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Compound Detail

CHEMBL541700

GALLINAMIDE A
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CC[C@H](C)[C@@H](C(=O)O[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C)/C=C/C(=O)N1C(=O)C=C(OC)[C@@H]1C)N(C)C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL541700
Name GALLINAMIDE A
Phase Preclinical
Structure Type MOL
InChI Key ASRBKZHDORPEHO-KYJIWOQOSA-N
20
Targets
34
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

592.8
MW (Da)
2.80
ALogP
8
HBA
2
HBD
134.3
PSA (Ų)
0.21
QED
1
Ro5 Violations
16
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C31H52N4O7
MW 592.78
Aromatic Rings 0
Heavy Atoms 42
NP-Likeness 1.02

Activity Summary

IC50 30 meas. best 9.59
Ki 3 meas. best 8.28
EC50 1 meas. best 7.55

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Cruzipain
CHEMBL3563
 IC50 9.59 9.24 0.3 2
Procathepsin L
CHEMBL3837
 IC50 8.33 8.065 4.7 4
Procathepsin L
CHEMBL5291
 Ki 8.28 8.28 5.3 1
Cathepsin B
CHEMBL4072
 IC50 8.13 6.4267 7.3 3
Procathepsin L
CHEMBL3837
 Ki 8.1 8.1 8.0 1
Falcipain 2
CHEMBL5800
 IC50 8.07 8.07 8.5 3
Falcipain-3
CHEMBL1250373
 IC50 7.66 7.66 22.0 1
Unchecked
CHEMBL612545
 IC50 7.66 7.255 22.0 2
SARS-CoV-2
CHEMBL4303835
 EC50 7.55 7.55 28.0 1
Plasmodium falciparum
CHEMBL364
 IC50 7.3 6.56 50.0 3
Cathepsin B
CHEMBL4072
 Ki 6.93 6.93 117.0 1
Cathepsin L2
CHEMBL3272
 IC50 6.85 6.595 140.0 2
Leishmania donovani
CHEMBL367
 IC50 5.03 5.03 9300.0 1
HeLa
CHEMBL399
 IC50 4.92 4.92 12000.0 1
PANC-1
CHEMBL614139
 IC50 4.51 4.51 31200.0 1
MDA-MB-231
CHEMBL400
 IC50 4.46 4.46 34900.0 1
4T1
CHEMBL612589
 IC50 4.46 4.46 34600.0 1
A549
CHEMBL392
 IC50 4.39 4.39 40400.0 1
MCF7
CHEMBL387
 IC50 4.34 4.34 45500.0 1
A-375
CHEMBL613859
 IC50 4.34 4.34 45600.0 1
HT-29
CHEMBL384
 IC50 4.28 4.28 53000.0 1
B16-F10
CHEMBL612656
 IC50 4.22 4.22 59700.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Cruzipain IC50 = 0.26 nM 9.59 Inhibition of recombinant Trypanosoma cruzi Cruzain expressed in Pichia pastoris... 31539239
Cruzipain IC50 = 1.3 nM 8.89 Inhibition of Trypanosoma cruzi cruzain using Z-FR-AMC as substrate preincubated... 35188371
Procathepsin L IC50 = 4.67 nM 8.33 Inhibition of human cathepsin L using fluorogenic substrate cbz-FR-AMC monitored... 31539239
Procathepsin L IC50 = 5.0 nM 8.3 Inhibition of recombinant human Cathepsin L using Z-Phe-Arg-aminomethylcoumarin ... 24364476
Procathepsin L IC50 = 5.0 nM 8.3 Inhibition of human cathepsin L 31539239
Procathepsin L Ki = 5.29 nM 8.28 Inhibition of mouse Cathepsin L assessed as Apparent inhibition constant using Z... 34730959
Cathepsin B IC50 = 7.34 nM 8.13 Inhibition of human recombinant Cathepsin B assessed remaining activity using Z-... 34730959
Procathepsin L Ki = 7.95 nM 8.1 Inhibition of human recombinant Cathepsin L assessed as Apparent inhibition cons... 34730959
Falcipain 2 IC50 = 8.5 nM 8.07 Inhibition of FP2' in Plasmodium falciparum trophozoite stage after 1 hr by SDS-... 25412465
Falcipain 2 IC50 = 8.5 nM 8.07 Inhibition of FP2 in Plasmodium falciparum trophozoite stage after 1 hr by SDS-P... 25412465
Falcipain 2 IC50 = 8.5 nM 8.07 Inhibition of Plasmodium falciparum D10 trophozite lysates FP-2 pretreated with ... 36996716
Unchecked IC50 = 22.0 nM 7.66 Inhibition of FP3 in Plasmodium falciparum trophozoite stage after 1 hr by SDS-P... 25412465
Falcipain-3 IC50 = 22.0 nM 7.66 Inhibition of Plasmodium falciparum D10 trophozite lysates FP-3 pretreated with ... 36996716
SARS-CoV-2 EC50 = 28.0 nM 7.55 Antiviral activity against SARS-COV-2 infected in African green monkey Vero E6 c... 37229831
Procathepsin L IC50 = 47.0 nM 7.33 Inhibition of recombinant human Cathepsin L using Z-Phe-Arg-aminomethylcoumarin ... 24364476
Plasmodium falciparum IC50 = 50.0 nM 7.3 Antiplasmodial activity against Plasmodium falciparum 3D7 25412465
Plasmodium falciparum IC50 = 50.0 nM 7.3 Antiplasmodial activity against Plasmodium falciparum D10 assessed as inhibition... 36996716
Cathepsin B Ki = 117.0 nM 6.93 Inhibition of human recombinant Cathepsin B assessed as Apparent inhibition cons... 34730959
Unchecked IC50 = 140.0 nM 6.85 Inhibition of FP1 in Plasmodium falciparum trophozoite stage after 1 hr by SDS-P... 25412465
Cathepsin L2 IC50 = 140.0 nM 6.85 Inhibition of human Cathepsin V using Z-Phe-Arg-aminomethylcoumarin as substrate... 24364476

Literature References

PubMed DOI Target Context # Activities
34730959 10.1021/acs.jmedchem.1c01494 SARS-CoV-2 10
34730959 10.1021/acs.jmedchem.1c01494 Procathepsin L 9
34730959 10.1021/acs.jmedchem.1c01494 Cathepsin B 8
24364476 10.1021/np400727r Procathepsin L 7
31539239 10.1021/acs.jmedchem.9b00294 Procathepsin L 5
24364476 10.1021/np400727r Unchecked 4
24364476 10.1021/np400727r Cathepsin L2 2
25412465 10.1021/jm501439w Falcipain 2 2
25412465 10.1021/jm501439w Unchecked 2
34730959 10.1021/acs.jmedchem.1c01494 Replicase polyprotein 1ab 2
24364476 10.1021/np400727r Cathepsin B 2
24364476 10.1021/np400727r Pro-cathepsin H 2
19161344 10.1021/np8003529 Trypanosoma cruzi 1
25412465 10.1021/jm501439w Plasmodium falciparum 1
30006166 10.1016/j.ejmech.2018.06.046 4T1 1
37229831 10.1016/j.ejmech.2023.115503 SARS-CoV-2 1
19161344 10.1021/np8003529 Leishmania donovani 1
30006166 10.1016/j.ejmech.2018.06.046 HT-29 1
30006166 10.1016/j.ejmech.2018.06.046 A-375 1
19161344 10.1021/np8003529 Plasmodium falciparum 1

Data from ChEMBL 36 via Core Engine