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Compound Detail

CHEMBL566757

DAPORINAD
🧪 Phase II
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🧪 Phase II
O=C(/C=C/c1cccnc1)NCCCCC1CCN(C(=O)c2ccccc2)CC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL566757
Name DAPORINAD
Phase Phase II
Structure Type MOL
InChI Key KPBNHDGDUADAGP-VAWYXSNFSA-N

Known Names

APO 866 APO-866 APO866 Daporinad FK 866 FK-866 FK866 K 22.175
37
Targets
113
Activities
4
Assay Types
24
PK Parameters
20
Publications
8
Known Names
3
Indications
1
Mechanisms

Molecular Properties

391.5
MW (Da)
3.93
ALogP
3
HBA
1
HBD
62.3
PSA (Ų)
0.55
QED
0
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Achiral

Flags

Natural Product

Extended Properties

Molecular Formula C24H29N3O2
MW 391.52
Aromatic Rings 2
Heavy Atoms 29
NP-Likeness -0.86

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Nicotinamide phosphoribosyltransferase inhibitor INHIBITOR Nicotinamide phosphoribosyltransferase ✓ ✓

Indications

Lymphoma, T-Cell, Cutaneous Melanoma Leukemia, Lymphocytic, Chronic, B-Cell

Activity Summary

IC50 102 meas. best 10.52
Ki 6 meas. best 9.7
EC50 4 meas. best 8.6
Kd 1 meas. best 8.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Nicotinamide phosphoribosyltransferase
CHEMBL1744525
 IC50 10.52 8.1752 0.0 23
Nicotinamide phosphoribosyltransferase
CHEMBL1744525
 Ki 9.7 9.1667 0.2 6
ML-2
CHEMBL614356
 IC50 9.62 9.62 0.2 1
A2780
CHEMBL614004
 IC50 9.55 8.8529 0.3 7
BXPC-3
CHEMBL614530
 IC50 9.52 9.52 0.3 1
MIA PaCa-2
CHEMBL614725
 IC50 9.47 8.9167 0.3 3
NAMALVA
CHEMBL614049
 IC50 9.43 9.43 0.4 1
MCF7
CHEMBL387
 IC50 9.39 7.9425 0.4 4
SH-SY5Y
CHEMBL614910
 IC50 9.3 9.035 0.5 2
Jurkat
CHEMBL397
 IC50 9.22 9.18 0.6 2
PANC-1
CHEMBL614139
 IC50 9.22 9.22 0.6 1
RPMI-8226
CHEMBL614882
 IC50 9.12 9.12 0.8 1
K562
CHEMBL385
 IC50 9.02 8.58 1.0 2
Huh-7
CHEMBL614039
 IC50 8.98 6.94 1.1 3
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 8.82 8.82 1.5 1
NB-4
CHEMBL614188
 IC50 8.7 8.7 2.0 1
SH-SY5Y
CHEMBL614910
 EC50 8.6 8.52 2.5 3
Nicotinamide phosphoribosyltransferase
CHEMBL3259474
 IC50 8.57 8.03 2.7 3
HeLa
CHEMBL399
 IC50 8.43 8.43 3.8 1
PC-3
CHEMBL390
 IC50 8.42 8.2933 3.8 3
NCI-H1975
CHEMBL614348
 IC50 8.32 8.32 4.8 1
DU-145
CHEMBL613508
 IC50 8.29 8.29 5.1 1
SK-OV-3
CHEMBL614925
 IC50 8.22 7.45 6.0 2
A-431
CHEMBL614069
 IC50 8.21 8.21 6.1 1
Unchecked
CHEMBL612545
 EC50 8.17 8.17 6.7 1
Nicotinamide phosphoribosyltransferase
CHEMBL1744525
 Kd 8.0 8.0 10.0 1
HCT-116
CHEMBL394
 IC50 7.96 6.395 10.9 4
MV4-11
CHEMBL613835
 IC50 7.82 7.82 15.3 1
HepG2
CHEMBL395
 IC50 7.73 6.61 18.7 3
A549
CHEMBL392
 IC50 7.55 5.43 28.0 4
Unchecked
CHEMBL612545
 IC50 7.47 7.47 33.6 1
LN-18
CHEMBL4296458
 IC50 7.47 7.47 33.6 1
CT26
CHEMBL613866
 IC50 7.46 7.435 34.9 2
LX-2
CHEMBL5465457
 IC50 6.68 6.68 210.0 1
B16
CHEMBL381
 IC50 6.66 6.66 219.0 1
HCCLM3
CHEMBL5465453
 IC50 6.4 6.2 400.0 2
U-87 MG
CHEMBL614247
 IC50 6.39 5.899 410.0 10
Cytochrome P450 3A4
CHEMBL340
 IC50 6.27 6.045 540.0 2
MDA-MB-231
CHEMBL400
 IC50 5.89 5.89 1300.0 1
Hep 3B2
CHEMBL4296437
 IC50 5.81 4.7833 1550.0 3
Cytochrome P450 2C9
CHEMBL3397
 IC50 5.44 5.44 3600.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 12337.0 ng.hr.mL-1 Mus musculus
AUC 6466.0 ng.hr.mL-1 Mus musculus
AUC 6466.0 ng.hr.mL-1 Mus musculus
CL 15.0 mL.min-1.kg-1 Homo sapiens
CL 67.0 mL.min-1.kg-1 Mus musculus
CL 27.0 mL.min-1.kg-1 Mus musculus
CL 15.0 mL.min-1.kg-1 Homo sapiens
CL 22.8 mL.min-1.kg-1 Mus musculus
CL 258.33 mL.min-1.kg-1 Mus musculus
CL 91.67 mL.min-1.kg-1 Homo sapiens
CL 22.8 mL.min-1.kg-1 Mus musculus
Cmax 37188.39 nM Mus musculus
Cmax 14000.0 nM Mus musculus
Cmax 6700.0 nM Rattus norvegicus
Fu 0.007 - Homo sapiens
Fu 0.033 - Mus musculus
T1/2 0.4 hr Mus musculus
T1/2 0.37 hr Mus musculus
T1/2 0.37 hr Mus musculus
T1/2 0.8333 hr Mus musculus
Tmax 0.25 hr Mus musculus
Vd 0.998 L.kg-1 Mus musculus
Vd 0.8 L.kg-1 Mus musculus
Vd 0.8 L.kg-1 Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Nicotinamide phosphoribosyltransferase IC50 = 0.0301 nM 10.52 Inhibition of NAMPT in human SH-SY5Y cells assessed as NAD depletion incubated f... -
Nicotinamide phosphoribosyltransferase IC50 = 0.15 nM 9.82 Inhibition of recombinant human NAMPT preincubated for 5 mins followed by NAM ad... 38060985
Nicotinamide phosphoribosyltransferase Ki = 0.2 nM 9.7 Displacement of fluorescent labelled OG488 from human full length FLAG-tagged NA... 31303996
ML-2 IC50 = 0.24 nM 9.62 Cytotoxicity against human ML-2 cells assessed as inhibition of cell viability a... 36787658
A2780 IC50 = 0.28 nM 9.55 Antiproliferative activity against human A2780 cells incubated for 72 hrs in car... 36563407
Nicotinamide phosphoribosyltransferase Ki = 0.3 nM 9.52 Binding affinity to NAMPT (unknown origin) assessed as inhibition constant 38580317
BXPC-3 IC50 = 0.3 nM 9.52 Antiproliferative activity against human BXPC-3 cells assessed as inhibition of ... 35724566
Nicotinamide phosphoribosyltransferase Ki = 0.3 nM 9.52 Noncompetitive inhibition of NAMPT (unknown origin) 23679915
Nicotinamide phosphoribosyltransferase Ki = 0.3 nM 9.52 Inhibition of NAMPT (unknown origin) assessed as inhibition constant 38722799
MIA PaCa-2 IC50 = 0.34 nM 9.47 Antitumor activity in human MIA PaCa-2 cells assessed as intracellular NAD+ depl... 36787658
NAMALVA IC50 = 0.37 nM 9.43 Cytotoxicity against human NAMALVA cells assessed as inhibition of cell viabilit... 36787658
MCF7 IC50 = 0.41 nM 9.39 Antiproliferative activity against human MCF7 cells assessed as inhibition of ce... 30992165
SH-SY5Y IC50 = 0.5 nM 9.3 Cytotoxicity against human SH-SY5Y cells assessed as reduction of total cellular... 19961183
Nicotinamide phosphoribosyltransferase IC50 = 0.56 nM 9.25 Inhibition of NAMPT (unknown origin) 37369332
Jurkat IC50 = 0.6 nM 9.22 Antiproliferative activity against human Jurkat cells assessed as inhibition of ... 35724566
PANC-1 IC50 = 0.6 nM 9.22 Antiproliferative activity against human PANC-1 cells assessed as inhibition of ... 35724566
Jurkat IC50 = 0.73 nM 9.14 Cytotoxicity against human Jurkat cells assessed as inhibition of cell viability... 36787658
RPMI-8226 IC50 = 0.76 nM 9.12 Cytotoxicity against human RPMI-8226 cells assessed as inhibition of cell viabil... 36787658
K562 IC50 = 0.96 nM 9.02 Antiproliferative activity against human K562 cells assessed as inhibition of ce... 30992165
Nicotinamide phosphoribosyltransferase IC50 = 1.0 nM 9.0 Inhibition of NAMPT in human A2780 cells assessed as decrease in cell viability ... 27541271

