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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:58 UTC
HMDB IDHMDB01186
Secondary Accession NumbersNone
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
N1-AcetylspermineChEBI
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 KeyInChIKey=GUNURVWAJRRUAV-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
  • Secondary carboxylic acid amide
  • Secondary amine
  • Secondary aliphatic amine
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • 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
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
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 QuantifiedNot ApplicableNot AvailableNot Available
Normal
  • Not Applicable
details
UrineDetected and Quantified0.02 (0.00-0.08) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot ApplicableAdult (>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 QuantifiedNot ApplicableAdult (>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 LinkHMDB01186
Metagene LinkHMDB01186
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. [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