ECMDB: 2,3-Dihydrodipicolinic acid (ECMDB04056) (M2MDB000588)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (4)XML

Proteins (8)

Record Information

Version

2.0

Creation Date

2012-05-31 14:03:48 -0600

Update Date

2015-06-03 15:54:41 -0600

Secondary Accession Numbers

ECMDB04056

Identification

Name:

2,3-Dihydrodipicolinic acid

Description

L-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

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha 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 Framework

Aliphatic heteromonocyclic compounds

External Descriptors

dihydrodipicolinic acid (CHEBI:48052 )

Physical Properties

State:

Solid

Charge:

-2

Melting point:

135.2

Experimental Properties:

Property	Value	Source
Water Solubility:	0.03	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	6.84 g/L	ALOGPS
logP	0.12	ALOGPS
logP	0.66	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	3.17	ChemAxon
pKa (Strongest Basic)	-1.1	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	86.96 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	39.36 m³·mol⁻¹	ChemAxon
Polarizability	15.08 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

SMPDB Pathways:

Lysine biosynthesis	PW000771
Secondary Metabolites: threonine biosynthesis from aspartate	PW000976

KEGG Pathways:

Lysine biosynthesis ec00300
Microbial metabolism in diverse environments ec01120

EcoCyc Pathways:

lysine biosynthesis I DAPLYSINESYN-PWY

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0077-9300000000-d72da8848d1f49469c23	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-0002-7910000000-ae5409fbe082d4832847	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-fa63cf428cc5d8471604	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01b9-1900000000-a3ffb331ab96000a39e1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00bc-9400000000-35fdba6f9d56521e4e19	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00b9-5900000000-c56aff84aa96cf6da852	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-5900000000-a51255d0609601301b43	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ue9-9000000000-65ec758152caf537e272	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-35bd5d728d4b6335059a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0900000000-681935e00eed4828fd0f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-9300000000-ba4f4cccfccf71d0b007	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-1900000000-2698c9ffb8a4caa90c8f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-9200000000-625e0679cd43f0dedb7f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f89-9000000000-7337376b7fa4e0a9a51d	View in MoNA
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer

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

Links

External Links:

Resource	Link
CHEBI ID	30620
HMDB ID	HMDB12247
Pubchem Compound ID	17
Kegg ID	C03340
ChemSpider ID	16
Wikipedia ID	Not Available
BioCyc ID	2-3-DIHYDRODIPICOLINATE
EcoCyc ID	2-3-DIHYDRODIPICOLINATE

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

2,3-Dihydrodipicolinic acid (ECMDB04056) (M2MDB000588)

Structure for #<Compound:0xa46e42c8>

Enzymes

Reactions

Reactions