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Compound Detail

CHEMBL256279

BENGAMIDE A
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CCCCCCCCCCCCCC(=O)O[C@H]1CC[C@H](NC(=O)[C@H](OC)[C@H](O)[C@@H](O)[C@H](O)/C=C/C(C)C)C(=O)NC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL256279
Name BENGAMIDE A
Phase Preclinical
Structure Type MOL
InChI Key NKASPYGDXVCCTA-HADZOMMTSA-N
6
Targets
11
Activities
1
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

584.8
MW (Da)
3.30
ALogP
8
HBA
5
HBD
154.4
PSA (Ų)
0.08
QED
1
Ro5 Violations
21
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C31H56N2O8
MW 584.80
Aromatic Rings 0
Heavy Atoms 41
NP-Likeness 1.19

Activity Summary

IC50 11 meas. best 9.4

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
HCT-116
CHEMBL394
 IC50 9.4 8.575 0.4 2
MDA-MB-435
CHEMBL614697
 IC50 9.0 9.0 1.0 1
Unchecked
CHEMBL612545
 IC50 7.12 7.12 75.0 1
Methionine aminopeptidase 2
CHEMBL3922
 IC50 6.4 5.68 400.0 2
RAW264.7
CHEMBL612557
 IC50 6.3 6.2 500.0 3
Methionine aminopeptidase 1
CHEMBL2474
 IC50 6.16 5.93 700.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
HCT-116 IC50 = 0.4 nM 9.4 Antiproliferative activity against human HCT116 cells after 96 hrs 28185457
MDA-MB-435 IC50 = 1.0 nM 9.0 Cytotoxicity against human MDA-MB-435 cells assessed as reduction in cell viabil... 28185457
HCT-116 IC50 = 18.0 nM 7.75 Cytotoxicity against human HCT116 cells after 48 hrs by SRB assay 22705020
Unchecked IC50 = 75.0 nM 7.12 Inhibition of LPS-stimulated NFkappaB activation transfected in mouse RAW264.7 c... 22705020
Methionine aminopeptidase 2 IC50 = 400.0 nM 6.4 Inhibition of human MetAP2 28185457
RAW264.7 IC50 = 500.0 nM 6.3 Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-... 22705020
RAW264.7 IC50 = 500.0 nM 6.3 Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-... 22705020
Methionine aminopeptidase 1 IC50 = 700.0 nM 6.16 Inhibition of human MetAP1 28185457
RAW264.7 IC50 = 1000.0 nM 6.0 Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-... 22705020
Methionine aminopeptidase 1 IC50 = 2000.0 nM 5.7 Inhibition of methionine aminopeptidase 1 19209899
Methionine aminopeptidase 2 IC50 = 11000.0 nM 4.96 Inhibition of methionine aminopeptidase 2 19209899

Literature References

PubMed DOI Target Context # Activities
22705020 10.1016/j.bmc.2012.05.043 RAW264.7 9
23634668 10.1021/jm400227z Unchecked 7
22705020 10.1016/j.bmc.2012.05.043 Unchecked 2
19209899 10.1021/np800817y Methionine aminopeptidase 2 1
28185457 10.1021/acs.jnatprod.6b00970 Methionine aminopeptidase 2 1
28185457 10.1021/acs.jnatprod.6b00970 Methionine aminopeptidase 1 1
28185457 10.1021/acs.jnatprod.6b00970 HCT-116 1
28185457 10.1021/acs.jnatprod.6b00970 MDA-MB-435 1
22705020 10.1016/j.bmc.2012.05.043 HCT-116 1
19209899 10.1021/np800817y Methionine aminopeptidase 1 1
18327911 10.1021/np700738k P388 1
10346943 10.1021/np980330l Saccharomyces cerevisiae 1
10346943 10.1021/np980330l Candida albicans 1
- 10.1021/np970050q Candida 1
18327911 10.1021/np700738k SF-295 1
18327911 10.1021/np700738k BXPC-3 1
18327911 10.1021/np700738k DU-145 1
18327911 10.1021/np700738k KM-20L2 1
18327911 10.1021/np700738k NCI-H460 1
18327911 10.1021/np700738k OVCAR-3 1

Data from ChEMBL 36 via Core Engine