Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000588
Identification
Name: 2,3-Dihydrodipicolinic acid
Description:L-2,3-Dihydrodipicolinate is involved in the lysine biosynthesis pathway. L-2,3-Dihydrodipicolinate is produced from a reaction between pyruvate and L-aspartate-semialdehyde, with water as a byproduct. The reaction is catalyzed by dihydrodipicolinate synthase.
Structure
Thumb
Synonyms:
  • 2,3-Di-H-Dipicolinate
  • 2,3-Di-H-Dipicolinic acid
  • 2,3-Dihydrodipicolinate
  • 2,3-DPA
  • Dihydrodipicolinate
  • Dihydrodipicolinic acid
  • L-2,3-Dihydrodipicolinate
  • L-2,3-Dihydrodipicolinic acid
Chemical Formula: C7H7NO4
Average Molecular Weight: 169.1348
Monoisotopic Molecular Weight: 169.037507717
InChI Key: UWOCFOFVIBZJGH-UHFFFAOYSA-N
InChI:InChI=1S/C7H7NO4/c9-6(10)4-2-1-3-5(8-4)7(11)12/h1-2,5H,3H2,(H,9,10)(H,11,12)
CAS number: 16052-12-3
IUPAC Name:2,3-dihydropyridine-2,6-dicarboxylic acid
Traditional IUPAC Name: 2,3-dihydrodipicolinic acid
SMILES:OC(=O)C1CC=CC(=N1)C(O)=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.
Kingdom Organic compounds
Super ClassOrganic acids and derivatives
Class Carboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct Parent Alpha amino acids and derivatives
Alternative Parents
Substituents
  • Alpha-amino acid or derivatives
  • Dihydropyridinecarboxylic acid derivative
  • Dihydropyridine
  • Hydropyridine
  • Dicarboxylic acid or derivatives
  • Ketimine
  • Azacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboxylic acid
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Imine
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular Framework Aliphatic heteromonocyclic compounds
External Descriptors Not Available
Physical Properties
State: Solid
Charge:-2
Melting point: 135.2
Experimental Properties:
PropertyValueSource
Water Solubility:0.03PhysProp
Predicted Properties
PropertyValueSource
Water Solubility6.84 mg/mLALOGPS
logP0.12ALOGPS
logP0.66ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)3.17ChemAxon
pKa (Strongest Basic)-1.1ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area86.96 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity39.36 m3·mol-1ChemAxon
Polarizability15.08 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-35bd5d728d4b6335059aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0900000000-681935e00eed4828fd0fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9300000000-ba4f4cccfccf71d0b007View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-fa63cf428cc5d8471604View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01b9-1900000000-a3ffb331ab96000a39e1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00bc-9400000000-35fdba6f9d56521e4e19View in MoNA
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID30620
HMDB IDHMDB12247
Pubchem Compound ID17
Kegg IDC03340
ChemSpider ID16
Wikipedia IDNot Available
BioCyc ID2-3-DIHYDRODIPICOLINATE
EcoCyc ID2-3-DIHYDRODIPICOLINATE

Enzymes

General function:
Involved in dihydrodipicolinate reductase activity
Specific function:
2,3,4,5-tetrahydrodipicolinate + NAD(P)(+) = 2,3-dihydrodipicolinate + NAD(P)H
Gene Name:
dapB
Locus Tag:
PA4759
Molecular weight:
28.3 kDa
Reactions
(S)-2,3,4,5-tetrahydrodipicolinate + NAD(P)(+) = (S)-2,3-dihydrodipicolinate + NAD(P)H.
General function:
Involved in catalytic activity
Specific function:
L-aspartate 4-semialdehyde + pyruvate = dihydrodipicolinate + 2 H(2)O
Gene Name:
dapA
Locus Tag:
PA1010
Molecular weight:
31.4 kDa
Reactions
L-aspartate 4-semialdehyde + pyruvate = dihydrodipicolinate + 2 H(2)O.