Compound Detail

CHEMBL275938

AURINTRICARBOXYLIC ACID

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O=C(O)C1=CC(=C(c2ccc(O)c(C(=O)O)c2)c2ccc(O)c(C(=O)O)c2)C=CC1=O

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL275938
Name	AURINTRICARBOXYLIC ACID
Phase	Preclinical
Structure Type	MOL
InChI Key	GIXWDMTZECRIJT-UHFFFAOYSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

422.4

MW (Da)

2.45

ALogP

HBA

HBD

169.4

PSA (Å²)

0.45

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula	C22H14O9
MW	422.35
Aromatic Rings	2
Heavy Atoms	31
NP-Likeness	0.42

Activity Summary

IC50 64 meas. best 7.92

EC50 2 meas. best 7.12

Ki 2 meas. best 8.3

Kd 1 meas. best 5.47

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Unchecked CHEMBL612545	Ki	8.3	8.3	5.0	1
Tyrosyl-DNA phosphodiesterase 1 CHEMBL1075138	IC50	7.92	7.79	12.0	2
DNA repair nuclease/redox regulator APEX1 CHEMBL5619	IC50	7.26	6.5067	55.0	3
DNA polymerase eta CHEMBL5542	IC50	7.12	7.12	75.0	2
DNA polymerase iota CHEMBL5391	IC50	7.12	7.12	75.0	1
Human immunodeficiency virus 1 CHEMBL378	EC50	7.12	5.835	76.0	2
DNA-3-methyladenine glycosylase CHEMBL3396943	IC50	6.7	6.7	200.0	1
Unchecked CHEMBL612545	IC50	6.52	5.8356	300.0	16
Complement component C9 CHEMBL4295693	IC50	6.3	6.3	500.0	1
GroEL/GroES CHEMBL4106139	IC50	6.24	6.145	570.0	2
Cystathionine gamma-lyase CHEMBL4295745	IC50	6.22	5.5729	600.0	7
Cystathionine gamma-lyase CHEMBL4295745	Ki	6.22	6.22	600.0	1
Cysteine protease ATG4B CHEMBL1741221	IC50	5.89	5.5225	1300.0	4
Cystathionine beta-synthase CHEMBL3399911	IC50	5.52	4.83	3000.0	3
HSP60/HSP10 CHEMBL4106131	IC50	5.5	5.5	3200.0	1
Cystathionine gamma-lyase CHEMBL4295745	Kd	5.47	5.47	3400.0	1
Human immunodeficiency virus 1 CHEMBL378	IC50	5.3	5.3	5000.0	1
Plasmodium falciparum CHEMBL364	IC50	5.3	5.1	5011.9	5
Inhibitor of nuclear factor kappa-B kinase subunit beta CHEMBL1991	IC50	5.27	5.27	5400.0	1
Oryctolagus cuniculus CHEMBL374	IC50	5.0	5.0	10000.0	1
MAP2K3/Myc proto-oncogene protein CHEMBL4888452	IC50	4.85	4.85	14060.0	1
Hepatitis C virus CHEMBL379	IC50	4.82	4.82	15000.0	1
Cruzipain CHEMBL3563	IC50	4.55	4.415	28000.0	2
Cystathionine gamma-lyase CHEMBL4680037	IC50	4.37	4.37	43200.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Unchecked	Ki	=	5.0	nM	8.3	Inhibition of Yersinia pestis YopH using p-nitrophenol as substrate by spectroph...	25468042
Tyrosyl-DNA phosphodiesterase 1	IC50	=	12.0	nM	7.92	Inhibition of recombinant TDP1 (unknown origin) using 5'-32P-labeled N14Y DNA su...	27687971
Tyrosyl-DNA phosphodiesterase 1	IC50	=	22.0	nM	7.66	Inhibition of recombinant TDP1 (unknown origin) expressed in Escherichia coli Ro...	27687971
DNA repair nuclease/redox regulator APEX1	IC50	=	55.0	nM	7.26	Inhibition of APE1 (unknown origin)	28161249
DNA repair nuclease/redox regulator APEX1	IC50	=	55.0	nM	7.26	Inhibition of human APE1 preincubated for 15 mins followed by substrate addition...	28161249
DNA polymerase eta	IC50	=	75.0	nM	7.12	Inhibition of human recombinant DNA polymerase eta expressed in Baculovirus expr...	27362876
DNA polymerase iota	IC50	=	75.0	nM	7.12	Inhibition of human recombinant DNA polymerase iota expressed in Baculovirus exp...	27362876
DNA polymerase eta	IC50	=	75.0	nM	7.12	Inhibition of recombinant human DNA polymerase eta expressed in baculovirus expr...	36621139
Human immunodeficiency virus 1	EC50	=	76.0	nM	7.12	Antiviral activity against HIV1 bearing HIV1 NL4-3 envelope infected in human He...	17646410
DNA-3-methyladenine glycosylase	IC50	=	200.0	nM	6.7	Inhibition of human purified MPG pre-incubated with compound for 10 mins followe...	25650313
Unchecked	IC50	=	300.0	nM	6.52	Inhibition of Hepatitis C virus genotype 1b (con1) full length C-terminal His-ta...	27474921
Unchecked	IC50	=	300.0	nM	6.52	Inhibition of HCV NS3 helicase DNA unwinding activity using fluorescent DNA subs...	27810598
Unchecked	IC50	=	300.0	nM	6.52	Inhibition of Hepatitis C virus genotype 1b NS3 helicase unwinding activity usin...	28089348
Unchecked	IC50	=	400.0	nM	6.4	Inhibition of DNA polymerase (unknown origin)	36621139
Unchecked	IC50	=	470.0	nM	6.33	Activation of miRNA (unknown origin)	30108932
Unchecked	IC50	=	470.0	nM	6.33	Inhibition of miRNA (unknown origin) by western blot analysis	30108932
Complement component C9	IC50	=	500.0	nM	6.3	Inhibition of C9 binding to C5b678 in zymogen activated human serum assessed as ...	28977749
GroEL/GroES	IC50	=	570.0	nM	6.24	Inhibition of Escherichia coli GroEL expressed in Escherichia coli DH5alpha/Esch...	30852084
Cystathionine gamma-lyase	IC50	=	600.0	nM	6.22	Inhibition of human CSE using L-Cys as the substrate by tandem well based HTS as...	30562026
Cystathionine gamma-lyase	Ki	=	600.0	nM	6.22	Competitive inhibition of human CSE using varying levels of L-Cys as substrate a...	30562026

