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Record Information
Version3.6
Creation Date2006-05-22 14:17:46 UTC
Update Date2017-07-18 21:42:23 UTC
HMDB IDHMDB02284
Secondary Accession NumbersNone
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 ).
Structure
Thumb
Synonyms
ValueSource
AcetylcadaverineHMDB
Monoacetyl cadaverineHMDB
N-(5-Aminopentyl)acetamideHMDB
MonoacetylcadaverineMeSH
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
DescriptionThis compound belongs to the class of chemical entities known as acetamides. These are organic compounds with the general formula RNHC(=O)CH3, where R= organyl group.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and 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
StatusDetected and Quantified
Origin
  • Endogenous
  • Microbial
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity41.42 m3·mol-1ChemAxon
Polarizability17.36 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Feces
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    UrineDetected and Quantified0.16 (0.04-0.87) umol/mmol creatinineAdult (>18 years old)BothNormal details
    UrineDetected but not Quantified Adult (>18 years old)BothNormal details
    UrineDetected and Quantified0.279 +/- 0.17 umol/mmol creatinineAdult (>18 years old)BothNot Available details
    Abnormal Concentrations
    BiofluidStatusValueAgeSexConditionReferenceDetails
    FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
    UrineDetected but not Quantified Adult (>18 years old)BothLeukemia details
    UrineDetected and Quantified0.460 +/- 0.232 umol/mmol creatinineAdult (>18 years old)BothLeukemia details
    Associated Disorders and Diseases
    Disease ReferencesNone
    Associated OMIM IDsNone
    DrugBank IDNot Available
    DrugBank Metabolite IDNot Available
    Phenol Explorer Compound IDNot Available
    Phenol Explorer Metabolite IDNot Available
    FoodDB IDFDB022947
    KNApSAcK IDNot Available
    Chemspider ID164295
    KEGG Compound IDNot Available
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkNot Available
    NuGOwiki LinkHMDB02284
    Metagene LinkHMDB02284
    METLIN IDNot Available
    PubChem Compound189087
    PDB IDNot Available
    ChEBI 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 ]