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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:34 UTC
Update Date2017-10-23 19:03:56 UTC
HMDB IDHMDB0002064
Secondary Accession Numbers
  • HMDB02064
Metabolite Identification
Common NameN-Acetylputrescine
DescriptionN-Acetylputrescine is a polyamine commonly occurring excreted in normal human urine (PMID 7775374 ). N-Acetylputrescine is the most abundant of all polyamines both in normal individuals and in patients with leukemia (PMID 9464484 ). N-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, but also contribute to the odor of such processes as bad breath and bacterial vaginosis. Putrescine is also found in semen. 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
ValueSource
AcetylputrescineHMDB
MonoacetylputrescineHMDB
N-(4-Aminobutyl)acetamideHMDB
N-Acetylputrescine monohydrochlorideMeSH
Chemical FormulaC6H14N2O
Average Molecular Weight130.1882
Monoisotopic Molecular Weight130.11061308
IUPAC NameN-(4-aminobutyl)acetamide
Traditional Nameacetylputrescine
CAS Registry Number18233-70-0
SMILES
CC(=O)NCCCCN
InChI Identifier
InChI=1S/C6H14N2O/c1-6(9)8-5-3-2-4-7/h2-5,7H2,1H3,(H,8,9)
InChI KeyKLZGKIDSEJWEDW-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as carboximidic acids. These are organic acids with the general formula RC(=N)-OH (R=H, organic group).
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboximidic acids and derivatives
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
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

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 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
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
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
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
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected and Quantified5.06 +/- 7.64 uMAdult (>18 years old)Male
    Normal
      • Sugimoto et al. (...
    details
    SalivaDetected and Quantified1.04 +/- 0.694 uMAdult (>18 years old)Female
    Normal
      • Sugimoto et al. (...
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    UrineDetected and Quantified1.18 (0.58-2.25) umol/mmol creatinineAdult (>18 years old)BothNormal details
    UrineDetected but not Quantified Adult (>18 years old)BothNormal details
    UrineDetected and Quantified0.827 +/- 0.615 umol/mmol creatinineAdult (>18 years old)BothNot Available details
    UrineDetected and Quantified1.2 +/- 0.079 umol/mmol creatinineAdult (>18 years old)BothNormal details
    UrineDetected and Quantified0.5 (0.4-0.7) umol/mmol creatinineAdult (>18 years old)Both
    Normal
    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 Quantified2.66 +/- 1.45 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 IDFDB022827
    KNApSAcK IDNot Available
    Chemspider ID109095
    KEGG Compound IDC02714
    BioCyc IDCPD-569
    BiGG ID1445791
    Wikipedia LinkNot Available
    METLIN ID3252
    PubChem Compound122356
    PDB IDNot Available
    ChEBI ID17768
    References
    Synthesis ReferenceNot Available
    Material Safety Data Sheet (MSDS)Download (PDF)
    General References
    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 ]
    2. 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 ]
    3. 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 ]
    4. 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. 1995 Jan;117(1):107-12. [PubMed:7775374 ]
    5. 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. 1994 Mar;115(3):584-9. [PubMed:8056776 ]

    Enzymes

    General function:
    Involved in N-acetyltransferase activity
    Specific function:
    Enzyme which catalyzes the acetylation of polyamines. Substrate specificity: norspermidine > spermidine = spermine >> N(1)acetylspermine = putrescine.
    Gene Name:
    SAT2
    Uniprot ID:
    Q96F10
    Molecular weight:
    19154.905
    Reactions
    Acetyl-CoA + Putrescine → Coenzyme A + N-Acetylputrescinedetails
    General function:
    Involved in N-acetyltransferase activity
    Specific function:
    Enzyme which catalyzes the acetylation of polyamines. Substrate specificity: norspermidine = spermidine >> spermine > N(1)-acetylspermine > putrescine. This highly regulated enzyme allows a fine attenuation of the intracellular concentration of polyamines. Also involved in the regulation of polyamine transport out of cells. Acts on 1,3-diaminopropane, 1,5-diaminopentane, putrescine, spermidine (forming N(1)- and N(8)-acetylspermidine), spermine, N(1)-acetylspermidine and N(8)-acetylspermidine.
    Gene Name:
    SAT1
    Uniprot ID:
    P21673
    Molecular weight:
    20023.8
    Reactions
    Acetyl-CoA + Putrescine → Coenzyme A + N-Acetylputrescinedetails
    General function:
    Involved in oxidoreductase activity
    Specific function:
    Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOB preferentially degrades benzylamine and phenylethylamine.
    Gene Name:
    MAOB
    Uniprot ID:
    P27338
    Molecular weight:
    58762.475
    Reactions
    N-Acetylputrescine + Water + Oxygen → N4-Acetylaminobutanal + Ammonia + Hydrogen peroxidedetails
    General function:
    Involved in oxidoreductase activity
    Specific function:
    Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
    Gene Name:
    MAOA
    Uniprot ID:
    P21397
    Molecular weight:
    59681.27
    Reactions
    N-Acetylputrescine + Water + Oxygen → N4-Acetylaminobutanal + Ammonia + Hydrogen peroxidedetails