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Compound Detail

CHEMBL269277

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

Basic Information

ChEMBL ID CHEMBL269277
Name BETULINIC ACID
Phase Phase I
Structure Type MOL
InChI Key QGJZLNKBHJESQX-FZFNOLFKSA-N

Known Names

.beta.-betulinic acid ALS-357 Betulic acid Betulinic acid Lupatic acid Mairin NSC-113090 NSC-677578
90
Targets
431
Activities
4
Assay Types
1
PK Parameters
20
Publications
8
Known Names
2
Indications

Molecular Properties

456.7
MW (Da)
7.09
ALogP
2
HBA
2
HBD
57.5
PSA (Ų)
0.44
QED
1
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product

Extended Properties

Molecular Formula C30H48O3
MW 456.71
Aromatic Rings 0
Heavy Atoms 33
NP-Likeness 3.07

Indications

Dysplastic Nevus Syndrome Melanoma

Activity Summary

IC50 307 meas. best 7.58
EC50 115 meas. best 6.05
Kd 6 meas. best 6.23
Ki 3 meas. best 5.11

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
HeLa
CHEMBL399
 IC50 7.58 5.0067 26.0 9
Jurkat
CHEMBL397
 IC50 7.57 6.07 26.9 2
HepG2
CHEMBL395
 IC50 7.44 5.0717 36.4 6
8505C
CHEMBL1075387
 IC50 6.48 5.2963 330.0 8
MCF7
CHEMBL387
 IC50 6.48 4.7555 330.0 20
A549
CHEMBL392
 IC50 6.48 4.8028 330.0 25
518A2
CHEMBL4483222
 IC50 6.48 6.48 330.0 1
A2780
CHEMBL614004
 IC50 6.48 5.14 330.0 9
Sindbis virus
CHEMBL613725
 IC50 6.34 6.32 457.1 2
Albumin
CHEMBL3253
 Kd 6.23 5.8233 593.0 3
Human alphaherpesvirus 1
CHEMBL377
 IC50 6.16 6.16 700.0 1
Human immunodeficiency virus 1
CHEMBL378
 EC50 6.05 5.875 899.5 8
G-protein coupled bile acid receptor 1
CHEMBL5409
 EC50 5.99 5.985 1030.0 2
ADMET
CHEMBL612558
 IC50 5.89 4.766 1300.0 10
Plasmodium falciparum
CHEMBL364
 EC50 5.85 5.85 1419.0 1
Unchecked
CHEMBL612545
 EC50 5.85 5.85 1400.0 1
H9
CHEMBL614806
 EC50 5.85 5.85 1400.0 4
Tyrosine-protein phosphatase non-receptor type 1
CHEMBL335
 IC50 5.82 5.82 1500.0 1
Human alphaherpesvirus 2
CHEMBL370
 IC50 5.8 5.8 1600.0 1
Nonstructural protein 5
CHEMBL4295629
 IC50 5.77 5.77 1700.0 2
Dengue virus
CHEMBL613757
 IC50 5.77 5.77 1700.0 1
Aldo-keto reductase family 1 member B10
CHEMBL5983
 IC50 5.7 5.7 2000.0 1
Nuclear receptor ROR-gamma
CHEMBL1741186
 IC50 5.66 5.66 2200.0 1
Leishmania donovani
CHEMBL367
 IC50 5.58 5.485 2600.0 2
Nuclear receptor ROR-gamma
CHEMBL1741186
 Kd 5.57 5.52 2700.0 2
Human immunodeficiency virus 1
CHEMBL378
 IC50 5.51 5.04 3100.0 4
Plasmodium falciparum
CHEMBL364
 IC50 5.46 5.21 3440.0 3
HT-29
CHEMBL384
 IC50 5.46 4.7445 3500.0 11
Human betaherpesvirus 5
CHEMBL371
 EC50 5.44 5.44 3620.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 5.44 4.8594 3610.0 36
NON-PROTEIN TARGET
CHEMBL3879801
 EC50 5.37 5.05 4300.0 6
BV-2
CHEMBL614781
 IC50 5.35 5.35 4500.0 1
DNA polymerase beta
CHEMBL4343
 IC50 5.19 5.02 6500.0 2
SW480
CHEMBL612544
 IC50 5.19 5.19 6400.0 4
8505C
CHEMBL1075387
 EC50 5.17 5.17 6700.0 2
SK-MEL-2
CHEMBL614917
 IC50 5.16 4.77 7000.0 4
5'-nucleotidase
CHEMBL5957
 IC50 5.14 5.14 7280.0 2
A549
CHEMBL392
 EC50 5.12 4.823 7600.0 10
5'-nucleotidase
CHEMBL5957
 Ki 5.11 5.11 7800.0 1
B16
CHEMBL381
 IC50 5.1 4.685 7900.0 2
Human alphaherpesvirus 1
CHEMBL377
 EC50 5.09 5.09 8200.0 1
Replicase polyprotein 1a
CHEMBL3927
 Ki 5.09 5.09 8200.0 1
OVCAR-3
CHEMBL614213
 IC50 5.08 4.57 8366.0 3
HeLa
CHEMBL399
 EC50 5.06 5.06 8800.0 1
HCT-15
CHEMBL612263
 IC50 5.06 4.9433 8700.0 3
A2780
CHEMBL614004
 EC50 5.06 4.994 8800.0 15
SUMO-activating enzyme
CHEMBL2095174
 IC50 5.03 4.955 9240.0 2
518A2
CHEMBL4483222
 EC50 5.03 4.976 9400.0 5
Replicase polyprotein 1a
CHEMBL3927
 IC50 5.0 5.0 10000.0 1
Replicase polyprotein 1ab
CHEMBL4523582
 IC50 5.0 5.0 10000.0 1

