Showing Compound Card for Diaminopimelic acid (CDB005132)

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Record Information
Version1.0
Created at2020-04-17 19:12:33 UTC
Updated at2020-11-18 16:39:25 UTC
CannabisDB IDCDB005132
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameDiaminopimelic acid
DescriptionDiaminopimelic acid, also known as LL-2,6-diaminopimelate or DAPA, 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. A Diaminopimelic acid in which both chiral centres have S configuration. Diaminopimelic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Diaminopimelic acid exists in all living species, ranging from bacteria to humans. Outside of the human body, Diaminopimelic acid has been detected, but not quantified in, several different foods, such as breadfruits, horned melons, daikon radish, malabar spinachs, and hard wheats. This could make diaminopimelic acid a potential biomarker for the consumption of these foods. Diaminopimelic acid is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(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
Chemical FormulaC7H14N2O4
Average Molecular Weight190.2
Monoisotopic Molecular Weight190.0954
IUPAC Name(2S,6S)-2,6-diaminoheptanedioic acid
Traditional Namediamino-pimelic acid
CAS Registry Number583-93-7
SMILES
N[C@@H](CCC[C@H](N)C(O)=O)C(O)=O
InChI Identifier
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
InChI KeyGMKMEZVLHJARHF-WHFBIAKZSA-N
Chemical Taxonomy
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:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point300 °CNot Available
Boiling Point426.7 °CWikipedia
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
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-d85213bd7ac426f10cd72012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001i-9100000000-add590f1b216bdb403342012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-001i-9000000000-de98ed3bb8c48b6f98522012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-2c8a0ca138ef6ea5ef432021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-003r-9600000000-19f54d2417fe44d0eba32021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-e8b0bbffeaa501a6fedd2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-91296097628a67dd97ef2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-e5c4e034dcab0695e0ce2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-002r-0900000000-2a19445fee9eade1d5382021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-00di-9000000000-f44538bc8ae3a51cbbc62021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-003r-9700000000-3baa36a29b4ed6172da02021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-004i-1900000000-cf39d89ce72ac9ddaf512021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0200-6900000000-6f21b7798408480c1bfc2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-001i-9300000000-6e778092666f89ff42112021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-28fbb202ae5558af75942021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-004i-1900000000-8a1ee3da7fbe94f840c22021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-8caae42eda716644fdc12021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0005-1900000000-be94a16bee7fad24d5d92016-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-5900000000-896859ce722942f9dd682016-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006t-9200000000-50c1b5a4f7b19e8ff0db2016-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-5ecd829b51ba774883f62016-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-1900000000-53b7aee01233b5b73d3e2016-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9400000000-2cc35eb21a44b2d472b52016-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0079-0900000000-a0ce1f9601e9b8d83ccf2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00dj-6900000000-cc22f522673c5549366c2021-09-22View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0001370
DrugBank IDDB03590
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022583
KNApSAcK IDC00007596
Chemspider ID388416
KEGG Compound IDC00666
BioCyc IDLL-DIAMINOPIMELATE
BiGG IDNot Available
Wikipedia LinkDiaminopimelic acid
METLIN ID352
PubChem Compound439283
PDB IDNot Available
ChEBI ID16026
References
General ReferencesNot Available