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Compound Detail

CHEMBL1098728

NEORAUTENOL
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CC1(C)C=Cc2cc3c(cc2O1)OC[C@H]1c2ccc(O)cc2O[C@@H]31
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1098728
Name NEORAUTENOL
Phase Preclinical
Structure Type MOL
InChI Key OGFFMQWYZCTXCM-KXBFYZLASA-N
9
Targets
10
Activities
2
Assay Types
0
PK Parameters
10
Publications
0
Known Names

Molecular Properties

322.4
MW (Da)
4.19
ALogP
4
HBA
1
HBD
47.9
PSA (Ų)
0.79
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 C20H18O4
MW 322.36
Aromatic Rings 2
Heavy Atoms 24
NP-Likeness 2.91

Activity Summary

IC50 9 meas. best 5.12
Ki 1 meas. best 4.66

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Tyrosine-protein phosphatase non-receptor type 1
CHEMBL335
 IC50 5.12 5.12 7600.0 1
NCI-H1299
CHEMBL612255
 IC50 4.82 4.82 15000.0 1
HCT-116
CHEMBL394
 IC50 4.76 4.76 17400.0 1
Sialidase
CHEMBL5189
 IC50 4.7 4.7 19820.0 1
Sialidase
CHEMBL5189
 Ki 4.66 4.66 21740.0 1
NCI-H460
CHEMBL396
 IC50 4.62 4.62 24200.0 1
A549
CHEMBL392
 IC50 4.61 4.61 24600.0 1
Hep 3B2
CHEMBL4296437
 IC50 4.54 4.54 28500.0 1
Sialidase
CHEMBL1075100
 IC50 4.28 4.28 53110.0 1
MDA-MB-231
CHEMBL400
 IC50 4.28 4.28 53100.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Tyrosine-protein phosphatase non-receptor type 1 IC50 = 7600.0 nM 5.12 Inhibition of human recombinant PTP1B assessed as p-nitrophenol production 19836230
NCI-H1299 IC50 = 15000.0 nM 4.82 Antitumor activity against human NCI-H1299 cells assessed as inhibition of cell ... 37271378
HCT-116 IC50 = 17400.0 nM 4.76 Antitumor activity against human HCT-116 cells assessed as inhibition of cell gr... 37271378
Sialidase IC50 = 19820.0 nM 4.7 Inhibition of Clostridium perfringens neuraminidase assessed as inhibition of 4-... 20363636
Sialidase Ki = 21740.0 nM 4.66 Noncompetitive inhibition of Clostridium perfringens neuraminidase 20363636
NCI-H460 IC50 = 24200.0 nM 4.62 Antitumor activity against human NCI-H460 cells assessed as inhibition of cell g... 37271378
A549 IC50 = 24600.0 nM 4.61 Antitumor activity against human A549 cells assessed as inhibition of cell growt... 37271378
Hep 3B2 IC50 = 28500.0 nM 4.54 Antitumor activity against human Hep3B cells assessed as inhibition of cell grow... 37271378
Sialidase IC50 = 53110.0 nM 4.28 Inhibition of Vibrio cholerae neuraminidase assessed as inhibition of 4-MU-NANA ... 20363636
MDA-MB-231 IC50 = 53100.0 nM 4.28 Antitumor activity against human MDA-MB-231 cells assessed as inhibition of cell... 37271378

Literature References

PubMed DOI Target Context # Activities
20363636 10.1016/j.bmc.2010.03.005 Sialidase 11
19836230 10.1016/j.bmcl.2009.09.108 MCF7 3
19836230 10.1016/j.bmcl.2009.09.108 Tyrosine-protein phosphatase non-receptor type 1 1
19836230 10.1016/j.bmcl.2009.09.108 MDA-MB-231 1
37271378 10.1016/j.bmcl.2023.129353 A549 1
37271378 10.1016/j.bmcl.2023.129353 NCI-H1299 1
37271378 10.1016/j.bmcl.2023.129353 NCI-H460 1
37271378 10.1016/j.bmcl.2023.129353 HCT-116 1
37271378 10.1016/j.bmcl.2023.129353 Hep 3B2 1
37271378 10.1016/j.bmcl.2023.129353 MDA-MB-231 1

Data from ChEMBL 36 via Core Engine