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Compound Detail

CHEMBL486627

DEOXYSHIKONIN
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CC(C)=CCCC1=CC(=O)c2c(O)ccc(O)c2C1=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL486627
Name DEOXYSHIKONIN
Phase Preclinical
Structure Type MOL
InChI Key VOMDIEGPEURZJO-UHFFFAOYSA-N
19
Targets
22
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

272.3
MW (Da)
3.15
ALogP
4
HBA
2
HBD
74.6
PSA (Ų)
0.65
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C16H16O4
MW 272.30
Aromatic Rings 1
Heavy Atoms 20
NP-Likeness 2.39

Activity Summary

IC50 21 meas. best 6.18
Ki 1 meas. best 4.92

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Vero
CHEMBL391
 IC50 6.18 6.18 660.0 1
SK-BR-3
CHEMBL613834
 IC50 6.16 6.16 690.0 1
MCF7
CHEMBL387
 IC50 6.1 6.1 790.0 1
SAOS-2
CHEMBL614894
 IC50 6.07 6.07 850.0 1
HeLa
CHEMBL399
 IC50 6.07 6.07 850.0 1
HepG2
CHEMBL395
 IC50 6.05 5.515 900.0 2
AU565
CHEMBL1075393
 IC50 6.04 6.04 920.0 1
DU-145
CHEMBL613508
 IC50 5.91 5.91 1240.0 1
COP9 signalosome complex subunit 5
CHEMBL4105809
 IC50 5.6 5.46 2510.0 2
PC-3
CHEMBL390
 IC50 5.37 5.37 4290.0 1
MDA-MB-231
CHEMBL400
 IC50 5.29 5.29 5080.0 1
HT-29
CHEMBL384
 IC50 5.29 5.29 5120.0 1
NIH3T3
CHEMBL614822
 IC50 5.23 5.23 5840.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 5.22 5.22 6020.0 1
A-375
CHEMBL613859
 IC50 5.17 5.17 6830.0 1
Unchecked
CHEMBL612545
 Ki 4.92 4.92 11900.0 1
LNCaP
CHEMBL612518
 IC50 4.91 4.91 12210.0 1
HCT-116
CHEMBL394
 IC50 4.81 4.81 15460.0 1
Unchecked
CHEMBL612545
 IC50 4.56 4.56 27500.0 1
Neuraminidase
CHEMBL1795169
 IC50 4.2 4.2 63400.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Vero IC50 = 660.0 nM 6.18 Cytotoxicity against african green monkey Vero cells after 48 hrs by MTT assay 20405844
SK-BR-3 IC50 = 690.0 nM 6.16 Cytotoxicity against human SKBR3 cells after 48 hrs by MTT assay 20405844
MCF7 IC50 = 790.0 nM 6.1 Cytotoxicity against human MCF7 cells after 48 hrs by MTT assay 20405844
HeLa IC50 = 850.0 nM 6.07 Cytotoxicity against human HeLa cells after 48 hrs by MTT assay 20405844
SAOS-2 IC50 = 850.0 nM 6.07 Cytotoxicity against human Saos2 cells after 48 hrs by MTT assay 20405844
HepG2 IC50 = 900.0 nM 6.05 Cytotoxicity against human HepG2 cells after 48 hrs by MTT assay 20405844
AU565 IC50 = 920.0 nM 6.04 Cytotoxicity against human AU565 cells after 48 hrs by MTT assay 20405844
DU-145 IC50 = 1240.0 nM 5.91 Cytotoxicity against human DU145 cells after 48 hrs by MTT assay 20405844
COP9 signalosome complex subunit 5 IC50 = 2510.0 nM 5.6 Inhibition of N-terminal His6-tagged CSN5 (2 to 257 residues) (unknown origin) t... 39129245
PC-3 IC50 = 4290.0 nM 5.37 Cytotoxicity against human PC3 cells after 48 hrs by MTT assay 20405844
COP9 signalosome complex subunit 5 IC50 = 4810.0 nM 5.32 Inhibition of N-terminal His6-tagged CSN5 (2 to 257 residues) (unknown origin) t... 39129245
HT-29 IC50 = 5120.0 nM 5.29 Cytotoxicity against human HT-29 cells after 48 hrs by MTT assay 20405844
MDA-MB-231 IC50 = 5080.0 nM 5.29 Cytotoxicity against human MDA-MB-231 cells after 48 hrs by MTT assay 20405844
NIH3T3 IC50 = 5840.0 nM 5.23 Cytotoxicity against mouse 3T3 cells after 48 hrs by MTT assay 20405844
NON-PROTEIN TARGET IC50 = 6020.0 nM 5.22 Cytotoxicity against human Hep3B cells after 48 hrs by MTT assay 20405844
A-375 IC50 = 6830.0 nM 5.17 Antiproliferative activity against human A-375 cells assessed as inhibition of c... 39129245
HepG2 IC50 = 10500.0 nM 4.98 Antiproliferative activity against human HepG2 cells assessed as inhibition of c... 39129245
Unchecked Ki = 11900.0 nM 4.92 Reversible inhibition of Clostridium perfringens ATCC 10543 sialidase Nan1 c-ter... 22300884
LNCaP IC50 = 12210.0 nM 4.91 Cytotoxicity against human LNCAP cells after 48 hrs by MTT assay 20405844
HCT-116 IC50 = 15460.0 nM 4.81 Antiproliferative activity against human HCT-116 cells assessed as inhibition of... 39129245

Literature References

PubMed DOI Target Context # Activities
22300884 10.1016/j.bmc.2012.01.011 Unchecked 8
39129245 10.1021/acs.jmedchem.4c01514 COP9 signalosome complex subunit 5 5
22300884 10.1016/j.bmc.2012.01.011 Neuraminidase 3
39129245 10.1021/acs.jmedchem.4c01514 Unchecked 3
- 10.1584/jpestics.23.54 Tobacco mosaic virus 2
3373224 10.1021/np50055a025 Trichophyton mentagrophytes 2
3373224 10.1021/np50055a025 Kocuria rosea 1
20405844 10.1021/np900778j HT-29 1
3373224 10.1021/np50055a025 Epidermophyton floccosum 1
3373224 10.1021/np50055a025 Trichophyton tonsurans var. sulfureum 1
3373224 10.1021/np50055a025 Trichophyton rubrum 1
3373224 10.1021/np50055a025 Saccharomyces 1
3373224 10.1021/np50055a025 Bacillus subtilis 1
3373224 10.1021/np50055a025 Micrococcus luteus 1
3373224 10.1021/np50055a025 Cyberlindnera jadinii 1
3373224 10.1021/np50055a025 Candida tropicalis 1
3373224 10.1021/np50055a025 Pichia norvegensis 1
3373224 10.1021/np50055a025 Meyerozyma guilliermondii 1
3373224 10.1021/np50055a025 Candida albicans 1
3373224 10.1021/np50055a025 Serratia marcescens 1

Data from ChEMBL 36 via Core Engine