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name Structure Reference Source Properties Activities Metabolism

dipicolinic acid

AlkaPlorer ID: AK005769

Synonym: 'Dipicolinic acid', 'Dipicolinate', 'SMR000034075', 'MLSMR', 'MLS000080748'

IUPAC Name: pyridine-2,6-dicarboxylic acid

Structure

SMILES: O=C(O)C1=CC=CC(C(=O)O)=N1

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InChI: InChI=1S/C7H5NO4/c9-6(10)4-2-1-3-5(8-4)7(11)12/h1-3H,(H,9,10)(H,11,12)

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InChIKey: WJJMNDUMQPNECX-UHFFFAOYSA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain
Cordyceps militaris Cordyceps Cordycipitaceae Hypocreales Sordariomycetes Ascomycota Fungi Eukaryota

Properties Information

Molecule Weight: 167.11999999999998

TPSA？: 87.49

MolLogP？: 0.4779999999999999

Number of H-Donors: 2

Number of H-Acceptors: 3

RingCount: 1

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Aeromonas hydrophila Beta-lactamase Activity 12.0 % 10.1128/aac.00866-06
Agaricus bisporus Tyrosinase Inhibition 99.0 % 10.1021/jm101266s
Bacillus anthracis Anthrax lethal factor Inhibition 83.0 % 10.1021/jm101266s
Bacillus anthracis Dihydrodipicolinate synthase Inhibition 80.0 % 10.1016/j.bmcl.2007.11.026
Bacillus cereus Beta-lactamase 2 IC50 21800.0 nM 10.1016/j.bmcl.2003.12.037
Bacillus subtilis 4'-phosphopantetheinyl transferase ffp Potency 3981.1 nM None
Escherichia coli Beta-lactamase TEM IC50 nan nM 10.1016/j.bmcl.2003.12.037
Escherichia coli Escherichia coli Ki 900000.0 nM 10.1021/jm00137a004
Escherichia coli K-12 Beta-lactamase AmpC IC50 nan nM 10.1016/j.bmcl.2003.12.037
Escherichia coli K-12 Beta-lactamase AmpC Potency 2818.4 nM None
Escherichia coli K-12 Dihydrodipicolinate synthase IC50 400000.0 nM 10.1039/C9MD00107G
Escherichia coli K-12 Dihydrodipicolinate synthase Ki 11000000.0 nM 10.1039/C9MD00107G
Giardia intestinalis Putative fructose-1,6-bisphosphate aldolase Potency 28183.8 nM None
Homo sapiens 2-amino-3-carboxymuconate-6-semialdehyde decarboxylase IC50 15200.0 nM 10.1021/acs.jmedchem.0c01762
Homo sapiens 2-amino-3-carboxymuconate-6-semialdehyde decarboxylase Ki 15200.0 nM 10.1021/acs.jmedchem.0c01762
Homo sapiens Arachidonate 15-lipoxygenase Potency 1000.0 nM None
Homo sapiens Arachidonate 5-lipoxygenase Inhibition 31.0 % 10.1021/jm101266s
Homo sapiens Casein kinase II alpha Delta Tm -0.5 degrees C 10.1016/j.bmc.2017.04.037
Homo sapiens Dihydrodipicolinate synthase-like, mitochondrial Ki 11000000.0 nM 10.1016/j.bmcl.2007.11.108
Homo sapiens DNA-(apurinic or apyrimidinic site) lyase Potency 7943.3 nM None
Homo sapiens Hematopoietic cell protein-tyrosine phosphatase 70Z-PEP Activity nan None 10.1016/j.bmcl.2014.06.016
Homo sapiens Hematopoietic cell protein-tyrosine phosphatase 70Z-PEP Inhibition nan % 10.1016/j.bmcl.2014.06.016
Homo sapiens Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Potency 794.3 nM None
Homo sapiens Lysine-specific demethylase 4D-like IC50 250000.0 nM 10.1021/acs.jmedchem.1c01694
Homo sapiens Lysine-specific demethylase 4D-like Potency 8912.5 nM None
Homo sapiens Matrix metalloproteinase-1 Inhibition 7.0 % 10.1021/jm101266s
Homo sapiens Matrix metalloproteinase-2 Inhibition -6.0 % 10.1021/jm101266s
Homo sapiens Matrix metalloproteinase 3 Inhibition 54.0 % 10.1021/jm101266s
Homo sapiens Matrix metalloproteinase 8 Inhibition 17.0 % 10.1021/jm101266s
Homo sapiens Matrix metalloproteinase 9 Inhibition -7.0 % 10.1021/jm101266s
Homo sapiens Thyroid stimulating hormone receptor Potency 1584.9 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 1412.5 nM None
Mus musculus Nitric oxide synthase, inducible Inhibition 20.0 % 10.1021/jm101266s
Mycobacterium tuberculosis Dihydrodipicolinate synthase Inhibition 75.0 % 10.1016/j.bmcl.2007.11.026
Pseudomonas aeruginosa Beta-lactamase VIM-1 IC50 41600.0 nM 10.1128/aac.00465-08
Pseudomonas aeruginosa Beta-lactamase VIM-2 IC50 1660.0 nM 10.1021/acs.jmedchem.7b00407
