Record Information
Version1.0
Creation Date2016-09-30 22:43:09 UTC
Update Date2020-06-04 20:46:15 UTC
BMDB IDBMDB0001256
Secondary Accession Numbers
  • BMDB01256
Metabolite Identification
Common 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 exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. 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 cattle, spermine is involved in the metabolic pathway called spermidine and spermine biosynthesis pathway. Spermine is a potentially toxic compound.
Structure
Thumb
Synonyms
ValueSource
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
Chemical FormulaC10H26N4
Average Molecular Weight202.3402
Monoisotopic Molecular Weight202.215746852
IUPAC Name(3-aminopropyl)({4-[(3-aminopropyl)amino]butyl})amine
Traditional Namespermine
CAS Registry Number71-44-3
SMILES
NCCCNCCCCNCCCN
InChI Identifier
InChI=1S/C10H26N4/c11-5-3-9-13-7-1-2-8-14-10-4-6-12/h13-14H,1-12H2
InChI KeyPFNFFQXMRSDOHW-UHFFFAOYSA-N
Chemical Taxonomy
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
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point29 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
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 Spectrum (1D, 500 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, D2O, experimental)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, D2O, experimental)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
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)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Brain
  • Epidermis
  • Erythrocyte
  • Fibroblasts
  • Intestine
  • Liver
  • Longissimus Thoracis Muscle
  • Milk
  • Neuron
  • Pancreas
  • Platelet
  • Prostate Tissue
  • Ruminal Fluid
  • Semimembranosus Muscle
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.2 +/- 0.2 uMNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
BrainExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
EpidermisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
ErythrocyteExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
FibroblastsExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
IntestineExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Longissimus Thoracis MuscleDetected and Quantified0.2 +/- 0.1 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
MilkDetected and Quantified1.0700 - 7.560 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified3.2 uMNot SpecifiedNot Specified
Normal
details
NeuronExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PancreasExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PlateletExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Prostate TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Ruminal FluidDetected and Quantified3 +/- 3 uMNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
Semimembranosus MuscleDetected and Quantified0.11 +/- 0.03 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
TestisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0001256
DrugBank IDDB00127
Phenol Explorer Compound IDNot Available
FooDB IDFDB003225
KNApSAcK IDC00001432
Chemspider ID1072
KEGG Compound IDC00750
BioCyc IDSPERMINE
BiGG ID35875
Wikipedia LinkSpermine
METLIN ID255
PubChem Compound1103
PDB IDNot Available
ChEBI ID15746
References
Synthesis ReferenceWrede, Fritz; Strack, Erich; Hettche, Otto. Spermine. VII. Z. physiol. Chem. (1928), 173 61-8.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Motyl T, Ploszaj T, Wojtasik A, Kukulska W, Podgurniak M: Polyamines in cow's and sow's milk. Comp Biochem Physiol B Biochem Mol Biol. 1995 Jul;111(3):427-33. [PubMed:7613766 ]

Enzymes

General function:
Amino acid transport and metabolism
Specific function:
Catalyzes the production of spermine from spermidine and decarboxylated S-adenosylmethionine (dcSAM).
Gene Name:
SMS
Uniprot ID:
Q3SZA5
Molecular weight:
41224.0
Reactions
S-Adenosylmethioninamine + Spermidine → 5'-Methylthioadenosine + Sperminedetails
General function:
Carbohydrate transport and metabolism
Specific function:
Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnicotinamide (NMN), 4-(4-(dimethylamino)styryl)-N-methylpyridinium (ASP), the endogenous compounds choline, guanidine, histamine, epinephrine, adrenaline, noradrenaline and dopamine, and the drugs quinine, and metformin. The transport of organic cations is inhibited by a broad array of compounds like tetramethylammonium (TMA), cocaine, lidocaine, NMDA receptor antagonists, atropine, prazosin, cimetidine, TEA and NMN, guanidine, cimetidine, choline, procainamide, quinine, tetrabutylammonium, and tetrapentylammonium. Translocates organic cations in an electrogenic and pH-independent manner. Translocates organic cations across the plasma membrane in both directions. Transports the polyamines spermine and spermidine. Transports pramipexole across the basolateral membrane of the proximal tubular epithelial cells. The choline transport is activated by MMTS. Regulated by various intracellular signaling pathways including inhibition by protein kinase A activation, and endogenously activation by the calmodulin complex, the calmodulin-dependent kinase II and LCK tyrosine kinase (By similarity).
Gene Name:
SLC22A1
Uniprot ID:
A7MBE0
Molecular weight:
62502.0