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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:46 UTC
Update Date2023-02-21 17:16:19 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?1676999778
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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-MetCCS_train_neg131.77130932474
[M+H]+MetCCS_train_pos132.9530932474
[M-H]-Not Available131.771http://allccs.zhulab.cn/database/detail?ID=AllCCS00000052
[M+H]+Not Available133.439http://allccs.zhulab.cn/database/detail?ID=AllCCS00000052
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+133.83131661259
DarkChem[M-H]-128.37331661259
DeepCCS[M+H]+135.70430932474
DeepCCS[M-H]-132.64530932474
DeepCCS[M-2H]-169.16930932474
DeepCCS[M+Na]+144.65730932474
AllCCS[M+H]+133.432859911
AllCCS[M+H-H2O]+129.432859911
AllCCS[M+NH4]+137.132859911
AllCCS[M+Na]+138.132859911
AllCCS[M-H]-134.532859911
AllCCS[M+Na-2H]-136.932859911
AllCCS[M+HCOO]-139.632859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N-Acetylcadaverine,1TMS,isomer #1CC(=O)NCCCCCN[Si](C)(C)C1610.2Semi standard non polar33892256
N-Acetylcadaverine,1TMS,isomer #1CC(=O)NCCCCCN[Si](C)(C)C1558.6Standard non polar33892256
N-Acetylcadaverine,1TMS,isomer #1CC(=O)NCCCCCN[Si](C)(C)C2102.9Standard polar33892256
N-Acetylcadaverine,1TMS,isomer #2CC(=O)N(CCCCCN)[Si](C)(C)C1478.6Semi standard non polar33892256
N-Acetylcadaverine,1TMS,isomer #2CC(=O)N(CCCCCN)[Si](C)(C)C1551.2Standard non polar33892256
N-Acetylcadaverine,1TMS,isomer #2CC(=O)N(CCCCCN)[Si](C)(C)C2299.7Standard polar33892256
N-Acetylcadaverine,2TMS,isomer #1CC(=O)N(CCCCCN[Si](C)(C)C)[Si](C)(C)C1583.2Semi standard non polar33892256
N-Acetylcadaverine,2TMS,isomer #1CC(=O)N(CCCCCN[Si](C)(C)C)[Si](C)(C)C1773.2Standard non polar33892256
N-Acetylcadaverine,2TMS,isomer #1CC(=O)N(CCCCCN[Si](C)(C)C)[Si](C)(C)C1775.0Standard polar33892256
N-Acetylcadaverine,2TMS,isomer #2CC(=O)NCCCCCN([Si](C)(C)C)[Si](C)(C)C1841.2Semi standard non polar33892256
N-Acetylcadaverine,2TMS,isomer #2CC(=O)NCCCCCN([Si](C)(C)C)[Si](C)(C)C1762.3Standard non polar33892256
N-Acetylcadaverine,2TMS,isomer #2CC(=O)NCCCCCN([Si](C)(C)C)[Si](C)(C)C1997.8Standard polar33892256
N-Acetylcadaverine,3TMS,isomer #1CC(=O)N(CCCCCN([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C1801.0Semi standard non polar33892256
N-Acetylcadaverine,3TMS,isomer #1CC(=O)N(CCCCCN([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C1917.4Standard non polar33892256
N-Acetylcadaverine,3TMS,isomer #1CC(=O)N(CCCCCN([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C1768.7Standard polar33892256
N-Acetylcadaverine,1TBDMS,isomer #1CC(=O)NCCCCCN[Si](C)(C)C(C)(C)C1860.7Semi standard non polar33892256
N-Acetylcadaverine,1TBDMS,isomer #1CC(=O)NCCCCCN[Si](C)(C)C(C)(C)C1770.2Standard non polar33892256
N-Acetylcadaverine,1TBDMS,isomer #1CC(=O)NCCCCCN[Si](C)(C)C(C)(C)C2143.0Standard polar33892256
N-Acetylcadaverine,1TBDMS,isomer #2CC(=O)N(CCCCCN)[Si](C)(C)C(C)(C)C1687.7Semi standard non polar33892256
N-Acetylcadaverine,1TBDMS,isomer #2CC(=O)N(CCCCCN)[Si](C)(C)C(C)(C)C1755.4Standard non polar33892256
N-Acetylcadaverine,1TBDMS,isomer #2CC(=O)N(CCCCCN)[Si](C)(C)C(C)(C)C2311.6Standard polar33892256
N-Acetylcadaverine,2TBDMS,isomer #1CC(=O)N(CCCCCN[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2074.0Semi standard non polar33892256
N-Acetylcadaverine,2TBDMS,isomer #1CC(=O)N(CCCCCN[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2154.8Standard non polar33892256
N-Acetylcadaverine,2TBDMS,isomer #1CC(=O)N(CCCCCN[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1998.0Standard polar33892256
N-Acetylcadaverine,2TBDMS,isomer #2CC(=O)NCCCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2263.0Semi standard non polar33892256
N-Acetylcadaverine,2TBDMS,isomer #2CC(=O)NCCCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2171.5Standard non polar33892256
N-Acetylcadaverine,2TBDMS,isomer #2CC(=O)NCCCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2095.2Standard polar33892256
N-Acetylcadaverine,3TBDMS,isomer #1CC(=O)N(CCCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2434.7Semi standard non polar33892256
N-Acetylcadaverine,3TBDMS,isomer #1CC(=O)N(CCCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2473.9Standard non polar33892256
N-Acetylcadaverine,3TBDMS,isomer #1CC(=O)N(CCCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2116.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - N-Acetylcadaverine GC-MS (Non-derivatized) - 70eV, Positivesplash10-001l-9000000000-06147dfcd9c450f9f4182017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Acetylcadaverine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylcadaverine 10V, Positive-QTOFsplash10-0ufs-3900000000-9d16b7430dbb509b83ed2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylcadaverine 20V, Positive-QTOFsplash10-0udi-9800000000-e75e37d1af196e17b6ea2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylcadaverine 40V, Positive-QTOFsplash10-05nf-9000000000-4ae88c31526f55eef5592016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylcadaverine 10V, Negative-QTOFsplash10-0006-2900000000-20b0aeef985ef2a34ffe2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylcadaverine 20V, Negative-QTOFsplash10-0udi-5900000000-e747329b2881eb734d0e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylcadaverine 40V, Negative-QTOFsplash10-052f-9000000000-ca12c55eb237562ff8e12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylcadaverine 10V, Positive-QTOFsplash10-004s-2900000000-8d912fec58d282ee38f22021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylcadaverine 20V, Positive-QTOFsplash10-000i-9200000000-d196f42d15b308ed06ec2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylcadaverine 40V, Positive-QTOFsplash10-052f-9000000000-c75b850b1f4d70c9dc3e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylcadaverine 10V, Negative-QTOFsplash10-0006-3900000000-d74b7ce74028d6624d602021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylcadaverine 20V, Negative-QTOFsplash10-0a4i-9000000000-9981f655f72c6898948d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylcadaverine 40V, Negative-QTOFsplash10-0006-9000000000-6887861a6c20fdd3a3dc2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
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
MarkerDB IDNot Available
Good Scents 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 ]