Dialanine (CHEM025365)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 22:21:03 UTC
Update Date2016-11-09 01:18:04 UTC
Accession NumberCHEM025365
Identification
Common NameDialanine
ClassSmall Molecule
DescriptionA dipeptide comprising D-alanine with a D-alanyl residue attached to the alpha-nitrogen. It is a component of bacterial peptidoglycan and forms an important target for development of antibacterial drugs .
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(D-Ala)2ChEBI
D-Ala-D-alaChEBI
H-D-Ala-D-ala-OHChEBI
Alanyl-D-alanineHMDB
Ala-alaHMDB
H-Ala-ala-OHHMDB
AlanylalanineHMDB
Alanylalanine, (D)-isomerHMDB
Alanylalanine, (D-ala)-(L-ala)-isomerHMDB
Alanylalanine, (L)-isomerHMDB
Alanylalanine, (L-ala)-(D-ala)-isomerHMDB
Alanylalanine, (L-ala)-(DL-ala)-isomerHMDB
DialanineHMDB
D-Alanyl-L-alanineHMDB
L-Alanyl-D-alanineHMDB
Di-L-alanineHMDB
D-AlanylalanineHMDB
L-Alanyl-L-alanineHMDB
N-D-Alanyl-L-alanineHMDB
N-L-Alanyl-D-alanineHMDB
Chemical FormulaC6H12N2O3
Average Molecular Mass160.171 g/mol
Monoisotopic Mass160.085 g/mol
CAS Registry Number923-16-0
IUPAC Name(2R)-2-[(2R)-2-aminopropanamido]propanoic acid
Traditional NameD-ala-D-ala
SMILESCC(N)C(O)=NC(C)C(O)=O
InChI IdentifierInChI=1S/C6H12N2O3/c1-3(7)5(9)8-4(2)6(10)11/h3-4H,7H2,1-2H3,(H,8,9)(H,10,11)
InChI KeyDEFJQIDDEAULHB-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentDipeptides
Alternative Parents
Substituents
  • Alpha-dipeptide
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Alanine or derivatives
  • Alpha-amino acid or derivatives
  • Amino acid or derivatives
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Amino acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Carbonyl group
  • Primary amine
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility70.7 g/LALOGPS
logP-2.6ALOGPS
logP-3.4ChemAxon
logS-0.36ALOGPS
pKa (Strongest Acidic)3.73ChemAxon
pKa (Strongest Basic)8.39ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area92.42 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity37.79 m³·mol⁻¹ChemAxon
Polarizability15.66 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f79-0900000000-5d9afc4a11f868ffd54eSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-0900000000-8c6c90ec8315f93e4ad4Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f79-0900000000-5d9afc4a11f868ffd54eSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-0900000000-8c6c90ec8315f93e4ad4Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-9100000000-b16775fe354ea161228eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00r6-9400000000-b5b87eed7f3175b80e2eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03dl-6900000000-90b25f3c22007ea839b5Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0a4i-0900000000-bd7876a01b4ebfb8700fSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0006-9000000000-8d6a984538d3c099b09fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0296-5900000000-799966b5c9620715d16aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9200000000-513a3e368e7c6334e54fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-9000000000-0724d314ee5219f1c728Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-2900000000-b6d1f12edd1486d8cbb4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-059i-9600000000-8635adeca87ba2d6a666Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00du-9000000000-17647b2edc99cfa2d13bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-052o-4900000000-aae09911d82d8cfafc1fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9100000000-fcc1d4e4f5652338825fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-f5f0d3e84942d47714c6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9100000000-a9556cdd03ea097d9213Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-2cbbf675159b82ddf5e8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-ac3751498e9cf095d11fSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0003459
FooDB IDFDB003740
Phenol Explorer IDNot Available
KNApSAcK IDC00019576
BiGG IDNot Available
BioCyc IDD-ALA-D-ALA
METLIN ID6937
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID4573916
ChEBI ID16576
PubChem Compound ID5460362
Kegg Compound IDC00993
YMDB IDNot Available
ECMDB IDECMDB23080
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=16030213
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=19053785
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=24440607
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=61706
5. Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735.
6. Neuhaus, Francis C. Enzymic synthesis of D-alanyl-D-alanine. Biochemical and Biophysical Research Communications (1960), 3 401-5.
7. Ladesic B, Tomasic J, Kveder S, Hrsak I: The metabolic fate of 14C-labeled immunoadjuvant peptidoglycan monomer. II. In vitro studies. Biochim Biophys Acta. 1981 Nov 18;678(1):12-7.
8. Franken N, Seidl PH, Kuchenbauer T, Kolb HJ, Schleifer KH, Weiss L, Tympner KD: Specific immunoglobulin A antibodies to a peptide subunit sequence of bacterial cell wall peptidoglycan. Infect Immun. 1984 Apr;44(1):182-7.
9. Tabata K, Ikeda H, Hashimoto S: ywfE in Bacillus subtilis codes for a novel enzyme, L-amino acid ligase. J Bacteriol. 2005 Aug;187(15):5195-202.
10. Jansen A, Turck M, Szekat C, Nagel M, Clever I, Bierbaum G: Role of insertion elements and yycFG in the development of decreased susceptibility to vancomycin in Staphylococcus aureus. Int J Med Microbiol. 2007 Jul;297(4):205-15. Epub 2007 Apr 5.
11. Kovac A, Majce V, Lenarsic R, Bombek S, Bostock JM, Chopra I, Polanc S, Gobec S: Diazenedicarboxamides as inhibitors of D-alanine-D-alanine ligase (Ddl). Bioorg Med Chem Lett. 2007 Apr 1;17(7):2047-54. Epub 2007 Jan 17.