Record Information
Version1.0
Creation date2010-04-08 22:05:42 UTC
Update date2018-05-29 00:37:28 UTC
Primary IDFDB003225
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameSpermine
DescriptionOccurs as phosphate in ox pancreas, yeast and meat products Spermine is a polyamine involved in cellular metabolism found in all eukaryotic cells. Formed from spermidine, it is found in a wide variety of organisms and tissues and is an essential growth factor in some bacteria. It is found as a polycation at physiological pH. Spermine is associated with nucleic acids and is thought to stabilize helical structure, in particular, in viruses.
CAS Number71-44-3
Structure
Thumb
Synonyms
SynonymSource
4,9-Diaza-1,12-dodecanediamineChEBI
4,9-Diazadodecane-1,12-diamineChEBI
N,N'-bis(3-aminopropyl)-1,4-butanediamineChEBI
1,5,10,14-TetraazatetradecaneHMDB
4,9-DiazadodecamethylenediamineHMDB
Diaminopropyl-tetramethylenediamineHMDB
DiaminopropyltetramethylenediamineHMDB
GerontineHMDB
MusculamineHMDB
N,N'-bis(3-aminopropyl)-1,4-tetramethylenediamineHMDB
N,N'-bis(3-aminopropyl)butane-1,4-diamineHMDB
N1,N4-Bis(3-aminopropyl)-1,4-butanediamineHMDB
NeuridineHMDB
SperminHMDB
Spermine dihydrateHMDB
Spermine purissHMDB
SPMHMDB
1,4-Bis(aminopropyl)butanediaminebiospider
Bis(3-aminopropyl)tetramethylenediaminedb_source
N,N'-Bis(3-aminopropyl)-1,4-butanediamine, 9CIdb_source
N,N'-Bis(3-aminopropyl)-1,4-diaminobutanebiospider
N,N'-Bis(3-aminopropyl)-1,4-tetramethylenediaminebiospider
N,N'-Bis(3-aminopropyl)butane-1,4-diaminebiospider
N,N'-bis(aminopropyl)-1,4-butanediaminebiospider
N1,N4-bis(3-aminopropyl)-1,4-butanediaminebiospider
Predicted Properties
PropertyValueSource
Water Solubility2.19 g/LALOGPS
logP-0.66ALOGPS
logP-1.5ChemAxon
logS-2ALOGPS
pKa (Strongest Basic)10.8ChemAxon
Physiological Charge4ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area76.1 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity62.56 m³·mol⁻¹ChemAxon
Polarizability26.69 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC10H26N4
IUPAC name(3-aminopropyl)({4-[(3-aminopropyl)amino]butyl})amine
InChI IdentifierInChI=1S/C10H26N4/c11-5-3-9-13-7-1-2-8-14-10-4-6-12/h13-14H,1-12H2
InChI KeyPFNFFQXMRSDOHW-UHFFFAOYSA-N
Isomeric SMILESNCCCNCCCCNCCCN
Average Molecular Weight202.3402
Monoisotopic Molecular Weight202.215746852
Classification
Description belongs to the class of organic compounds known as dialkylamines. These are organic compounds containing a dialkylamine group, characterized by two alkyl groups bonded to the amino nitrogen.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassAmines
Direct ParentDialkylamines
Alternative Parents
Substituents
  • Secondary aliphatic amine
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Primary aliphatic amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 59.36%; H 12.95%; N 27.69%DFC
Melting Point29 oC
Boiling PointBp0.5 141-142°DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
Charge+4
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (x TMS)splash10-014u-1900000000-e9620319823eaeccecccView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (x TMS)splash10-00s6-3900000000-d7da5cd1c0be289412eeView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-00r6-1900000000-861e0541e2eb67219b93View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS)splash10-00di-7900000000-9706a16d903df3f9e094View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS)splash10-00di-5900000000-eb1574dc4aea2972932bView in MoNA
GC-MSGC-MS Spectrum - GC-MS (5 TMS)splash10-00ei-8900000000-710d44c573ed398f7db9View in MoNA
GC-MSGC-MS Spectrum - GC-MS (5 TMS)splash10-00s6-3900000000-cb82c1371fa767015cffView in MoNA
GC-MSGC-MS Spectrum - GC-MS (6 TMS)splash10-00rf-1900000000-ca3a2df44acb740134cdView in MoNA