Pharmacokinetic Data

Parameter Value Units Species
Ka 1.685 10'6/M Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
HeLa IC50 = 26.0 nM 7.58 Cytotoxicity against human HeLa cells after 72 hrs by MTT assay 19674909
Jurkat IC50 = 26.9 nM 7.57 Cytotoxicity against human Jurkat cells after 72 hrs by XTT assay 19674909
HepG2 IC50 = 36.4 nM 7.44 Cytotoxicity against human HepG2 cells after 72 hrs by MTT assay 19674909
A549 IC50 = 330.0 nM 6.48 Antitumor activity against human A549 cells by SRB assay 31499360
A2780 IC50 = 330.0 nM 6.48 Antitumor activity against human A2780 cells by SRB assay 31499360
8505C IC50 = 330.0 nM 6.48 Antitumor activity against human 8505C cells by SRB assay 31499360
518A2 IC50 = 330.0 nM 6.48 Antitumor activity against human 518A2 cells by SRB assay 31499360
MCF7 IC50 = 330.0 nM 6.48 Antitumor activity against human MCF7 cells by SRB assay 31499360
Sindbis virus IC50 = 457.09 nM 6.34 Antiviral activity against Sindbis virus infected in BHK cells assessed as inhib... 19839605
Sindbis virus IC50 = 500.0 nM 6.3 Antiviral activity against Sindbis virus infected in BHK cells assessed as inhib... 19839605
Albumin Kd = 593.0 nM 6.23 Binding affinity to human serum albumin with excitation at 285 nm by fluorescenc... 26112446
Human alphaherpesvirus 1 IC50 = 700.0 nM 6.16 Antiviral activity against HSV-1 KOS infected in African green monkey RC-37 cell... 26112446
Human immunodeficiency virus 1 EC50 = 899.5 nM 6.05 Antiviral activity against Human immunodeficiency virus 1 infected human H9 cell... -
G-protein coupled bile acid receptor 1 EC50 = 1030.0 nM 5.99 Agonist activity at TGR5 (unknown origin) expressed in CHO cells assessed as act... 38691888
G-protein coupled bile acid receptor 1 EC50 = 1040.0 nM 5.98 Agonist activity at TGR5 expressed in CHO cells by CRE-driven luciferase reporte... 19911773
Albumin Kd = 1300.0 nM 5.89 Binding affinity to human serum albumin with excitation at 295 nm after 30 mins ... 26112446
ADMET IC50 = 1300.0 nM 5.89 Cytotoxicity against human WI 38 cells after 48 hrs by WST-8 assay 15730243
Plasmodium falciparum EC50 = 1419.0 nM 5.85 Antimalarial activity against ring stage Plasmodium falciparum 3D7 infected in t... 30503412
Human immunodeficiency virus 1 EC50 = 1400.0 nM 5.85 Concentration required to inhibit 50% of HIV-1 (human immunodeficiency virus-1) ... 15501054
H9 EC50 = 1400.0 nM 5.85 Cytotoxicity against mock-infected human H9 cells 11141100

Literature References

PubMed DOI Target Context # Activities
30910472 10.1016/j.bmc.2019.03.033 HCT-116 30
29120172 10.1021/acs.jnatprod.7b00177 Unchecked 20
23973824 10.1016/j.ejmech.2013.07.012 A549 19
32237724 10.1021/acs.jnatprod.9b01212 BMDM 14
19839605 10.1021/np9003245 Semliki Forest virus 10
37236000 10.1016/j.ejmech.2023.115472 Unchecked 10
26592171 10.1016/j.bmcl.2015.10.035 LLC-PK1 8
30910472 10.1016/j.bmc.2019.03.033 DLD-1 8
37236000 10.1016/j.ejmech.2023.115472 Nuclear receptor ROR-gamma 8
28500966 10.1016/j.ejmech.2017.04.062 Unchecked 6
30910472 10.1016/j.bmc.2019.03.033 ADMET 6
19716700 10.1016/j.bmcl.2009.08.048 HepG2 6
32237724 10.1021/acs.jnatprod.9b01212 Mus musculus 6
18842418 10.1016/j.bmc.2008.09.053 Zinc finger protein GLI1 6
26629862 10.1016/j.ejmech.2015.11.018 NON-PROTEIN TARGET 6
17663539 10.1021/jm070295s SARS-CoV 5
30840925 10.1016/j.ejmech.2019.02.057 Unchecked 5
19481937 10.1016/j.bmcl.2009.05.050 Unchecked 5
2832544 10.1021/np50054a031 Unchecked 5
14640549 10.1021/jm020854p K562 5

Data from ChEMBL 36 via Core Engine