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Record Information
Version3.6
Creation Date2006-05-22 14:17:39 UTC
Update Date2017-09-14 00:33:32 UTC
HMDB IDHMDB0002172
Secondary Accession Numbers
  • HMDB02172
Metabolite Identification
Common NameN1,N12-Diacetylspermine
DescriptionN1,N12-Diacetylspermine is a polyamine commonly occurring in normal human urine (PMID 7775374 ). It has been reported that urinary N1,N12-Diacetylspermine can be used as a marker to efficiently detect colorectal and breast cancers at early stages (PMID 15837752 ).
Structure
Thumb
Synonyms
ValueSource
DASpmChEBI
N',n''-diacetylspermineMeSH
DiacetylspermineMeSH
Chemical FormulaC14H30N4O2
Average Molecular Weight286.4136
Monoisotopic Molecular Weight286.236876224
IUPAC NameN-[3-({4-[(3-acetamidopropyl)amino]butyl}amino)propyl]acetamide
Traditional NameN(1),N(12)-diacetylspermine
CAS Registry Number61345-83-3
SMILES
CC(=O)NCCCNCCCCNCCCNC(C)=O
InChI Identifier
InChI=1S/C14H30N4O2/c1-13(19)17-11-5-9-15-7-3-4-8-16-10-6-12-18-14(2)20/h15-16H,3-12H2,1-2H3,(H,17,19)(H,18,20)
InChI KeyNPDTUDWGJMBVEP-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
  • Secondary amine
  • Secondary aliphatic amine
  • Carboximidic acid
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
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 Solubility0.11 mg/mLALOGPS
logP-0.18ALOGPS
logP-1.8ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)15.99ChemAxon
pKa (Strongest Basic)10.78ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area82.26 Å2ChemAxon
Rotatable Bond Count13ChemAxon
Refractivity81.45 m3·mol-1ChemAxon
Polarizability35.39 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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000j-1290000000-204fd298d8648eb559faView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ufs-5980000000-6a3574952b41f068c5f8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0596-8900000000-64c9b2e7b01bf25fd8beView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-1090000000-59a2a54cb8b30d5401e7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052u-4190000000-a343244608f9fef3983cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-a6138905f79c3078381eView in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    UrineDetected but not Quantified Adult (>18 years old)BothNormal details
    UrineDetected and Quantified0.006 +/- 0.006 umol/mmol creatinineAdult (>18 years old)BothNot Available details
    UrineDetected and Quantified0.00679 (0.000 -0.0260) umol/mmol creatinineAdult (>18 years old)BothNormal details
    Abnormal Concentrations
    BiofluidStatusValueAgeSexConditionReferenceDetails
    UrineDetected but not Quantified Adult (>18 years old)BothLeukemia details
    UrineDetected and Quantified0.268 +/- 0.166 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 IDFDB022884
    KNApSAcK IDNot Available
    Chemspider ID117134
    KEGG Compound IDC03413
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkNot Available
    NuGOwiki LinkHMDB0002172
    METLIN ID6525
    PubChem Compound132680
    PDB IDNot Available
    ChEBI ID28101
    References
    Synthesis ReferenceNot Available
    Material Safety Data Sheet (MSDS)Not Available
    General References
    1. van den Berg GA, Muskiet FA, Kingma AW, van der Slik W, Halie MR: Simultaneous gas-chromatographic determination of free and acetyl-conjugated polyamines in urine. Clin Chem. 1986 Oct;32(10):1930-7. [PubMed:3757213 ]
    2. 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 ]
    3. Enjoji M, Kotoh K, Nakamuta M: [Factors affecting the increase of urinary diacetylspermine levels : a study in patients with liver diseases]. Rinsho Byori. 2006 Feb;54(2):126-31. [PubMed:16548232 ]
    4. Shimpo K, Chihara T, Hibiya M, Ito S, Nagatsu T: [Amines and pteridines]. Nihon Rinsho. 1996 Jun;54(6):1515-20. [PubMed:8691603 ]
    5. Hiramatsu K, Takahashi K, Yamaguchi T, Matsumoto H, Miyamoto H, Tanaka S, Tanaka C, Tamamori Y, Imajo M, Kawaguchi M, Toi M, Mori T, Kawakita M: N(1),N(12)-Diacetylspermine as a sensitive and specific novel marker for early- and late-stage colorectal and breast cancers. Clin Cancer Res. 2005 Apr 15;11(8):2986-90. [PubMed:15837752 ]
    6. Hiramatsu K, Sugimoto M, Kamei S, Hoshino M, Kinoshita K, Iwasaki K, Kawakita M: Diagnostic and prognostic usefulness of N1,N8-diacetylspermidine and N1,N12-diacetylspermine in urine as novel markers of malignancy. J Cancer Res Clin Oncol. 1997;123(10):539-45. [PubMed:9393587 ]

    Enzymes

    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,N12-Diacetylspermine + Oxygen + Water → N1-Acetylspermidine + 3-Acetamidobutanal + Hydrogen peroxidedetails