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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2018-05-20 20:23:10 UTC
HMDB IDHMDB0001186
Secondary Accession Numbers
  • HMDB01186
Metabolite Identification
Common NameN1-Acetylspermine
DescriptionN1-Acetylspermine 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. N1-Acetylspermine is considered to be a practically insoluble (in water) and relatively neutral molecule. N1-Acetylspermine has been detected in multiple biofluids, such as urine and blood. Within the cell, N1-acetylspermine is primarily located in the cytoplasm. N1-Acetylspermine exists in all eukaryotes, ranging from yeast to humans.
Structure
Thumb
Synonyms
ValueSource
N'-acetylspermineHMDB
N'-monoacetylspermineHMDB
N(1)-AcetylspermineHMDB
N-(3-((4-((3-Aminopropyl)amino)butyl)amino)propyl)-acetamideHMDB
N-AcetylspermineHMDB
Chemical FormulaC12H28N4O
Average Molecular Weight244.3769
Monoisotopic Molecular Weight244.226311538
IUPAC NameN-[3-({4-[(3-aminopropyl)amino]butyl}amino)propyl]acetamide
Traditional NameN(1)-acetylspermine
CAS Registry Number25593-72-0
SMILES
CC(=O)NCCCNCCCCNCCCN
InChI Identifier
InChI=1S/C12H28N4O/c1-12(17)16-11-5-10-15-8-3-2-7-14-9-4-6-13/h14-15H,2-11,13H2,1H3,(H,16,17)
InChI KeyGUNURVWAJRRUAV-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Amino acid or derivatives
  • Secondary carboxylic acid amide
  • Secondary aliphatic amine
  • Secondary amine
  • Amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

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 Solubility0.37 g/LALOGPS
logP-0.42ALOGPS
logP-1.6ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)16.3ChemAxon
pKa (Strongest Basic)10.97ChemAxon
Physiological Charge3ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area79.18 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity72 m³·mol⁻¹ChemAxon
Polarizability30.68 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-053u-9500000000-5c7387f6650bc2bf5ef8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0097-0960000000-75020060f674e61ca7f5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-01ot-9500000000-f7fc690c89dd182bd5eeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-001i-9100000000-1d31e6d5c8f815f68e8cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0002-0090000000-09b81054799f3b804bf7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-00ba-0920000000-661cc70e5955c3a4423eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0ik9-1900000000-99bd1a086e687629194dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0il0-5900000000-181066e0b9be9cd09644View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-001i-9300000000-0ab0b3f7fb3eb674343eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-00b9-0910000000-0ded9399ebe4b3d25073View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-0udi-0900000000-54a2cb1d413b63cacb96View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-03di-0900000000-2b9ff6380c30a974293fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-0udi-1900000000-92a251b4b894d28948c1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-03di-0900000000-4a8af7c0a23d4640e59aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0wc1-1910000000-df55bc991e81a351aaaaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0002-0090000000-c97bc5d03865a29035daView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00ba-0920000000-661cc70e5955c3a4423eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0ik9-1900000000-99bd1a086e687629194dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0il0-5900000000-340f89e5c24ffe902e34View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-9300000000-0ab0b3f7fb3eb674343eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-00b9-0910000000-e41b450aa8714c83814bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0wc1-1910000000-df55bc991e81a351aaaaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-1190000000-fdfc5d534abbe87c4ab3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udl-5390000000-a40765d256460b16ca9dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9100000000-2077f0d214e318d0356aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ufs-1590000000-3b92c9c12eeed9205679View 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)
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    UrineDetected and Quantified0.02 (0.00-0.08) umol/mmol creatinineAdult (>18 years old)BothNormal details
    UrineDetected but not Quantified Adult (>18 years old)BothNormal details
    UrineDetected and Quantified0.010 +/ 0.006 umol/mmol creatinineAdult (>18 years old)BothNot Available details
    Abnormal Concentrations
    BiospecimenStatusValueAgeSexConditionReferenceDetails
    UrineDetected but not Quantified Adult (>18 years old)BothLeukemia details
    UrineDetected and Quantified0.239 +/- 0.123 umol/mmol creatinineAdult (>18 years old)BothLeukemia details
    Associated Disorders and Diseases
    Disease References
    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 IDsNone
    DrugBank IDNot Available
    Phenol Explorer Compound IDNot Available
    FoodDB IDFDB022474
    KNApSAcK IDNot Available
    Chemspider ID892
    KEGG Compound IDC02567
    BioCyc IDN1-ACETYLSPERMINE
    BiGG IDNot Available
    Wikipedia LinkNot Available
    METLIN ID3369
    PubChem Compound916
    PDB IDSP5
    ChEBI ID17312
    References
    Synthesis ReferenceNot Available
    Material Safety Data Sheet (MSDS)Download (PDF)
    General References
    1. Fogel WA, Maslinski C: The FAD dependent amine oxidases in relation to developmental state of enterocyte. J Neural Transm Suppl. 1994;41:95-9. [PubMed:7931271 ]

