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Compound Detail

CHEMBL367881

(+)-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 CHEMBL367881
Name (+)-USNIC ACID
Phase Preclinical
Structure Type MOL
InChI Key WEYVVCKOOFYHRW-SFHVURJKSA-N
15
Targets
28
Activities
1
Assay Types
1
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 28 meas. best 7.16

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
4-hydroxyphenylpyruvate dioxygenase
CHEMBL2242740
 IC50 7.16 7.16 70.0 1
HL-60
CHEMBL383
 IC50 5.77 5.1167 1700.0 3
HaCaT
CHEMBL614392
 IC50 5.68 5.68 2100.0 1
Plasmodium berghei
CHEMBL612653
 IC50 5.64 5.64 2300.0 1
RAW264.7
CHEMBL612557
 IC50 5.33 5.11 4700.0 2
Plasmodium falciparum
CHEMBL364
 IC50 4.82 4.575 15300.0 2
Tyrosine-protein phosphatase non-receptor type 1
CHEMBL335
 IC50 4.79 4.79 16400.0 1
U-251
CHEMBL615022
 IC50 4.71 4.71 19500.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 4.64 4.64 23000.0 1
L1210
CHEMBL386
 IC50 4.58 4.58 26400.0 1
CHO
CHEMBL613853
 IC50 4.52 4.51 30000.0 2
PMNL
CHEMBL613706
 IC50 4.38 4.38 42000.0 1
Enoyl-[acyl-carrier-protein] reductase [NADH] FabI
CHEMBL1857
 IC50 4.33 4.33 47000.0 1
K562
CHEMBL385
 IC50 4.28 4.28 52800.0 1
DU-145
CHEMBL613508
 IC50 4.24 4.24 57400.0 1

Pharmacokinetic Data

Parameter Value Units Species
T1/2 1.322 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
4-hydroxyphenylpyruvate dioxygenase IC50 = 70.0 nM 7.16 Inhibition of Arabidopsis thaliana HPPD expressed in Escherichia coli JM105 usin... 28128559
HL-60 IC50 = 1700.0 nM 5.77 Cytotoxicity against human HL60 cells after 48 hrs by WST-1 assay 24725159
HaCaT IC50 = 2100.0 nM 5.68 Antiproliferative activity against human HaCaT cells 10395495
Plasmodium berghei IC50 = 2300.0 nM 5.64 Antiplasmodial activity against liver stage of Plasmodium berghei ANKA expressin... 23806111
RAW264.7 IC50 = 4700.0 nM 5.33 Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-... 23099095
HL-60 IC50 = 5400.0 nM 5.27 Cytotoxicity against human HL60 cells after 24 hrs by WST-1 assay 24725159
RAW264.7 IC50 = 12800.0 nM 4.89 Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-... 23099095
Plasmodium falciparum IC50 = 15300.0 nM 4.82 Antiplasmodial activity after 48 hrs against Plasmodium falciparum K1 in human e... 17234416
Tyrosine-protein phosphatase non-receptor type 1 IC50 = 16400.0 nM 4.79 Inhibition of human recombinant PTP1B 18288807
U-251 IC50 = 19500.0 nM 4.71 Cytotoxicity against human U251 RCB 0641 cells after 72 hrs by MTT assay 18558490
NON-PROTEIN TARGET IC50 = 23000.0 nM 4.64 Cytotoxicity against mouse 3LL CRL 1642 cells after 48 hrs by MTT assay 18558490
L1210 IC50 = 26400.0 nM 4.58 Cytotoxicity against mouse L1210 ATCC CCL 219 cells after 48 hrs by MTT assay 18558490
CHO IC50 = 30000.0 nM 4.52 Cytotoxicity against polyamine transport-deficient mutant CHO cells after 48 hrs... 18558490
CHO IC50 = 31300.0 nM 4.5 Cytotoxicity against CHO cells after 48 hrs by MTT assay 18558490
PMNL IC50 = 42000.0 nM 4.38 Inhibition of LTB4 biosynthesis in A-23187-stimulated bovine PMNL cells 10395494
Enoyl-[acyl-carrier-protein] reductase [NADH] FabI IC50 = 47000.0 nM 4.33 Inhibition of Escherichia coli FabI using 2-dodecenoyl-CoA as substrate at pH 8 23806111
Plasmodium falciparum IC50 = 47300.0 nM 4.33 Antiplasmodial activity against blood stage of chloroquine and pyrimethamine-res... 23806111
HL-60 IC50 = 48500.0 nM 4.31 Cytotoxicity against human HL60 cells after 72 hrs 24725159
K562 IC50 = 52800.0 nM 4.28 Cytotoxicity against human K562 ATCC CCL 243 cells after 72 hrs by MTT assay 18558490
DU-145 IC50 = 57400.0 nM 4.24 Cytotoxicity against human DU145 ATCC HTB 81 cells after 72 hrs by MTT assay 18558490

Literature References

PubMed DOI Target Context # Activities
18558490 10.1016/j.bmc.2008.05.069 L1210 10
23434134 10.1016/j.bmc.2013.01.045 HaCaT 8
23434134 10.1016/j.bmc.2013.01.045 Mus musculus 7
23806111 10.1021/np400083k Unchecked 6
9083483 10.1021/jm960759e Human immunodeficiency virus type 1 integrase 5
24725159 10.1021/np4008574 No relevant target 4
23434134 10.1016/j.bmc.2013.01.045 Unchecked 4
36652792 10.1016/j.bmc.2023.117157 ADMET 3
23806111 10.1021/np400083k Plasmodium berghei 3
24725159 10.1021/np4008574 HL-60 3
23099095 10.1016/j.bmcl.2012.09.084 RAW264.7 2
36652792 10.1016/j.bmc.2023.117157 HeLa 2
23806111 10.1021/np400083k Danio rerio 2
20116906 10.1016/j.ejmech.2009.12.055 Fructose-1,6-bisphosphatase 1 2
10395495 10.1021/np980378z HaCaT 2
10395494 10.1021/np9803777 Unchecked 2
24725159 10.1021/np4008574 Vero 2
30396105 10.1016/j.ejmech.2018.10.055 Tyrosyl-DNA phosphodiesterase 1 2
24725159 10.1021/np4008574 HeLa 2
18558490 10.1016/j.bmc.2008.05.069 CHO 2

Data from ChEMBL 36 via Core Engine