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Compound Detail

CHEMBL24171

BERGAPTEN
🧪 Phase III
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🧪 Phase III
COc1c2ccoc2cc2oc(=O)ccc12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL24171
Name BERGAPTEN
Phase Phase III
Structure Type MOL
InChI Key BGEBZHIAGXMEMV-UHFFFAOYSA-N

Known Names

5-methoxypsoralen Bergaptan Bergapten Bergaptene Geralen Heraclin Majudin Methoxsalen related compound a NSC-95437
11
Targets
22
Activities
3
Assay Types
0
PK Parameters
20
Publications
9
Known Names
2
Indications

Molecular Properties

216.2
MW (Da)
2.55
ALogP
4
HBA
0
HBD
52.6
PSA (Ų)
0.59
QED
0
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Achiral

Flags

Natural Product
USAN Stem -erg-

Extended Properties

Molecular Formula C12H8O4
MW 216.19
Aromatic Rings 3
Heavy Atoms 16
NP-Likeness 1.04

Indications

Psoriasis Dermatitis, Atopic

ATC Classification

D05BA03
bergapten
Level 1: DERMATOLOGICALS
Level 2: ANTIPSORIATICS

Activity Summary

IC50 14 meas. best 7.1
Kd 5 meas. best 4.39
Ki 3 meas. best 7.22

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Cytochrome P450 1A1
CHEMBL2231
 Ki 7.22 7.22 60.0 1
Cytochrome P450 1A2
CHEMBL3356
 Ki 7.22 7.22 60.0 1
Cytochrome P450 1A1
CHEMBL2231
 IC50 7.1 7.1 80.0 1
Cytochrome P450 1A2
CHEMBL3356
 IC50 7.05 7.05 90.0 1
HT-1080
CHEMBL614580
 IC50 6.05 5.6233 900.0 3
Unchecked
CHEMBL612545
 IC50 5.76 5.27 1750.0 3
HL-60
CHEMBL383
 IC50 5.47 5.47 3350.0 1
Cytochrome P450 2A6
CHEMBL5282
 Ki 4.92 4.92 12000.0 1
Amine oxidase [flavin-containing] A
CHEMBL1951
 IC50 4.86 4.86 13800.0 1
Cytochrome P450 1B1
CHEMBL4878
 IC50 4.82 4.82 15300.0 1
HeLa
CHEMBL399
 IC50 4.79 4.79 16300.0 1
Fusarium solani
CHEMBL612506
 IC50 4.56 4.56 27700.0 1
Potassium voltage-gated channel subfamily A member 2
CHEMBL2086
 Kd 4.39 4.39 41000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Cytochrome P450 1A2 Ki = 60.0 nM 7.22 Inhibition of human recombinant CYP1A2 expressed in HEK293 cells using 3-cyano-7... 30108931
Cytochrome P450 1A1 Ki = 60.0 nM 7.22 Inhibition of human recombinant CYP1A1 expressed in HEK293 cells using 7-ethoxyr... 30108931
Cytochrome P450 1A1 IC50 = 80.0 nM 7.1 Inhibition of human recombinant CYP1A1 expressed in HEK293 cells using 7-ethoxyr... 30108931
Cytochrome P450 1A2 IC50 = 90.0 nM 7.05 Inhibition of human recombinant CYP1A2 expressed in HEK293 cells using 3-cyano-7... 30108931
HT-1080 IC50 = 900.0 nM 6.05 Inhibition of cell growth after irradiation at UVA dose of 6.5 J/cmE-2 in HT1080... 12873520
Unchecked IC50 = 1750.0 nM 5.76 Selectivity for Kv1.3 potassium channel over Kv1.5 potassium channel 19056148
HT-1080 IC50 = 1800.0 nM 5.75 Inhibition of cell growth after irradiation at UVA dose of 3.2 J/cmE-2 in HT1080... 12873520
HL-60 IC50 = 3350.0 nM 5.47 The compound was tested in vitro for growth inhibition against HL-60(human promy... 10543884
Unchecked IC50 = 6500.0 nM 5.19 Inhibition of calf thymus DNA topoisomerase 1 assessed as pUC19 DNA relaxation b... 19736019
HT-1080 IC50 = 8500.0 nM 5.07 Inhibition of cell growth after irradiation at UVA dose of 2.6 J/cmE-2 in HT1080... 12873520
Cytochrome P450 2A6 Ki = 12000.0 nM 4.92 Mechanism based inhibition of human cytochrome P450 2A6 measured by coumarin 7-h... 16248836
Amine oxidase [flavin-containing] A IC50 = 13800.0 nM 4.86 Inhibition of MAO-A (unknown origin) 23517722
Unchecked IC50 = 13800.0 nM 4.86 Inhibition of mouse brain monoamine oxidase 23517722
Cytochrome P450 1B1 IC50 = 15300.0 nM 4.82 Inhibition of human recombinant CYP1B1 expressed in HEK293 cells using 7-ethoxyr... 30108931
HeLa IC50 = 16300.0 nM 4.79 The compound was tested in vitro for growth inhibition against HeLa(human cervix... 10543884
Fusarium solani IC50 = 27700.0 nM 4.56 Fungistatic activity against Fusarium solani assessed as growth inhibition 12568545
Potassium voltage-gated channel subfamily A member 2 Kd = 41000.0 nM 4.39 Blockade of peak K+ currents against Kv1.2 gene 9804693

Literature References

PubMed DOI Target Context # Activities
3069958 10.1021/np50060a016 Salmonella typhimurium 13
23291118 10.1016/j.ejmech.2012.11.043 ADMET 5
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
30108931 10.1039/C7MD00388A Cytochrome P450 1A1 4
15161195 10.1021/jf0497298 Lactuca sativa 4
9804693 10.1021/jm981032o ADMET 3
19736019 10.1016/j.bmc.2009.04.023 Unchecked 3
31464439 10.1021/acs.jnatprod.9b00547 HepG2 3
12873520 10.1016/s0960-894x(03)00529-8 HT-1080 3
30108931 10.1039/C7MD00388A Cytochrome P450 1A2 3
9804693 10.1021/jm981032o Potassium voltage-gated channel subfamily A member 1 3
9804693 10.1021/jm981032o Nucleic Acid 2
25891102 10.1016/j.bmcl.2015.04.003 Tyrosine-protein phosphatase non-receptor type 1 2
23291118 10.1016/j.ejmech.2012.11.043 Radical scavenging activity 2
10543884 10.1021/jm9910829 HeLa 2
10543884 10.1021/jm9910829 HL-60 2
21625478 10.1371/journal.pone.0019825 Polymerase acidic protein 2
11170668 10.1021/np000406p HSC-2 2
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M1 2
9157191 10.1021/np960407a Mus musculus 2

Data from ChEMBL 36 via Core Engine