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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2014-06-04 18:34:44 UTC
HMDB IDHMDB00002
Secondary Accession NumbersNone
Metabolite Identification
Common Name1,3-Diaminopropane
Description1,3-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
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 FormulaC3H10N2
Average Molecular Weight74.1249
Monoisotopic Molecular Weight74.08439833
IUPAC Namepropane-1,3-diamine
Traditional Name1,3-diaminopropane
CAS Registry Number109-76-2
SMILES
NCCCN
InChI Identifier
InChI=1S/C3H10N2/c4-2-1-3-5/h1-5H2
InChI KeyXFNJVJPLKCPIBV-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAliphatic Acyclic Compounds
ClassAlkylamines
Sub ClassPolyamines
Other Descriptors
  • Alkylamines
  • alkane-alpha,omega-diamine(ChEBI)
Substituents
  • N/A
Direct ParentPolyamines
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-12 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-1.43HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility437 g/LALOGPS
logP-1.4ALOGPS
logP-1.4ChemAxon
logS0.77ALOGPS
pKa (Strongest Basic)10.47ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area52.04ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity22.73ChemAxon
Polarizability9.06ChemAxon
Spectra
SpectraGC-MSMS/MSLC-MS1D NMR2D NMR
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Beta-Alanine MetabolismSMP00007map00410
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.04 +/- 0.03 uMAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified0.16 (0.02-0.69) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified2.55 (0.18-5.85) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.015 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified1.2 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.13 +/- 0.13 uMAdult (>18 years old)FemaleBreast cancer details
UrineDetected and Quantified0.96 (0.12-2.11) umol/mmol creatinineAdult (>18 years old)Both
Leukemia
details
Associated Disorders and Diseases
Disease References
Perillyl alcohol administration for cancer treatment
  1. 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
Leukemia
  1. 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
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB005274
KNApSAcK IDC00007404
Chemspider ID415
KEGG Compound IDC00986
BioCyc IDCPD-313
BiGG ID36543
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00002
Metagene LinkHMDB00002
METLIN ID5081
PubChem Compound428
PDB ID13D
ChEBI ID15725
References
Synthesis ReferenceTakayanagi, 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
  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
  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
  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
  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
  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
  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
  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
  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
  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

Enzymes

General function:
Involved in spermine synthase activity
Specific function:
Catalyzes the production of spermine from spermidine and decarboxylated S-adenosylmethionine (dcSAM).
Gene Name:
SMS
Uniprot ID:
P52788
Molecular weight:
35278.2
References
  1. Oredsson SM, Anehus S, Heby O: Reversal of the growth inhibitory effect of alpha-difluoromethylornithine by putrescine but not by other divalent cations. Mol Cell Biochem. 1984 Sep;64(2):163-72. Pubmed: 6438490
General function:
Involved in peptidyl-lysine modification to hypusine
Specific function:
Catalyzes the NAD-dependent oxidative cleavage of spermidine and the subsequent transfer of the butylamine moiety of spermidine to the epsilon-amino group of a specific lysine residue of the eIF-5A precursor protein to form the intermediate deoxyhypusine residue.
Gene Name:
DHPS
Uniprot ID:
P49366
Molecular weight:
40970.28
Reactions
[eIF5A-precursor]-lysine + Spermidine → [eIF5A-precursor]-deoxyhypusine + 1,3-Diaminopropanedetails
References
  1. Park JH, Wolff EC, Folk JE, Park MH: Reversal of the deoxyhypusine synthesis reaction. Generation of spermidine or homospermidine from deoxyhypusine by deoxyhypusine synthase. J Biol Chem. 2003 Aug 29;278(35):32683-91. Epub 2003 Jun 4. Pubmed: 12788913
General function:
Involved in copper ion binding
Specific function:
Catalyzes the degradation of compounds such as putrescine, histamine, spermine, and spermidine, substances involved in allergic and immune responses, cell proliferation, tissue differentiation, tumor formation, and possibly apoptosis. Placental DAO is thought to play a role in the regulation of the female reproductive function.
Gene Name:
ABP1
Uniprot ID:
P19801
Molecular weight:
85377.1
General function:
Involved in copper ion binding
Specific function:
Cell adhesion protein that participates in lymphocyte recirculation by mediating the binding of lymphocytes to peripheral lymph node vascular endothelial cells in an L-selectin-independent fashion. Has a monoamine oxidase activity. May play a role in adipogenesis.
Gene Name:
AOC3
Uniprot ID:
Q16853
Molecular weight:
84621.27
Reactions
1,3-Diaminopropane + Oxygen + Water → 3-Aminopropionaldehyde + Ammonia + Hydrogen peroxidedetails
General function:
Involved in copper ion binding
Specific function:
Has a monoamine oxidase activity with substrate specificity for 2-phenylethylamine and tryptamine. May play a role in adipogenesis. May be a critical modulator of signal transmission in retina.
Gene Name:
AOC2
Uniprot ID:
O75106
Molecular weight:
80515.11
Reactions
1,3-Diaminopropane + Oxygen + Water → 3-Aminopropionaldehyde + Ammonia + Hydrogen peroxidedetails
General function:
Involved in adenosylmethionine decarboxylase activity
Specific function:
Not Available
Gene Name:
AMD1
Uniprot ID:
P17707
Molecular weight:
21301.015
References
  1. Pegg AE, Shuttleworth K, Hibasami H: Specificity of mammalian spermidine synthase and spermine synthase. Biochem J. 1981 Aug 1;197(2):315-20. Pubmed: 6798961
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
ODC1
Uniprot ID:
P11926
Molecular weight:
51147.73