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Compound Detail

CHEMBL217299

DOXANTHRINE
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Oc1cc2c(cc1O)C1c3ccccc3CNC1CO2
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL217299
Name DOXANTHRINE
Phase Preclinical
Structure Type MOL
InChI Key QDUNOUQOKOYLCH-UHFFFAOYSA-N
9
Targets
12
Activities
2
Assay Types
0
PK Parameters
8
Publications
0
Known Names

Molecular Properties

269.3
MW (Da)
2.09
ALogP
4
HBA
3
HBD
61.7
PSA (Ų)
0.64
QED
0
Ro5 Violations
0
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C16H15NO3
MW 269.30
Aromatic Rings 2
Heavy Atoms 20
NP-Likeness 1.14

Activity Summary

Ki 10 meas. best 8.7
EC50 2 meas. best 7.5

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Alpha-2C adrenergic receptor
CHEMBL1916
 Ki 8.7 8.7 2.0 1
D(1B) dopamine receptor
CHEMBL1850
 Ki 8.15 8.15 7.0 1
Alpha-2B adrenergic receptor
CHEMBL1942
 Ki 8.0 8.0 10.0 1
D(1A) dopamine receptor
CHEMBL5067
 Ki 7.66 7.66 22.0 1
D(1A) dopamine receptor
CHEMBL2056
 EC50 7.5 7.5 32.0 1
D(4) dopamine receptor
CHEMBL219
 Ki 7.05 7.05 90.0 1
D(1A) dopamine receptor
CHEMBL2056
 Ki 7.01 7.01 98.0 1
D(4) dopamine receptor
CHEMBL219
 EC50 6.96 6.96 110.0 1
Alpha-2A adrenergic receptor
CHEMBL1867
 Ki 6.75 6.75 180.0 1
D(3) dopamine receptor
CHEMBL234
 Ki 6.41 6.41 390.0 1
D(2) dopamine receptor
CHEMBL217
 Ki 5.72 5.575 1910.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Alpha-2C adrenergic receptor Ki = 2.0 nM 8.7 Binding affinity to human cloned adrenergic alpha 2C receptor receptor 17154515
D(1B) dopamine receptor Ki = 7.0 nM 8.15 Binding affinity to human cloned dopamine D5 receptor 17154515
Alpha-2B adrenergic receptor Ki = 10.0 nM 8.0 Binding affinity to human cloned adrenergic alpha 2B receptor receptor 17154515
D(1A) dopamine receptor Ki = 22.0 nM 7.66 Displacement of [3H]SCH-23390 from dopamine D1-like receptor in porcine striata ... 17154515
D(1A) dopamine receptor EC50 = 32.0 nM 7.5 Activity at human dopamine D1 receptor expressed in HEK293 cells assessed as sti... 17154515
D(4) dopamine receptor Ki = 90.0 nM 7.05 Binding affinity to human cloned dopamine D4 receptor 17154515
D(1A) dopamine receptor Ki = 98.0 nM 7.01 Binding affinity to human cloned dopamine D1 receptor 17154515
D(4) dopamine receptor EC50 = 110.0 nM 6.96 Activity at human dopamine D4.4 receptor expressed in HEK293 cells assessed as i... 17154515
Alpha-2A adrenergic receptor Ki = 180.0 nM 6.75 Binding affinity to human cloned adrenergic alpha 2A receptor 17154515
D(3) dopamine receptor Ki = 390.0 nM 6.41 Binding affinity to human cloned dopamine D3 receptor 17154515
D(2) dopamine receptor Ki = 1910.0 nM 5.72 Binding affinity to human cloned dopamine D2 receptor 17154515
D(2) dopamine receptor Ki = 3700.0 nM 5.43 Displacement of [3H]spiperone from dopamine D2-like receptor in porcine striata ... 17154515

Literature References

PubMed DOI Target Context # Activities
17154515 10.1021/jm0604979 D(1A) dopamine receptor 4
17154515 10.1021/jm0604979 D(2) dopamine receptor 4
17154515 10.1021/jm0604979 D(4) dopamine receptor 3
17154515 10.1021/jm0604979 D(3) dopamine receptor 1
17154515 10.1021/jm0604979 Alpha-2A adrenergic receptor 1
17154515 10.1021/jm0604979 Alpha-2B adrenergic receptor 1
17154515 10.1021/jm0604979 Alpha-2C adrenergic receptor 1
17154515 10.1021/jm0604979 D(1B) dopamine receptor 1

Data from ChEMBL 36 via Core Engine