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Compound Detail

CHEMBL46294

DIHYDROFOLIC ACID
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Nc1nc(=O)c2c([nH]1)NCC(CNc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)=N2
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL46294
Name DIHYDROFOLIC ACID
Phase Preclinical
Structure Type MOL
InChI Key OZRNSSUDZOLUSN-LBPRGKRZSA-N
2
Targets
11
Activities
2
Assay Types
0
PK Parameters
10
Publications
0
Known Names

Molecular Properties

443.4
MW (Da)
0.01
ALogP
9
HBA
7
HBD
211.9
PSA (Ų)
0.28
QED
1
Ro5 Violations
9
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C19H21N7O6
MW 443.42
Aromatic Rings 2
Heavy Atoms 32
NP-Likeness -0.14

Activity Summary

Kd 10 meas. best 6.68
Ki 1 meas. best 5.51

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Dihydrofolate reductase
CHEMBL1809
 Kd 6.68 5.94 210.0 10
Dihydrofolate synthase/folylpolyglutamate synthase
CHEMBL3309008
 Ki 5.51 5.51 3100.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Dihydrofolate reductase Kd = 210.0 nM 6.68 Thermodynamic Dissociation Constant for compound-Phe31-dihydrofolate reductase (... 3275776
Dihydrofolate reductase Kd = 220.0 nM 6.66 Thermodynamic dissociation constant of compound for wild type Escherichia coli d... 1495020
Dihydrofolate reductase Kd = 240.0 nM 6.62 Thermodynamic Dissociation Constant for compound-Phe31-dihydrofolate reductase (... 3275776
Dihydrofolate reductase Kd = 243.0 nM 6.61 Thermodynamic dissociation constant of compound for mutant T46A Escherichia coli... 1495020
Dihydrofolate reductase Kd = 2000.0 nM 5.7 Thermodynamic dissociation constant of compound for mutant T46N Escherichia coli... 1495020
Dihydrofolate reductase Kd = 2400.0 nM 5.62 Thermodynamic dissociation constant of compound for mutant T46S Escherichia coli... 1495020
Dihydrofolate reductase Kd = 2600.0 nM 5.58 Thermodynamic Dissociation Constant for compound-Tyr31-dihydrofolate reductase (... 3275776
Dihydrofolate reductase Kd = 2900.0 nM 5.54 Thermodynamic Dissociation Constant for compound-Tyr31-dihydrofolate reductase (... 3275776
Dihydrofolate synthase/folylpolyglutamate synthase Ki = 3100.0 nM 5.51 Inhibition of Escherichia coli K-12 recombinant His-tagged folylpoly-gamma-gluta... 18724364
Dihydrofolate reductase Kd = 6200.0 nM 5.21 Thermodynamic Dissociation Constant for compound-Val31-dihydrofolate reductase (... 3275776
Dihydrofolate reductase Kd = 6600.0 nM 5.18 Thermodynamic Dissociation Constant for compound-Val31-dihydrofolate reductase (... 3275776

Literature References

PubMed DOI Target Context # Activities
1495020 10.1021/jm00093a026 Dihydrofolate reductase 8
3275776 10.1021/jm00396a019 Dihydrofolate reductase 6
10841789 10.1021/jm990322h Human immunodeficiency virus type 1 integrase 3
8627598 10.1021/jm950793d Homo sapiens 3
8627598 10.1021/jm950793d Mus musculus 2
8627598 10.1021/jm950793d Unchecked 2
1495020 10.1021/jm00093a026 Bifunctional dihydrofolate reductase-thymidylate synthase 2
18724364 10.1038/nchembio.108 Dihydrofolate synthase/folylpolyglutamate synthase 2
410932 10.1021/jm00221a038 Thymidylate synthase 2
410932 10.1021/jm00221a038 Dihydrofolate reductase 2

Data from ChEMBL 36 via Core Engine