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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2009-04-06 16:19:43 UTC
Update Date2019-07-23 05:57:26 UTC
HMDB IDHMDB0012130
Secondary Accession Numbers
  • HMDB0059657
  • HMDB0062589
  • HMDB12130
  • HMDB59657
  • HMDB62589
Metabolite Identification
Common Name​2,3,4,5-Tetrahydro-2-pyridinecarboxylic acid
Description2,3,4,5-Tetrahydro-2-pyridinecarboxylic acid (CAS: 3038-89-9), also known as 2,3,4,5-tetrahydropiperidine-2-carboxylate and 1-piperideine-6-carboxylic acid, is a cyclic intermediate in lysine degradation. L-Lysine is an essential amino acid that is a necessary building block for all protein in the body and It plays a major role in calcium absorption; building muscle protein; recovering from surgery or sports injuries; and the body's production of hormones, enzymes, and antibodies. In the lysine degradation pathway, 2,3,4,5-tetrahydro-2-pyridinecarboxylic acid is a substrate for L-aminoadipate-semialdehyde dehydrogenase (amaA) and can be formed by the spontaneous cyclization of 2-aminoadipate-6-semialdehyde. 2,3,4,5-Tetrahydro-2-pyridinecarboxylic acid is also an intermediate in glycine, serine, and threonine metabolism. It is a substrate for peroxisomal sarcosine oxidase.
Structure
Data?1563861446
Synonyms
ValueSource
(S)-2,3,4,5-Tetrahydropyridine-2-carboxylic acidChEBI
delta1-Piperideine-6-L-carboxylateChEBI
Delta(1)-Piperideine-6-L-carboxylic acidChEBI
delta1-Piperideine-6-L-carboxylic acidGenerator
Δ1-piperideine-6-L-carboxylateGenerator
Δ1-piperideine-6-L-carboxylic acidGenerator
delta(1)-Piperideine-6-L-carboxylateGenerator
Δ(1)-piperideine-6-L-carboxylateGenerator
Δ(1)-piperideine-6-L-carboxylic acidGenerator
(S)-1-Piperideine-6-carboxylateHMDB
(S)-2,3,4,5-Tetrahydropyridine-2-carboxylateGenerator
(2S)-2,3,4,5-Tetrahydro-2-pyridinecarboxylic acidHMDB
(S)-2,3,4,5-Tetrahydro-2-pyridinecarboxylic acidHMDB
(S)-2,3,4,5-Tetrahydropiperidine-2-carboxylateHMDB
(S)-2,3,4,5-Tetrahydropiperidine-2-carboxylic acidHMDB
1-Piperideine-6-carboxylateHMDB
1-Piperideine-6-carboxylic acidHMDB
2,3,4,5-Tetrahydro-2-pyridinecarboxylic acidHMDB
2,3,4,5-Tetrahydropicolinic acidHMDB
delta1-Piperideine-6-carboxylateHMDB
delta1-Piperideine-6-carboxylic acidHMDB
delta1-Piperidine-6-carboxylateHMDB
delta1-Piperidine-6-carboxylic acidHMDB
Δ1-Piperidine-6-carboxylateHMDB
Δ1-Piperidine-6-carboxylic acidHMDB
δ1-Piperideine-6-carboxylateHMDB
δ1-Piperideine-6-carboxylic acidHMDB
Chemical FormulaC6H9NO2
Average Molecular Weight127.1412
Monoisotopic Molecular Weight127.063328537
IUPAC Name(2S)-2,3,4,5-tetrahydropyridine-2-carboxylic acid
Traditional Name(2S)-2,3,4,5-tetrahydropyridine-2-carboxylic acid
CAS Registry Number73980-78-6
SMILES
OC(=O)[C@@H]1CCCC=N1
InChI Identifier
InChI=1S/C6H9NO2/c8-6(9)5-3-1-2-4-7-5/h4-5H,1-3H2,(H,8,9)/t5-/m0/s1
InChI KeyCSDPVAKVEWETFG-YFKPBYRVSA-N
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
  • Tetrahydropyridine
  • Hydropyridine
  • Azacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic oxide
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Imine
  • Carbonyl group
  • Organic nitrogen compound
  • Organopnictogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility8.53 g/LALOGPS
logP0.36ALOGPS
logP-1.8ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)2ChemAxon
pKa (Strongest Basic)6.22ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area49.66 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity32 m³·mol⁻¹ChemAxon
Polarizability12.69 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f9x-9000000000-7bc5d56fa658fac7e9e0JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-001i-9100000000-26047328d0a1182e46edJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01t9-3900000000-7acf87e49673fc08eeaaJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-9400000000-6ae0da8e10e93ebebb84JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f8c-9000000000-a147c4de8fc31bccca5dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-2900000000-f6e66950933f111873a1JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-7900000000-c03c466dc61aeb1bfe71JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9000000000-45b9069abf74b9d12e30JSpectraViewer | MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC00450
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound24771808
PDB IDNot Available
ChEBI ID49014
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Metabolizes sarcosine, L-pipecolic acid and L-proline.
Gene Name:
PIPOX
Uniprot ID:
Q9P0Z9
Molecular weight:
44065.515
Reactions
L-Pipecolic acid + Oxygen → ​2,3,4,5-Tetrahydro-2-pyridinecarboxylic acid + Hydrogen peroxidedetails