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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-08-16 03:37:56 UTC
HMDB IDHMDB0001186
Secondary Accession Numbers
  • HMDB01186
Metabolite Identification
Common NameN1-Acetylspermine
DescriptionN1-Acetylspermine is a polyamine that has been postulated to be an intermediate in the conversion of spermine to spermidine.
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 chemical entities known as acetamides. These are organic compounds with the general formula RNHC(=O)CH3, where R= organyl group.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and 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
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count12ChemAxon
Refractivity72 m3·mol-1ChemAxon
Polarizability30.68 Å3ChemAxon
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-MSNot Available
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 , positivesplash10-0il0-5900000000-340f89e5c24ffe902e34View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00b9-0910000000-e41b450aa8714c83814bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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
    BiofluidStatusValueAgeSexConditionReferenceDetails
    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 ReferencesNone
    Associated OMIM IDsNone
    DrugBank IDNot Available
    DrugBank Metabolite IDNot Available
    Phenol Explorer Compound IDNot Available
    Phenol Explorer Metabolite IDNot Available
    FoodDB IDFDB022474
    KNApSAcK IDNot Available
    Chemspider ID892
    KEGG Compound IDC02567
    BioCyc IDN1-ACETYLSPERMINE
    BiGG IDNot Available
    Wikipedia LinkNot Available
    NuGOwiki LinkHMDB0001186
    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 ]

    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
    General function:
    Amino acid transport and metabolism
    Specific function:
    Catalyzes the biosynthesis of guanidinoacetate, the immediate precursor of creatine. Creatine plays a vital role in energy metabolism in muscle tissues. May play a role in embryonic and central nervous system development. May be involved in the response to heart failure by elevating local creatine synthesis.
    Gene Name:
    GATM
    Uniprot ID:
    P50440
    Molecular weight:
    48455.01
    General function:
    Involved in zinc ion binding
    Specific function:
    Involved in the regulation of homocysteine metabolism. Converts betaine and homocysteine to dimethylglycine and methionine, respectively. This reaction is also required for the irreversible oxidation of choline.
    Gene Name:
    BHMT
    Uniprot ID:
    Q93088
    Molecular weight:
    44998.205
    General function:
    Involved in oxidoreductase activity
    Specific function:
    Not Available
    Gene Name:
    SARDH
    Uniprot ID:
    Q9UL12
    Molecular weight:
    101035.985
    General function:
    Involved in carboxy-lyase activity
    Specific function:
    Catalyzes the biosynthesis of histamine from histidine.
    Gene Name:
    HDC
    Uniprot ID:
    P19113
    Molecular weight:
    74139.825
    General function:
    Involved in catalytic activity
    Specific function:
    Not Available
    Gene Name:
    ODC1
    Uniprot ID:
    P11926
    Molecular weight:
    51147.73
    General function:
    Secondary metabolites biosynthesis, transport and catabolism
    Specific function:
    Flavoenzyme which catalyzes the oxidation of spermine to spermidine. Can also use N(1)-acetylspermine and spermidine as substrates, with different affinity depending on the isoform (isozyme) and on the experimental conditions. 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. May contribute to beta-alanine production via aldehyde dehydrogenase conversion of 3-amino-propanal.
    Gene Name:
    SMOX
    Uniprot ID:
    Q9NWM0
    Molecular weight:
    65006.29
    General function:
    Involved in agmatinase activity
    Specific function:
    Not Available
    Gene Name:
    AGMAT
    Uniprot ID:
    Q9BSE5
    Molecular weight:
    37660.065
    General function:
    Involved in oxidation reduction
    Specific function:
    Converts trimethyllysine (TML) into hydroxytrimethyllysine (HTML).
    Gene Name:
    TMLHE
    Uniprot ID:
    Q9NVH6
    Molecular weight:
    44048.895
    General function:
    Involved in zinc ion binding
    Specific function:
    Involved in the regulation of homocysteine metabolism. Converts homocysteine to methionine using S-methylmethionine (SMM) as a methyl donor.
    Gene Name:
    BHMT2
    Uniprot ID:
    Q9H2M3
    Molecular weight:
    33166.69
    General function:
    Involved in GTP binding
    Specific function:
    Not Available
    Gene Name:
    GIMAP1
    Uniprot ID:
    Q8WWP7
    Molecular weight:
    34368.9
    General function:
    Involved in GTP binding
    Specific function:
    Not Available
    Gene Name:
    GIMAP2
    Uniprot ID:
    Q9UG22
    Molecular weight:
    38016.9
    General function:
    Involved in GTP binding
    Specific function:
    Exhibits intrisinic GTPase activity. Shows a higher affinity for GDP over GTP (about 12-fold higher), and binding shows an absolute requirement for magnesium
    Gene Name:
    GIMAP4
    Uniprot ID:
    Q9NUV9
    Molecular weight:
    37533.5
    General function:
    Involved in GTP binding
    Specific function:
    Required for mitochondrial integrity and T-cell survival. May contribute to T-cell quiescence
    Gene Name:
    GIMAP5
    Uniprot ID:
    Q96F15
    Molecular weight:
    34845.7
    General function:
    Involved in GTP binding
    Specific function:
    Not Available
    Gene Name:
    GIMAP6
    Uniprot ID:
    Q6P9H5
    Molecular weight:
    32948.6
    General function:
    Involved in GTP binding
    Specific function:
    Not Available
    Gene Name:
    GIMAP7
    Uniprot ID:
    Q8NHV1
    Molecular weight:
    34508.2
    General function:
    Involved in GTP binding
    Specific function:
    Exerts an anti-apoptotic effect in the immune system and is involved in responses to infections
    Gene Name:
    GIMAP8
    Uniprot ID:
    Q8ND71
    Molecular weight:
    74889.6
    General function:
    Involved in oxidoreductase activity
    Specific function:
    Decreases the sensitivity of PDP1 to magnesium ions, and this inhibition is reversed by the polyamine spermine
    Gene Name:
    PDPR
    Uniprot ID:
    Q8NCN5
    Molecular weight:
    99363.7
    General function:
    Involved in enzyme inhibitor activity
    Specific function:
    Binds to, and destabilizes, ornithine decarboxylase which is then degraded. Also inhibits cellular uptake of polyamines by inactivating the polyamine uptake transporter. SMAD1/OAZ1/PSMB4 complex mediates the degradation of the CREBBP/EP300 repressor SNIP1
    Gene Name:
    OAZ1
    Uniprot ID:
    P54368
    Molecular weight:
    25405.3
    General function:
    Involved in leucine zipper domain binding
    Specific function:
    Part of the MIS12 complex which is required for normal chromosome alignment and segregation and kinetochore formation during mitosis. May act as a cotranscription partner of NFE2L2 involved in regulation of polyamine-induced transcription of SSAT
    Gene Name:
    PMF1
    Uniprot ID:
    Q6P1K2
    Molecular weight:
    23339.2