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Compound Detail

CHEMBL307341

AURAPTENE
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CC(C)=CCC/C(C)=C/COc1ccc2ccc(=O)oc2c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL307341
Name AURAPTENE
Phase Preclinical
Structure Type MOL
InChI Key RSDDHGSKLOSQFK-RVDMUPIBSA-N
14
Targets
22
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

298.4
MW (Da)
4.86
ALogP
3
HBA
0
HBD
39.4
PSA (Ų)
0.56
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C19H22O3
MW 298.38
Aromatic Rings 2
Heavy Atoms 22
NP-Likeness 1.41

Activity Summary

IC50 21 meas. best 10.46
Ki 1 meas. best 5.72

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Amine oxidase [flavin-containing] A
CHEMBL3681
 IC50 10.46 10.46 0.0 1
Melatonin receptor type 1A
CHEMBL1945
 Ki 5.72 5.72 1900.0 1
Unchecked
CHEMBL612545
 IC50 5.2 5.18 6300.0 2
Mitochondrial complex I (NADH dehydrogenase)
CHEMBL2363065
 IC50 4.99 4.86 10200.0 2
Leishmania major
CHEMBL612879
 IC50 4.77 4.77 17100.0 1
Polyunsaturated fatty acid lipoxygenase ALOX15
CHEMBL2903
 IC50 4.62 4.62 23900.0 1
BT-549
CHEMBL614072
 IC50 4.62 4.62 24000.0 1
3T3-L1
CHEMBL614510
 IC50 4.33 4.33 47000.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 4.24 4.165 58000.0 2
PC-3
CHEMBL390
 IC50 4.19 4.19 65000.0 1
LoVo
CHEMBL614721
 IC50 4.18 4.18 66000.0 1
MDA-MB-231
CHEMBL400
 IC50 4.1 4.1 80000.0 1
A549
CHEMBL392
 IC50 4.09 4.09 82000.0 1
SK-MEL-28
CHEMBL614919
 IC50 4.06 4.06 87000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Amine oxidase [flavin-containing] A IC50 = 0.0346 nM 10.46 Inhibition of mouse brain MAO-A 23517722
Melatonin receptor type 1A Ki = 1900.0 nM 5.72 Displacement of 2-[125I]iodomelatonin from human MT1 receptor expressed in CHO c... 29144746
Unchecked IC50 = 6300.0 nM 5.2 Inhibition of soybean 15-lipoxygenase by MBTH-DMAB method 23047230
Unchecked IC50 = 7000.0 nM 5.16 Antiviral activity against Influenza A virus (A/California/07/09(H1N1)) pdm09 in... 28501512
Mitochondrial complex I (NADH dehydrogenase) IC50 = 10200.0 nM 4.99 Inhibition of mitochondrial ETC complex 1 in human T47D cells assessed as inhibi... 23434131
Leishmania major IC50 = 17100.0 nM 4.77 Antileishmanial activity against promastigote form of Leishmania major assessed ... 32668302
Mitochondrial complex I (NADH dehydrogenase) IC50 = 18800.0 nM 4.73 Inhibition of mitochondrial ETC complex 1 in human T47D cells assessed as inhibi... 23434131
Polyunsaturated fatty acid lipoxygenase ALOX15 IC50 = 23900.0 nM 4.62 Inhibition of recombinant human 15-lipoxygenase by MBTH-DMAB method 23047230
BT-549 IC50 = 24000.0 nM 4.62 Antiproliferative activity against human BT549 cells after 24 hrs by MTT assay 29144746
3T3-L1 IC50 = 47000.0 nM 4.33 Anticorpulence activity against mouse 3T3L1 cells assessed as inhibition of lipi... 19054677
NON-PROTEIN TARGET IC50 = 58000.0 nM 4.24 Cytotoxicity against human OE21 cells after 72 hrs by MTT assay 21696954
PC-3 IC50 = 65000.0 nM 4.19 Cytotoxicity against human PC3 cells after 72 hrs by MTT assay 21696954
LoVo IC50 = 66000.0 nM 4.18 Cytotoxicity against human LoVo cells after 72 hrs by MTT assay 21696954
MDA-MB-231 IC50 = 80000.0 nM 4.1 Antiproliferative activity against human MDA-MB-231 cells after 24 hrs by MTT as... 29144746
NON-PROTEIN TARGET IC50 = 82000.0 nM 4.09 Cytotoxicity against human U373 cells after 72 hrs by MTT assay 21696954
A549 IC50 = 82000.0 nM 4.09 Cytotoxicity against human A549 cells after 72 hrs by MTT assay 21696954
SK-MEL-28 IC50 = 87000.0 nM 4.06 Cytotoxicity against human SK-MEL-28 cells after 72 hrs by MTT assay 21696954

Literature References

PubMed DOI Target Context # Activities
22472691 10.1016/j.bmcl.2012.03.057 Bile acid receptor 8
23434131 10.1016/j.bmc.2013.01.048 Unchecked 6
29730190 10.1016/j.ejmech.2018.04.051 Melan-a 5
23306152 10.3390/ijms14011293 Aspergillus fumigatus 5
19679472 10.1016/j.bmcl.2009.07.110 Mus musculus 4
23306152 10.3390/ijms14011293 Aspergillus flavus 4
21696954 10.1016/j.bmcl.2011.05.089 NON-PROTEIN TARGET 4
29144746 10.1021/acs.jnatprod.7b00853 BT-549 3
29144746 10.1021/acs.jnatprod.7b00853 Unchecked 3
29144746 10.1021/acs.jnatprod.7b00853 MDA-MB-231 3
28844340 10.1016/j.ejmech.2017.08.038 Mus musculus 3
29730190 10.1016/j.ejmech.2018.04.051 No relevant target 2
25205194 10.1016/j.bmcl.2014.08.038 NON-PROTEIN TARGET 2
23434131 10.1016/j.bmc.2013.01.048 Mitochondrial complex I (NADH dehydrogenase) 2
28501512 10.1016/j.bmcl.2017.04.091 Unchecked 2
21880488 10.1016/j.bmcl.2011.08.005 PANC-1 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
15081016 10.1016/j.bmcl.2004.02.009 Mus musculus 2
29144746 10.1021/acs.jnatprod.7b00853 MCF7 2
28525281 10.1021/acs.jnatprod.7b00173 Aryl hydrocarbon receptor 2

Data from ChEMBL 36 via Core Engine