Record Information
Version1.0
Creation date2015-05-07 20:35:52 UTC
Update date2019-11-26 03:21:59 UTC
Primary IDFDB030951
Secondary Accession Numbers
  • FDB022583
Chemical Information
FooDB NameL,L-diaminopimelate
DescriptionDiaminopimelic acid, also known as ll-2,6-diaminopimelate or ll-2,6-diaminoheptanedioic acid, is a member of the class of compounds known as L-alpha-amino acids. L-alpha-amino acids are alpha amino acids which have the L-configuration of the alpha-carbon atom. Thus, diaminopimelic acid is considered to be a fatty acid lipid molecule. Diaminopimelic acid is soluble (in water) and a moderately acidic compound (based on its pKa). Diaminopimelic acid can be found in a number of food items such as quinoa, allium (onion), star anise, and dock, which makes diaminopimelic acid a potential biomarker for the consumption of these food products. Diaminopimelic acid can be found primarily in blood, feces, and urine. Diaminopimelic acid exists in all living species, ranging from bacteria to humans. Diaminopimelic acid is a characteristic of certain cell walls of some bacteria. Diaminopimelic acid is often found in the peptide linkages of NAM-NAG chains that make up the cell wall of gram-negative bacteria. When provided, they exhibit normal growth. When in deficiency, they still grow but with the inability to make new cell wall proteoglycan .
CAS Number583-93-7
Structure
Thumb
Synonyms
SynonymSource
(S,S)-2,6-Diaminopimelic acidChEBI
(S-(R*,r*))-2,6-diaminoheptanedioic acidChEBI
L,L-2,6-Diaminopimelic acidChEBI
LL-2,6-DiaminoheptanedioateChEBI
LL-2,6-DiaminopimelateChEBI
LL-2,6-Diaminopimelic acidKegg
(S,S)-2,6-DiaminopimelateGenerator
(S-(R*,r*))-2,6-diaminoheptanedioateGenerator
L,L-2,6-DiaminopimelateGenerator
LL-2,6-Diaminoheptanedioic acidGenerator
DiaminopimelateGenerator
( (R*,s*)-2,6-diamino-heptanedioateHMDB
( (R*,s*)-2,6-diamino-heptanedioic acidHMDB
(2R,6S)-2,6-diamino-HeptanedioateHMDB
(2R,6S)-2,6-diamino-Heptanedioic acidHMDB
(R*,s*)-2,6-diamino-heptanedioateHMDB
(R*,s*)-2,6-diamino-heptanedioic acidHMDB
2,6-diamino-HeptanedioateHMDB
2,6-diamino-Heptanedioic acidHMDB
2,6-DiaminoheptanedioateHMDB
2,6-Diaminoheptanedioic acidHMDB
2,6-DiaminopimelateHMDB
2,6-Diaminopimelic acidHMDB, MeSH
a,A'-diaminopimelateHMDB
a,A'-diaminopimelic acidHMDB
a,e-DiaminopimelateHMDB
a,e-Diaminopimelic acidHMDB
D,L-DiaminopimelateHMDB
D,L-meso-DiaminoheptanedioateHMDB
D,L-meso-Diaminoheptanedioic acidHMDB
DAPAHMDB
DL-2,6-DiaminoheptanedioateHMDB
DL-2,6-Diaminoheptanedioic acidHMDB
DL-2,6-DiaminopimelateHMDB
DL-2,6-Diaminopimelic acidHMDB
L,L-2,6-DiaminoheptanedioateHMDB
L,L-2,6-Diaminoheptanedioic acidHMDB
L,L-DiaminopimelateHMDB
meso-1-alpha,epsilon-DiaminopimelateHMDB
meso-2,6-diamino-HeptanedioateHMDB
meso-2,6-diamino-Heptanedioic acidHMDB
meso-2,6-DiaminoheptanedioateHMDB
meso-2,6-Diaminoheptanedioic acidHMDB
meso-alpha,Alpha'-diaminopimelateHMDB
meso-alpha,Alpha'-diaminopimelic acidHMDB
meso-alpha,epsilon-DiaminopimelateHMDB
meso-alpha,epsilon-Diaminopimelic acidHMDB
meso-DiaminoheptanedioateHMDB
meso-Diaminoheptanedioic acidHMDB
meso-DiaminopimelateHMDB
Acid, diaminopimelicMeSH, HMDB
2,6 Diaminopimelic acidMeSH, HMDB
Acid, 2,6-diaminopimelicMeSH, HMDB
Diamino-pimelateGenerator, HMDB
Diaminopimelic acidMeSH
Predicted Properties
PropertyValueSource
Water Solubility14.1 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity43.64 m³·mol⁻¹ChemAxon
Polarizability18.93 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC7H14N2O4
IUPAC name(2S,6S)-2,6-diaminoheptanedioic acid
InChI IdentifierInChI=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
InChI KeyGMKMEZVLHJARHF-WHFBIAKZSA-N
Isomeric SMILESN[C@@H](CCC[C@H](N)C(O)=O)C(O)=O
Average Molecular Weight190.1971
Monoisotopic Molecular Weight190.095356946
Classification
Description 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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative Parents
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
  • Amine
  • Organic oxygen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSDiaminopimelic acid, 4 TMS, GC-MS Spectrumsplash10-0umi-1950000000-749403a0eb6d05c7903eSpectrum
GC-MSDiaminopimelic acid, 4 TMS, GC-MS Spectrumsplash10-0uk9-1980000000-1b092f9141e7549bee24Spectrum
GC-MSDiaminopimelic acid, non-derivatized, GC-MS Spectrumsplash10-0umi-1950000000-749403a0eb6d05c7903eSpectrum
GC-MSDiaminopimelic acid, non-derivatized, GC-MS Spectrumsplash10-0uk9-1980000000-1b092f9141e7549bee24Spectrum
Predicted GC-MSDiaminopimelic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00dm-9500000000-5d0aafd0747a1090e055Spectrum
Predicted GC-MSDiaminopimelic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-014i-4590000000-b941e92697a8b7800912Spectrum
Predicted GC-MSDiaminopimelic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-004l-0900000000-d85213bd7ac426f10cd7Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001i-9100000000-add590f1b216bdb40334Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-001i-9000000000-de98ed3bb8c48b6f9852Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-2c8a0ca138ef6ea5ef43Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-003r-9600000000-19f54d2417fe44d0eba3Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-e8b0bbffeaa501a6feddSpectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-91296097628a67dd97efSpectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-e5c4e034dcab0695e0ceSpectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-002r-0900000000-2a19445fee9eade1d538Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-00di-9000000000-f44538bc8ae3a51cbbc6Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-003r-9700000000-3baa36a29b4ed6172da0Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-004i-1900000000-cf39d89ce72ac9ddaf51Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0200-6900000000-6f21b7798408480c1bfcSpectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-001i-9300000000-6e778092666f89ff4211Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-28fbb202ae5558af7594Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-004i-1900000000-8a1ee3da7fbe94f840c2Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-8caae42eda716644fdc1Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0005-1900000000-be94a16bee7fad24d5d9Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-5900000000-896859ce722942f9dd68Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006t-9200000000-50c1b5a4f7b19e8ff0dbSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-5ecd829b51ba774883f6Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-1900000000-53b7aee01233b5b73d3eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9400000000-2cc35eb21a44b2d472b5Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0079-0900000000-a0ce1f9601e9b8d83ccfSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00dj-6900000000-cc22f522673c5549366cSpectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference