Human Metabolome Database Version 3.5

Showing metabocard for Cadaverine (HMDB02322)

Record Information
Version 3.5
Creation Date 2006-05-22 08:17:48 -0600
Update Date 2013-02-08 17:11:44 -0700
HMDB ID HMDB02322
Secondary Accession Numbers None
Metabolite Identification
Common 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. 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).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  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 Formula C5H14N2
Average Molecular Weight 102.1781
Monoisotopic Molecular Weight 102.115698458
IUPAC Name pentane-1,5-diamine
Traditional IUPAC Name pentane-1,5-diamine
CAS Registry Number 462-94-2
SMILES NCCCCCN
InChI Identifier InChI=1S/C5H14N2/c6-4-2-1-3-5-7/h1-7H2
InChI Key VHRGRCVQAFMJIZ-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
  • Microbial
Biofunction Not Available
Application Not Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
State Liquid
Experimental Properties
Property Value Reference
Melting Point 9 °C Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
LogP -0.27 ALOGPS
LogP -0.4 ChemAxon
LogS -0.06 ALOGPS
pKa (strongest basic) 10.51 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 52.04 A2 ChemAxon
Rotatable Bond Count 4 ChemAxon
Refractivity 31.98 ChemAxon
Polarizability 13.11 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 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)
MS/MS Spectrum LC-ESI-QTOF (UPLC Q-Tof Premier, Waters)
MS/MS Spectrum GC-MS
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Intestine
  • Epidermis
  • Prostate
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Urine Detected and Quantified
0.40 (0.01-0.82) umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected but not Quantified
Not Applicable Adult (>18 years old) Both Normal
Urine Detected and Quantified
0.217 +/- .208 umol/mmol creatinine Adult (>18 years old) Both Not Available
Urine Detected and Quantified
0.058 +/- 0.0067 umol/mmol creatinine Adult (>18 years old) Both Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified 0.22 +/- 0.11 uM Adult (>18 years old) Both Comment Kidney disease
Blood Detected and Quantified 0.16 +/- 0.09 uM Adult (>18 years old) Both Comment Kidney disease
Urine Detected but not Quantified Not Applicable Adult (>18 years old) Both Leukemia
Urine Detected and Quantified 0.991 +/- 0.936 umol/mmol creatinine Adult (>18 years old) Both Leukemia
Urine Detected and Quantified 0.18 +/- 0.044 umol/mmol creatinine Adult (>18 years old) Both Pancreatic cancer
Associated Disorders and Diseases
Disease References
Kidney disease
  • 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 Link_out
      Thyroid cancer
      • 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 Link_out
          Associated OMIM IDs None
          DrugBank ID DB03854 Link_out
          DrugBank Metabolite ID Not Available
          Phenol Explorer Compound ID Not Available
          Phenol Explorer Metabolite ID Not Available
          FoodDB ID FDB001493
          KNApSAcK ID C00001403 Link_out
          Chemspider ID 13866593 Link_out
          KEGG Compound ID C01672 Link_out
          BioCyc ID CADAVERINE Link_out
          BiGG ID Not Available
          Wikipedia Link Cadaverine Link_out
          NuGOwiki Link HMDB02322 Link_out
          Metagene Link HMDB02322 Link_out
          METLIN ID 3236 Link_out
          PubChem Compound 273 Link_out
          PDB ID N2P Link_out
          ChEBI ID 18127 Link_out
          References
          Synthesis Reference Not Available
          Material Safety Data Sheet (MSDS) Download (PDF)
          General References
          1. 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 Link_out
          2. 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 Link_out
          3. 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 Link_out
          4. 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 Link_out
          5. 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 Link_out
          6. 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 Link_out
          7. 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 Link_out
          8. 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 Link_out
          9. 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 Link_out
          10. 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 Link_out
          11. 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 Link_out
          12. 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 Link_out
          13. 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
          14. 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 Link_out
          15. 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 Link_out
          16. 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
          17. 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 Link_out

          Enzymes
          Name: Spermidine synthase
          Reactions:
          S-Adenosylmethioninamine + Cadaverine unknown 5'-Methylthioadenosine + Aminopropylcadaverine details
          Gene Name: SRM
          Uniprot ID: P19623 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Membrane primary amine oxidase
          Reactions:
          Cadaverine + Water + Oxygen unknown 5-Aminopentanal + 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:
          Cadaverine + Water + Oxygen unknown 5-Aminopentanal + Ammonia + Hydrogen peroxide details
          Gene Name: AOC2
          Uniprot ID: O75106 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA