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Compound Detail

CHEMBL170518

PROSTRATIN
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CC(=O)O[C@@]12C[C@@H](C)[C@@]3(O)[C@@H](C=C(CO)C[C@]4(O)C(=O)C(C)=C[C@@H]34)[C@@H]1C2(C)C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL170518
Name PROSTRATIN
Phase Preclinical
Structure Type MOL
InChI Key BOJKFRKNLSCGHY-HXGSDTCMSA-N
10
Targets
30
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

390.5
MW (Da)
1.53
ALogP
6
HBA
3
HBD
104.1
PSA (Ų)
0.49
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C22H30O6
MW 390.48
Aromatic Rings 0
Heavy Atoms 28
NP-Likeness 3.28

Activity Summary

EC50 25 meas. best 10.22
Ki 5 meas. best 8.32

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Human immunodeficiency virus 1
CHEMBL378
 EC50 10.22 7.2189 0.1 9
Protein kinase C alpha type
CHEMBL2213
 Ki 8.32 8.32 4.8 1
Unchecked
CHEMBL612545
 Ki 7.9 7.9 12.5 1
Protein kinase C gamma type
CHEMBL2938
 Ki 7.66 7.66 21.8 1
Protein kinase C, PKC; classical/novel
CHEMBL2096620
 Ki 6.72 6.7 190.0 2
Chikungunya virus
CHEMBL4296563
 EC50 6.7 5.9522 200.0 9
Human immunodeficiency virus
CHEMBL613758
 EC50 6.65 6.65 226.0 1
Protein kinase C (PKC)
CHEMBL2093867
 EC50 6.55 6.3733 280.0 3
Human immunodeficiency virus 2
CHEMBL380
 EC50 6.05 6.05 900.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 EC50 5.58 5.575 2600.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Human immunodeficiency virus 1 EC50 = 0.06 nM 10.22 Antiviral activity against Human immunodeficiency virus 1 infected in human C816... 21534540
Human immunodeficiency virus 1 EC50 = 3.3 nM 8.48 Reversal of HIV-1 latency in human J-Lat 10.6 cells assessed as increase in GFP ... 33540228
Protein kinase C alpha type Ki = 4.8 nM 8.32 Ability to displace bound [20-3H]-PDBU from a recombinant single isozyme (PKCalp... 11384235
Human immunodeficiency virus 1 EC50 = 11.0 nM 7.96 Reversal of HIV-1 latency in human J-Lat 8.4 cells assessed as increase in GFP e... 33540228
Unchecked Ki = 12.5 nM 7.9 Displacement of [3H]PDBu from Protein kinase C in vitro 1597853
Protein kinase C gamma type Ki = 21.8 nM 7.66 Displacement of 3H-PDBu from recombinant human PKCgamma incubated for 25 mins by... 33540228
Human immunodeficiency virus 1 EC50 = 45.0 nM 7.35 Reversal of HIV-1 latency in human J-Lat 9.2 cells assessed as increase in GFP e... 33540228
Protein kinase C, PKC; classical/novel Ki = 190.0 nM 6.72 Displacement of [3H]PDBu binding to Protein kinase C of CEM cells with 10% fetal... 1597853
Chikungunya virus EC50 = 200.0 nM 6.7 Antiviral activity against Chikungunya virus LR2006 OPY1 infected in African gre... 28689975
Chikungunya virus EC50 = 200.0 nM 6.7 Antiviral activity against Chikungunya virus SGP011 infected in African green mo... 28689975
Protein kinase C, PKC; classical/novel Ki = 210.0 nM 6.68 Displacement of [3H]PDBu from Protein kinase C of CEM cells 1597853
Human immunodeficiency virus EC50 = 226.0 nM 6.65 Antiviral activity against HIV NL4.3 harboring renilla luciferase infected in hu... 28925702
Protein kinase C (PKC) EC50 = 280.0 nM 6.55 Activation of PKC in human U1 cells infected with latent HIV-1 assessed as rever... 30413535
Human immunodeficiency virus 1 EC50 = 294.0 nM 6.53 Reversal of HIV-1 latency in human ACH-2 cells assessed as increase in GFP posit... 33540228
Human immunodeficiency virus 1 EC50 = 294.0 nM 6.53 HIV1-latency reversing activity in human ACH-2 cell line incubated for 48 hrs 37224601
Protein kinase C (PKC) EC50 = 294.0 nM 6.53 Activation of PKC in human ACH-2 cells infected with latent HIV-1 assessed as re... 30413535
Chikungunya virus EC50 = 300.0 nM 6.52 Antiviral activity against Chikungunya virus SGP011 by qRT-PCR analysis 28689975
Chikungunya virus EC50 = 400.0 nM 6.4 Antiviral activity against Chikungunya virus SGP011 infected in African green mo... 28689975
Chikungunya virus EC50 = 500.0 nM 6.3 Antiviral activity against Chikungunya virus CNR20235 infected in buffalo green ... 28689975
Human immunodeficiency virus 1 EC50 = 768.0 nM 6.12 Reactivation of HIV-1 latency infected in GFP-fused human J-Lat C11 cells assess... 33540228

Literature References

PubMed DOI Target Context # Activities
27731641 10.1021/acs.jnatprod.6b00603 Protein kinase C (PKC) 27
28689975 10.1016/j.bmc.2017.06.049 Chikungunya virus 8
33540228 10.1016/j.ejmech.2021.113213 Human immunodeficiency virus 1 6
30413535 10.1074/jbc.ra118.005798 U1 5
30413535 10.1074/jbc.ra118.005798 ADMET 5
30413535 10.1074/jbc.ra118.005798 ACH-2 cell line 5
35522580 10.1021/acs.jnatprod.1c01225 Human immunodeficiency virus 1 4
25970561 10.1021/acs.jnatprod.5b00073 Unchecked 3
30413535 10.1074/jbc.ra118.005798 J-Lat 6.3 3
1597853 10.1021/jm00089a006 Protein kinase C, PKC; classical/novel 2
30413535 10.1074/jbc.ra118.005798 Unchecked 2
33721994 10.1021/acs.jnatprod.0c01039 Human immunodeficiency virus 2
28925702 10.1021/acs.jnatprod.7b00113 Unchecked 2
30413535 10.1074/jbc.ra118.005798 Protein kinase C (PKC) 2
11689073 10.1021/jm010258f Panel NCI-60 (60 carcinoma cell lines) 1
26225771 10.1371/journal.ppat.1005066 Unchecked 1
17512094 10.1016/j.ejmech.2007.03.016 KB 1
3236005 10.1021/np50060a003 Mus musculus 1
11384235 10.1021/jm010052e Protein kinase C alpha type 1
11384235 10.1021/jm010052e No relevant target 1

Data from ChEMBL 36 via Core Engine