Literature References

PubMed DOI Target Context # Activities
38651495 10.1021/acs.jmedchem.3c02482 U-87 MG 24
38691889 10.1016/j.ejmech.2024.116444 Hep 3B2 13
28165742 10.1021/acs.jmedchem.6b01392 Mus musculus 12
36787658 10.1016/j.ejmech.2023.115170 ML-2 10
36787658 10.1016/j.ejmech.2023.115170 Jurkat 10
24164086 10.1021/jm4009949 Mus musculus 9
31400709 10.1016/j.ejmech.2019.111576 ADMET 9
38691889 10.1016/j.ejmech.2024.116444 Unchecked 8
36787658 10.1016/j.ejmech.2023.115170 RPMI-8226 7
36595482 10.1021/acs.jmedchem.2c01954 A549 5
28165742 10.1021/acs.jmedchem.6b01392 Liver 5
28165742 10.1021/acs.jmedchem.6b01392 Unchecked 5
33239261 10.1016/j.ejmech.2020.113022 Epidermal growth factor receptor 4
35640078 10.1021/acs.jmedchem.2c00077 A549/TR 4
37369332 10.1016/j.bmcl.2023.129393 A2780 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
36563407 10.1021/acs.jmedchem.2c01990 ADMET 4
36563407 10.1021/acs.jmedchem.2c01990 A2780 3
35724566 10.1016/j.ejmech.2022.114504 Jurkat 3
36595482 10.1021/acs.jmedchem.2c01954 Unchecked 3

Data from ChEMBL 36 via Core Engine