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Compound Detail

CHEMBL470029

OLEANONIC ACID
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CC1(C)CC[C@]2(C(=O)O)CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CCC(=O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]2C1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL470029
Name OLEANONIC ACID
Phase Preclinical
Structure Type MOL
InChI Key FMIMFCRXYXVFTA-FUAOEXFOSA-N
17
Targets
31
Activities
1
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

454.7
MW (Da)
7.44
ALogP
2
HBA
1
HBD
54.4
PSA (Ų)
0.42
QED
1
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C30H46O3
MW 454.70
Aromatic Rings 0
Heavy Atoms 33
NP-Likeness 3.31

Activity Summary

IC50 31 meas. best 9.66

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Tissue factor
CHEMBL4081
 IC50 9.66 9.66 0.2 1
Pancreatic triacylglycerol lipase
CHEMBL1812
 IC50 6.31 6.31 490.0 1
Tyrosine-protein phosphatase non-receptor type 1
CHEMBL335
 IC50 5.46 5.3175 3500.0 4
Tyrosine-protein phosphatase non-receptor type 2
CHEMBL3807
 IC50 5.25 5.25 5630.0 1
CCRF-CEM
CHEMBL382
 IC50 5.02 4.92 9500.0 2
CEM-DNR
CHEMBL614547
 IC50 4.77 4.77 17000.0 1
Unchecked
CHEMBL612545
 IC50 4.76 4.7033 17400.0 3
Glycogen phosphorylase, muscle form
CHEMBL4696
 IC50 4.75 4.75 17782.8 4
SK-MEL
CHEMBL614914
 IC50 4.51 4.51 31000.0 1
Nitric oxide synthase, inducible
CHEMBL4481
 IC50 4.43 4.43 37000.0 1
Mus musculus
CHEMBL375
 IC50 4.43 4.43 37000.0 2
RAW264.7
CHEMBL612557
 IC50 4.42 4.235 38500.0 2
J774.A1
CHEMBL614040
 IC50 4.41 4.41 38800.0 1
HCT-116
CHEMBL394
 IC50 4.35 4.35 45000.0 2
U2OS
CHEMBL615023
 IC50 4.31 4.31 48500.0 2
A549
CHEMBL392
 IC50 4.3 4.3 49500.0 2
ADMET
CHEMBL612558
 IC50 4.06 4.06 87720.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Tissue factor IC50 = 0.221 nM 9.66 Inhibition of LPS-induced tissue factor procoagulant activity in human THP1 cell... 28109788
Pancreatic triacylglycerol lipase IC50 = 490.0 nM 6.31 Inhibition of Pancreatic lipase (unknown origin) using 4-MUO as fluorescent subs... 37490786
Tyrosine-protein phosphatase non-receptor type 1 IC50 = 3500.0 nM 5.46 Inhibition of human recombinant PTP1B after 30 mins 18798681
Tyrosine-protein phosphatase non-receptor type 1 IC50 = 5320.0 nM 5.27 Inhibition of PTP1B by pNPP assay 18707891
Tyrosine-protein phosphatase non-receptor type 1 IC50 = 5320.0 nM 5.27 Inhibition of PTP1B (unknown origin) -
Tyrosine-protein phosphatase non-receptor type 1 IC50 = 5320.0 nM 5.27 Inhibition of PTP1B (unknown origin) -
Tyrosine-protein phosphatase non-receptor type 2 IC50 = 5630.0 nM 5.25 Inhibition of TCPTP by pNPP assay 18707891
CCRF-CEM IC50 = 9500.0 nM 5.02 Cytotoxicity against human CCRF-CEM cells assessed as reduction in cell viabilit... 36174412
CCRF-CEM IC50 = 15100.0 nM 4.82 Cytotoxicity against human CCRF-CEM cells incubated for 72 hrs by MTS assay 31677446
CEM-DNR IC50 = 17000.0 nM 4.77 Cytotoxicity against human CEM-DNR cells assessed as reduction in cell viability... 36174412
Unchecked IC50 = 17400.0 nM 4.76 Cytotoxicity against human CEM-DNR-bulk cells incubated for 72 hrs by MTS assay 31677446
Glycogen phosphorylase, muscle form IC50 = 17900.0 nM 4.75 Inhibition of rabbit muscle GPa 16546381
Glycogen phosphorylase, muscle form IC50 = 18000.0 nM 4.75 Inhibition of rabbit muscle glycogen phosphorylase A assessed as phosphate relea... 18517260
Glycogen phosphorylase, muscle form IC50 = 17782.79 nM 4.75 Inhibition of rabbit muscle glycogen phosphorylase A assessed as release of phos... 21439694
Glycogen phosphorylase, muscle form IC50 = 17900.0 nM 4.75 Inhibition of rabbit muscle glycogen phosphorylase A assessed as release of phos... 21439694
Unchecked IC50 = 21000.0 nM 4.68 Cytotoxicity against human K562-Tax cells assessed as reduction in cell viabilit... 36174412
Unchecked IC50 = 21500.0 nM 4.67 Cytotoxicity against human K562-TAX cells incubated for 72 hrs by MTS assay 31677446
SK-MEL IC50 = 31000.0 nM 4.51 Compound was tested for its cytotoxicity against human malignant melanoma cell l... 10450948
Mus musculus IC50 = 37100.0 nM 4.43 Inhibitory activity on IFN-gamma-induced nitric oxide production in mouse macrop... -
Mus musculus IC50 = 37000.0 nM 4.43 50 percent inhibitory concentration of compound to inhibit nitric oxide producti... 10794703

Literature References

PubMed DOI Target Context # Activities
20964318 10.1021/np100064m Tyrosine-protein phosphatase non-receptor type 1 2
10794703 10.1021/jm000008j Mus musculus 2
36174412 10.1016/j.ejmech.2022.114777 Unchecked 2
21439694 10.1016/j.ejmech.2011.02.053 Glycogen phosphorylase, muscle form 2
31677446 10.1016/j.ejmech.2019.111806 HCT-116 2
19171409 10.1016/j.ejmech.2008.12.024 NON-PROTEIN TARGET 2
25113933 10.1016/j.bmcl.2014.07.056 RAW264.7 2
31677446 10.1016/j.ejmech.2019.111806 Unchecked 2
- 10.1007/s00044-010-9529-5 Tyrosine-protein phosphatase non-receptor type 1 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
9748372 10.1021/np9800710 H9 1
36174412 10.1016/j.ejmech.2022.114777 MRC5 1
18707891 10.1016/j.bmc.2008.07.080 Tyrosine-protein phosphatase non-receptor type 2 1
18517260 10.1021/jm8000949 Glycogen phosphorylase, muscle form 1
9748372 10.1021/np9800710 Human immunodeficiency virus 1 1
9748372 10.1021/np9800710 ADMET 1
17116667 10.1128/aac.00642-06 Helicobacter pylori 1
16546381 10.1016/j.bmcl.2006.03.009 Glycogen phosphorylase, muscle form 1
10450948 10.1016/s0960-894x(99)00314-5 Unchecked 1
10450948 10.1016/s0960-894x(99)00314-5 SK-MEL 1

Data from ChEMBL 36 via Core Engine