Record Information
Version2.0
Creation Date2012-05-31 14:03:48 -0600
Update Date2015-06-03 15:54:41 -0600
Secondary Accession Numbers
  • ECMDB04056
Identification
Name:2,3-Dihydrodipicolinic acid
DescriptionL-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
Weight:Average: 169.1348
Monoisotopic: 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
Description 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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids and derivatives
Alternative Parents
Substituents
  • Alpha-amino acid or derivatives
  • Dihydropyridinecarboxylic acid derivative
  • Dihydropyridine
  • Dicarboxylic acid or derivatives
  • Hydropyridine
  • Ketimine
  • Carboxylic acid
  • Azacycle
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Imine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Carbonyl group
  • Organic oxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-2
Melting point:135.2
Experimental Properties:
PropertyValueSource
Water Solubility:0.03PhysProp
Predicted Properties
PropertyValueSource
Water Solubility6.84 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity39.36 m³·mol⁻¹ChemAxon
Polarizability15.08 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Lysine biosynthesisPW000771 ThumbThumb?image type=greyscaleThumb?image type=simple
Secondary Metabolites: threonine biosynthesis from aspartatePW000976 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
  • Lysine biosynthesis ec00300
  • Microbial metabolism in diverse environments ec01120
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0077-9300000000-d72da8848d1f49469c23View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0002-7910000000-ae5409fbe082d4832847View in MoNA
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
Uniprot ID:
P04036
Molecular weight:
28756
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
Uniprot ID:
P0A6L2
Molecular weight:
31270
Reactions
L-aspartate 4-semialdehyde + pyruvate = dihydrodipicolinate + 2 H(2)O.
General function:
Involved in catalytic activity
Specific function:
Specific function unknown
Gene Name:
yjhH
Uniprot ID:
P39359
Molecular weight:
32721
General function:
Involved in catalytic activity
Specific function:
Unknown Function
Gene Name:
yagE
Uniprot ID:
P75682
Molecular weight:
33316