Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:10:11 UTC
HMDB IDHMDB01256
Secondary Accession NumbersNone
Metabolite Identification
Common NameSpermine
DescriptionSpermine 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. 1,5,10,14-Tetraazatetradecane
  2. 4,9-Diaza-1,12-dodecanediamine
  3. 4,9-Diazadodecamethylenediamine
  4. 4,9-Diazadodecane-1,12-diamine
  5. Diaminopropyl-tetramethylenediamine
  6. Diaminopropyltetramethylenediamine
  7. Gerontine
  8. Musculamine
  9. N,N'-Bis(3-aminopropyl)-1,4-Butanediamine
  10. N,N'-Bis(3-aminopropyl)-1,4-tetramethylenediamine
  11. N,N'-Bis(3-aminopropyl)butane-1,4-diamine
  12. N1,N4-bis(3-aminopropyl)-1,4-butanediamine
  13. Neuridine
  14. Spermin
  15. Spermine
  16. Spermine dihydrate
  17. Spermine puriss
  18. SPM
Chemical FormulaC10H26N4
Average Molecular Weight202.3402
Monoisotopic Molecular Weight202.215746852
IUPAC Name(3-aminopropyl)({4-[(3-aminopropyl)amino]butyl})amine
Traditional IUPAC 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
KingdomOrganic Compounds
Super ClassAliphatic Acyclic Compounds
ClassAlkylamines
Sub ClassPolyamines
Other Descriptors
  • Alkylamines
  • polyazaalkane(ChEBI)
  • tetraamine(ChEBI)
Substituents
  • N/A
Direct ParentPolyamines
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Arginine and proline metabolism
  • Component of beta-Alanine metabolism
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
water solubility2.19 g/LALOGPS
logP-0.66ALOGPS
logP-1.5ChemAxon
logS-2ALOGPS
pKa (strongest basic)11.1ChemAxon
physiological charge4ChemAxon
hydrogen acceptor count4ChemAxon
hydrogen donor count4ChemAxon
polar surface area76.1ChemAxon
rotatable bond count11ChemAxon
refractivity62.56ChemAxon
polarizability26.4ChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Saliva
  • Urine
Tissue Location
  • Brain
  • Erythrocyte
  • Fibroblasts
  • Intestine
  • Liver
  • Muscle
  • Neuron
  • Pancreas
  • Platelet
  • Prostate
  • Skin
  • Testes
Pathways
NameSMPDB LinkKEGG Link
Spermidine and Spermine BiosynthesisSMP00445Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified9.97 +/- 3.26 uMAdult (>18 years old)MaleNormal
  • Geigy Scient...
Cerebrospinal Fluid (CSF)Detected and Quantified0.14 +/- 0.01 uMAdult (>18 years old)BothNormal
SalivaDetected and Quantified0.04 uMAdult (>18 years old)BothNormal
UrineDetected and Quantified0.08 (0.01-0.28) umol/mmol creatinineAdult (>18 years old)BothNormal
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal
UrineDetected and Quantified0.058 +/- 0.026 umol/mmol creatinineAdult (>18 years old)BothNot Available
UrineDetected and Quantified0.019 umol/mmol creatinineAdult (>18 years old)BothNormal
UrineDetected and Quantified0.13 +/- 0.065 umol/mmol creatinineAdult (>18 years old)BothNormal
  • Geigy Scient...
  • West Cadwell...
  • Basel, Switz...
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReference
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothLeukemia
UrineDetected and Quantified0.463 +/- 0.214 umol/mmol creatinineAdult (>18 years old)BothLeukemia
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00127
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB003225
KNApSAcK IDC00001432
Chemspider ID1072
KEGG Compound IDC00750
BioCyc IDSPERMINE
BiGG ID35875
Wikipedia LinkSpermine
NuGOwiki LinkHMDB01256
Metagene LinkHMDB01256
METLIN ID255
PubChem Compound1103
PDB IDSPM
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. 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
  2. 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
  3. 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
  4. 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
  5. 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
  6. 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
  7. 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
  8. 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
  9. 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
  10. 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
  11. 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
  12. 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

Enzymes

Gene Name:
SAT2
Uniprot ID:
Q96F10
Gene Name:
SAT1
Uniprot ID:
P21673
Gene Name:
XDH
Uniprot ID:
P47989
Gene Name:
SMS
Uniprot ID:
P52788
Reactions
S-Adenosylmethioninamine + Spermidine unknown 5'-Methylthioadenosine + Sperminedetails
Gene Name:
SRM
Uniprot ID:
P19623
Reactions
S-Adenosylmethioninamine + Spermidine unknown 5'-Methylthioadenosine + Sperminedetails
Gene Name:
BBOX1
Uniprot ID:
O75936
Gene Name:
SARDH
Uniprot ID:
Q9UL12
Gene Name:
HDC
Uniprot ID:
P19113
Gene Name:
ODC1
Uniprot ID:
P11926
Gene Name:
SMOX
Uniprot ID:
Q9NWM0
Reactions
Spermine + Oxygen + Water unknown Spermidine + 3-Aminopropionaldehyde + Hydrogen peroxidedetails
Gene Name:
AGMAT
Uniprot ID:
Q9BSE5
Gene Name:
OAZ1
Uniprot ID:
P54368
Gene Name:
PMF1
Uniprot ID:
Q6P1K2

Transporters

Gene Name:
SLC22A4
Uniprot ID:
Q9H015
Gene Name:
SLC22A1
Uniprot ID:
O15245