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Record Information
Creation Date2006-05-22 14:17:48 UTC
Update Date2014-10-09 20:54:01 UTC
Secondary Accession NumbersNone
Metabolite Identification
Common NameCadaverine
DescriptionCadaverine is a foul-smelling diamine formed by bacterial decarboxylation of lysine that occurs during protein hydrolysis during putrefaction of animal tissue. However, this diamine is not purely associated with putrefaction. It is also produced in small quantities by mammals. In particular, it is partially responsible for the distinctive smell of urine and semen. Elevated levels of cadaverine have been found in the urine of some patients with defects in lysine metabolism. Cadaverine is toxic in large doses. In rats it had a low acute oral toxicity of more than 2000 mg/kg body weight (Wikipedia).
  1. 1,5-Diaminopentane
  2. 1,5-Diaminopentane dihydrochloride
  3. 1,5-Pentamethylenediamine
  4. 1,5-Pentanediamine
  5. Cadaverin
  6. Cadaverine dihydrochloride
  7. Pentamethylenediamine
  8. Pentamethylenediamine dihydrochloride
  9. Pentane-1,5-diamine
Chemical FormulaC5H14N2
Average Molecular Weight102.1781
Monoisotopic Molecular Weight102.115698458
IUPAC Namepentane-1,5-diamine
Traditional Namepentane-1,5-diamine
CAS Registry Number462-94-2
InChI Identifier
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAliphatic Acyclic Compounds
Sub ClassPolyamines
Other Descriptors
  • Alkylamines
  • alkane-alpha,omega-diamine(ChEBI)
  • N/A
Direct ParentPolyamines
StatusDetected and Quantified
  • Endogenous
  • Microbial
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
Experimental Properties
Melting Point9 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility89.1 g/LALOGPS
pKa (Strongest Basic)10.51ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area52.04ChemAxon
Rotatable Bond Count4ChemAxon
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Saliva
  • Urine
Tissue Location
  • Epidermis
  • Intestine
  • Prostate
PathwaysNot Available
Normal Concentrations
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
    • Dame, ZT. et al. ...
UrineDetected and Quantified0.40 (0.01-0.82) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.217 +/- .208 umol/mmol creatinineAdult (>18 years old)BothNot Available details
UrineDetected and Quantified0.058 +/- 0.0067 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BloodDetected and Quantified0.22 +/- 0.11 uMAdult (>18 years old)Both
Kidney disease
BloodDetected and Quantified0.16 +/- 0.09 uMAdult (>18 years old)Both
Kidney disease
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothLeukemia details
UrineDetected and Quantified0.991 +/- 0.936 umol/mmol creatinineAdult (>18 years old)BothLeukemia details
UrineDetected and Quantified0.18 +/- 0.044 umol/mmol creatinineAdult (>18 years old)BothPancreatic cancer details
Associated Disorders and Diseases
Disease References
Thyroid cancer
  1. Loser C, Folsch UR, Paprotny C, Creutzfeldt W: Polyamine concentrations in pancreatic tissue, serum, and urine of patients with pancreatic cancer. Pancreas. 1990 Mar;5(2):119-27. Pubmed: 2315288
Kidney disease
  1. Takagi T, Chung TG, Saito A: Determination of polyamines in hydrolysates of uremic plasma by high-performance cation-exchange column chromatography. J Chromatogr. 1983 Feb 11;272(2):279-85. Pubmed: 6833425
Associated OMIM IDsNone
DrugBank IDDB03854
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB001493
KNApSAcK IDC00001403
Chemspider ID13866593
KEGG Compound IDC01672
BiGG IDNot Available
Wikipedia LinkCadaverine
NuGOwiki LinkHMDB02322
Metagene LinkHMDB02322
PubChem Compound273
ChEBI ID18127
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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
  2. 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