Pseudomonas aeruginosa Beta-lactamase VIM-2 Inhibition 60.0 % 10.1021/acs.jmedchem.7b00407
Pseudomonas aeruginosa Class B carbapenemase VIM-13 IC50 48000.0 nM 10.1128/aac.00465-08
Pseudomonas aeruginosa Metallo beta-lactamase Activity 2.0 % 10.1128/aac.00866-06
Pseudomonas aeruginosa Metallo beta-lactamase Activity 72.0 % 10.1128/aac.00866-06
Serratia marcescens Metallo-beta-lactamase type 2 IC50 3030.0 nM 10.1021/acs.jmedchem.7b00407
Serratia marcescens Metallo-beta-lactamase type 2 Inhibition 60.0 % 10.1021/acs.jmedchem.7b00407
Stenotrophomonas maltophilia Beta-lactamase L1 Activity 92.0 % 10.1128/aac.00866-06
Stenotrophomonas maltophilia Beta-lactamase L1 IC50 7800.0 nM 10.1016/j.bmcl.2003.12.037
Streptomyces coelicolor (strain ATCC BAA-471 / A3(2) / M145) Dihydrodipicolinate synthase IC50 400000.0 nM 10.1016/0960-894X(94)85023-2
None No relevant target Activity nan None 10.1021/acs.jmedchem.7b00407
None No relevant target Inhibition 95.0 % 10.1039/d0md00320d
None Unchecked Activity 20.0 % 10.1021/acs.jmedchem.7b00407
None Unchecked Activity 77.0 % 10.1128/aac.00866-06
None Unchecked Activity 88.0 % 10.1128/aac.00866-06
None Unchecked Activity 95.0 % 10.1128/aac.00866-06
None Unchecked Activity 96.0 % 10.1128/aac.00866-06
None Unchecked Activity nan None 10.1021/acs.jmedchem.7b00407
None Unchecked Activity nan None 10.1021/jm800936s
None Unchecked FC 2.0 None 10.1021/acs.jmedchem.1c00362
None Unchecked FC 16.0 None 10.1021/acs.jmedchem.1c00362
None Unchecked FC 32.0 None 10.1021/acs.jmedchem.1c00362
None Unchecked FC 64.0 None 10.1021/acs.jmedchem.1c00362
None Unchecked FC 128.0 None 10.1021/acs.jmedchem.1c00362
None Unchecked IC50 410.0 nM 10.1021/acs.jmedchem.7b00407
None Unchecked IC50 520.0 nM 10.1021/acs.jmedchem.7b00407
None Unchecked IC50 1130.0 nM 10.1016/j.ejmech.2021.113747
None Unchecked IC50 6200.0 nM 10.1016/j.bmcl.2018.11.025
None Unchecked IC50 7800.0 nM 10.1016/j.ejmech.2014.02.008
None Unchecked IC50 8800.0 nM 10.1016/j.bmcl.2018.11.025
None Unchecked IC50 10000.0 nM 10.1021/acs.jmedchem.1c00362
None Unchecked IC50 21800.0 nM 10.1016/j.ejmech.2014.02.008
None Unchecked IC50 23600.0 nM 10.1016/j.bmcl.2018.11.025
None Unchecked IC50 29000.0 nM 10.1021/acs.jmedchem.1c00362
None Unchecked IC50 29400.0 nM 10.1016/j.bmcl.2018.11.025
None Unchecked IC50 61500.0 nM 10.1016/j.bmcl.2018.11.025
None Unchecked IC50 64000.0 nM 10.1021/acs.jmedchem.1c01694
None Unchecked IC50 88400.0 nM 10.1016/j.bmcl.2018.11.025
None Unchecked IC50 120000.0 nM 10.1021/jm800936s
None Unchecked IC50 250000.0 nM 10.1021/jm800936s
None Unchecked IC50 500000.0 nM 10.1021/acs.jmedchem.8b01363
None Unchecked IC50 501187.23 nM 10.1021/acs.jmedchem.8b01363
None Unchecked IC50 nan None 10.1016/j.bmcl.2018.11.025
None Unchecked Inhibition 1.0 % 10.1016/j.bmcl.2007.11.026
None Unchecked Inhibition 60.0 % 10.1021/acs.jmedchem.7b00407
None Unchecked Inhibition 67.0 % 10.1016/j.bmcl.2007.11.026
None Unchecked Inhibition 76.0 % 10.1016/j.bmcl.2007.11.026
None Unchecked Inhibition nan % 10.1021/acs.jmedchem.7b00407
None Unchecked Ki 3000.0 nM 10.1128/aac.00083-07
None Unchecked Ki 92000.0 nM 10.1016/j.bmcl.2013.12.114
None Unchecked Ki 2700000.0 nM 10.1016/j.bmcl.2013.12.114
None Unchecked MIC 0.031 ug.mL-1 10.1021/acs.jmedchem.1c00362
None Unchecked MIC 0.063 ug.mL-1 10.1021/acs.jmedchem.1c00362
None Unchecked MIC 0.125 ug.mL-1 10.1021/acs.jmedchem.1c00362
None Unchecked MIC 0.25 ug.mL-1 10.1021/acs.jmedchem.1c00362
None Unchecked MIC 0.5 ug.mL-1 10.1021/acs.jmedchem.1c00362
None Unchecked MIC 1.0 ug.mL-1 10.1021/acs.jmedchem.1c00362
None Unchecked MIC 16.0 ug.mL-1 10.1021/acs.jmedchem.1c00362
None Unchecked Potency 36.6 nM None

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT022643 O=C(O)C1=CCC=C(C(=O)O)N1>>O=C(O)c1cccc(C(=O)O)n1 RXN-5321
AKRT022657 O=C(O)C1=N[C@H](C(=O)O)CC=C1>>O=C(O)c1cccc(C(=O)O)n1 47092
AKRT022665 O=C(O)C1=N[C@H](C(=O)O)C[C@H](O)C1>>O=C(O)c1cccc(C(=O)O)n1 RXN-5041
AKRT023348 O=C(O)c1cccc(C(=O)O)n1>>O=C(O)C1=CCC=C(C(=O)O)N1 MNXR176877