Human Metabolome Database Version 3.5

Showing metabocard for 1,3-Diaminopropane (HMDB00002)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:07:44 -0700
HMDB ID HMDB00002
Secondary Accession Numbers None
Metabolite Identification
Common Name 1,3-Diaminopropane
Description 1,3-Diaminopropane is a stable, flammable and highly hydroscopic fluid. It is a polyamine that is normally quite toxic if swallowed, inhaled or absorbed through the skin. It is a catabolic byproduct of spermidine. It is also a precursor in the enzymatic synthesis of beta-alanine. 1, 3-Diaminopropane is involved in the arginine/proline metabolic pathways and the beta-alanine metabolic pathway.
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 1,3-Diamino-N-propane
  2. 1,3-Propanediamine
  3. 1,3-Propylenediamine
  4. 1,3-Trimethylenediamine
  5. 3-Aminopropylamine
  6. a,w-Propanediamine
  7. Propane-1,3-diamine
  8. Trimethylenediamine
Chemical Formula C3H10N2
Average Molecular Weight 74.1249
Monoisotopic Molecular Weight 74.08439833
IUPAC Name propane-1,3-diamine
Traditional IUPAC Name 1,3-diaminopropane
CAS Registry Number 109-76-2
SMILES NCCCN
InChI Identifier InChI=1S/C3H10N2/c4-2-1-3-5/h1-5H2
InChI Key XFNJVJPLKCPIBV-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aliphatic Acyclic Compounds
Class Alkylamines
Sub Class Polyamines
Other Descriptors
  • Alkylamines
  • alkane-alpha,omega-diamine(ChEBI)
Substituents
  • N/A
Direct Parent Polyamines
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations
  • Cytoplasm
Physical Properties
State Liquid
Experimental Properties
Property Value Reference
Melting Point -12 °C Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP -1.43 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
LogP -1.41 ALOGPS
LogP -1.4 ChemAxon
LogS 0.77 ALOGPS
pKa (strongest basic) 10.47 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 52.04 A2 ChemAxon
Rotatable Bond Count 2 ChemAxon
Refractivity 22.73 ChemAxon
Polarizability 9.06 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 2 ChemAxon
Spectra
Gas-MS Spectrum
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum EI-B (HITACHI RMU-6L)
MS/MS Spectrum EI-B (HITACHI RMU-6M)
MS/MS Spectrum CI-B (HITACHI M-80)
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 50
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies )
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)
[1H,13C] 2D NMR Spectrum
[1H,1H] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location Not Available
Pathways
Name SMPDB Link KEGG Link
Beta-Alanine Metabolism SMP00007 map00410 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
0.04 +/- 0.03 uM Adult (>18 years old) Female Normal
Urine Detected and Quantified
0.16 (0.02-0.69) umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
2.55 (0.18-5.85) umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
0.015 umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
1.2 umol/mmol creatinine Adult (>18 years old) Both Comment Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified 0.13 +/- 0.13 uM Adult (>18 years old) Female Breast cancer
Urine Detected and Quantified 0.96 (0.12-2.11) umol/mmol creatinine Adult (>18 years old) Both Comment Leukemia
Associated Disorders and Diseases
Disease References
Perillyl alcohol administration for cancer treatment
  • Byun JA, Lee SH, Jung BH, Choi MH, Moon MH, Chung BC: Analysis of polyamines as carbamoyl derivatives in urine and serum by liquid chromatography-tandem mass spectrometry. Biomed Chromatogr. 2008 Jan;22(1):73-80. Pubmed: 17668437 Link_out
      Leukemia
      • Lee SH, Suh JW, Chung BC, Kim SO: Polyamine profiles in the urine of patients with leukemia. Cancer Lett. 1998 Jan 9;122(1-2):1-8. Pubmed: 9464484 Link_out
          Associated OMIM IDs None
          DrugBank ID Not Available
          DrugBank Metabolite ID Not Available
          Phenol Explorer Compound ID Not Available
          Phenol Explorer Metabolite ID Not Available
          FoodDB ID FDB005274
          KNApSAcK ID C00007404 Link_out
          Chemspider ID 415 Link_out
          KEGG Compound ID C00986 Link_out
          BioCyc ID CPD-313 Link_out
          BiGG ID 36543 Link_out
          Wikipedia Link Not Available
          NuGOwiki Link HMDB00002 Link_out
          Metagene Link HMDB00002 Link_out
          METLIN ID 5081 Link_out
          PubChem Compound 428 Link_out
          PDB ID 13D Link_out
          ChEBI ID 15725 Link_out
          References
          Synthesis Reference Takayanagi, Yasuyuki; Oohinata, Takahiro. Preparation of 1,3-diaminopropane from acrylonitrile and ammonia. Jpn. Kokai Tokkyo Koho (1994), 5 pp.
