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Compound Detail

CHEMBL51628

UMBELLIFERONE
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O=c1ccc2ccc(O)cc2o1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL51628
Name UMBELLIFERONE
Phase Preclinical
Structure Type MOL
InChI Key ORHBXUUXSCNDEV-UHFFFAOYSA-N
20
Targets
52
Activities
3
Assay Types
30
PK Parameters
20
Publications
0
Known Names

Molecular Properties

162.1
MW (Da)
1.50
ALogP
3
HBA
1
HBD
50.4
PSA (Ų)
0.60
QED
0
Ro5 Violations
0
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C9H6O3
MW 162.14
Aromatic Rings 2
Heavy Atoms 12
NP-Likeness 1.11

Activity Summary

IC50 39 meas. best 6.32
Ki 12 meas. best 7.6
EC50 1 meas.

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Carbonic anhydrase 9
CHEMBL3594
 Ki 7.6 6.64 24.9 4
Carbonic anhydrase 12
CHEMBL3242
 Ki 7.35 6.53 45.1 3
SK-MEL-28
CHEMBL614919
 IC50 6.32 6.32 480.0 1
Zn finger protein
CHEMBL1293200
 Ki 6.12 6.12 754.0 1
SK-MEL3
CHEMBL614920
 IC50 5.8 5.74 1600.0 2
MCF7
CHEMBL387
 IC50 5.54 5.54 2900.0 1
MDA-MB-231
CHEMBL400
 IC50 5.43 5.43 3700.0 1
Induced myeloid leukemia cell differentiation protein Mcl-1
CHEMBL4361
 Ki 5.42 5.42 3810.0 1
HT-29
CHEMBL384
 IC50 5.36 5.0 4350.0 2
HCT-116
CHEMBL394
 IC50 5.09 5.09 8050.0 1
SMMC-7721
CHEMBL613831
 IC50 4.7 4.7 19900.0 1
A549
CHEMBL392
 IC50 4.68 4.68 21110.0 1
Induced myeloid leukemia cell differentiation protein Mcl-1
CHEMBL4361
 IC50 4.68 4.68 21040.0 1
Unchecked
CHEMBL612545
 IC50 4.68 4.3733 20880.0 3
Aldo-keto reductase family 1 member B1
CHEMBL1900
 IC50 4.64 4.64 22900.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 4.48 4.48 33000.0 1
Seed linoleate 13S-lipoxygenase-1
CHEMBL4586
 IC50 4.37 4.37 43000.0 1
HeLa
CHEMBL399
 IC50 4.37 4.37 42350.0 1
V79
CHEMBL614074
 IC50 4.24 4.24 58000.0 1
Carbonic anhydrase 1
CHEMBL261
 Ki 4.23 4.23 58400.0 3
LoVo
CHEMBL614721
 IC50 4.01 4.01 97000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 123.03 uL.min-1.(10^6cells)-1 Homo sapiens
CL 140000.0 mL.min-1.g-1 Homo sapiens
CL 280000.0 mL.min-1.g-1 Mus musculus
CL 902.32 mL.min-1.g-1 Mus musculus
CL 138.6 mL.min-1.g-1 Homo sapiens
CL 306.0 mL.min-1.kg-1 Rattus norvegicus
CL 289.2 mL.min-1.kg-1 Homo sapiens
T1/2 0.1233 hr Mus musculus
T1/2 0.13 hr Canis lupus familiaris
T1/2 0.12 hr Rattus norvegicus
T1/2 0.25 hr Macaca mulatta
T1/2 0.235 hr Homo sapiens
T1/2 0.3517 hr Homo sapiens
T1/2 0.185 hr Rattus norvegicus
T1/2 0.17 hr Canis lupus familiaris
T1/2 0.1983 hr Mus musculus
T1/2 0.4433 hr Homo sapiens
T1/2 0.2583 hr Homo sapiens
T1/2 0.2583 hr Homo sapiens
T1/2 0.08333 hr Homo sapiens
t1/2 - - Mus musculus
T1/2 0.05 hr Homo sapiens
T1/2 0.01333 hr Mus musculus
t1/2 - - Homo sapiens
T1/2 0.2588 hr Homo sapiens
T1/2 0.02567 hr Mus musculus
T1/2 0.08667 hr Homo sapiens
T1/2 0.1233 hr Mus musculus
T1/2 0.01833 hr Rattus norvegicus
T1/2 0.1 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Carbonic anhydrase 9 Ki = 24.9 nM 7.6 Inhibition of human carbonic anhydrase 9 incubated for 15 mins prior to testing ... 29197732
Carbonic anhydrase 12 Ki = 45.1 nM 7.35 Inhibition of human carbonic anhydrase 12 incubated for 15 mins prior to testing... 29197732
Carbonic anhydrase 9 Ki = 478.0 nM 6.32 Inhibition of human recombinant CA9 after 6 hrs by stopped flow CO2 hydration as... 22077347
Carbonic anhydrase 9 Ki = 482.0 nM 6.32 Inhibition of human recombinant CA9 catalytic domain by stopped-flow CO2 hydrati... 21067924
Carbonic anhydrase 9 Ki = 480.0 nM 6.32 Inhibition of human carbonic anhydrase 9 catalytic domain by Stopped-Flow CO2 Hy... 26688270
SK-MEL-28 IC50 = 480.0 nM 6.32 Anticancer activity against human SK-MEL-28 cells assessed as reduction in cell ... 37197457
Zn finger protein Ki = 754.0 nM 6.12 Inhibition of human recombinant CA12 catalytic domain by stopped-flow CO2 hydrat... 21067924
Carbonic anhydrase 12 Ki = 754.0 nM 6.12 Inhibition of human recombinant CA12 after 6 hrs by stopped flow CO2 hydration a... 22077347
Carbonic anhydrase 12 Ki = 750.0 nM 6.12 Inhibition of human carbonic anhydrase 12 catalytic domain by Stopped-Flow CO2 H... 26688270
SK-MEL3 IC50 = 1600.0 nM 5.8 Anticancer activity against human SK-MEL3 cells assessed as reduction in cell vi... 37197457
SK-MEL3 IC50 = 2100.0 nM 5.68 Anticancer activity against human SK-MEL3 cells assessed as reduction in cell vi... 37197457
MCF7 IC50 = 2900.0 nM 5.54 Antiproliferative activity against human MCF7 cells after 24 hrs by MTT assay 29144746
MDA-MB-231 IC50 = 3700.0 nM 5.43 Antiproliferative activity against human MDA-MB-231 cells after 24 hrs by MTT as... 29144746
Induced myeloid leukemia cell differentiation protein Mcl-1 Ki = 3810.0 nM 5.42 Displacement of FAM-Bid peptide from recombinant N-terminal His6x-tagged human M... 33218896
HT-29 IC50 = 4350.0 nM 5.36 Cytotoxicity against human HT-29 cells after 96 hrs by MTT assay 23746477
HCT-116 IC50 = 8050.0 nM 5.09 Cytotoxicity against human HCT116 cells after 96 hrs by MTT assay 23746477
SMMC-7721 IC50 = 19900.0 nM 4.7 Antiproliferative activity against human SMMC7721 cells after 48 hrs by MTT assa... 28720504
Unchecked IC50 = 20880.0 nM 4.68 Cytotoxicity against human C3PV cells assessed as reduction in cell viability in... 37197457
Induced myeloid leukemia cell differentiation protein Mcl-1 IC50 = 21040.0 nM 4.68 Displacement of FAM-Bid peptide from recombinant N-terminal His6x-tagged human M... 33218896
A549 IC50 = 21110.0 nM 4.68 Antiproliferative activity against human A549 cells after 48 hrs by MTT assay 28720504

Literature References

PubMed DOI Target Context # Activities
21417376 10.1021/np100621c Mus musculus 27
16190766 10.1021/jm0580149 Rattus norvegicus 16
21680063 10.1016/j.ejmech.2011.05.052 J774 9
31244112 10.1021/acs.jmedchem.9b00525 ADMET 8
10543892 10.1021/np990048u Salmonella typhimurium 6
28829592 10.1021/acs.jmedchem.7b00930 ADMET 6
32787099 10.1021/acs.jmedchem.0c00565 ADMET 6
23306152 10.3390/ijms14011293 Aspergillus fumigatus 5
37421373 10.1021/acs.jmedchem.3c00976 ADMET 5
23306152 10.3390/ijms14011293 Aspergillus flavus 4
28829592 10.1021/acs.jmedchem.7b00930 Unchecked 4
19150597 10.1016/j.bmcl.2008.12.098 Radical scavenging activity 4
21696954 10.1016/j.bmcl.2011.05.089 NON-PROTEIN TARGET 4
35993890 10.1021/acs.jmedchem.2c00589 ADMET 4
27474926 10.1016/j.ejmech.2016.07.026 NON-PROTEIN TARGET 4
37261954 10.1021/acs.jmedchem.3c00279 ADMET 4
29236486 10.1021/acs.jnatprod.7b00665 Influenza A virus 3
29730190 10.1016/j.ejmech.2018.04.051 Melan-a 3
29236486 10.1021/acs.jnatprod.7b00665 A549 3
22381334 10.1124/dmd.111.043596 Hepatocyte 3

Data from ChEMBL 36 via Core Engine