Record Information
Version2.0
Creation Date2012-05-31 13:48:23 -0600
Update Date2015-09-13 12:56:10 -0600
Secondary Accession Numbers
  • ECMDB01256
Identification
Name:Spermine
Description:Spermine is a biogenic polyamine 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 all pH values. Spermine is associated with nucleic acids, particularly in viruses, and is thought to stabilize the helical structure.
Structure
Thumb
Synonyms:
  • 1,5,10,14-Tetraazatetradecane
  • 4,9-Diaza-1,12-dodecanediamine
  • 4,9-Diazadodecamethylenediamine
  • 4,9-Diazadodecane-1,12-diamine
  • Diaminopropyl-tetramethylenediamine
  • Diaminopropyltetramethylenediamine
  • Gerontine
  • Musculamine
  • N,N'-Bis(3-aminopropyl)-1,4-Butanediamine
  • N,N'-Bis(3-aminopropyl)-1,4-tetramethylenediamine
  • N,N'-Bis(3-aminopropyl)butane-1,4-diamine
  • N1,N4-bis(3-aminopropyl)-1,4-butanediamine
  • Neuridine
  • Spermin
  • Spermine
  • Spermine dihydrate
  • Spermine dihydric acid
  • Spermine puriss
  • SPM
Chemical Formula:C10H26N4
Weight:Average: 202.3402
Monoisotopic: 202.215746852
InChI Key:PFNFFQXMRSDOHW-UHFFFAOYSA-N
InChI:InChI=1S/C10H26N4/c11-5-3-9-13-7-1-2-8-14-10-4-6-12/h13-14H,1-12H2
CAS number:71-44-3
IUPAC Name:(3-aminopropyl)({4-[(3-aminopropyl)amino]butyl})amine
Traditional IUPAC Name:spermine
SMILES:NCCCNCCCCNCCCN
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as dialkylamines. These are organic compounds containing a dialkylamine group, characterized by two alkyl groups bonded to the amino nitrogen.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic nitrogen compounds
Sub ClassOrganonitrogen compounds
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
Physical Properties
State:Solid
Charge:4
Melting point:29 °C
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility2.19 mg/mLALOGPS
logP-0.66ALOGPS
logP-1.5ChemAxon
logS-2ALOGPS
pKa (Strongest Basic)11.1ChemAxon
Physiological Charge4ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area76.1 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity62.56 m3·mol-1ChemAxon
Polarizability26.69 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Glutathione metabolismPW000833 Pw000833Pw000833 greyscalePw000833 simple
beta-Alanine metabolismPW000896 Pw000896Pw000896 greyscalePw000896 simple
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not 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)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-MSsplash10-053r-9300000000-2ce22d19e72f10b80f34View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-014u-1900000000-e9620319823eaeccecccView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-00s6-3900000000-d7da5cd1c0be289412eeView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-00r6-1900000000-861e0541e2eb67219b93View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-00di-7900000000-9706a16d903df3f9e094View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-00di-5900000000-eb1574dc4aea2972932bView in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-00ei-8900000000-710d44c573ed398f7db9View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-00s6-3900000000-cb82c1371fa767015cffView in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-00rf-1900000000-ca3a2df44acb740134cdView in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-00y0-1900000000-7ba8e67861945901b381View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-01bl-1900000000-5a4875c4cf337f0cff9cView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-000i-7900000000-4e66988ec8e890a03e13View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-00rf-2900000000-9d5a63fbbd1662e5dc43View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-01w1-4900000000-f7c07f1cee7101fc31d7View 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 Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • Cipolla BG, Ziade J, Bansard JY, Moulinoux JP, Staerman F, Quemener V, Lobel B, Guille F: Pretherapeutic erythrocyte polyamine spermine levels discriminate high risk relapsing patients with M1 prostate carcinoma. Cancer. 1996 Sep 1;78(5):1055-65. Pubmed: 8780544
  • El Baze P, Milano G, Verrando P, Renee N, Ortonne JP: Polyamine levels in normal human skin. A comparative study of pure epidermis, pure dermis, and suction blister fluid. Arch Dermatol Res. 1983;275(4):218-21. Pubmed: 6625645
  • Hosseinkhani H, Azzam T, Tabata Y, Domb AJ: Dextran-spermine polycation: an efficient nonviral vector for in vitro and in vivo gene transfection. Gene Ther. 2004 Jan;11(2):194-203. Pubmed: 14712304
  • Jensen PK, Therkelsen AJ: Selective inhibition of fibroblasts by spermine in primary cultures of normal human skin epithelial cells. In Vitro. 1982 Oct;18(10):867-71. Pubmed: 7173947
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Lorenz B, Francis F, Gempel K, Boddrich A, Josten M, Schmahl W, Schmidt J, Lehrach H, Meitinger T, Strom TM: Spermine deficiency in Gy mice caused by deletion of the spermine synthase gene. Hum Mol Genet. 1998 Mar;7(3):541-7. Pubmed: 9467015
  • Loser C, Folsch UR, Paprotny C, Creutzfeldt W: Polyamines in colorectal cancer. Evaluation of polyamine concentrations in the colon tissue, serum, and urine of 50 patients with colorectal cancer. Cancer. 1990 Feb 15;65(4):958-66. Pubmed: 2297664
  • Mollica F, Li Volti S, Rapisarda A, Longo G, Pavone L, Vanella A: Increased erythrocytic spermine in Duchenne muscular dystrophy. Pediatr Res. 1980 Nov;14(11):1196-8. Pubmed: 7454431
  • Proctor MS, Fletcher HV Jr, Shukla JB, Rennert OM: Elevated spermidine and spermine levels in the blood of psoriasis patients. J Invest Dermatol. 1975 Oct;65(4):409-11. Pubmed: 1176793
  • Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411
  • Swift TA, Dias JA: Effects of the polyamine spermine on binding of follicle-stimulating hormone to membrane-bound immature bovine testis receptors. Biochim Biophys Acta. 1986 Feb 21;885(2):221-30. Pubmed: 3004602
  • Uehara N, Shirakawa S, Uchino H, Saeki Y: Elevated contents of spermidine and spermine in the erythrocytes of cancer patients. Cancer. 1980 Jan 1;45(1):108-11. Pubmed: 7350997
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Venza M, Visalli M, Cicciu D, Teti D: Determination of polyamines in human saliva by high-performance liquid chromatography with fluorescence detection. J Chromatogr B Biomed Sci Appl. 2001 Jun 5;757(1):111-7. Pubmed: 11419735
  • Vijayendran, C., Barsch, A., Friehs, K., Niehaus, K., Becker, A., Flaschel, E. (2008). "Perceiving molecular evolution processes in Escherichia coli by comprehensive metabolite and gene expression profiling." Genome Biol 9:R72. Pubmed: 18402659
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:Wrede, Fritz; Strack, Erich; Hettche, Otto. Spermine. VII. Z. physiol. Chem. (1928), 173 61-8.
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID15746
HMDB IDHMDB01256
Pubchem Compound ID1103
Kegg IDC00750
ChemSpider ID1072
WikipediaSpermine
BioCyc IDSPERMINE
EcoCyc IDSPERMINE
Ligand ExpoSPM

Enzymes

General function:
Involved in catalytic activity
Specific function:
Catalyzes the production of spermidine from putrescine and decarboxylated S-adenosylmethionine (dcSAM), which serves as an aminopropyl donor
Gene Name:
speE
Uniprot ID:
P09158
Molecular weight:
32321
Reactions
S-adenosylmethioninamine + putrescine = 5'-S-methyl-5'-thioadenosine + spermidine.