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Compound Detail

CHEMBL74898

AYANIN
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COc1cc(O)c2c(=O)c(OC)c(-c3ccc(OC)c(O)c3)oc2c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL74898
Name AYANIN
Phase Preclinical
Structure Type MOL
InChI Key KPCRYSMUMBNTCK-UHFFFAOYSA-N
15
Targets
21
Activities
1
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

344.3
MW (Da)
2.90
ALogP
7
HBA
2
HBD
98.4
PSA (Ų)
0.75
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C18H16O7
MW 344.32
Aromatic Rings 3
Heavy Atoms 25
NP-Likeness 1.19

Activity Summary

IC50 21 meas. best 6.34

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Broad substrate specificity ATP-binding cassette transporter ABCG2
CHEMBL5393
 IC50 6.34 5.9167 460.0 3
rhinovirus A2
CHEMBL612678
 IC50 5.75 5.75 1800.0 1
Respiratory syncytial virus
CHEMBL612679
 IC50 5.21 5.21 6100.0 1
Unchecked
CHEMBL612545
 IC50 5.03 5.03 9400.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 4.96 4.728 10840.0 5
ATP-dependent translocase ABCB1
CHEMBL4302
 IC50 4.89 4.89 13000.0 1
J774.A1
CHEMBL614040
 IC50 4.75 4.75 17800.0 1
NCI-H157
CHEMBL614783
 IC50 4.73 4.73 18640.0 1
HeLa
CHEMBL399
 IC50 4.71 4.71 19470.0 1
HOP-62
CHEMBL614643
 IC50 4.7 4.7 20060.0 1
NCI-H522
CHEMBL614387
 IC50 4.69 4.69 20210.0 1
A549
CHEMBL392
 IC50 4.68 4.68 20790.0 1
BV-2
CHEMBL614781
 IC50 4.6 4.6 25100.0 1
M14
CHEMBL614317
 IC50 4.43 4.43 37070.0 1
Multidrug resistance-associated protein 1
CHEMBL3004
 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 = 460.0 nM 6.34 Inhibition of BCRP expressed in MDCK cells using Hoechst 33342 staining 21354800
Broad substrate specificity ATP-binding cassette transporter ABCG2 IC50 = 680.0 nM 6.17 Inhibition of BCRP expressed in MCF-7 MX cells using Hoechst 33342 staining 21354800
rhinovirus A2 IC50 = 1800.0 nM 5.75 Antiviral activity against HRV2 HGP infected in human HeLa cells assessed as pro... 36749598
Broad substrate specificity ATP-binding cassette transporter ABCG2 IC50 = 5700.0 nM 5.24 Inhibition of ABCG2 expressed in human NCI-H460 cells assessed as inhibition of ... 21275386
Respiratory syncytial virus IC50 = 6100.0 nM 5.21 Antiviral activity against RSV A2 infected in human HEp-2 cells assessed as redu... 36749598
Unchecked IC50 = 9400.0 nM 5.03 Inhibition of P-gp expressed in A2780adr cells by calcein AM accumulation assay 21354800
NON-PROTEIN TARGET IC50 = 10840.0 nM 4.96 Anticancer activity against human SKBR cells by HTS assay 25139569
ATP-dependent translocase ABCB1 IC50 = 13000.0 nM 4.89 Inhibition of MDR1 expressed in MDCK cells using rhodamine 123 staining by flow ... 21354800
NON-PROTEIN TARGET IC50 = 12790.0 nM 4.89 Anticancer activity against human H460 cells by HTS assay 25139569
NON-PROTEIN TARGET IC50 = 16230.0 nM 4.79 Anticancer activity against human M4E cells by HTS assay 25139569
J774.A1 IC50 = 17800.0 nM 4.75 Anti-inflammatory activity in mouse J774.A1 cells assessed as suppression of LPS... 37683361
NCI-H157 IC50 = 18640.0 nM 4.73 Anticancer activity against human NCI-H157 cells by HTS assay 25139569
HeLa IC50 = 19470.0 nM 4.71 Anticancer activity against human HeLa cells by HTS assay 25139569
HOP-62 IC50 = 20060.0 nM 4.7 Anticancer activity against human HOP62 cells by HTS assay 25139569
NCI-H522 IC50 = 20210.0 nM 4.69 Anticancer activity against human NCI-H522 cells by HTS assay 25139569
A549 IC50 = 20790.0 nM 4.68 Anticancer activity against human A549 cells by HTS assay 25139569
NON-PROTEIN TARGET IC50 = 21920.0 nM 4.66 Anticancer activity against human NCI-H1944 cells by HTS assay 25139569
BV-2 IC50 = 25100.0 nM 4.6 Anti-inflammatory activity in mouse BV-2 cells assessed as inhibition of LPS-ind... 37683361
M14 IC50 = 37070.0 nM 4.43 Anticancer activity against human M14 cells by HTS assay 25139569
NON-PROTEIN TARGET IC50 = 45970.0 nM 4.34 Anticancer activity against human LOXIMVI cells by HTS assay 25139569

Literature References

PubMed DOI Target Context # Activities
24853321 10.1016/j.bmc.2014.04.053 B16-F0 12
11575945 10.1021/np010122k NON-PROTEIN TARGET 10
25139569 10.1016/j.bmcl.2014.08.006 NON-PROTEIN TARGET 9
22647223 10.1016/j.ejmech.2012.04.044 Thrombin 4
21493073 10.1016/j.bmc.2011.03.040 3T3-L1 4
24853321 10.1016/j.bmc.2014.04.053 ADMET 3
9632366 10.1021/jm970842h Tubulin 2
36749598 10.1021/acs.jnatprod.2c01007 Respiratory syncytial virus 2
36749598 10.1021/acs.jnatprod.2c01007 ADMET 2
36749598 10.1021/acs.jnatprod.2c01007 HeLa 2
21354800 10.1016/j.bmc.2010.12.043 Unchecked 2
21354800 10.1016/j.bmc.2010.12.043 Broad substrate specificity ATP-binding cassette transporter ABCG2 2
21354800 10.1016/j.bmc.2010.12.043 Multidrug resistance-associated protein 1 1
37683361 10.1016/j.ejmech.2023.115791 BV-2 1
21354800 10.1016/j.bmc.2010.12.043 MCF7 1
21354800 10.1016/j.bmc.2010.12.043 A2780 1
25139569 10.1016/j.bmcl.2014.08.006 A549 1
25139569 10.1016/j.bmcl.2014.08.006 NCI-H157 1
20356063 10.1021/np100065v Unchecked 1
20356063 10.1021/np100065v KB 1

Data from ChEMBL 36 via Core Engine