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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:46 UTC
Update Date2020-02-26 21:24:01 UTC
HMDB IDHMDB0002284
Secondary Accession Numbers
  • HMDB02284
Metabolite Identification
Common NameN-Acetylcadaverine
DescriptionN-Acetylcadaverine is the acetylated form of the polyamine cadaverine. Cadaverine is produced by the breakdown of amino acids in living and dead organisms and is toxic in large doses. Cadaverine is largely responsible for the foul odor of putrefying flesh, but also contributes to the odor of such processes as bad breath and bacterial vaginosis. Cadaverine is also found in semen. Polyamines (and their acetylated forms) are known to be closely related with cell growth, cell proliferation, and synthesis of proteins and nucleic acids. Their concentrations are adjusted either by regulating the activity levels of the biosynthetic and catabolic reactions or by controlling the net direction of polyamine acetylation-deacetylation. In Alzheimer's disease (AD), the neurotoxic amyloid β-peptide is known to up-regulate polyamine metabolism by increasing ornithine decarboxylase activity and polyamine uptake by initiating free radical damage. Because of these findings, polyamines have been considered to play an important role in response to neurodegenerative conditions. Altered levels of polyamines have been found in tissue, hair and body fluids of patients with neuromuscular diseases and neurodegenerative conditions. (PMID: 17723614 ). N-Acetylcadaverine has been found to be a metabolite of several bacteria species (https://www.sciencedirect.com/science/article/pii/S209580991730423X).
Structure
Data?1582752241
Synonyms
ValueSource
Monoacetyl cadaverineChEBI
MonoacetylcadaverineChEBI
AcetylcadaverineHMDB
N-(5-Aminopentyl)acetamideHMDB
Chemical FormulaC7H16N2O
Average Molecular Weight144.2147
Monoisotopic Molecular Weight144.126263144
IUPAC NameN-(5-aminopentyl)acetamide
Traditional NameN-acetylcadaverine
CAS Registry Number32343-73-0
SMILES
CC(=O)NCCCCCN
InChI Identifier
InChI=1S/C7H16N2O/c1-7(10)9-6-4-2-3-5-8/h2-6,8H2,1H3,(H,9,10)
InChI KeyRMOIHHAKNOFHOE-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as acetamides. These are organic compounds with the general formula RNHC(=O)CH3, where R= organyl group.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassCarboxylic acid derivatives
Direct ParentAcetamides
Alternative Parents
Substituents
  • Acetamide
  • Secondary carboxylic acid amide
  • Amino acid or derivatives
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility23.7 g/LALOGPS
logP-0.4ALOGPS
logP-0.58ChemAxon
logS-0.78ALOGPS
pKa (Strongest Acidic)16.53ChemAxon
pKa (Strongest Basic)10.21ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area55.12 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity41.42 m³·mol⁻¹ChemAxon
Polarizability17.36 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001l-9000000000-06147dfcd9c450f9f418Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ufs-3900000000-9d16b7430dbb509b83edSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-9800000000-e75e37d1af196e17b6eaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05nf-9000000000-4ae88c31526f55eef559Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-2900000000-20b0aeef985ef2a34ffeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-5900000000-e747329b2881eb734d0eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9000000000-ca12c55eb237562ff8e1Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.16 (0.04-0.87) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.279 +/- 0.17 umol/mmol creatinineAdult (>18 years old)BothNot Available details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothLeukemia details
UrineDetected and Quantified0.460 +/- 0.232 umol/mmol creatinineAdult (>18 years old)BothLeukemia details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
Leukemia
  1. Lee SH, Suh JW, Chung BC, Kim SO: Polyamine profiles in the urine of patients with leukemia. Cancer Lett. 1998 Jan 9;122(1-2):1-8. [PubMed:9464484 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022947
KNApSAcK IDNot Available
Chemspider ID164295
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound189087
PDB IDNot Available
ChEBI ID88824
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceSugita, Yuzo; Yoshimura, Yoshinori; Okada, Masato. Manufacture of monoacetylpolyamines with diacetylpolyamine amidohydrolase or microorganisms. Jpn. Kokai Tokkyo Koho (1992), 11 pp. CODEN: JKXXAF JP 04234992 A 19920824 Heisei. CAN 118:21079 AN 1993:21079
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Abdel-Monem MM, Ohno K: Polyamine metabolism II: N-(Monoaminoalkyl)- and N-(polyaminoalkyl)acetamides in human urine. J Pharm Sci. 1977 Aug;66(8):1195-7. [PubMed:894508 ]
  2. Lee SH, Kim SO, Lee HD, Chung BC: Estrogens and polyamines in breast cancer: their profiles and values in disease staging. Cancer Lett. 1998 Nov 13;133(1):47-56. [PubMed:9929159 ]
  3. Paik MJ, Lee S, Cho KH, Kim KR: Urinary polyamines and N-acetylated polyamines in four patients with Alzheimer's disease as their N-ethoxycarbonyl-N-pentafluoropropionyl derivatives by gas chromatography-mass spectrometry in selected ion monitoring mode. Anal Chim Acta. 2006 Aug 18;576(1):55-60. Epub 2006 Feb 24. [PubMed:17723614 ]