Showing Compound Card for Cadaverine (CDB006154)

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Record Information
Version1.0
Created at2020-03-18 23:21:55 UTC
Updated at2020-12-07 19:06:56 UTC
CannabisDB IDCDB006154
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameCadaverine
DescriptionCadaverine, also known as 1,5-diaminopentane, belongs to the class of organic compounds known as monoalkylamines. These are organic compounds containing a primary aliphatic amine group. Cadaverine is a strong basic compound (based on its pKa). Cadaverine is a foul-smelling diamine formed by bacterial decarboxylation of lysine that occurs during protein hydrolysis during putrefaction of animal and/or plant tissue. However, cadaverine 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 has been shown to bind to mammalian trace amine associated receptors TAAR6 and TAAR8 ( PMID: 29324768 ) and to act as a “necromone” triggering avoidance or attractive responses, which are fundamental for the survival of a wide range of species. Cadaverine is toxic in large doses. In rats it has a low acute oral toxicity of more than 2000 mg/kg body weight ( PMID: 9207896 ). Cadaverine can be naturally found in some bacterial species including Corynebacterium (PMID: 27872963 ). In addition many plants have been found to synthesize it. For instance, plants from the Leguminosae family have been shown to produce cadaverine and use it as a precursor in the biosynthesis of quinolizidine alkaloids. Quinolizidine alkaloids are secondary metabolites that are involved in insect defense and also display therapeutic pharmacological properties.
Structure
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MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
SynonymsNot Available
Chemical FormulaC5H14N2
Average Molecular Weight102.18
Monoisotopic Molecular Weight102.1157
IUPAC Name(3R,3aS,5S)-3,8-dimethyl-5-(prop-1-en-2-yl)-1,2,3,3a,4,5,6,7-octahydroazulene
Traditional Name(1R,7S,8aS)-1,4-dimethyl-7-(prop-1-en-2-yl)-1,2,3,5,6,7,8,8a-octahydroazulene
CAS Registry Number462-94-2
SMILES
NCCCCCN
InChI Identifier
InChI=1S/C5H14N2/c6-4-2-1-3-5-7/h1-7H2
InChI KeyVHRGRCVQAFMJIZ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentSesquiterpenoids
Alternative Parents
Substituents
  • Sesquiterpenoid
  • Branched unsaturated hydrocarbon
  • Polycyclic hydrocarbon
  • Cyclic olefin
  • Unsaturated aliphatic hydrocarbon
  • Unsaturated hydrocarbon
  • Olefin
  • Hydrocarbon
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect

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Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point9 °CNot Available
Boiling Point179.1 °CWikipedia
Water SolubilityNot AvailableNot Available
logP0.0Wikipedia
Predicted Properties
PropertyValueSource
logP5.61ALOGPS
logP4.46ChemAxon
logS-4ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity67.26 m³·mol⁻¹ChemAxon
Polarizability26.26 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available2020-06-30View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound91753506
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Izquierdo C, Gomez-Tamayo JC, Nebel JC, Pardo L, Gonzalez A: Identifying human diamine sensors for death related putrescine and cadaverine molecules. PLoS Comput Biol. 2018 Jan 11;14(1):e1005945. doi: 10.1371/journal.pcbi.1005945. eCollection 2018 Jan. [PubMed:29324768 ]
  2. Til HP, Falke HE, Prinsen MK, Willems MI: Acute and subacute toxicity of tyramine, spermidine, spermine, putrescine and cadaverine in rats. Food Chem Toxicol. 1997 Mar-Apr;35(3-4):337-48. doi: 10.1016/s0278-6915(97)00121-x. [PubMed:9207896 ]
  3. Wendisch VF: Microbial Production of Amino Acid-Related Compounds. Adv Biochem Eng Biotechnol. 2017;159:255-269. doi: 10.1007/10_2016_34. [PubMed:27872963 ]