          Material Safety Data Sheet (MSDS) Download (PDF)
          General References
          1. van den Berg GA, Muskiet FA, Kingma AW, van der Slik W, Halie MR: Simultaneous gas-chromatographic determination of free and acetyl-conjugated polyamines in urine. Clin Chem. 1986 Oct;32(10):1930-7. Pubmed: 3757213 Link_out
          2. Kim KR, Paik MJ, Kim JH, Dong SW, Jeong DH: Rapid gas chromatographic profiling and screening of biologically active amines. J Pharm Biomed Anal. 1997 Jun;15(9-10):1309-18. Pubmed: 9226558 Link_out
          3. Bremer HJ, Kohne E: The excretion of diamines in human urine. II. Cadaverine, putrescine, 1,3-diaminopropane, 2,2'-dithiobis(ethylamine) and spermidine in urine of patients with cystinuria and cystinlysinuria. Clin Chim Acta. 1971 May;32(3):407-18. Pubmed: 5096953 Link_out
          4. Fleisher JH, Russell DH: Estimation of urinary diamines and polyamines by thin-layer chromatography. J Chromatogr. 1975 Jul 16;110(2):335-40. Pubmed: 1150841 Link_out
          5. Blackburn P, Peterson CM: Thiol-disulfide interchange between cystine and N-2-mercaptoethyl-1, 3-diaminopropane as a potential treatment for cystinuria. Anal Biochem. 1984 Jan;136(1):31-8. Pubmed: 6324613 Link_out
          6. Aigner-Held R, Campbell RA, Daves GD Jr: Polyamine-pyridoxal Schiff bases in urine. Proc Natl Acad Sci U S A. 1979 Dec;76(12):6652-5. Pubmed: 293750 Link_out
          7. Somayaji VV, Guay V, Peng Z, Sykes TR, Noujaim AA: Synthesis and evaluation of a new bifunctional chelating agent for the preparation of radioimmunoconjugates. Q J Nucl Med. 1995 Dec;39(4):300-10. Pubmed: 8624793 Link_out
          8. van den Berg GA, Schaaf JM, Nagel GT, Teelken AW, Muskiet FA: Determination of polyamines and metabolites in cerebrospinal fluid by isotope dilution mass fragmentography, and a clinical application. Clin Chim Acta. 1987 Jun 15;165(2-3):147-54. Pubmed: 3308180 Link_out
          9. Muskiet FA, van den Berg GA, Kingma AW, Fremouw-Ottevangers DC, Halie MR: Total polyamines and their non-alpha-amino acid metabolites simultaneously determined in urine by capillary gas chromatography, with nitrogen-phosphorus detector; and some clinical applications. Clin Chem. 1984 May;30(5):687-95. Pubmed: 6713628 Link_out
          10. Lee SH, Suh JW, Chung BC, Kim SO: Polyamine profiles in the urine of patients with leukemia. Cancer Lett. 1998 Jan 9;122(1-2):1-8. Pubmed: 9464484 Link_out

          Enzymes
          Name: Spermine synthase
          Reactions: Not Available
          Gene Name: SMS
          Uniprot ID: P52788 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Deoxyhypusine synthase
          Reactions:
          [eIF5A-precursor]-lysine + Spermidine unknown [eIF5A-precursor]-deoxyhypusine + 1,3-Diaminopropane details
          Gene Name: DHPS
          Uniprot ID: P49366 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Amiloride-sensitive amine oxidase [copper-containing]
          Reactions: Not Available
          Gene Name: ABP1
          Uniprot ID: P19801 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Membrane primary amine oxidase
          Reactions:
          1,3-Diaminopropane + Oxygen + Water unknown 3-Aminopropionaldehyde + Ammonia + Hydrogen peroxide details
          Gene Name: AOC3
          Uniprot ID: Q16853 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Retina-specific copper amine oxidase
          Reactions:
          1,3-Diaminopropane + Oxygen + Water unknown 3-Aminopropionaldehyde + Ammonia + Hydrogen peroxide details
          Gene Name: AOC2
          Uniprot ID: O75106 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: S-adenosylmethionine decarboxylase proenzyme
          Reactions: Not Available
          Gene Name: AMD1
          Uniprot ID: P17707 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Ornithine decarboxylase
          Reactions: Not Available
          Gene Name: ODC1
          Uniprot ID: P11926 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA