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Compound Detail

CHEMBL12850

DEHYDROABIETIC ACID
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CC(C)c1ccc2c(c1)CC[C@H]1[C@](C)(C(=O)O)CCC[C@]21C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL12850
Name DEHYDROABIETIC ACID
Phase Preclinical
Structure Type MOL
InChI Key NFWKVWVWBFBAOV-MISYRCLQSA-N
16
Targets
38
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

300.4
MW (Da)
4.90
ALogP
1
HBA
1
HBD
37.3
PSA (Ų)
0.84
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 C20H28O2
MW 300.44
Aromatic Rings 1
Heavy Atoms 22
NP-Likeness 1.94

Activity Summary

IC50 35 meas. best 7.56
EC50 3 meas. best 4.38

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Lysine--tRNA ligase
CHEMBL5575
 IC50 7.56 7.56 27.7 1
EJ
CHEMBL614292
 IC50 4.6 4.6 25120.0 1
Jurkat
CHEMBL397
 IC50 4.59 4.59 25510.0 1
5637
CHEMBL612565
 IC50 4.56 4.56 27590.0 1
PC-3
CHEMBL390
 IC50 4.55 4.42 28100.0 2
HeLa
CHEMBL399
 IC50 4.55 4.5325 28430.0 4
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 4.54 4.4275 28720.0 4
HCT-116
CHEMBL394
 IC50 4.45 4.45 35240.0 1
Cyclin-dependent kinase 2/cyclin E1
CHEMBL1907605
 IC50 4.44 4.44 36290.0 1
Retinoic acid receptor RXR-beta
CHEMBL1870
 EC50 4.38 4.38 42000.0 1
Retinoic acid receptor RXR-gamma
CHEMBL2004
 EC50 4.38 4.38 42000.0 1
Retinoic acid receptor RXR-alpha
CHEMBL2061
 EC50 4.38 4.38 42000.0 1
A549
CHEMBL392
 IC50 4.25 4.145 55650.0 4
SK-OV-3
CHEMBL614925
 IC50 4.18 4.115 65960.0 4
HepG2
CHEMBL395
 IC50 4.12 4.0875 76760.0 4
NCI-H460
CHEMBL396
 IC50 4.12 4.084 75050.0 5

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Lysine--tRNA ligase IC50 = 27.7 nM 7.56 Inhibition of SYK (unknown origin) by mobility shift assay 29578342
EJ IC50 = 25120.0 nM 4.6 Cytotoxicity against human EJ cells assessed as growth inhibition after 72 hrs b... 23707051
Jurkat IC50 = 25510.0 nM 4.59 Cytotoxicity against human Jurkat cells assessed as growth inhibition after 72 h... 23707051
5637 IC50 = 27590.0 nM 4.56 Cytotoxicity against human 5637 cells assessed as growth inhibition after 72 hrs... 23707051
HeLa IC50 = 28430.0 nM 4.55 Cytotoxicity against human HeLa cells assessed as growth inhibition after 72 hrs... 23707051
PC-3 IC50 = 28100.0 nM 4.55 Cytotoxicity against human PC3 cells assessed as growth inhibition after 72 hrs ... 23707051
NON-PROTEIN TARGET IC50 = 28720.0 nM 4.54 Cytotoxic activity against human Bel7404 cells assessed as inhibition of cell gr... 26706349
HeLa IC50 = 29350.0 nM 4.53 Cytotoxicity against human HeLa cells after 48 hrs by MTT assay 24565905
HeLa IC50 = 29350.0 nM 4.53 Cytotoxicity against human HeLa cells after 48 hrs by MTT assay 25462253
NON-PROTEIN TARGET IC50 = 30250.0 nM 4.52 Cytotoxic activity against human HCT116 cells assessed as inhibition of cell gro... 26706349
HeLa IC50 = 30350.0 nM 4.52 Anticancer activity against human HeLa cells assessed as inhibition of cell grow... 38389893
NON-PROTEIN TARGET IC50 = 34700.0 nM 4.46 Cytotoxicity against human Bel7404 cells after 48 hrs by MTT assay 24565905
HCT-116 IC50 = 35240.0 nM 4.45 Cytotoxicity against human HCT116 cells after 48 hrs by MTT assay 24565905
Cyclin-dependent kinase 2/cyclin E1 IC50 = 36290.0 nM 4.44 Inhibition of human recombinant C-terminal His6-tagged full length human Cdk2/hu... 26706349
Retinoic acid receptor RXR-alpha EC50 = 42000.0 nM 4.38 Transactivation of human Gal4-fused RXRalpha LBD expressed in HEK293T cells afte... 29901398
Retinoic acid receptor RXR-gamma EC50 = 42000.0 nM 4.38 Transactivation of human Gal4-fused RXRgamma LBD expressed in HEK293T cells afte... 29901398
Retinoic acid receptor RXR-beta EC50 = 42000.0 nM 4.38 Transactivation of human Gal4-fused RXRbeta LBD expressed in HEK293T cells after... 29901398
PC-3 IC50 = 51310.0 nM 4.29 Cytotoxic activity against human PC3 cells assessed as reduction in cell viabili... 28011223
A549 IC50 = 55650.0 nM 4.25 Cytotoxic activity against human A549 cells assessed as inhibition of cell growt... 26706349
NON-PROTEIN TARGET IC50 = 65060.0 nM 4.19 Cytotoxic activity against human SKOV3 cells assessed as inhibition of cell grow... 26706349

Literature References

PubMed DOI Target Context # Activities
29650291 10.1016/j.bmcl.2018.03.062 Staphylococcus aureus 6
27777007 10.1016/j.bmcl.2016.10.018 Staphylococcus aureus 6
10869208 10.1021/np0000217 Unchecked 4
12502340 10.1021/np020258y Unchecked 4
19892441 10.1016/j.ejmech.2009.10.010 Vero 4
26812172 10.1021/acs.jnatprod.5b01053 NON-PROTEIN TARGET 3
29901398 10.1021/acs.jmedchem.8b00494 Retinoic acid receptor RXR-alpha 3
26706349 10.1016/j.ejmech.2015.12.008 NON-PROTEIN TARGET 3
25466709 10.1016/j.bmcl.2014.11.034 Trametes versicolor 2
29459209 10.1016/j.bmcl.2018.02.014 HUVEC 2
25466709 10.1016/j.bmcl.2014.11.034 Gloeophyllum trabeum 2
19892441 10.1016/j.ejmech.2009.10.010 Human alphaherpesvirus 1 2
28485933 10.1021/acs.jnatprod.7b00081 Danio rerio 2
29901398 10.1021/acs.jmedchem.8b00494 Retinoic acid receptor RXR-gamma 2
29578342 10.1021/acs.jnatprod.7b01082 Lysine--tRNA ligase 2
29901398 10.1021/acs.jmedchem.8b00494 Retinoid X receptor 2
26812172 10.1021/acs.jnatprod.5b01053 C6 2
29901398 10.1021/acs.jmedchem.8b00494 Retinoic acid receptor RXR-beta 2
12608857 10.1021/np020380x Staphylococcus aureus 2
- 10.1039/C5MD00498E Leishmania donovani 2

Data from ChEMBL 36 via Core Engine