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Compound Detail

CHEMBL271321

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COc1cc(-c2oc3ccccc3c(=O)c2O)ccc1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL271321
Phase Preclinical
Structure Type MOL
InChI Key YONDROKMQHIDPQ-UHFFFAOYSA-N
2
Targets
8
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

284.3
MW (Da)
2.88
ALogP
5
HBA
2
HBD
79.9
PSA (Ų)
0.76
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C16H12O5
MW 284.27
Aromatic Rings 3
Heavy Atoms 21
NP-Likeness 0.91

Activity Summary

EC50 7 meas. best 7.05
IC50 1 meas. best 4.66

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Aorta
CHEMBL613606
 EC50 7.05 5.91 89.1 7
SK-MEL-1
CHEMBL614916
 IC50 4.66 4.66 22000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Aorta EC50 = 89.13 nM 7.05 Effect on acetylcholine-induced vasorelaxation in xanthine/xanthine oxidase expo... 18307286
Aorta EC50 = 275.42 nM 6.56 Effect on acetylcholine-induced vasorelaxation in pyrogallol exposed Sprague-Daw... 18307286
Aorta EC50 = 870.96 nM 6.06 Vasorelaxant activity against U46619-induced contraction in endothelium-intact S... 18307286
Aorta EC50 = 1659.59 nM 5.78 Vasorelaxant activity against U46619-induced contraction in endothelium-denuded ... 18307286
Aorta EC50 = 4466.84 nM 5.35 Vascular activity in KPSS precontracted Sprague-Dawley rat thoracic aorta assess... 18307286
Aorta EC50 = 4786.3 nM 5.32 Vasorelaxant activity against KCl-induced contraction in endothelium-intact Spra... 18307286
Aorta EC50 = 5623.41 nM 5.25 Vasorelaxant activity against KCl-induced contraction in endothelium-denuded Spr... 18307286
SK-MEL-1 IC50 = 22000.0 nM 4.66 Cytotoxicity against human SK-MEL-1 cells assessed as reduction in cell viabilit... 29032930

Literature References

PubMed DOI Target Context # Activities
18307286 10.1021/jm070352h Aorta 17
26191362 10.1021/acsmedchemlett.5b00043 Unchecked 2
25262941 10.1016/j.bmc.2014.08.038 Melanocyte-stimulating hormone receptor 2
25262941 10.1016/j.bmc.2014.08.038 Adrenocorticotropic hormone receptor 2
25262941 10.1016/j.bmc.2014.08.038 Melanocortin receptor 3 2
25262941 10.1016/j.bmc.2014.08.038 Melanocortin receptor 4 2
25262941 10.1016/j.bmc.2014.08.038 Melanin-concentrating hormone receptor 1 1
29032930 10.1016/j.bmc.2017.09.043 SK-MEL-1 1
25262941 10.1016/j.bmc.2014.08.038 C5a anaphylatoxin chemotactic receptor 1 1
25262941 10.1016/j.bmc.2014.08.038 Parathyroid hormone/parathyroid hormone-related peptide receptor 1
25262941 10.1016/j.bmc.2014.08.038 Adenosine receptor A3 1
25262941 10.1016/j.bmc.2014.08.038 Adenosine receptor A2a 1
25262941 10.1016/j.bmc.2014.08.038 Adenosine receptor A1 1
25262941 10.1016/j.bmc.2014.08.038 D(1B) dopamine receptor 1
25262941 10.1016/j.bmc.2014.08.038 D(1A) dopamine receptor 1
25262941 10.1016/j.bmc.2014.08.038 Muscarinic acetylcholine receptor M1 1
25262941 10.1016/j.bmc.2014.08.038 Orexin receptor type 2 1
25262941 10.1016/j.bmc.2014.08.038 5-hydroxytryptamine receptor 2C 1
25262941 10.1016/j.bmc.2014.08.038 Neuromedin-U receptor 1 1
25262941 10.1016/j.bmc.2014.08.038 Melanocortin receptor 5 1

Data from ChEMBL 36 via Core Engine