(2S,4S)-4-Hydroxy-2,3,4,5-tetrahydrodipicolinate (ECMDB23778) (M2MDB004261)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (4)XML
Proteins (1276)
Record Information
Version2.0
Creation Date2015-06-04 15:15:06 -0600
Update Date2015-09-17 15:41:57 -0600
Secondary Accession Numbers
  • ECMDB23778
Identification
Name:(2S,4S)-4-Hydroxy-2,3,4,5-tetrahydrodipicolinate
DescriptionThe 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
MOLSDFPDBSMILESInChI
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
Weight:Average: 185.136
Monoisotopic: 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
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
  • Dicarboxylic acid or derivatives
  • Hydropyridine
  • Ketimine
  • Secondary alcohol
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboxylic acid
  • Azacycle
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Imine
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility13.3 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity39.74 m³·mol⁻¹ChemAxon
Polarizability16.67 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Tetrahydrodipicolinate + NAD + NADP + Water <> (2S,4S)-4-Hydroxy-2,3,4,5-tetrahydrodipicolinate + NADH + NADPH + Hydrogen ion
Pyruvic acid + L-Aspartate-semialdehyde <> (2S,4S)-4-Hydroxy-2,3,4,5-tetrahydrodipicolinate + Water
L-Aspartate-semialdehyde + Pyruvic acid > Hydrogen ion + Water + (2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinate + (2S,4S)-4-Hydroxy-2,3,4,5-tetrahydrodipicolinate
(2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinate + Hydrogen ion + NADPH + (2S,4S)-4-Hydroxy-2,3,4,5-tetrahydrodipicolinate + NADPH > Water + NADP + (S)-2,3,4,5-tetrahydrodipicolinate
SMPDB Pathways:
Lysine biosynthesisPW000771 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
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 IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. Dihydrodipicolinate reductase
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.
Protein Details
2. Dihydrodipicolinate synthase
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.
Protein Details
3. Uncharacterized protein yjhH
General function:
Involved in catalytic activity
Specific function:
Specific function unknown
Gene Name:
yjhH
Uniprot ID:
P39359
Molecular weight:
32721
Protein Details
4. Uncharacterized protein yagE
General function:
Involved in catalytic activity
Specific function:
Unknown Function
Gene Name:
yagE
Uniprot ID:
P75682
Molecular weight:
33316