  3. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411
  4. Wolrath H, Forsum U, Larsson PG, Boren H: Analysis of bacterial vaginosis-related amines in vaginal fluid by gas chromatography and mass spectrometry. J Clin Microbiol. 2001 Nov;39(11):4026-31. Pubmed: 11682525
  5. Gabastou JM, Nugon-Baudon L, Robert Y, Manuel C, Vaissade P, Bourgeon E, Sibeud M, Szylit O, Bourlioux P: [Digestive amines of bacterial origin and behavior disorders. Apropos of a case] Pathol Biol (Paris). 1996 Apr;44(4):275-81. Pubmed: 8763591
  6. Cooke M, Leeves N, White C: Time profile of putrescine, cadaverine, indole and skatole in human saliva. Arch Oral Biol. 2003 Apr;48(4):323-7. Pubmed: 12663078
  7. Becker K, Csikos M, Sardy M, Szalai ZS, Horvath A, Karpati S: Identification of two novel nonsense mutations in the transglutaminase 1 gene in a Hungarian patient with congenital ichthyosiform erythroderma. Exp Dermatol. 2003 Jun;12(3):324-9. Pubmed: 12823447
  8. Goldberg S, Kozlovsky A, Gordon D, Gelernter I, Sintov A, Rosenberg M: Cadaverine as a putative component of oral malodor. J Dent Res. 1994 Jun;73(6):1168-72. Pubmed: 8046106
  9. Wakisaka K, Arano Y, Uezono T, Akizawa H, Ono M, Kawai K, Ohomomo Y, Nakayama M, Saji H: A novel radioiodination reagent for protein radiopharmaceuticals with L-lysine as a plasma-stable metabolizable linkage to liberate m-iodohippuric acid after lysosomal proteolysis. J Med Chem. 1997 Aug 1;40(16):2643-52. Pubmed: 9258371
  10. Kai M, Ogata T, Haraguchi K, Ohkura Y: High-performance liquid chromatographic determination of free and total polyamines in human serum as fluorescamine derivatives. J Chromatogr. 1979 Jun 11;163(2):151-60. Pubmed: 541366
  11. Konikoff F, Goldman G, Halpern Z, Somjen GJ, Gilat T: Polyamines--potential nucleating factors in bile. Liver. 1990 Jun;10(3):173-6. Pubmed: 2385158
  12. Fujita K, Nagatsu T, Shinpo K, Maruta K, Teradaira R, Nakamura M: Improved analysis for urinary polyamines by use of high-voltage electrophoresis on paper. Clin Chem. 1980 Oct;26(11):1577-82. Pubmed: 7418205
  13. Kohler H, Rodrigues SP, Maurelli AT, McCormick BA: Inhibition of Salmonella typhimurium enteropathogenicity by piperidine, a metabolite of the polyamine cadaverine. J Infect Dis. 2002 Oct 15;186(8):1122-30. Epub 2002 Sep 20. Pubmed: 12355363
  14. Chen KC, Amsel R, Eschenbach DA, Holmes KK: Biochemical diagnosis of vaginitis: determination of diamines in vaginal fluid. J Infect Dis. 1982 Mar;145(3):337-45. Pubmed: 7061879
  15. Kubilus J, Baden HP: Isolation of two immunologically related transglutaminase substrates from cultured human keratinocytes. In Vitro. 1982 May;18(5):447-55. Pubmed: 6180968
  16. Kubota S, Okada M, Imahori K, Ohsawa N: A new simple enzymatic assay method for urinary polyamines in humans. Cancer Res. 1983 May;43(5):2363-7. Pubmed: 6831460
  17. Hallak A, Rosenberg R, Gilat T, Somjen GJ: Determination of free polyamines in human bile by high-performance liquid chromatography. Clin Sci (Lond). 1993 Oct;85(4):451-4. Pubmed: 8222511


General function:
Involved in catalytic activity
Specific function:
Catalyzes the production of spermidine from putrescine and decarboxylated S-adenosylmethionine (dcSAM). Has a strong preference for putrescine as substrate, and has very low activity towards 1,3-diaminopropane. Has extremely low activity towards spermidine.
Gene Name:
Uniprot ID:
Molecular weight:
S-Adenosylmethioninamine + Cadaverine → 5'-Methylthioadenosine + Aminopropylcadaverinedetails
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:
Uniprot ID:
Molecular weight:
Cadaverine + Water + Oxygen → 5-Aminopentanal + 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:
Uniprot ID:
Molecular weight:
Cadaverine + Water + Oxygen → 5-Aminopentanal + Ammonia + Hydrogen peroxidedetails