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Compound Detail

CHEMBL461903

(-)-USNIC ACID
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CC(=O)C1=C(O)C=C2Oc3c(C(C)=O)c(O)c(C)c(O)c3[C@]2(C)C1=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL461903
Name (-)-USNIC ACID
Phase Preclinical
Structure Type MOL
InChI Key WEYVVCKOOFYHRW-GOSISDBHSA-N
11
Targets
14
Activities
1
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

344.3
MW (Da)
2.13
ALogP
7
HBA
3
HBD
121.1
PSA (Ų)
0.55
QED
0
Ro5 Violations
2
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 1
Heavy Atoms 25
NP-Likeness 1.98

Activity Summary

IC50 14 meas. best 4.95

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
MCF7
CHEMBL387
 IC50 4.95 4.62 11200.0 2
MDA-MB-231
CHEMBL400
 IC50 4.88 4.8633 13100.0 3
MDA-MB-468
CHEMBL614335
 IC50 4.86 4.86 13700.0 1
SK-BR-3
CHEMBL613834
 IC50 4.84 4.84 14400.0 1
BT-474
CHEMBL614529
 IC50 4.82 4.82 15100.0 1
T47D
CHEMBL614361
 IC50 4.8 4.8 15900.0 1
L1210
CHEMBL386
 IC50 4.76 4.76 17400.0 1
U-251
CHEMBL615022
 IC50 4.71 4.71 19700.0 1
K562
CHEMBL385
 IC50 4.66 4.66 21800.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 4.46 4.46 35100.0 1
DU-145
CHEMBL613508
 IC50 4.34 4.34 45900.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
MCF7 IC50 = 11200.0 nM 4.95 Antiproliferative activity against human MCF7 cells incubated for 72 hrs by MTT ... 28245124
MDA-MB-231 IC50 = 13100.0 nM 4.88 Antiproliferative activity against human MDA-MB-231 cells incubated for 72 hrs b... 28245124
MDA-MB-468 IC50 = 13700.0 nM 4.86 Antiproliferative activity against human MDA-MB-468 cells incubated for 72 hrs b... 28245124
MDA-MB-231 IC50 = 13700.0 nM 4.86 Antimigratory activity in human MDA-MB-231 cells assessed as inhibition of cell ... 28245124
MDA-MB-231 IC50 = 14200.0 nM 4.85 Anti-invasive activity in human MDA-MB-231 cells after 24 hrs by microscopic ana... 28245124
SK-BR-3 IC50 = 14400.0 nM 4.84 Antiproliferative activity against human SK-BR-3 cells incubated for 72 hrs by M... 28245124
BT-474 IC50 = 15100.0 nM 4.82 Antiproliferative activity against human BT-474 cells incubated for 72 hrs by MT... 28245124
T47D IC50 = 15900.0 nM 4.8 Antiproliferative activity against human T47D cells incubated for 72 hrs by MTT ... 28245124
L1210 IC50 = 17400.0 nM 4.76 Cytotoxicity against mouse L1210 ATCC CCL 219 cells after 48 hrs by MTT assay 18558490
U-251 IC50 = 19700.0 nM 4.71 Cytotoxicity against human U251 RCB 0641 cells after 72 hrs by MTT assay 18558490
K562 IC50 = 21800.0 nM 4.66 Cytotoxicity against human K562 ATCC CCL 243 cells after 72 hrs by MTT assay 18558490
NON-PROTEIN TARGET IC50 = 35100.0 nM 4.46 Cytotoxicity against mouse 3LL CRL 1642 cells after 48 hrs by MTT assay 18558490
DU-145 IC50 = 45900.0 nM 4.34 Cytotoxicity against human DU145 ATCC HTB 81 cells after 72 hrs by MTT assay 18558490
MCF7 IC50 = 51700.0 nM 4.29 Cytotoxicity against human MCF7 ATCC HTB 22 cells after 72 hrs by MTT assay 18558490

Literature References

PubMed DOI Target Context # Activities
28245124 10.1021/acs.jnatprod.6b00917 MDA-MB-231 6
28245124 10.1021/acs.jnatprod.6b00917 Serine/threonine-protein kinase mTOR 4
28245124 10.1021/acs.jnatprod.6b00917 MCF7 3
160461 10.1021/jm00197a019 No relevant target 3
- 10.1016/0305-1978(94)90001-9 Spodoptera littoralis 2
18558490 10.1016/j.bmc.2008.05.069 CHO 2
28245124 10.1021/acs.jnatprod.6b00917 mTORC2 2
18558490 10.1016/j.bmc.2008.05.069 DU-145 1
23099095 10.1016/j.bmcl.2012.09.084 MDCK 1
23099095 10.1016/j.bmcl.2012.09.084 Unchecked 1
18558490 10.1016/j.bmc.2008.05.069 U-251 1
18558490 10.1016/j.bmc.2008.05.069 K562 1
18558490 10.1016/j.bmc.2008.05.069 MCF7 1
7964789 10.1021/np50109a009 Staphylococcus aureus 1
18558490 10.1016/j.bmc.2008.05.069 L1210 1
7964789 10.1021/np50109a009 Pseudomonas aeruginosa 1
7964789 10.1021/np50109a009 Candida albicans 1
7964789 10.1021/np50109a009 Mycolicibacterium smegmatis 1
7964789 10.1021/np50109a009 Klebsiella pneumoniae 1
7964789 10.1021/np50109a009 Salmonella enterica subsp. enterica serovar Gallinarum 1

Data from ChEMBL 36 via Core Engine