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Compound Detail

CHEMBL296567

DIHYDROBETULONIC ACID
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CC(C)[C@@H]1CC[C@]2(C(=O)O)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CCC(=O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL296567
Name DIHYDROBETULONIC ACID
Phase Preclinical
Structure Type MOL
InChI Key OUAPNSVTUJNUMW-SVAFSPIFSA-N
11
Targets
29
Activities
1
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

456.7
MW (Da)
7.38
ALogP
2
HBA
1
HBD
54.4
PSA (Ų)
0.47
QED
1
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C30H48O3
MW 456.71
Aromatic Rings 0
Heavy Atoms 33
NP-Likeness 2.94

Activity Summary

IC50 29 meas. best 5.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
CCRF-CEM
CHEMBL382
 IC50 5.7 5.308 2000.0 5
K562
CHEMBL385
 IC50 5.6 5.215 2500.0 4
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 5.4 5.4 4000.0 1
HCT-116
CHEMBL394
 IC50 5.39 4.796 4100.0 5
A549
CHEMBL392
 IC50 5.23 4.8467 5900.0 3
Unchecked
CHEMBL612545
 IC50 4.96 4.67 11000.0 4
MRC5
CHEMBL614181
 IC50 4.93 4.93 11700.0 1
BJ
CHEMBL614358
 IC50 4.65 4.65 22600.0 1
U2OS
CHEMBL615023
 IC50 4.57 4.565 27000.0 2
Semliki Forest virus
CHEMBL613724
 IC50 4.52 4.515 30199.5 2
CEM-DNR
CHEMBL614547
 IC50 4.32 4.32 48000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
CCRF-CEM IC50 = 2000.0 nM 5.7 Cytotoxicity against human CEM cells after 72 hrs by MTT assay 17371067
K562 IC50 = 2500.0 nM 5.6 Cytotoxicity against human K562 cells after 72 hrs by MTT assay 22551630
CCRF-CEM IC50 = 4000.0 nM 5.4 Cytotoxicity against human CCRF-CEM cells after 72 hrs by MTT assay 22551630
K562 IC50 = 4000.0 nM 5.4 Cytotoxicity against human paclitaxel resistant K562 cells after 72 hrs by MTT a... 22551630
NON-PROTEIN TARGET IC50 = 4000.0 nM 5.4 Cytotoxicity against human CCRF-CEM cells after 72 hrs by MTS assay 27236068
HCT-116 IC50 = 4100.0 nM 5.39 Cytotoxicity against human HCT116 cells after 72 hrs by MTT assay 22551630
A549 IC50 = 5900.0 nM 5.23 Cytotoxicity against human A549 cells after 72 hrs by MTT assay 22551630
HCT-116 IC50 = 6100.0 nM 5.21 Cytotoxicity against human p53-deficient HCT116 cells after 72 hrs by MTT assay 22551630
CCRF-CEM IC50 = 6200.0 nM 5.21 Cytotoxicity against human CCRF-CEM cells incubated for 72 hrs by MTS assay 31677446
CCRF-CEM IC50 = 6300.0 nM 5.2 Cytotoxicity against human CCRF-CEM cells assessed as reduction in cell viabilit... 36174412
CCRF-CEM IC50 = 9400.0 nM 5.03 Cytotoxicity against human daunorubicine resistant CEM cells after 72 hrs by MTT... 22551630
Unchecked IC50 = 11100.0 nM 4.96 Cytotoxicity against human K562-TAX cells incubated for 72 hrs by MTS assay 31677446
Unchecked IC50 = 11000.0 nM 4.96 Cytotoxicity against human K562-Tax cells assessed as reduction in cell viabilit... 36174412
K562 IC50 = 11600.0 nM 4.94 Cytotoxicity against human K562 cells incubated for 72 hrs by MTS assay 31677446
MRC5 IC50 = 11700.0 nM 4.93 Cytotoxicity against human MRC5 cells after 72 hrs by MTT assay 22551630
K562 IC50 = 12000.0 nM 4.92 Cytotoxicity against human K562 cells assessed as reduction in cell viability in... 36174412
A549 IC50 = 22000.0 nM 4.66 Cytotoxicity against human A549 cells assessed as reduction in cell viability in... 36174412
BJ IC50 = 22600.0 nM 4.65 Cytotoxicity against human BJ cells after 72 hrs by MTT assay 22551630
A549 IC50 = 22200.0 nM 4.65 Cytotoxicity against human A549 cells incubated for 72 hrs by MTS assay 31677446
U2OS IC50 = 27000.0 nM 4.57 Cytotoxicity against human U2OS cells assessed as reduction in cell viability in... 36174412

Literature References

PubMed DOI Target Context # Activities
19839605 10.1021/np9003245 Semliki Forest virus 3
22551630 10.1016/j.bmc.2012.03.066 CCRF-CEM 2
36174412 10.1016/j.ejmech.2022.114777 Unchecked 2
31677446 10.1016/j.ejmech.2019.111806 HCT-116 2
31677446 10.1016/j.ejmech.2019.111806 Unchecked 2
22551630 10.1016/j.bmc.2012.03.066 HCT-116 2
22551630 10.1016/j.bmc.2012.03.066 K562 2
19839605 10.1021/np9003245 ADMET 2
11527742 10.1016/s0960-894x(01)00460-7 SK-MEL-2 2
17371067 10.1021/np060436d CCRF-CEM 1
11527742 10.1016/s0960-894x(01)00460-7 PC-3 1
9873420 10.1016/s0960-894x(98)00295-9 SK-MEL-2 1
22551630 10.1016/j.bmc.2012.03.066 A549 1
11527742 10.1016/s0960-894x(01)00460-7 UACC-257 1
22551630 10.1016/j.bmc.2012.03.066 BJ 1
22551630 10.1016/j.bmc.2012.03.066 MRC5 1
27236068 10.1016/j.ejmech.2016.05.029 NON-PROTEIN TARGET 1
36174412 10.1016/j.ejmech.2022.114777 MRC5 1
11527742 10.1016/s0960-894x(01)00460-7 M14 1
11527742 10.1016/s0960-894x(01)00460-7 HCT-116 1

Data from ChEMBL 36 via Core Engine