NAV

Dipicolinic acid

Identification

Generic Name
Dipicolinic acid
DrugBank Accession Number
DB04267
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 167.1189
Monoisotopic: 167.021857653
Chemical Formula
C7H5NO4
Synonyms
  • 2,6-dicarboxypyridine
  • 2,6-Dipicolinic acid
  • 2,6-pyridinedicarboxylic acid
External IDs
  • NSC-176
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
U4-hydroxy-tetrahydrodipicolinate reductaseNot AvailableEscherichia coli (strain K12)
U4-hydroxy-tetrahydrodipicolinate reductaseNot AvailableMycobacterium tuberculosis
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
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Technetium Tc-99m oxidronateDipicolinic acid may decrease effectiveness of Technetium Tc-99m oxidronate as a diagnostic agent.
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Sodium dipicolinateNot Available4220-17-1FYWQWZBZNHKKSQ-UHFFFAOYSA-M

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as pyridinecarboxylic acids. These are compounds containing a pyridine ring bearing a carboxylic acid group.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Pyridines and derivatives
Sub Class
Pyridinecarboxylic acids and derivatives
Direct Parent
Pyridinecarboxylic acids
Alternative Parents
Dicarboxylic acids and derivatives / Heteroaromatic compounds / Carboxylic acids / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives
Substituents
Aromatic heteromonocyclic compound / Azacycle / Carboxylic acid / Carboxylic acid derivative / Dicarboxylic acid or derivatives / Heteroaromatic compound / Hydrocarbon derivative / Organic nitrogen compound / Organic oxide / Organic oxygen compound
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
pyridinedicarboxylic acid (CHEBI:46837)
Affected organisms
Not Available

Chemical Identifiers

UNII
UE81S5CQ0G
CAS number
499-83-2
InChI Key
WJJMNDUMQPNECX-UHFFFAOYSA-N
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)
IUPAC Name
pyridine-2,6-dicarboxylic acid
SMILES
OC(=O)C1=CC=CC(=N1)C(O)=O

References

General References
Not Available
Human Metabolome Database
HMDB0033161
PubChem Compound
10367
PubChem Substance
46505713
ChemSpider
9940
BindingDB
26116
ChEBI
46837
ChEMBL
CHEMBL284104
ZINC
ZINC000000105246
PDBe Ligand
PDC
Wikipedia
Dipicolinic_acid
PDB Entries
1arz / 1c3v / 1p9l / 2pc2 / 2pe7 / 2pes / 3lgr / 3ojo / 4ih3 / 4irw …
show 7 more

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility3.46 mg/mLALOGPS
logP0.54ALOGPS
logP-0.44Chemaxon
logS-1.7ALOGPS
pKa (Strongest Acidic)0.55Chemaxon
pKa (Strongest Basic)7.02Chemaxon
Physiological Charge-2Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area87.49 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity37.67 m3·mol-1Chemaxon
Polarizability14.57 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.8629
Blood Brain Barrier+0.8069
Caco-2 permeable+0.5766
P-glycoprotein substrateNon-substrate0.7647
P-glycoprotein inhibitor INon-inhibitor0.9933
P-glycoprotein inhibitor IINon-inhibitor0.9944
Renal organic cation transporterNon-inhibitor0.9369
CYP450 2C9 substrateNon-substrate0.8305
CYP450 2D6 substrateNon-substrate0.8963
CYP450 3A4 substrateNon-substrate0.8162
CYP450 1A2 substrateNon-inhibitor0.9829
CYP450 2C9 inhibitorNon-inhibitor0.9767
CYP450 2D6 inhibitorNon-inhibitor0.9626
CYP450 2C19 inhibitorNon-inhibitor0.9758
CYP450 3A4 inhibitorNon-inhibitor0.9806
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9957
Ames testNon AMES toxic0.9858
CarcinogenicityNon-carcinogens0.9079
BiodegradationReady biodegradable0.7704
Rat acute toxicity1.9310 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9884
hERG inhibition (predictor II)Non-inhibitor0.9864
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MS (2 TMS)GC-MSsplash10-0f92-5970000000-e5aa4bc3f23f554c51c2
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-01ba-5900000000-32b3c0674b6807262c0a
GC-MS Spectrum - EI-BGC-MSsplash10-0kor-9400000000-4be19de76ddc678df43f
GC-MS Spectrum - EI-BGC-MSsplash10-0kor-7900000000-48c091dd3ea56a6cad7d
GC-MS Spectrum - EI-BGC-MSsplash10-0g29-9200000000-bbc0b97db569b40d51b6
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0002-1950000000-1221ab338705f508fac4
GC-MS Spectrum - GC-MSGC-MSsplash10-0f92-5970000000-e5aa4bc3f23f554c51c2
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-0900000000-a5289d738ec0dc242d6f
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-0900000000-d1ecb7618061f844f1c0
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0zfr-0900000000-a37a801a9050182360e8
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9200000000-49a1b0911fdd08bf3f9c
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0pb9-6900000000-148d64e628747f223807
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9000000000-4818e0f36e7689d1f42f
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-136.9528613
predicted
DarkChem Lite v0.1.0
[M-H]-137.1340613
predicted
DarkChem Lite v0.1.0
[M-H]-137.2154613
predicted
DarkChem Lite v0.1.0
[M-H]-137.4611613
predicted
DarkChem Lite v0.1.0
[M-H]-126.89719
predicted
DeepCCS 1.0 (2019)
[M+H]+137.8086613
predicted
DarkChem Lite v0.1.0
[M+H]+137.6470613
predicted
DarkChem Lite v0.1.0
[M+H]+137.5748613
predicted
DarkChem Lite v0.1.0
[M+H]+137.3258613
predicted
DarkChem Lite v0.1.0
[M+H]+130.72453
predicted
DeepCCS 1.0 (2019)
[M+Na]+137.6589613
predicted
DarkChem Lite v0.1.0
[M+Na]+137.4073613
predicted
DarkChem Lite v0.1.0
[M+Na]+137.5694613
predicted
DarkChem Lite v0.1.0
[M+Na]+139.94925
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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Details1. 4-hydroxy-tetrahydrodipicolinate reductase
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Oxidoreductase activity, acting on ch or ch2 groups, nad or nadp as acceptor
Specific Function
Catalyzes the conversion of 4-hydroxy-tetrahydrodipicolinate (HTPA) to tetrahydrodipicolinate. Can use both NADH and NADPH as a reductant, with NADH being twice as effective as NADPH.
Gene Name
dapB
Uniprot ID
P04036
Uniprot Name
4-hydroxy-tetrahydrodipicolinate reductase
Molecular Weight
28756.34 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
Details2. 4-hydroxy-tetrahydrodipicolinate reductase
Kind
Protein
Organism
Mycobacterium tuberculosis
Pharmacological action
Unknown
General Function
Catalyzes the conversion of 4-hydroxy-tetrahydrodipicolinate (HTPA) to tetrahydrodipicolinate (Probable). Can use both NADH and NADPH as a reductant, with NADH being 6-fold as effective as NADPH.
Specific Function
4-hydroxy-tetrahydrodipicolinate reductase
Gene Name
dapB
Uniprot ID
P9WP23
Uniprot Name
4-hydroxy-tetrahydrodipicolinate reductase
Molecular Weight
25733.14 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52