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Compound Detail

CHEMBL464274

DEHYDROHIRSUTANONOL
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O=C(/C=C/CCc1ccc(O)c(O)c1)CCc1ccc(O)c(O)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL464274
Name DEHYDROHIRSUTANONOL
Phase Preclinical
Structure Type MOL
InChI Key VWHYFMQKJYFLCC-DUXPYHPUSA-N
7
Targets
20
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

328.4
MW (Da)
3.20
ALogP
5
HBA
4
HBD
98.0
PSA (Ų)
0.46
QED
0
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C19H20O5
MW 328.36
Aromatic Rings 2
Heavy Atoms 24
NP-Likeness 1.29

Activity Summary

IC50 15 meas. best 6.1
EC50 4 meas. best 5.6
Ki 1 meas. best 5.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
RAW264.7
CHEMBL612557
 IC50 6.1 5.18 800.0 5
Trypanosoma brucei brucei
CHEMBL612851
 EC50 5.6 5.55 2500.0 2
Replicase polyprotein 1ab
CHEMBL4523582
 IC50 5.39 5.39 4100.0 1
Unchecked
CHEMBL612545
 IC50 5.39 5.01 4100.0 5
Unchecked
CHEMBL612545
 Ki 5.0 5.0 10000.0 1
No relevant target
CHEMBL2362975
 IC50 4.87 4.8 13400.0 3
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 4.85 4.85 14000.0 1
Leishmania mexicana
CHEMBL612880
 EC50 4.77 4.77 17000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
RAW264.7 IC50 = 800.0 nM 6.1 Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-... 33422907
Trypanosoma brucei brucei EC50 = 2500.0 nM 5.6 Antitrypanosomal activity against Trypanosoma brucei brucei 427 after 48 hrs by ... 20004045
Trypanosoma brucei brucei EC50 = 3200.0 nM 5.5 Antitrypanosomal activity against diminazene-resistant Trypanosoma brucei brucei... 20004045
Unchecked IC50 = 4100.0 nM 5.39 Inhibition of C-terminal 6His-tagged SARS-CoV papain-like protease expressed in ... 32511912
Unchecked IC50 = 4100.0 nM 5.39 Inhibition of SARS-CoV C-terminal 6His-tagged papain-like protease expressed in ... 32845145
Unchecked IC50 = 4100.0 nM 5.39 Inhibition of SARS CoV papain-like protease using Arg-Leu-Arg-Gly-Gly-AMC as sub... 33618158
Replicase polyprotein 1ab IC50 = 4100.0 nM 5.39 Inhibition of C-terminal his6-tagged recombinant SARS-CoV-2 3CL protease express... 33352046
RAW264.7 IC50 = 5000.0 nM 5.3 Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-... 33422907
RAW264.7 IC50 = 5800.0 nM 5.24 Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-... 33422907
Unchecked Ki = 10000.0 nM 5.0 Noncompetitive inhibition of SARS-CoV C-terminal 6His-tagged papain-like proteas... 32845145
No relevant target IC50 = 13400.0 nM 4.87 Antioxidant activity assessed as DPPH radical scavenging activity incubated for ... 33422907
NON-PROTEIN TARGET IC50 = 14000.0 nM 4.85 Antifibrotic activity against rat HSC-T6 cells assessed as inhibition of prolife... 21504848
RAW264.7 IC50 = 14100.0 nM 4.85 Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-... 33422907
No relevant target IC50 = 16800.0 nM 4.78 Antioxidant activity assessed as nitroblue tetrazolium superoxide radical scaven... 33422907
Leishmania mexicana EC50 = 17000.0 nM 4.77 Antileishmanial activity against Leishmania mexicana MNYC/BZ/62/M379 amastigotes... 20004045
No relevant target IC50 = 17600.0 nM 4.75 Antioxidant activity assessed as nitroblue tetrazolium superoxide radical scaven... 33422907
Unchecked IC50 = 36200.0 nM 4.44 Inhibition of C-terminal 6His-tagged SARS-CoV 3C-like protease expressed in Esch... 32511912
Unchecked IC50 = 36200.0 nM 4.44 Inhibition of SARS CoV 3C-like protease using 12-mer fluorogenic peptide Dabcyl-... 33618158
RAW264.7 IC50 = 39000.0 nM 4.41 Cytotoxicity against mouse RAW264.7 cells assessed as reduction in cell viabilit... 33422907

Literature References

PubMed DOI Target Context # Activities
33422907 10.1016/j.bmc.2020.115971 Unchecked 11
33422907 10.1016/j.bmc.2020.115971 RAW264.7 10
33422907 10.1016/j.bmc.2020.115971 Mus musculus 8
21504848 10.1016/j.bmcl.2011.03.074 NON-PROTEIN TARGET 4
23465614 10.1016/j.bmcl.2013.01.127 3T3-L1 4
20004045 10.1016/j.ejmech.2009.11.035 Trypanosoma brucei brucei 3
33422907 10.1016/j.bmc.2020.115971 No relevant target 3
21504848 10.1016/j.bmcl.2011.03.074 Unchecked 2
33618158 10.1016/j.ejmech.2021.113294 Unchecked 2
32511912 10.1021/acs.jmedchem.0c00606 Unchecked 2
32845145 10.1021/acs.jmedchem.0c00626 Unchecked 2
21504848 10.1016/j.bmcl.2011.03.074 ADMET 1
33422907 10.1016/j.bmc.2020.115971 Nuclear factor NF-kappa-B complex 1
33352046 10.1021/acs.jnatprod.0c00968 Replicase polyprotein 1ab 1
9834165 10.1021/np9801460 Protein kinase C alpha type 1
20004045 10.1016/j.ejmech.2009.11.035 HEK293 1
20004045 10.1016/j.ejmech.2009.11.035 Leishmania mexicana 1
20004045 10.1016/j.ejmech.2009.11.035 Leishmania major 1
20045319 10.1016/j.bmcl.2009.12.057 Unchecked 1
20045319 10.1016/j.bmcl.2009.12.057 ADMET 1

Data from ChEMBL 36 via Core Engine