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Record Information
Version3.6
Creation Date2006-05-22 14:17:48 UTC
Update Date2016-09-22 21:06:44 UTC
HMDB IDHMDB02322
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).
Structure
Thumb
Synonyms
ValueSource
1,5-DiaminopentaneChEBI
1,5-PentamethylenediamineChEBI
1,5-PentanediamineChEBI
DAPEChEBI
PentamethylenediamineChEBI
PENTANE-1,5-diamineChEBI
1,5-Diaminopentane dihydrochlorideHMDB
CadaverinHMDB
Cadaverine dihydrochlorideHMDB
Pentamethylenediamine dihydrochlorideHMDB
Chemical FormulaC5H14N2
Average Molecular Weight102.1781
Monoisotopic Molecular Weight102.115698458
IUPAC Namepentane-1,5-diamine
Traditional Namecadaverine
CAS Registry Number462-94-2
SMILES
NCCCCCN
InChI Identifier
InChI=1S/C5H14N2/c6-4-2-1-3-5-7/h1-7H2
InChI KeyInChIKey=VHRGRCVQAFMJIZ-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as monoalkylamines. These are organic compounds containing an primary aliphatic amine group.
KingdomOrganic compounds
Super ClassOrganonitrogen compounds
ClassAmines
Sub ClassPrimary amines
Direct ParentMonoalkylamines
Alternative Parents
Substituents
  • Hydrocarbon derivative
  • Primary aliphatic amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Microbial
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point9 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
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
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue Location
  • Epidermis
  • Intestine
  • Prostate
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableNot SpecifiedBoth
Normal
details
FecesDetected and Quantified217.268 +/- 239.777 uMNot SpecifiedNot Specified
Normal
details
FecesDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected and Quantified7.40 +/- 22.4 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected and Quantified1.32 +/- 1.41 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified2.50 +/- 2.62 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified2.74 +/- 5.58 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
    • Zerihun T. Dame, ...
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
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
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.22 +/- 0.11 uMAdult (>18 years old)Both
Kidney disease
details
BloodDetected and Quantified0.16 +/- 0.09 uMAdult (>18 years old)Both
Kidney disease
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Irritable bowel syndrome
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Ulcerative colitis
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Not SpecifiedPancreatic cancer details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Not SpecifiedPeriodontal diseases details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothOral cancer details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)FemaleBreast cancer details
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. [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. [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
BioCyc IDCADAVERINE
BiGG IDNot Available
Wikipedia LinkCadaverine
NuGOwiki LinkHMDB02322
Metagene LinkHMDB02322
METLIN ID3236
PubChem Compound273
PDB IDN2P
ChEBI ID18127
References
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. [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. [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. [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. [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. [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. [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. [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. [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. [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. [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. [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. [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. [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. [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. [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. [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. [8222511 ]

Enzymes

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:
SRM
Uniprot ID:
P19623
Molecular weight:
33824.455
Reactions
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:
AOC3
Uniprot ID:
Q16853
Molecular weight:
84621.27
Reactions
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:
AOC2
Uniprot ID:
O75106
Molecular weight:
80515.11
Reactions
Cadaverine + Water + Oxygen → 5-Aminopentanal + Ammonia + Hydrogen peroxidedetails