    Only showing the first 10 proteins. There are 29 proteins in total.

    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
    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
    General function:
    Amino acid transport and metabolism
    Specific function:
    Flavoenzyme which catalyzes the oxidation of N(1)-acetylspermine to spermidine and is thus involved in the polyamine back-conversion. Can also oxidize N(1)-acetylspermidine to putrescine. Substrate specificity: N(1)-acetylspermine = N(1)-acetylspermidine > N(1),N(12)-diacylspermine >> spermine. Does not oxidize spermidine. Plays an important role in the regulation of polyamine intracellular concentration and has the potential to act as a determinant of cellular sensitivity to the antitumor polyamine analogs.
    Gene Name:
    PAOX
    Uniprot ID:
    Q6QHF9
    Molecular weight:
    55512.64
    Reactions
    N1-Acetylspermine + Oxygen + Water → Spermidine + Acetamidopropanal + Hydrogen peroxidedetails
    General function:
    Involved in oxidoreductase activity, acting on CH-OH group of donors
    Specific function:
    Not Available
    Gene Name:
    CHDH
    Uniprot ID:
    Q8NE62
    Molecular weight:
    65358.005
    General function:
    Involved in oxidoreductase activity
    Specific function:
    Not Available
    Gene Name:
    DMGDH
    Uniprot ID:
    Q9UI17
    Molecular weight:
    96810.135
    General function:
    Involved in spermine synthase activity
    Specific function:
    Catalyzes the production of spermine from spermidine and decarboxylated S-adenosylmethionine (dcSAM).
    Gene Name:
    SMS
    Uniprot ID:
    P52788
    Molecular weight:
    35278.2
    General function:
    Involved in oxidoreductase activity
    Specific function:
    Converts gamma-trimethylaminobutyraldehyde into gamma-butyrobetaine. Catalyzes the irreversible oxidation of a broad range of aldehydes to the corresponding acids in an NAD-dependent reaction.
    Gene Name:
    ALDH9A1
    Uniprot ID:
    P49189
    Molecular weight:
    56291.485
    General function:
    Involved in iron ion binding
    Specific function:
    Catalyzes the formation of L-carnitine from gamma-butyrobetaine.
    Gene Name:
    BBOX1
    Uniprot ID:
    O75936
    Molecular weight:
    44714.6
    General function:
    Involved in transferase activity, transferring pentosyl groups
    Specific function:
    Catalyzes the reversible phosphorylation of S-methyl-5'-thioadenosine (MTA) to adenine and 5-methylthioribose-1-phosphate. Involved in the breakdown of MTA, a major by-product of polyamine biosynthesis. Responsible for the first step in the methionine salvage pathway after MTA has been generated from S-adenosylmethionine. Has broad substrate specificity with 6-aminopurine nucleosides as preferred substrates.
    Gene Name:
    MTAP
    Uniprot ID:
    Q13126
    Molecular weight:
    31235.76
    General function:
    Involved in adenosylmethionine decarboxylase activity
    Specific function:
    Not Available
    Gene Name:
    AMD1
    Uniprot ID:
    P17707
    Molecular weight:
    21301.015

    Only showing the first 10 proteins. There are 29 proteins in total.