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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:23:02 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 a very strong basic compound (based on its pKa). N1-Acetylspermine exists in all living species, ranging from bacteria to humans. Outside of the human body, N1-Acetylspermine has been detected, but not quantified in, several different foods, such as purple lavers, jutes, yams, pineapples, and fireweeds. This could make N1-acetylspermine a potential biomarker for the consumption of these foods. N1-Acetylspermine is a polyamine that has been postulated to be an intermediate in the conversion of spermine to spermidine.
Structure
Data?1582752182
Synonyms
ValueSource
N'-acetylspermineHMDB
N'-monoacetylspermineHMDB
N(1)-AcetylspermineHMDB
N-(3-((4-((3-Aminopropyl)amino)butyl)amino)propyl)-acetamideHMDB
N-AcetylspermineHMDB
N1-AcetylspermineChEBI
MonoacetylspermineHMDB
N1-MonoacetylspermineHMDB
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
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
  • 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)10.79ChemAxon
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-053u-9500000000-5c7387f6650bc2bf5ef8Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0097-0960000000-75020060f674e61ca7f5Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-01ot-9500000000-f7fc690c89dd182bd5eeSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-001i-9100000000-1d31e6d5c8f815f68e8cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0002-0090000000-09b81054799f3b804bf7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-00ba-0920000000-661cc70e5955c3a4423eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0ik9-1900000000-99bd1a086e687629194dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0il0-5900000000-181066e0b9be9cd09644Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-001i-9300000000-0ab0b3f7fb3eb674343eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-00b9-0910000000-0ded9399ebe4b3d25073Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-0udi-0900000000-54a2cb1d413b63cacb96Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-03di-0900000000-2b9ff6380c30a974293fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-0udi-1900000000-92a251b4b894d28948c1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-03di-0900000000-4a8af7c0a23d4640e59aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0wc1-1910000000-df55bc991e81a351aaaaSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0002-0090000000-c97bc5d03865a29035daSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00ba-0920000000-661cc70e5955c3a4423eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0ik9-1900000000-99bd1a086e687629194dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0il0-5900000000-340f89e5c24ffe902e34Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-9300000000-0ab0b3f7fb3eb674343eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-00b9-0910000000-e41b450aa8714c83814bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0wc1-1910000000-df55bc991e81a351aaaaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-1190000000-fdfc5d534abbe87c4ab3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udl-5390000000-a40765d256460b16ca9dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9100000000-2077f0d214e318d0356aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ufs-1590000000-3b92c9c12eeed9205679Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Placenta
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
    FooDB IDFDB022474
    KNApSAcK IDNot Available
    Chemspider ID892
    KEGG Compound IDC02567
    BioCyc IDN1-ACETYLSPERMINE
    BiGG IDNot Available
    Wikipedia LinkNot Available
    METLIN ID3369
    PubChem Compound916
    PDB IDNot Available
    ChEBI ID17312
    Food Biomarker OntologyNot Available
    VMH IDN1SPRM
    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 ]
    2. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

    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.