7 nM 7.71 Inhibition of recombinant human CYP1B1 expressed in supersomes using ethoxyresor... 28458135
Cytochrome P450 1B1 IC50 = 20.0 nM 7.7 Inhibition of human CYP1B1 by EROD assay 20696580
Cytochrome P450 1A1 IC50 = 95.0 nM 7.02 Inhibition of human CYP1A1 by EROD assay 20696580
Cytochrome P450 1A1 IC50 = 94.7 nM 7.02 Inhibition of recombinant human CYP1A1 expressed in supersomes using ethoxyresor... 28458135
RAW264.7 IC50 = 240.0 nM 6.62 Inhibition of NO production in LPS-stimulated mouse RAW264.7 cells pre-incubated... 25176187
Neutrophil IC50 = 400.0 nM 6.4 Inhibition of oxidative burst in PMA-stimulated human neutrophils assessed as in... 23871908
Cytochrome P450 1A2 IC50 = 1118.0 nM 5.95 Inhibition of human CYP1A2 by EROD assay 20696580
Monocyte IC50 = 2600.0 nM 5.58 Inhibition of procoagulant activity in monocyte from human blood assessed as cou... 8882428
Neutrophil IC50 = 2800.0 nM 5.55 Inhibition of oxidative burst in PMA-stimulated human neutrophils assessed as in... 23871908
Multidrug resistance-associated protein 1 IC50 = 3000.0 nM 5.52 Inhibition of MRP1 19725578
RAW264.7 IC50 = 3100.0 nM 5.51 Antiinflammatory activity in mouse RAW264.7 cells assessed as suppression of LPS... 37683361
Neutrophil IC50 = 7100.0 nM 5.15 Inhibition of oxidative burst in PMA-stimulated human neutrophils assessed as in... 23871908
Neutrophil IC50 = 8600.0 nM 5.07 Inhibition of oxidative burst in PMA-stimulated human neutrophils assessed as in... 23871908
Xanthine dehydrogenase/oxidase IC50 = 14000.0 nM 4.85 Inhibition of cow milk xanthine oxidase 3379415
RAW264.7 IC50 = 14200.0 nM 4.85 Antiinflammatory activity against mouse RAW264.7 cells assessed as inhibition of... 19778086
Monocyte IC50 = 22000.0 nM 4.66 Inhibition of TNFalpha expression in LPS-stimulated human monocytes treated 30 m... 10096854
NON-PROTEIN TARGET IC50 = 27140.0 nM 4.57 Anti-platelet activity in rat platelet rich plasma assessed as inhibition of ADP... 26096681
ADMET IC50 = 36000.0 nM 4.44 Inhibition of mouse Hepa-1c1c7 cells by MTT assay 14510590

Literature References

PubMed DOI Target Context # Activities
21209248 10.1124/dmd.110.037333 Catechol O-methyltransferase 15
25190466 10.1016/j.bmcl.2014.07.093 MDA-MB-231 14
25190466 10.1016/j.bmcl.2014.07.093 Nuclear factor NF-kappa-B complex 13
16797983 10.1016/j.bmcl.2006.06.011 Rattus norvegicus 9
21209248 10.1124/dmd.110.037333 Rattus norvegicus 8
1593282 10.1021/np50081a012 Unchecked 6
21209248 10.1124/dmd.110.037333 ADMET 5
23871908 10.1016/j.ejmech.2013.06.019 Neutrophil 4
19807106 10.1021/jm900964r Peroxisome proliferator-activated receptor gamma 2
19807106 10.1021/jm900964r Peroxisome proliferator-activated receptor alpha 2
21209248 10.1124/dmd.110.037333 Kidney 2
21209248 10.1124/dmd.110.037333 Liver 2
23265844 10.1016/j.bmc.2012.11.040 Peroxisome proliferator-activated receptor delta 2
25190466 10.1016/j.bmcl.2014.07.093 ADMET 2
21209248 10.1124/dmd.110.037333 Small intestine 2
21209248 10.1124/dmd.110.037333 Lung 2
14510590 10.1021/np0302100 Unchecked 2
7775983 10.1021/np50117a005 Unchecked 2
25176187 10.1016/j.bmcl.2014.08.004 RAW264.7 2
3379415 10.1021/np50056a030 Xanthine dehydrogenase/oxidase 2

Data from ChEMBL 36 via Core Engine