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Compound Detail

CHEMBL479579

PHOSPHORAMIDON
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CC(C)C[C@H](NP(=O)(O)O[C@@H]1O[C@@H](C)[C@H](O)[C@@H](O)[C@H]1O)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL479579
Name PHOSPHORAMIDON
Phase Preclinical
Structure Type MOL
InChI Key ZPHBZEQOLSRPAK-XLCYBJAPSA-N
8
Targets
40
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

543.5
MW (Da)
0.23
ALogP
8
HBA
8
HBD
210.7
PSA (Ų)
0.18
QED
2
Ro5 Violations
11
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C23H34N3O10P
MW 543.51
Aromatic Rings 2
Heavy Atoms 37
NP-Likeness 0.93

Activity Summary

IC50 36 meas. best 9.4
Ki 4 meas. best 8.4

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Neprilysin
CHEMBL3768
 IC50 9.4 8.7733 0.4 3
Neprilysin
CHEMBL3369
 IC50 9.22 7.8525 0.6 8
Endothelin-converting enzyme 1
CHEMBL4791
 IC50 9.1 6.495 0.8 10
Neprilysin
CHEMBL1944
 IC50 8.7 7.652 2.0 5
Neprilysin
CHEMBL3369
 Ki 8.4 8.4 4.0 1
Thermolysin
CHEMBL3392
 Ki 7.55 7.55 28.0 1
Thermolysin
CHEMBL3392
 IC50 7.48 7.48 33.0 1
Elastase
CHEMBL1075146
 Ki 7.24 7.24 57.0 1
Unchecked
CHEMBL612545
 IC50 6.22 5.115 600.0 6
Endothelin-converting enzyme 1
CHEMBL2340
 IC50 5.51 5.51 3100.0 1
Unchecked
CHEMBL612545
 Ki 5.16 5.16 6980.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Neprilysin IC50 = 0.4 nM 9.4 Inhibition of enkephalinase activity in membranes prepared from rabbit 2585440
Neprilysin IC50 = 0.6 nM 9.22 Inhibition of enkephalinase activity in synaptic membranes prepared from rat str... 2585440
Endothelin-converting enzyme 1 IC50 = 0.8 nM 9.1 Inhibitory activity against human bronchiolar smooth muscle Endothelin-convertin... 7783143
Neprilysin IC50 = 2.0 nM 8.7 Inhibitory activity against big ET-1 of Neutral endopeptidase 7783143
Neprilysin IC50 = 2.0 nM 8.7 Inhibition of neutral endopeptidase in human fibroblasts homogenates using gluta... 21937235
Neprilysin Ki = 4.0 nM 8.4 Binding affinity towards enkephalinase (metalloendopeptidase, E.C.3.4.24.11) of ... 2993614
Neprilysin IC50 = 4.2 nM 8.38 Inhibitory activity against neutral endopeptidase (NEP)prepared from microsomal ... -
Neprilysin IC50 = 4.2 nM 8.38 compound was tested for inhibitory activity against neutral endopeptidase (NEP) -
Neprilysin IC50 = 6.0 nM 8.22 Inhibitory activity against Leu-enkeph of Neutral endopeptidase 7783143
Endothelin-converting enzyme 1 IC50 = 17.0 nM 7.77 Inhibition of human recombinant ECE1 by fluorimetry 19596577
Neprilysin IC50 = 26.0 nM 7.58 Evaluation of in vitro inhibitory activity against Neutral endopeptidase 8544178
Neprilysin IC50 = 27.0 nM 7.57 In vitro inhibition of Neutral endopeptidase (NEP) enzyme 8120868
Thermolysin Ki = 28.0 nM 7.55 Inhibitory constant against thermolysin. 1588550
Neprilysin IC50 = 30.0 nM 7.52 Inhibition of human somatic NEP 19899765
Neprilysin IC50 = 30.0 nM 7.52 In vitro inhibition of rat neutral endopeptidase 10669576
Neprilysin IC50 = 30.0 nM 7.52 Inhibitory activity against neutral endopeptidase (NEP). 9554884
Neprilysin IC50 = 30.0 nM 7.52 Inhibition of neutral endopeptidase 24.11(NEP) -
Thermolysin IC50 = 33.0 nM 7.48 Inhibitory activity against thermolysin with 0.5 uM [Leu5]-enkephalin (NEN) 7783143
Neprilysin IC50 = 34.0 nM 7.47 Inhibition of rat kidney NEP using glutaryl-Ala-Ala-beta-naphthylamide as substr... 32337993
Elastase Ki = 57.0 nM 7.24 Inhibition of Pseudomonas aeruginosa LasB elastase using aminobenzoyl-Ala-Gly-Le... 26804741

Literature References

PubMed DOI Target Context # Activities
- 10.1016/S0960-894X(97)00159-5 Endothelin-converting enzyme 1 2
2585440 10.1021/jm00132a005 Neprilysin 2
12852763 10.1021/jm021089h Neprilysin 2
7783143 10.1021/jm00012a011 Neprilysin 2
17933532 10.1016/j.bmcl.2007.09.084 Unchecked 2
31703818 10.1016/j.ejmech.2019.111812 Unchecked 2
10669576 10.1021/jm990507o Endothelin-converting enzyme 1 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
10669576 10.1021/jm990507o Neprilysin 1
10669576 10.1021/jm990507o Unchecked 1
- 10.1016/S0960-894X(01)80341-3 Endothelin-converting enzyme 1 1
- 10.1016/S0960-894X(01)80341-3 Neprilysin 1
- 10.1016/S0960-894X(01)80341-3 Unchecked 1
8421284 10.1021/jm00053a023 Endothelin-converting enzyme 1 1
1588550 10.1021/jm00088a002 Thermolysin 1
26804741 10.1021/acs.jmedchem.5b01698 Elastase 1
9554884 10.1021/jm970787c Neprilysin 1
- 10.1016/0960-894X(96)00211-9 Endothelin-converting enzyme 1 1
9554884 10.1021/jm970787c Endothelin-converting enzyme 1 1
- 10.1016/S0960-894X(97)00159-5 Neprilysin 1

Data from ChEMBL 36 via Core Engine