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Compound Detail

CHEMBL476121

XANTHOMICROL
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COc1c(OC)c(O)c2c(=O)cc(-c3ccc(O)cc3)oc2c1OC
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL476121
Name XANTHOMICROL
Phase Preclinical
Structure Type MOL
InChI Key SAMBWAJRKKEEOR-UHFFFAOYSA-N
7
Targets
8
Activities
2
Assay Types
0
PK Parameters
15
Publications
0
Known Names

Molecular Properties

344.3
MW (Da)
2.90
ALogP
7
HBA
2
HBD
98.4
PSA (Ų)
0.75
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C18H16O7
MW 344.32
Aromatic Rings 3
Heavy Atoms 25
NP-Likeness 1.35

Activity Summary

IC50 6 meas. best 6.27
Ki 2 meas. best 6.08

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Aldo-keto reductase family 1 member B1
CHEMBL2622
 IC50 6.27 6.27 537.0 1
Mu-type opioid receptor
CHEMBL2858
 Ki 6.08 6.08 830.0 1
Unchecked
CHEMBL612545
 IC50 5.46 5.055 3500.0 2
Delta-type opioid receptor
CHEMBL3222
 Ki 5.44 5.44 3600.0 1
B16-F10
CHEMBL612656
 IC50 5.42 5.42 3800.0 1
Peroxisome proliferator-activated receptor gamma
CHEMBL235
 IC50 5.27 5.27 5400.0 1
THP-1
CHEMBL614245
 IC50 5.09 5.09 8100.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Aldo-keto reductase family 1 member B1 IC50 = 537.03 nM 6.27 Inhibition of rat lens aldose reductase 18585047
Mu-type opioid receptor Ki = 830.0 nM 6.08 Displacement of [3H]DAMGO from mu opioid receptor in CD1 mouse whole brain minus... 25562563
Unchecked IC50 = 3500.0 nM 5.46 Inhibition of PMA-stimulated pro MMP9 production in human SRA 01/04 cells after ... 22047798
Delta-type opioid receptor Ki = 3600.0 nM 5.44 Displacement of [3H]DPDPE from delta opioid receptor in CD1 mouse whole brain mi... 25562563
B16-F10 IC50 = 3800.0 nM 5.42 Anti-inflammatory activity in LPS-stimulated mouse B16-F10 cells assessed as red... 37683361
Peroxisome proliferator-activated receptor gamma IC50 = 5400.0 nM 5.27 Antagonist activity at PPARgamma (unknown origin) expressed in human LNCaP cells... 34433102
THP-1 IC50 = 8100.0 nM 5.09 Anti-inflammatory activity in LPS-stimulated human THP-1 cells assessed as reduc... 37683361
Unchecked IC50 = 22300.0 nM 4.65 Inhibition of TNFalpha-stimulated pro MMP9 production in human SRA 01/04 cells a... 22047798

Literature References

PubMed DOI Target Context # Activities
22047798 10.1016/j.bmc.2011.10.001 Unchecked 3
25562563 10.1021/np500671v Mus musculus 3
18585047 10.1016/j.bmc.2008.06.004 Aldo-keto reductase family 1 member B1 1
22047798 10.1016/j.bmc.2011.10.001 ADMET 1
- 10.1007/s00044-011-9767-1 Entamoeba histolytica 1
23199882 10.1016/j.bmcl.2012.10.133 NON-PROTEIN TARGET 1
25562563 10.1021/np500671v Delta-type opioid receptor 1
25562563 10.1021/np500671v Mu-type opioid receptor 1
25562563 10.1021/np500671v Unchecked 1
34433102 10.1016/j.bmc.2021.116368 Peroxisome proliferator-activated receptor gamma 1
35748331 10.1021/acs.jnatprod.1c01093 Staphylococcus aureus 1
35748331 10.1021/acs.jnatprod.1c01093 Streptococcus mutans 1
35748331 10.1021/acs.jnatprod.1c01093 Treponema denticola 1
37683361 10.1016/j.ejmech.2023.115791 THP-1 1
37683361 10.1016/j.ejmech.2023.115791 B16-F10 1

Data from ChEMBL 36 via Core Engine