Literature References

PubMed	DOI	Target Context	# Activities
30562026	10.1021/acs.jmedchem.8b01720	Cystathionine gamma-lyase	28
30562026	10.1021/acs.jmedchem.8b01720	Unchecked	16
1704065	10.1021/jm00105a052	MT4	11
25468042	10.1016/j.bmc.2014.10.042	Unchecked	7
18333608	10.1021/jm701500e	Unchecked	6
19734910	10.1038/nchembio.215	Plasmodium falciparum	5
1704065	10.1021/jm00105a052	HuT78	5
1704065	10.1021/jm00105a052	Unchecked	5
30852084	10.1016/j.bmcl.2019.02.028	GroEL/GroES	4
27474921	10.1016/j.ejmech.2016.07.035	Unchecked	4
30562026	10.1021/acs.jmedchem.8b01720	Cystathionine beta-synthase	4
27529560	10.1021/acs.jmedchem.6b00794	Unchecked	4
27517808	10.1016/j.ejmech.2016.07.073	Cysteine protease ATG4B	3
28161249	10.1016/j.bmc.2017.01.028	DNA repair nuclease/redox regulator APEX1	2
1704066	10.1021/jm00105a053	HuT78	2
27529560	10.1021/acs.jmedchem.6b00794	3'-5' exonuclease crn-4	2
18333608	10.1021/jm701500e	Cruzipain	2
1704066	10.1021/jm00105a053	Human immunodeficiency virus 1	2
1704065	10.1021/jm00105a052	CCRF-CEM	2
22197397	10.1016/j.bmc.2011.11.061	Hepatitis C virus	2

Data from ChEMBL 36 via Core Engine