Record Information
Version2.0
Creation Date2012-05-31 13:55:18 -0600
Update Date2015-09-13 12:56:12 -0600
Secondary Accession Numbers
  • ECMDB02064
Identification
Name:N-Acetylputrescine
DescriptionN-Acetylputrescine is the N-acetylated form of the naturally occurring polyamine called putrescine. The N-acetylation is mediated by the enzyme diamine N-acetyltransferase. Putrescine is related to cadaverine (another polyamine). Both are produced by the breakdown of amino acids in living and dead organisms and both are toxic in large doses. Putrescine and cadaverine are largely responsible for the foul odor of putrefying flesh. Putrescine attacks s-adenosyl methionine and converts it to spermidine. Spermidine in turn attacks another s-adenosyl methionine and converts it to spermine. Putrescine is synthesized in small quantities by healthy living cells by the action of ornithine decarboxylase.
Structure
Thumb
Synonyms:
  • Acetylputrescine
  • Monoacetylputrescine
  • N-(4-Aminobutyl)acetamide
Chemical Formula:C6H14N2O
Weight:Average: 130.1882
Monoisotopic: 130.11061308
InChI Key:KLZGKIDSEJWEDW-UHFFFAOYSA-N
InChI:InChI=1S/C6H14N2O/c1-6(9)8-5-3-2-4-7/h2-5,7H2,1H3,(H,8,9)
CAS number:18233-70-0
IUPAC Name:N-(4-aminobutyl)acetamide
Traditional IUPAC Name:acetylputrescine
SMILES:CC(=O)NCCCCN
Chemical Taxonomy
Description belongs to the class of organic compounds known as carboximidic acids. These are organic acids with the general formula RC(=N)-OH (R=H, organic group).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboximidic acids and derivatives
Sub ClassCarboximidic acids
Direct ParentCarboximidic acids
Alternative Parents
Substituents
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidic acid
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility141 g/LALOGPS
logP-0.84ALOGPS
logP-1ChemAxon
logS0.04ALOGPS
pKa (Strongest Acidic)16.48ChemAxon
pKa (Strongest Basic)9.9ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area55.12 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity36.82 m³·mol⁻¹ChemAxon
Polarizability15.28 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:
  • Arginine and proline metabolism ec00330
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00di-2900000000-5ce6ea5fec8a535152b1View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00di-9700000000-99b6d1613ba71642630cView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00di-9700000000-f5b3a7431b349387eaf4View in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0fl9-3900000000-4e71aaf5516b6c95b4c8View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-00dr-5900000000-7f05a246fd26bf66b402View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-2900000000-5ce6ea5fec8a535152b1View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9700000000-99b6d1613ba71642630cView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9700000000-f5b3a7431b349387eaf4View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0fl9-3900000000-4e71aaf5516b6c95b4c8View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00dr-5900000000-7f05a246fd26bf66b402View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0fl9-3900000000-4e71aaf5516b6c95b4c8View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00dr-5900000000-7f05a246fd26bf66b402View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9000000000-8aea84b2256cb4c80b28View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03k9-3900000000-059ca8ad6ad85938c0f9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-9000000000-9dc7efc6c0f52e2a1622View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00di-9100000000-cf5d10d7ed6eaebc6417View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-001i-0900000000-409c4453575d652233d4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0229-9700000000-128ded2b5a97118c2d5dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-00di-9000000000-170cecf2246d1432d9b1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-00di-9000000000-4921ba95eaa0b725f1e9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-00dl-9000000000-6822cd785ae4293a429cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-03k9-4900000000-bee7a2928577d361331eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-0900000000-409c4453575d652233d4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0229-9700000000-128ded2b5a97118c2d5dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-9000000000-170cecf2246d1432d9b1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-9000000000-4921ba95eaa0b725f1e9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00dl-9000000000-6822cd785ae4293a429cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03k9-4900000000-bee7a2928577d361331eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-014i-3900000000-4c6930587dbe03729b9cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-01q9-0900000000-9782f79bcff20398ee5eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-00dl-9000000000-005452a2f31ffdc3b2f5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-000i-9000000000-2615125feb868f3112f3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q0-9600000000-b7657fac110a60062e9bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0079-9000000000-9489cb75eca41b783e8eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0abc-9000000000-4d6f44ed73fd53b37795View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-5900000000-f9c8118634ba3d7bb53cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9200000000-7baa5995e911a5894fd3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9000000000-2afae62bc17432205556View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Abdel-Monem MM, Ohno K: Polyamine metabolism I: Synthesis of dansyl derivatives of N-(monoaminoalkyl)- and N-(polyaminoalkyl)acetamides and elucidation in urine of a cancer patient. J Pharm Sci. 1977 Aug;66(8):1089-94. Pubmed: 197226
  • Hiramatsu K, Kamei S, Sugimoto M, Kinoshita K, Iwasaki K, Kawakita M: An improved method of determining free and acetylated polyamines by HPLC involving an enzyme reactor and an electrochemical detector. J Biochem (Tokyo). 1994 Mar;115(3):584-9. Pubmed: 8056776
  • Hiramatsu K, Sugimoto M, Kamei S, Hoshino M, Kinoshita K, Iwasaki K, Kawakita M: Determination of amounts of polyamines excreted in urine: demonstration of N1,N8-diacetylspermidine and N1,N12-diacetylspermine as components commonly occurring in normal human urine. J Biochem (Tokyo). 1995 Jan;117(1):107-12. Pubmed: 7775374
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • 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
  • Loser C, Folsch UR, Paprotny C, Creutzfeldt W: Polyamines in colorectal cancer. Evaluation of polyamine concentrations in the colon tissue, serum, and urine of 50 patients with colorectal cancer. Cancer. 1990 Feb 15;65(4):958-66. Pubmed: 2297664
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID17768
HMDB IDHMDB02064
Pubchem Compound ID122356
Kegg IDC02714
ChemSpider ID109095
Wikipedia IDNot Available
BioCyc IDCPD-569
EcoCyc IDCPD-569

Enzymes

General function:
Involved in N-acetyltransferase activity
Specific function:
Regulates polyamine concentration by their degradation. Acts on spermidine, forming N(1)- and N(8)-acetylspermidine
Gene Name:
speG
Uniprot ID:
P0A951
Molecular weight:
21887
Reactions
Acetyl-CoA + an alkane-alpha,omega-diamine = CoA + an N-acetyldiamine.