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Spermine (FDB003225)

Record Information
Version1.0
Creation date2010-04-08 22:05:42 UTC
Update date2020-09-17 15:38:52 UTC
Primary IDFDB003225
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameSpermine
DescriptionSpermine, also known as gerontine or musculamine, 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. Spermine is a drug which is used for nutritional supplementation, also for treating dietary shortage or imbalance. Spermine is a very strong basic compound (based on its pKa). Spermine exists in all living species, ranging from bacteria to humans. 5'-methylthioadenosine and spermine can be biosynthesized from S-adenosylmethioninamine and spermidine through the action of the enzyme spermine synthase. In humans, spermine is involved in spermidine and spermine biosynthesis. Outside of the human body, Spermine is found, on average, in the highest concentration within a few different foods, such as milk (cow), oats, and white wines and in a lower concentration in red wines. Spermine has also been detected, but not quantified in, several different foods, such as annual wild rices, fruits, breadfruits, saffrons, and kelps. This could make spermine a potential biomarker for the consumption of these foods. Spermine is a potentially toxic compound.
CAS Number71-44-3
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Industrial application:

Physico-Chemical Properties
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-053u-9100000000-5a106273203d28e4a7012014-09-20View Spectrum
GC-MSSpermine, x TMS, GC-MS Spectrumsplash10-014u-1900000000-e9620319823eaeccecccSpectrum
GC-MSSpermine, x TMS, GC-MS Spectrumsplash10-00s6-3900000000-d7da5cd1c0be289412eeSpectrum
GC-MSSpermine, non-derivatized, GC-MS Spectrumsplash10-00r6-1900000000-861e0541e2eb67219b93Spectrum
GC-MSSpermine, 5 TMS, GC-MS Spectrumsplash10-00di-7900000000-9706a16d903df3f9e094Spectrum
GC-MSSpermine, 5 TMS, GC-MS Spectrumsplash10-00di-5900000000-eb1574dc4aea2972932bSpectrum
GC-MSSpermine, 5 TMS, GC-MS Spectrumsplash10-00ei-8900000000-710d44c573ed398f7db9Spectrum
GC-MSSpermine, 5 TMS, GC-MS Spectrumsplash10-00s6-3900000000-cb82c1371fa767015cffSpectrum
GC-MSSpermine, 6 TMS, GC-MS Spectrumsplash10-00rf-1900000000-ca3a2df44acb740134cdSpectrum
GC-MSSpermine, 6 TMS, GC-MS Spectrumsplash10-00y0-1900000000-7ba8e67861945901b381Spectrum
GC-MSSpermine, non-derivatized, GC-MS Spectrumsplash10-014u-1900000000-e9620319823eaeccecccSpectrum
GC-MSSpermine, non-derivatized, GC-MS Spectrumsplash10-00s6-3900000000-d7da5cd1c0be289412eeSpectrum
GC-MSSpermine, non-derivatized, GC-MS Spectrumsplash10-00r6-1900000000-861e0541e2eb67219b93Spectrum
GC-MSSpermine, non-derivatized, GC-MS Spectrumsplash10-00di-7900000000-9706a16d903df3f9e094Spectrum
GC-MSSpermine, non-derivatized, GC-MS Spectrumsplash10-00di-5900000000-eb1574dc4aea2972932bSpectrum
GC-MSSpermine, non-derivatized, GC-MS Spectrumsplash10-00ei-8900000000-710d44c573ed398f7db9Spectrum
GC-MSSpermine, non-derivatized, GC-MS Spectrumsplash10-00s6-3900000000-cb82c1371fa767015cffSpectrum
GC-MSSpermine, non-derivatized, GC-MS Spectrumsplash10-00rf-1900000000-ca3a2df44acb740134cdSpectrum
GC-MSSpermine, non-derivatized, GC-MS Spectrumsplash10-00y0-1900000000-7ba8e67861945901b381Spectrum
GC-MSSpermine, non-derivatized, GC-MS Spectrumsplash10-01bl-1900000000-5a4875c4cf337f0cff9cSpectrum
GC-MSSpermine, non-derivatized, GC-MS Spectrumsplash10-000i-7900000000-4e66988ec8e890a03e13Spectrum
GC-MSSpermine, non-derivatized, GC-MS Spectrumsplash10-00rf-2900000000-9d5a63fbbd1662e5dc43Spectrum
GC-MSSpermine, non-derivatized, GC-MS Spectrumsplash10-01w1-4900000000-f7c07f1cee7101fc31d7Spectrum
Predicted GC-MSSpermine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-053r-9300000000-2ce22d19e72f10b80f34Spectrum
Predicted GC-MSSpermine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0w29-2940000000-a8b05c7cfaea58c5d82d2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-03di-1900000000-75ac3953e5378c465a622012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-001i-9000000000-e3b84db5723912be8a4f2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0udi-0930000000-4bb02118dea11e2101f82012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0006-9000000000-468357ae06dea8985d852012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00b9-6900000000-cf244bbfdbb5b7889d7a2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-004i-0900000000-c5af077deeab934c36b72012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0udi-0940000000-098121f449eb29dd74be2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0006-9000000000-167ef7503b0827eb212f2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-03di-0900000000-feb04e188e675948f7952012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-004i-0900000000-93e15f4592fe9bbeb3672012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0udi-0090000000-c22e98adb3dc62b1eb772012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-01t9-0900000000-76aa5e4bf523c2027cba2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-03di-4900000000-b762c20d8a09a78cf9312012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-001i-9300000000-0428cb6df2b593ded5672012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-001i-9000000000-c319f927047d78e2b69b2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-004i-0900000000-b4f106f6fe26766fbf732012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-03di-0900000000-29d4a223bb44ded927b52012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-01q9-9500000000-d1b7e914e9ccee2d0f662012-08-31View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udr-2970000000-268b93360fb5eaa19e492015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a73-9810000000-ee919f22493191f567082015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9200000000-f7cb18a7a6036554cb6b2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-ea2e2f233958fa61cd8b2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-3390000000-0ade7d389047531a84ee2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fu-9200000000-e760ec8b3259e54992ce2015-05-27View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
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
Food Biomarker OntologyNot Available
VMH IDNot Available
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).