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Compound Detail

CHEMBL489354

MALABARICONE B
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O=C(CCCCCCCCc1ccc(O)cc1)c1c(O)cccc1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL489354
Name MALABARICONE B
Phase Preclinical
Structure Type MOL
InChI Key KOAPDMKKECXPHX-UHFFFAOYSA-N
9
Targets
18
Activities
2
Assay Types
0
PK Parameters
17
Publications
0
Known Names

Molecular Properties

342.4
MW (Da)
4.96
ALogP
4
HBA
3
HBD
77.8
PSA (Ų)
0.42
QED
0
Ro5 Violations
10
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C21H26O4
MW 342.43
Aromatic Rings 2
Heavy Atoms 25
NP-Likeness 0.54

Activity Summary

IC50 13 meas. best 6.4
Ki 5 meas. best 6.3

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Sialidase A
CHEMBL4105839
 IC50 6.4 6.4 400.0 1
Sialidase A
CHEMBL4105839
 Ki 6.3 6.3 500.0 1
Cholinesterase
CHEMBL5763
 Ki 6.25 6.25 560.0 1
Phosphatidylcholine:ceramide cholinephosphotransferase 2
CHEMBL3112379
 IC50 6.0 5.8 1000.0 2
Cholinesterase
CHEMBL5763
 IC50 5.75 5.75 1760.0 1
Acetylcholinesterase
CHEMBL220
 IC50 5.74 5.74 1840.0 1
Phosphatidylcholine:ceramide cholinephosphotransferase 1
CHEMBL3611965
 IC50 5.7 5.58 2000.0 2
Acetylcholinesterase
CHEMBL220
 Ki 5.36 5.36 4330.0 1
Unchecked
CHEMBL612545
 Ki 5.25 5.245 5600.0 2
Unchecked
CHEMBL612545
 IC50 5.24 4.76 5700.0 3
MCF7
CHEMBL387
 IC50 5.16 5.16 6860.0 1
Pancreatic alpha-amylase
CHEMBL5730
 IC50 4.89 4.89 12890.0 1
Albumin
CHEMBL3728
 IC50 4.39 4.39 40340.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Sialidase A IC50 = 400.0 nM 6.4 Inhibition of Streptococcus pneumoniae sialidase NanA using 4-methylumbelliferyl... 28551100
Sialidase A Ki = 500.0 nM 6.3 Competitive inhibition of Streptococcus pneumoniae sialidase NanA using 4-methyl... 28551100
Cholinesterase Ki = 560.0 nM 6.25 Mixed inhibition of equine serum BChE using S-butyrylthiocholine chloride as sub... 27236720
Phosphatidylcholine:ceramide cholinephosphotransferase 2 IC50 = 1000.0 nM 6.0 Noncompetitive inhibition of SMS2 (unknown origin) stably expressed in mouse ZS ... 31413799
Cholinesterase IC50 = 1760.0 nM 5.75 Inhibition of equine serum BChE using S-butyrylthiocholine chloride as substrate... 27236720
Acetylcholinesterase IC50 = 1840.0 nM 5.74 Inhibition of AChE (unknown origin) using acetylthiocholine iodide as substrate ... 27236720
Phosphatidylcholine:ceramide cholinephosphotransferase 1 IC50 = 2000.0 nM 5.7 Noncompetitive inhibition of SMS1 (unknown origin) stably expressed in mouse ZS ... 31413799
Phosphatidylcholine:ceramide cholinephosphotransferase 2 IC50 = 2500.0 nM 5.6 Inhibition of SMS2 (unknown origin) stably expressed in mouse ZS cells using C6-... 31413799
Phosphatidylcholine:ceramide cholinephosphotransferase 1 IC50 = 3500.0 nM 5.46 Inhibition of SMS1 (unknown origin) stably expressed in mouse ZS cells using C6-... 31413799
Acetylcholinesterase Ki = 4330.0 nM 5.36 Mixed inhibition of AChE (unknown origin) using acetylthiocholine iodide as subs... 27236720
Unchecked Ki = 5600.0 nM 5.25 Noncompetitive inhibition of Streptococcus pneumoniae sialidase NanB using 4-met... 28551100
Unchecked Ki = 5800.0 nM 5.24 Noncompetitive inhibition of Streptococcus pneumoniae sialidase NanC using 4-met... 28551100
Unchecked IC50 = 5700.0 nM 5.24 Inhibition of Streptococcus pneumoniae sialidase NanB using 4-methylumbelliferyl... 28551100
MCF7 IC50 = 6860.0 nM 5.16 Cytotoxicity against human MCF7 cells after 72 hrs by MTT assay 20805034
Pancreatic alpha-amylase IC50 = 12890.0 nM 4.89 Inhibition of porcine pancreatic alpha-amylase using starch as substrate after 3... 29789207
Unchecked IC50 = 14300.0 nM 4.84 Inhibition of Streptococcus pneumoniae sialidase NanC using 4-methylumbelliferyl... 28551100
Albumin IC50 = 40340.0 nM 4.39 Antiglycation activity in bovine serum albumin assessed as inhibition of advance... 29789207
Unchecked IC50 = 63700.0 nM 4.2 Inhibition of rat intestinal alpha-glucosidase using p-nitrophenyl alpha-D-gluco... 29789207

Literature References

PubMed DOI Target Context # Activities
1955885 10.1021/np50075a017 Candida albicans 6
28551100 10.1016/j.bmcl.2017.05.055 Unchecked 6
29789207 10.1016/j.bmc.2018.05.020 L6 5
27236720 10.1016/j.bmcl.2016.05.046 Cholinesterase 3
27236720 10.1016/j.bmcl.2016.05.046 Acetylcholinesterase 3
28551100 10.1016/j.bmcl.2017.05.055 Sialidase A 3
27236720 10.1016/j.bmcl.2016.05.046 Unchecked 2
31413799 10.1021/acsmedchemlett.9b00171 Phosphatidylcholine:ceramide cholinephosphotransferase 2 2
31413799 10.1021/acsmedchemlett.9b00171 Phosphatidylcholine:ceramide cholinephosphotransferase 1 2
1955885 10.1021/np50075a017 Staphylococcus aureus 2
1955885 10.1021/np50075a017 Enterococcus durans 2
1955885 10.1021/np50075a017 Bacillus subtilis 2
20805034 10.1016/j.bmc.2010.08.011 MCF7 1
29789207 10.1016/j.bmc.2018.05.020 Pancreatic alpha-amylase 1
29789207 10.1016/j.bmc.2018.05.020 Unchecked 1
29789207 10.1016/j.bmc.2018.05.020 Albumin 1
20805034 10.1016/j.bmc.2010.08.011 Nucleic Acid 1

Data from ChEMBL 36 via Core Engine