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Compound Detail

CHEMBL2364573

NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE
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NC(=O)c1ccc[n+]([C@H]2O[C@@H](COP(=O)([O-])OP(=O)(O)OC[C@H]3O[C@@H](n4cnc5c(N)ncnc54)[C@H](OP(=O)(O)O)[C@@H]3O)[C@H](O)[C@@H]2O)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2364573
Name NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE
Phase Preclinical
Structure Type MOL
InChI Key XJLXINKUBYWONI-DQQFMEOOSA-N
3
Targets
9
Activities
2
Assay Types
0
PK Parameters
9
Publications
0
Known Names

Molecular Properties

743.4
MW (Da)
-3.53
ALogP
19
HBA
8
HBD
367.6
PSA (Ų)
0.06
QED
3
Ro5 Violations
13
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C21H28N7O17P3
MW 743.41
Aromatic Rings 3
Heavy Atoms 48
NP-Likeness 0.78

Activity Summary

Kd 7 meas. best 6.66
Ki 2 meas. best 8.33

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL1939
 Ki 8.33 8.085 4.7 2
Dihydrofolate reductase
CHEMBL1809
 Kd 6.66 6.4633 220.0 6
2-dehydropantoate 2-reductase
CHEMBL4855
 Kd 5.24 5.24 5800.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 4.7 nM 8.33 Binding affinity was evaluated as inhibition of recombinant wild type (WT) Plasm... 9554869
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 14.5 nM 7.84 Binding affinity was evaluated as inhibition of mutant (C59R + S108N) Plasmodium... 9554869
Dihydrofolate reductase Kd = 220.0 nM 6.66 Thermodynamic Dissociation Constant for compound-Val31-dihydrofolate reductase (... 3275776
Dihydrofolate reductase Kd = 300.0 nM 6.52 Thermodynamic Dissociation Constant for compound-Val31-dihydrofolate reductase (... 3275776
Dihydrofolate reductase Kd = 340.0 nM 6.47 Thermodynamic Dissociation Constant for compound-Tyr31-dihydrofolate reductase (... 3275776
Dihydrofolate reductase Kd = 380.0 nM 6.42 Thermodynamic Dissociation Constant for compound-Phe31-dihydrofolate reductase (... 3275776
Dihydrofolate reductase Kd = 400.0 nM 6.4 Thermodynamic Dissociation Constant for compound-Tyr31-dihydrofolate reductase (... 3275776
Dihydrofolate reductase Kd = 490.0 nM 6.31 Thermodynamic Dissociation Constant for compound-Phe31-dihydrofolate reductase (... 3275776
2-dehydropantoate 2-reductase Kd = 5800.0 nM 5.24 Binding affinity to Escherichia coli KPR 16884311

Literature References

PubMed DOI Target Context # Activities
3275776 10.1021/jm00396a019 Dihydrofolate reductase 6
1495020 10.1021/jm00093a026 Dihydrofolate reductase 4
8627598 10.1021/jm950793d Homo sapiens 3
9554869 10.1021/jm970845u Bifunctional dihydrofolate reductase-thymidylate synthase 2
8627598 10.1021/jm950793d Mus musculus 2
8627598 10.1021/jm950793d Unchecked 2
9554869 10.1021/jm970845u Unchecked 1
7310833 10.1021/jm00144a035 Choline O-acetyltransferase 1
16884311 10.1021/jm060490r 2-dehydropantoate 2-reductase 1

Data from ChEMBL 36 via Core Engine