GC-MSGC-MS Spectrum - GC-MS (6 TMS)splash10-00y0-1900000000-7ba8e67861945901b381View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014u-1900000000-e9620319823eaeccecccView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00s6-3900000000-d7da5cd1c0be289412eeView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00r6-1900000000-861e0541e2eb67219b93View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-7900000000-9706a16d903df3f9e094View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-5900000000-eb1574dc4aea2972932bView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00ei-8900000000-710d44c573ed398f7db9View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00s6-3900000000-cb82c1371fa767015cffView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00rf-1900000000-ca3a2df44acb740134cdView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00y0-1900000000-7ba8e67861945901b381View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-01bl-1900000000-5a4875c4cf337f0cff9cView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000i-7900000000-4e66988ec8e890a03e13View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00rf-2900000000-9d5a63fbbd1662e5dc43View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-01w1-4900000000-f7c07f1cee7101fc31d7View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-053r-9300000000-2ce22d19e72f10b80f34View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0w29-2940000000-a8b05c7cfaea58c5d82dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-03di-1900000000-75ac3953e5378c465a62View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-001i-9000000000-e3b84db5723912be8a4fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0udi-0930000000-4bb02118dea11e2101f8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0006-9000000000-468357ae06dea8985d85View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00b9-6900000000-cf244bbfdbb5b7889d7aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-004i-0900000000-c5af077deeab934c36b7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0udi-0940000000-098121f449eb29dd74beView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0006-9000000000-167ef7503b0827eb212fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-03di-0900000000-feb04e188e675948f795View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-004i-0900000000-93e15f4592fe9bbeb367View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0udi-0090000000-c22e98adb3dc62b1eb77View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-01t9-0900000000-76aa5e4bf523c2027cbaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-03di-4900000000-b762c20d8a09a78cf931View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-001i-9300000000-0428cb6df2b593ded567View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-001i-9000000000-c319f927047d78e2b69bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-004i-0900000000-b4f106f6fe26766fbf73View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-03di-0900000000-29d4a223bb44ded927b5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-01q9-9500000000-d1b7e914e9ccee2d0f66View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udr-2970000000-268b93360fb5eaa19e49View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a73-9810000000-ee919f22493191f56708View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9200000000-f7cb18a7a6036554cb6bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-ea2e2f233958fa61cd8bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-3390000000-0ade7d389047531a84eeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fu-9200000000-e760ec8b3259e54992ceView in MoNA
MSMass Spectrum (Electron Ionization)splash10-053u-9100000000-5a106273203d28e4a701View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider ID1072
ChEMBL IDCHEMBL23194
KEGG Compound IDC00750
Pubchem Compound ID1103
Pubchem Substance IDNot Available
ChEBI ID15746
Phenol-Explorer IDNot Available
DrugBank IDDB00127
HMDB IDHMDB01256
CRC / DFC (Dictionary of Food Compounds) IDCTQ89-F:CTQ89-F
EAFUS IDNot Available
Dr. Duke IDSPERMINE
BIGG ID35875
KNApSAcK IDC00001432
HET IDSPM
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDSpermine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
immunosuppressant35705 An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.CHEBI
Enzymes
NameGene NameUniProt ID
Glycine amidinotransferase, mitochondrialGATMP50440
Histidine decarboxylaseHDCP19113
Spermidine synthaseSRMP19623
Diamine acetyltransferase 2SAT2Q96F10
Diamine acetyltransferase 1SAT1P21673
Spermine synthaseSMSP52788
S-methyl-5'-thioadenosine phosphorylaseMTAPQ13126
Ornithine decarboxylaseODC1P11926
Ornithine decarboxylase antizyme 1OAZ1P54368
Pathways
NameSMPDB LinkKEGG Link
Spermidine and Spermine BiosynthesisSMP00445 Not Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).