Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000457
Identification
Name: Cadaverine
Description:Cadaverine 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. Cadaverine is toxic in large doses. In rats it had a low acute oral toxicity of more than 2000 mg/kg body weight (Wikipedia).
Structure
Thumb
Synonyms:
  • 1,5-Diaminopentane
  • 1,5-Diaminopentane dihydrochloride
  • 1,5-Pentamethylenediamine
  • 1,5-Pentanediamine
  • BioDex 1-
  • Cadaverin
  • Cadaverine dihydrochloride
  • Diaminopentane
  • Pentamethylenediamine
  • Pentamethylenediamine dihydrochloride
  • Pentane-1,5-diamine
Chemical Formula: C5H14N2
Average Molecular Weight: 102.1781
Monoisotopic Molecular Weight: 102.115698458
InChI Key: VHRGRCVQAFMJIZ-UHFFFAOYSA-N
InChI:InChI=1S/C5H14N2/c6-4-2-1-3-5-7/h1-7H2
CAS number: 462-94-2
IUPAC Name:pentane-1,5-diamine
Traditional IUPAC Name: cadaverine
SMILES:NCCCCCN
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as monoalkylamines. These are organic compounds containing an primary aliphatic amine group.
Kingdom Organic compounds
Super ClassOrganonitrogen compounds
Class Amines
Sub ClassPrimary amines
Direct Parent Monoalkylamines
Alternative Parents
Substituents
  • Hydrocarbon derivative
  • Primary aliphatic amine
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Liquid
Charge:2
Melting point: 9 °C
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility89.1 mg/mLALOGPS
logP-0.27ALOGPS
logP-0.4ChemAxon
logS-0.06ALOGPS
pKa (Strongest Basic)10.51ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area52.04 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity31.98 m3·mol-1ChemAxon
Polarizability13.11 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-00di-2900000000-c1c59035a5dd2cf2397aView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-00di-1900000000-c7101e746f630b0d4f42View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-00di-1900000000-48b12a5bc6a62e9ed804View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-00di-7900000000-020b1654fcdd9f9fd0a0View in MoNA
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-00di-1900000000-3523119399e33cc99ffdView in MoNA
GC-MSGC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-9000000000-5817f0beec3a79f3a6c7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-9000000000-22d437e302afdf2f75c0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000f-9000000000-afba702d0bfb9c128a1aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0f79-9700000000-4e9a9316d1a1ba6cc539View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-000i-9000000000-e7f100cf1764df7c5c7dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-00kr-9000000000-dd3cb46607a44329a47eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-000f-9000000000-e695dd1988dad38b7ab2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-000f-9000000000-c7e19ea45810c9ff2ec7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0udi-0900000000-b90d873498daae7ae4d4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udr-8900000000-b4ffc99460cf006c6219View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fri-9300000000-10f9aa1be57f6e3ac50cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05mo-9000000000-df0b7a89c9648f6777c5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udr-8900000000-b4ffc99460cf006c6219View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fri-9300000000-10f9aa1be57f6e3ac50cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05mo-9000000000-df0b7a89c9648f6777c5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-c3c054bb552dc70cebbdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1900000000-d860072ec6a6efa13b55View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0g0x-9100000000-932b1baf4ef30ebec4fcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-c3c054bb552dc70cebbdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1900000000-d860072ec6a6efa13b55View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0g0x-9100000000-932b1baf4ef30ebec4fcView in MoNA
MSMass Spectrum (Electron Ionization)splash10-001i-9000000000-3462b2adf27a78b2134eView in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • Hamana, K. (1996). "Distribution of diaminopropane and acetylspermidine in Enterobacteriaceae." Can J Microbiol 42:107-114. Pubmed: 8742354
  • 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
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • 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
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
  • 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
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
ResourceLink
CHEBI ID18127
HMDB IDHMDB02322
Pubchem Compound ID273
Kegg IDC01672
ChemSpider ID13866593
WikipediaCadaverine
BioCyc IDCADAVERINE
EcoCyc IDCADAVERINE
Ligand ExpoN2P

Enzymes

General function:
Involved in catalytic activity
Specific function:
Catalyzes the production of spermidine from putrescine and decarboxylated S-adenosylmethionine (dcSAM), which serves as an aminopropyl donor
Gene Name:
speE
Locus Tag:
PA1687
Molecular weight:
32.2 kDa
Reactions
S-adenosylmethioninamine + putrescine = 5'-S-methyl-5'-thioadenosine + spermidine.

Transporters