Record Information
Version1.0
Creation date2010-04-08 22:04:59 UTC
Update date2018-05-28 23:06:06 UTC
Primary IDFDB001493
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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 .; Cadaverine is a foul-smelling molecule produced by protein hydrolysis during putrefaction of animal tissue. Cadaverine is a toxic diamine with the formula NH2(CH2)5NH2, which is similar to putrescine. Cadaverine is also known by the names 1,5-pentanediamine and pentamethylenediamine.
CAS Number462-94-2
Structure
Thumb
Synonyms
SynonymSource
CadaverineChEBI
Pentane-1,5-diaminiumChEBI
1,5-Amylene diaminebiospider
1,5-Diamino-n-pentanebiospider
1,5-Diaminopentanebiospider
1,5-Diaminopentane dihydrochloridebiospider
1,5-Pentamethylenediaminebiospider
1,5-Pentanediaminebiospider
Alpha,omega-pentanediaminebiospider
Animal conIInebiospider
BioDex 1-biospider
Cadaverinbiospider
Cadaverine dihydrochloridebiospider
DAPEChEBI
Diaminopentanebiospider
H2N(CH2)5NH2biospider
Pentamethylenediaminebiospider
Pentamethylenediamine dihydrochloridebiospider
Pentane-1,5-diaminebiospider
Predicted Properties
PropertyValueSource
Water Solubility0.27 g/LALOGPS
logP-2ALOGPS
logP-0.4ChemAxon
logS-2.8ALOGPS
pKa (Strongest Basic)10.51ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area55.28 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity54.57 m³·mol⁻¹ChemAxon
Polarizability13.8 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC5H16N2
IUPAC namepentane-1,5-bis(aminium)
InChI IdentifierInChI=1S/C5H14N2/c6-4-2-1-3-5-7/h1-7H2/p+2
InChI KeyVHRGRCVQAFMJIZ-UHFFFAOYSA-P
Isomeric SMILES[NH3+]CCCCC[NH3+]
Average Molecular Weight104.1939
Monoisotopic Molecular Weight104.131348522
Classification
DescriptionThis compound belongs to the class of organic compounds known as quaternary ammonium salts. These are compounds containing positively charged polyatomic ion of the structure NR4+, R being an alkyl group or an aryl group.
KingdomOrganic compounds
Super ClassOrganonitrogen compounds
ClassQuaternary ammonium salts
Sub ClassNot Available
Direct ParentQuaternary ammonium salts
Alternative Parents
Substituents
  • Quaternary ammonium salt
  • Hydrocarbon derivative
  • Amine
  • Organic cation
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting Point9 oC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
SpectraNot Available
ChemSpider ID13866593
ChEMBL IDCHEMBL119296
KEGG Compound IDC01672
Pubchem Compound ID273
Pubchem Substance IDNot Available
ChEBI ID18127
Phenol-Explorer IDNot Available
DrugBank IDDB03854
HMDB IDHMDB02322
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDCADAVERINE
BIGG IDNot Available
KNApSAcK IDC00001403
HET IDN2P
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDCadaverine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
phytohormonal26158 A plant growth regulator that modulates the formation of stems, leaves and flowers, as well as the development and ripening of fruit. The term includes endogenous and non-endogenous compounds (e.g. active compounds produced by bacteria on the leaf surface) as well as semi-synthetic and fully synthetic compounds.DUKE
toxic52209 A role played by the molecular entity or part thereof which causes the development of a pathological process.DUKE
Enzymes
NameGene NameUniProt ID
Spermidine synthaseSRMP19623
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.