2,6-Diaminopimelic Acid

Identification

Name
2,6-Diaminopimelic Acid
Accession Number
DB03590  (EXPT00541)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 190.1971
Monoisotopic: 190.095356946
Chemical Formula
C7H14N2O4
InChI Key
GMKMEZVLHJARHF-WHFBIAKZSA-N
InChI
InChI=1S/C7H14N2O4/c8-4(6(10)11)2-1-3-5(9)7(12)13/h4-5H,1-3,8-9H2,(H,10,11)(H,12,13)/t4-,5-/m0/s1
IUPAC Name
(2S,6S)-2,6-diaminoheptanedioic acid
SMILES
N[[email protected]@H](CCC[[email protected]](N)C(O)=O)C(O)=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UUDP-N-acetylmuramoyl-L-alanyl-D-glutamate--2,6-diaminopimelate ligaseNot AvailableEscherichia coli (strain K12)
UMeso-diaminopimelate D-dehydrogenaseNot AvailableCorynebacterium glutamicum (strain ATCC 13032 / DSM 20300 / JCM 1318 / LMG 3730 / NCIMB 10025)
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB01370
KEGG Compound
C00666
PubChem Compound
439283
PubChem Substance
46506904
ChemSpider
388416
ChEBI
57609
HET
API

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility14.1 mg/mLALOGPS
logP-4.1ALOGPS
logP-5.5ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)1.85ChemAxon
pKa (Strongest Basic)9.83ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area126.64 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity43.64 m3·mol-1ChemAxon
Polarizability18.93 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.7354
Blood Brain Barrier+0.6515
Caco-2 permeable-0.8734
P-glycoprotein substrateNon-substrate0.6551
P-glycoprotein inhibitor INon-inhibitor0.9848
P-glycoprotein inhibitor IINon-inhibitor0.9828
Renal organic cation transporterNon-inhibitor0.9465
CYP450 2C9 substrateNon-substrate0.8431
CYP450 2D6 substrateNon-substrate0.8525
CYP450 3A4 substrateNon-substrate0.8037
CYP450 1A2 substrateNon-inhibitor0.9433
CYP450 2C9 inhibitorNon-inhibitor0.965
CYP450 2D6 inhibitorNon-inhibitor0.9684
CYP450 2C19 inhibitorNon-inhibitor0.97
CYP450 3A4 inhibitorNon-inhibitor0.8785
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9969
Ames testNon AMES toxic0.7749
CarcinogenicityNon-carcinogens0.8989
BiodegradationReady biodegradable0.8595
Rat acute toxicity0.9661 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.986
hERG inhibition (predictor II)Non-inhibitor0.9849
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)GC-MSsplash10-0umi-1950000000-749403a0eb6d05c7903e
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)GC-MSsplash10-0uk9-1980000000-1b092f9141e7549bee24
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0umi-1950000000-749403a0eb6d05c7903e
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0uk9-1980000000-1b092f9141e7549bee24
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-004l-0900000000-d85213bd7ac426f10cd7
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-001i-9100000000-add590f1b216bdb40334
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-001i-9000000000-de98ed3bb8c48b6f9852
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
L-alpha-amino acids
Alternative Parents
Medium-chain fatty acids / Amino fatty acids / Dicarboxylic acids and derivatives / Amino acids / Carboxylic acids / Organopnictogen compounds / Organic oxides / Monoalkylamines / Hydrocarbon derivatives / Carbonyl compounds
Substituents
L-alpha-amino acid / Medium-chain fatty acid / Amino fatty acid / Dicarboxylic acid or derivatives / Fatty acid / Fatty acyl / Amino acid / Carboxylic acid / Organopnictogen compound / Organic nitrogen compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
2,6-diaminopimelic acid (CHEBI:16026) / Dicarboxylic acids (LMFA01170102)

Targets

Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Udp-n-acetylmuramoylalanyl-d-glutamate-2,6-diaminopimelate ligase activity
Specific Function
Catalyzes the addition of meso-diaminopimelic acid to the nucleotide precursor UDP-N-acetylmuramoyl-L-alanyl-D-glutamate (UMAG) in the biosynthesis of bacterial cell-wall peptidoglycan. Is also abl...
Gene Name
murE
Uniprot ID
P22188
Uniprot Name
UDP-N-acetylmuramoyl-L-alanyl-D-glutamate--2,6-diaminopimelate ligase
Molecular Weight
53343.13 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Corynebacterium glutamicum (strain ATCC 13032 / DSM 20300 / JCM 1318 / LMG 3730 / NCIMB 10025)
Pharmacological action
Unknown
General Function
Diaminopimelate dehydrogenase activity
Specific Function
Catalyzes the reversible NADPH-dependent reductive amination of L-2-amino-6-oxopimelate, the acyclic form of L-tetrahydrodipicolinate, to generate the meso compound, D,L-2,6-diaminopimelate. Probab...
Gene Name
ddh
Uniprot ID
P04964
Uniprot Name
Meso-diaminopimelate D-dehydrogenase
Molecular Weight
35199.135 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]

Drug created on June 13, 2005 07:24 / Updated on November 09, 2017 03:30