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Record Information
Version1.0
Created at2020-11-23 19:38:55 UTC
Updated at2021-08-12 19:51:58 UTC
NP-MRD IDNP0002726
Secondary Accession NumbersNone
Natural Product Identification
Common NameDL-alpha,epsilon-Diaminopimelic acid
Provided ByBMRBBMRB logo
DescriptionMeso-diaminopimelate 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. It was first documented in 2001 (PMID: 11262151). Based on a literature review a significant number of articles have been published on meso-diaminopimelate (PMID: 17984079) (PMID: 20803494) (PMID: 22339732) (PMID: 23325104).
Structure
Thumb
Synonyms
ValueSource
Meso-diaminoheptanedioic acidChEBI
Meso-2,6-diaminopimelateKegg
Meso-2,6-diaminopimelic acidKegg
Meso-diaminoheptanedioateKegg
Meso-diaminopimelic acidGenerator
meso-2,6-Diaminoheptanedioic acidGenerator
Chemical FormulaC7H14N2O4
Average Mass190.1971 Da
Monoisotopic Mass190.09536 Da
IUPAC Name(2R,6S)-2,6-diaminoheptanedioic acid
Traditional Namediaminopimelic acid
CAS Registry NumberNot Available
SMILES
[H][C@](N)(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+
InChI KeyGMKMEZVLHJARHF-SYDPRGILSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, experimental)Wishart Lab2021-06-20View Spectrum
Species
Species of OriginNot Available
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
  • D-alpha-amino acid
  • 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
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
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
Polarizability18.68 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID89700
KEGG Compound IDC00680
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDiaminopimelic_acid
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID16488
Good Scents IDNot Available
References
General References
  1. Borruat G, Roten CA, Fay LB, Karamata D: A high-performance liquid chromatography method for the detection of diaminopimelic acid in urine. Anal Biochem. 2001 Apr 1;291(1):11-6. [PubMed:11262151 ]
  2. Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
  3. Toth GK, Hetenyi A, Ilisz I, Peter A: A simple chromatographic route for the isolation of meso diaminopimelic acid. Chirality. 2011 Feb;23(2):133-7. doi: 10.1002/chir.20888. Epub 2010 Aug 27. [PubMed:20803494 ]
  4. Usha V, Lloyd AJ, Lovering AL, Besra GS: Structure and function of Mycobacterium tuberculosis meso-diaminopimelic acid (DAP) biosynthetic enzymes. FEMS Microbiol Lett. 2012 May;330(1):10-6. doi: 10.1111/j.1574-6968.2012.02527.x. Epub 2012 Mar 7. [PubMed:22339732 ]
  5. Saito Y, Yoshimura Y, Wakamatsu H, Takahata H: A facile synthesis of fully protected meso-diaminopimelic acid (DAP) and its application to the preparation of lipophilic N-acyl iE-DAP. Molecules. 2013 Jan 16;18(1):1162-73. doi: 10.3390/molecules18011162. [PubMed:23325104 ]