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
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 PropertiesNot Available
Chemical FormulaC10H26N4
IUPAC name
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 - 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
EI-MS/GC-MSNot Available
MS/MSNot Available
NMRNot Available
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).