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Human Metabolome Database Version 3.5

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Showing metabocard for 2,4-Diaminobutyric acid (HMDB02362)

Record Information
Version 3.5
Creation Date 2006-05-22 08:17:50 -0600
Update Date 2013-02-08 17:11:48 -0700
HMDB ID HMDB02362
Secondary Accession Numbers None
Metabolite Identification
Common Name 2,4-Diaminobutyric acid
Description 2,4-Diaminobutyric acid is a non-physiological, cationic amino acid analogue that is transported into cells by System A with potent antitumoral activity in vitro against human glioma cells, the result of the pronounced concentrated uptake of DAB in glioma cells to the extent that a cellular lysis could occur due to osmotic reasons. (PMID: 1561943 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (RS)-2,4-Diaminobutyric acid
  2. 2,4-Diamino-butanoate
  3. 2,4-Diamino-butanoic acid
  4. 2,4-Diamino-butyric acid
  5. 2,4-Diamino-N-butyric acid
  6. 2,4-Diaminobutanoate
  7. 2,4-Diaminobutanoic acid
  8. 2,4-Diaminobutyrate
  9. alpha,gamma-Diaminobutyrate
  10. alpha,gamma-Diaminobutyric acid
  11. DL-2,4-Diamino-N-butyric acid
  12. DL-2,4-Diaminobutanoate
  13. DL-2,4-Diaminobutanoic acid
  14. DL-2,4-Diaminobutyric acid
  15. DL-alpha,gamma-Diaminobutyric acid
Chemical Formula C4H10N2O2
Average Molecular Weight 118.1344
Monoisotopic Molecular Weight 118.074227574
IUPAC Name 2,4-diaminobutanoic acid
Traditional IUPAC Name 2,4-diaminobutyric acid
CAS Registry Number 305-62-4
SMILES NCCC(N)C(O)=O
InChI Identifier InChI=1S/C4H10N2O2/c5-2-1-3(6)4(7)8/h3H,1-2,5-6H2,(H,7,8)
InChI Key OGNSCSPNOLGXSM-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Amino Acids, Peptides, and Analogues
Class Amino Acids and Derivatives
Sub Class Alpha Amino Acids and Derivatives
Other Descriptors
  • Aliphatic Acyclic Compounds
  • diamino acid(ChEBI)
  • short-chain fatty acid(ChEBI)
  • straight-chain saturated fatty acid(ChEBI)
Substituents
  • Carboxylic Acid
  • Polyamine
  • Primary Aliphatic Amine (Alkylamine)
Direct Parent Alpha Amino Acids and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Drug
Biofunction
  • Protein synthesis, amino acid biosynthesis
Application Not Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP -4.64 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
Water Solubility 270 g/L ALOGPS
LogP -3.66 ALOGPS
LogP -4 ChemAxon
LogS 0.36 ALOGPS
pKa (strongest acidic) 2.55 ChemAxon
pKa (strongest basic) 10.25 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 89.34 A2 ChemAxon
Rotatable Bond Count 3 ChemAxon
Refractivity 28.56 ChemAxon
Polarizability 11.79 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 1 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Expected and not Quantified
Not Applicable Not Available Not Available Normal Inferred from detection in urine
Urine Detected and Quantified
Article_icon
0.1 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022978
KNApSAcK ID Not Available
Chemspider ID 457 Link_out
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB02362 Link_out
Metagene Link HMDB02362 Link_out
METLIN ID Not Available
PubChem Compound 470 Link_out
PDB ID Not Available
ChEBI ID 64307 Link_out
References
Synthesis Reference Talbot, Guy; Gaudry, Roger; Berlinguet, Louis. Synthesis of 4-aminobutyric acid and 2,4-diaminobutyric acid from butyrolactone. Canadian Journal of Chemistry (1958), 36 593-6.
Material Safety Data Sheet (MSDS) Download (PDF)
General References Not Available