Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000840
Identification
Name: Tetrahydrodipicolinate
Description:Tetrahydrodipicolinate is involved in amino-acid biosynthesis, specifically L-lysine biosynthesis via the DAP pathway
Structure
Thumb
Synonyms:
  • Δ1-piperideine-2,6-dicarboxylate
  • Δ1-piperideine-2,6-dicarboxylic acid
  • Δ1-piperideine-2,6-dicarboxylate
  • (S)-2,3,4,5-tetrahydropyridine-2,6-dicarboxylate
  • (S)-2,3,4,5-tetrahydropyridine-2,6-dicarboxylate
  • (S)-2,3,4,5-tetrahydropyridine-2,6-dicarboxylic acid
  • 2,3,4,5-Tetrahydro-2,6-dipicolinate
  • 2,3,4,5-Tetrahydro-2,6-dipicolinic acid
  • 2,3,4,5-Tetrahydro-2,6-pyridinedicarboxylate
  • 2,3,4,5-Tetrahydro-2,6-pyridinedicarboxylic acid
  • 2,3,4,5-Tetrahydrodipicolinate
  • 2,3,4,5-Tetrahydrodipicolinic acid
  • 2,3,4,5-Tetrahydropyridine-2,6-dicarboxylate
  • 2,3,4,5-Tetrahydropyridine-2,6-dicarboxylic acid
  • 2,3,4,5-THDPA
  • Delta1-piperideine-2,6-dicarboxylate
  • Delta1-piperideine-2,6-dicarboxylic acid
  • L-2,3,4,5-Tetrahydrodipicolinate
  • L-2,3,4,5-Tetrahydrodipicolinic acid
  • Tetrahydrodipicolinate
  • Tetrahydrodipicolinic acid
  • Tetrahydropyridine-2,6-dicarboxylate
  • Tetrahydropyridine-2,6-dicarboxylic acid
  • Thdpa
  • δ1-Piperideine-2,6-dicarboxylate
  • δ1-Piperideine-2,6-dicarboxylic acid
Chemical Formula: C7H9NO4
Average Molecular Weight: 171.1507
Monoisotopic Molecular Weight: 171.053157781
InChI Key: CXMBCXQHOXUCEO-UHFFFAOYSA-N
InChI:InChI=1S/C7H9NO4/c9-6(10)4-2-1-3-5(8-4)7(11)12/h4H,1-3H2,(H,9,10)(H,11,12)
CAS number: 2353-17-5
IUPAC Name:2,3,4,5-tetrahydropyridine-2,6-dicarboxylic acid
Traditional IUPAC Name: thdpa
SMILES:OC(=O)C1CCCC(=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
  • Tetrahydropyridine
  • 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: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility6.49 mg/mLALOGPS
logP0.18ALOGPS
logP0.66ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)3.28ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area86.96 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity38.27 m3·mol-1ChemAxon
Polarizability15.74 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, Positivesplash10-0fk9-0900000000-c67011d10b18a0d87130View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-2900000000-a7bbcc2a988fc7512c89View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-9200000000-ce850c0759cdaecbf496View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-0204d30834bac9fc03e7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00fr-1900000000-6180db32249ad7119393View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-003u-9300000000-d4c458eb9535a9595faaView 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 ID32976
HMDB IDHMDB12289
Pubchem Compound ID632
Kegg IDC03972
ChemSpider ID612
Wikipedia IDNot Available
BioCyc IDDELTA1-PIPERIDEINE-2-6-DICARBOXYLATE
EcoCyc IDDELTA1-PIPERIDEINE-2-6-DICARBOXYLATE