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Compound Detail

CHEMBL334918

MAACKIAIN
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Oc1ccc2c(c1)OC[C@H]1c3cc4c(cc3O[C@@H]21)OCO4
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL334918
Name MAACKIAIN
Phase Preclinical
Structure Type MOL
InChI Key HUKSJTUUSUGIDC-ZBEGNZNMSA-N

Known Names

(+/-)-Maackiain
5
Targets
7
Activities
2
Assay Types
0
PK Parameters
20
Publications
1
Known Names

Molecular Properties

284.3
MW (Da)
2.73
ALogP
5
HBA
1
HBD
57.1
PSA (Ų)
0.81
QED
0
Ro5 Violations
0
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C16H12O5
MW 284.27
Aromatic Rings 2
Heavy Atoms 21
NP-Likeness 2.06

Activity Summary

IC50 5 meas. best 6.17
Ki 2 meas. best 7.27

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Amine oxidase [flavin-containing] B
CHEMBL2039
 Ki 7.27 7.27 54.0 1
Amine oxidase [flavin-containing] B
CHEMBL2039
 IC50 6.17 6.17 680.0 1
Unchecked
CHEMBL612545
 Ki 5.68 5.68 2100.0 1
HMC1
CHEMBL4296432
 IC50 5.52 5.52 3010.0 1
Unchecked
CHEMBL612545
 IC50 5.5 5.5 3200.0 1
RAW264.7
CHEMBL612557
 IC50 4.57 4.57 27000.0 1
Amine oxidase [flavin-containing] A
CHEMBL1951
 IC50 4.07 4.07 85800.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Amine oxidase [flavin-containing] B Ki = 54.0 nM 7.27 Competitive inhibition of recombinant human MAO-B expressed in baculovirus infec... 27575476
Amine oxidase [flavin-containing] B IC50 = 680.0 nM 6.17 Inhibition of recombinant human MAO-B expressed in baculovirus infected BTI inse... 27575476
Unchecked Ki = 2100.0 nM 5.68 Inhibition of Clostridium perfringens neuraminidase by Lineweaver-Burke plot 18938076
HMC1 IC50 = 3010.0 nM 5.52 Inhibition of A23187-induced IL-6 production in human HMC1 cells incubated for 3... 25467151
Unchecked IC50 = 3200.0 nM 5.5 Inhibition of Clostridium perfringens neuraminidase 18938076
RAW264.7 IC50 = 27000.0 nM 4.57 Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-... 25592708
Amine oxidase [flavin-containing] A IC50 = 85800.0 nM 4.07 Inhibition of recombinant human MAO-A expressed in baculovirus infected BTI inse... 27575476

Literature References

PubMed DOI Target Context # Activities
27575476 10.1016/j.bmcl.2016.08.044 Amine oxidase [flavin-containing] B 5
26248805 10.1016/j.bmcl.2015.07.076 ADMET 3
17764956 10.1016/j.bmc.2007.08.011 NON-PROTEIN TARGET 3
26248805 10.1016/j.bmcl.2015.07.076 NON-PROTEIN TARGET 3
17158054 10.1016/j.bmc.2006.09.024 U-937 3
25592708 10.1016/j.bmcl.2014.12.012 RAW264.7 2
18938076 10.1016/j.bmcl.2008.10.033 Unchecked 2
9322358 10.1021/np970236p NON-PROTEIN TARGET 1
27575476 10.1016/j.bmcl.2016.08.044 Amine oxidase [flavin-containing] A 1
23571415 10.1124/mol.112.084152 Solute carrier organic anion transporter family member 1B3 1
23571415 10.1124/mol.112.084152 Solute carrier organic anion transporter family member 1B1 1
22280816 10.1016/j.ejmech.2011.12.029 Mycobacterium tuberculosis 1
9322358 10.1021/np970236p Unchecked 1
14698175 10.1016/j.bmcl.2003.10.044 Mus musculus 1
9322358 10.1021/np970236p Quinone oxidoreductase 1
10843587 10.1021/np990567x HL-60 1
17764956 10.1016/j.bmc.2007.08.011 HL-60 1
17764956 10.1016/j.bmc.2007.08.011 HCT-15 1
17764956 10.1016/j.bmc.2007.08.011 MDA-MB-435 1
17374486 10.1016/j.bmc.2007.03.011 Sodium/glucose cotransporter 2 1

Data from ChEMBL 36 via Core Engine