Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB004261
Identification
Name: (2S,4S)-4-Hydroxy-2,3,4,5-tetrahydrodipicolinate
Description:The dicarboxylic acid dianion formed from (2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinic acid by proton loss from both carboxy groups; major species present at pH 7.3
Structure
Thumb
Synonyms:
  • (2S,4S)-4-Hydroxy-2,3,4,5-tetrahydrodipicolinate
  • (2S,4S)-4-Hydroxy-2,3,4,5-tetrahydrodipicolinic acid
  • (4S)-4-Hydroxy-2,3,4,5-tetrahydro-(2S)-dipicolinate
  • (4S)-4-Hydroxy-2,3,4,5-tetrahydro-(2S)-dipicolinic acid
Chemical Formula: C7H7NO5
Average Molecular Weight: 185.136
Monoisotopic Molecular Weight: 185.033519489
InChI Key: DVTPRYHENFBCII-UHFFFAOYSA-L
InChI:InChI=1S/C7H9NO5/c9-3-1-4(6(10)11)8-5(2-3)7(12)13/h3-4,9H,1-2H2,(H,10,11)(H,12,13)/p-2
CAS number: Not Available
IUPAC Name:(2S,4S)-4-hydroxy-2,3,4,5-tetrahydropyridine-2,6-dicarboxylic acid
Traditional IUPAC Name: (2S,4S)-4-hydroxy-2,3,4,5-tetrahydropyridine-2,6-dicarboxylic acid
SMILES:OC1CC(N=C(C1)C([O-])=O)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
  • Dicarboxylic acid or derivatives
  • Hydropyridine
  • Ketimine
  • Secondary alcohol
  • Carboxylic acid
  • Azacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Imine
  • Hydrocarbon derivative
  • Organic oxide
  • Organonitrogen compound
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular Framework Aliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State: Not Available
Charge:-2
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility13.3 mg/mLALOGPS
logP-1.1ALOGPS
logP-0.64ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)3.13ChemAxon
pKa (Strongest Basic)-2.3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area107.19 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity39.74 m3·mol-1ChemAxon
Polarizability16.45 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, Positivesplash10-00dr-0900000000-a63724a1637e2369bfe3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-1900000000-98f3056d244f69428f0fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-7900000000-1f8ebafcd345462c8c15View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-09518370641f45a53d6cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01b9-9200000000-cdf4dacf370b1394d932View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-a3cc68fec7aabf43edd7View in MoNA
References
References: Not Available
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID67205
HMDB IDNot Available
Pubchem Compound ID53323638
Kegg IDC20258
ChemSpider ID26386323
Wikipedia IDNot Available
BioCyc IDNot Available

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.