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Compound Detail

CHEMBL76447

NOBILETIN
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COc1ccc(-c2cc(=O)c3c(OC)c(OC)c(OC)c(OC)c3o2)cc1OC
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL76447
Name NOBILETIN
Phase Preclinical
Structure Type MOL
InChI Key MRIAQLRQZPPODS-UHFFFAOYSA-N
11
Targets
18
Activities
1
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

402.4
MW (Da)
3.51
ALogP
8
HBA
0
HBD
85.6
PSA (Ų)
0.59
QED
0
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C21H22O8
MW 402.40
Aromatic Rings 3
Heavy Atoms 29
NP-Likeness 0.84

Activity Summary

IC50 18 meas. best 5.36

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Broad substrate specificity ATP-binding cassette transporter ABCG2
CHEMBL5393
 IC50 5.36 5.335 4400.0 2
A2780/Taxol
CHEMBL4483224
 IC50 5.05 5.05 9000.0 1
A549/TR
CHEMBL4483226
 IC50 5.05 5.05 9000.0 1
Monocyte
CHEMBL614076
 IC50 5.0 5.0 10000.0 1
ATP-dependent translocase ABCB1
CHEMBL4302
 IC50 4.94 4.94 11500.0 1
Unchecked
CHEMBL612545
 IC50 4.77 4.725 17000.0 4
HT-29
CHEMBL384
 IC50 4.62 4.62 24000.0 1
LNCaP C4-2
CHEMBL4296460
 IC50 4.52 4.52 30300.0 1
CWR22R
CHEMBL612657
 IC50 4.44 4.44 36530.0 1
HL-60
CHEMBL383
 IC50 4.38 4.38 41500.0 1
3T3-L1
CHEMBL614510
 IC50 4.3 4.3 50000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Broad substrate specificity ATP-binding cassette transporter ABCG2 IC50 = 4400.0 nM 5.36 Inhibition of BCRP expressed in MCF-7 MX cells using Hoechst 33342 staining 21354800
Broad substrate specificity ATP-binding cassette transporter ABCG2 IC50 = 4900.0 nM 5.31 Inhibition of BCRP expressed in MDCK cells using Hoechst 33342 staining 21354800
A549/TR IC50 = 9000.0 nM 5.05 Antiproliferative activity against human A549/Taxol cells overexpressing ABCB1 a... 35751979
A2780/Taxol IC50 = 9000.0 nM 5.05 Antiproliferative activity against human A2780/Taxol cells overexpressing ABCB1 ... 35751979
Monocyte IC50 = 10000.0 nM 5.0 Inhibition of TNFalpha expression in LPS-stimulated human monocytes treated 30 m... 10096854
ATP-dependent translocase ABCB1 IC50 = 11500.0 nM 4.94 TP_TRANSPORTER: inhibition of Daunorubicin efflux in NIH-3T3-G185 cells 11743742
Unchecked IC50 = 17000.0 nM 4.77 Inhibition of TNF-alpha-induced proMMP9 production in human SRA 01/04 cells afte... 21723726
Unchecked IC50 = 17000.0 nM 4.77 Inhibition of TNFalpha-stimulated pro MMP9 production in human SRA 01/04 cells a... 22047798
Unchecked IC50 = 20900.0 nM 4.68 Inhibition of PMA-induced proMMP9 production in human SRA 01/04 cells after 24 h... 21723726
Unchecked IC50 = 20900.0 nM 4.68 Inhibition of PMA-stimulated pro MMP9 production in human SRA 01/04 cells after ... 22047798
HT-29 IC50 = 24000.0 nM 4.62 Anticancer activity against human HT-29 cells after 72 hrs by MTT assay 19054677
LNCaP C4-2 IC50 = 30300.0 nM 4.52 Antiproliferative activity against human C4-2 cells incubated for 24 hrs by CCK-... 36459083
CWR22R IC50 = 36530.0 nM 4.44 Antiproliferative activity against human 22Rv1 cells incubated for 24 hrs by CCK... 36459083
HL-60 IC50 = 41500.0 nM 4.38 Antiproliferative activity against HL60 after 24 hrs 17391969
3T3-L1 IC50 = 50000.0 nM 4.3 Anticorpulence activity against mouse 3T3L1 cells assessed as inhibition of lipi... 19054677

Literature References

PubMed DOI Target Context # Activities
35290062 10.1021/acs.jnatprod.1c00971 MNT-1 10
19268587 10.1016/j.bmcl.2009.02.002 Unchecked 8
18282757 10.1016/j.bmc.2008.01.058 SH-SY5Y 5
21493073 10.1016/j.bmc.2011.03.040 3T3-L1 5
28559058 10.1016/j.bmc.2017.05.041 Amyloid-beta precursor protein 4
23199882 10.1016/j.bmcl.2012.10.133 NON-PROTEIN TARGET 4
15568779 10.1021/np034007g Salmonella typhimurium 4
17644380 10.1016/j.bmcl.2007.06.096 RAW264.7 3
3069957 10.1021/np50060a006 Salmonella typhimurium 3
35751979 10.1016/j.ejmech.2022.114542 A2780/Taxol 3
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
21354800 10.1016/j.bmc.2010.12.043 Broad substrate specificity ATP-binding cassette transporter ABCG2 2
21723726 10.1016/j.bmcl.2011.05.121 Unchecked 2
11982408 10.1021/jf011382a Phytophthora citrophthora 2
22047798 10.1016/j.bmc.2011.10.001 Unchecked 2
15640378 10.1124/dmd.104.002337 Solute carrier organic anion transporter family member 2B1 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
11982408 10.1021/jf011382a Citrus 2
15504753 10.1038/sj.bjp.0706008 ATP-dependent translocase ABCB1 2
17391969 10.1016/j.bmc.2007.03.021 HL-60 2

Data from ChEMBL 36 via Core Engine