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Human Metabolome Database Version 3.5

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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 | 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 Comments
Blood Detected and Quantified
Article_icon
0.04 +/- 0.03 uM Adult (>18 years old) Female Normal Not Available
Urine Detected and Quantified
Article_icon
0.16 (0.02-0.69) umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
Article_icon
2.55 (0.18-5.85) umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
Article_icon
0.015 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
Article_icon
1.2 umol/mmol creatinine Adult (>18 years old) Both Normal urine by NMR
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
0.13 +/- 0.13 uM Adult (>18 years old) Female Breast cancer Not Available
Urine Detected and Quantified
Article_icon
0.96 (0.12-2.11) umol/mmol creatinine Adult (>18 years old) Both Leukemia Initial stage of 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
      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:
      • S-adenosylmethioninamine + spermidine = S-methyl-5'-thioadenosine + spermine [RN:R02869]
      Gene Name: SMS
      Uniprot ID: P52788 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Deoxyhypusine synthase
      Reactions:
      • (1) [eIF5A-precursor]-lysine + spermidine = [eIF5A-precursor]-deoxyhypusine + propane-1,3-diamine [RN:R05329]
      • (2) (1a) spermidine + NAD+ = dehydrospermidine + NADH [RN:R07477]
      • (3) (1b) dehydrospermidine + [enzyme]-lysine = N-(4-aminobutylidene)-[enzyme]-lysine + propane-1,3-diamine [RN:R07479]
      • (4) (1c) N-(4-aminobutylidene)-[enzyme]-lysine + [eIF5A-precursor]-lysine = N-(4-aminobutylidene)-[eIF5A-precursor]-lysine + [enzyme]-lysine [RN:R07480]
      • (5) (1d) N-(4-aminobutylidene)-[eIF5A-precursor]-lysine + NADH + H+ = [eIF5A-precursor]-deoxyhypusine + NAD+ [RN:R07478]
      Gene Name: DHPS
      Uniprot ID: P49366 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Amiloride-sensitive amine oxidase [copper-containing]
      Reactions:
      • histamine + H2O + O2 = (imidazol-4-yl)acetaldehyde + NH3 + H2O2 [RN:R02150]
      Gene Name: ABP1
      Uniprot ID: P19801 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Membrane primary amine oxidase
      Reactions:
      • RCH2NH2 + H2O + O2 = RCHO + NH3 + H2O2 [RN:R01853]
      Gene Name: AOC3
      Uniprot ID: Q16853 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Retina-specific copper amine oxidase
      Reactions:
      • RCH2NH2 + H2O + O2 = RCHO + NH3 + H2O2 [RN:R01853]
      Gene Name: AOC2
      Uniprot ID: O75106 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: S-adenosylmethionine decarboxylase proenzyme
      Reactions:
      • S-adenosyl-L-methionine = (5-deoxy-5-adenosyl)(3-aminopropyl)methylsulfonium salt + CO2 [RN:R00178]
      Gene Name: AMD1
      Uniprot ID: P17707 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Ornithine decarboxylase
      Reactions:
      • L-ornithine = putrescine + CO2 [RN:R00670]
      Gene Name: ODC1
      Uniprot ID: P11926 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA