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Human Metabolome Database Version 3.5

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Showing metabocard for Spermine (HMDB01256)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:10:11 -0700
HMDB ID HMDB01256
Secondary Accession Numbers None
Metabolite Identification
Common 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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C10H26N4
Average Molecular Weight 202.3402
Monoisotopic Molecular Weight 202.215746852
IUPAC Name (3-aminopropyl)({4-[(3-aminopropyl)amino]butyl})amine
Traditional IUPAC Name spermine
CAS Registry Number 71-44-3
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 Key PFNFFQXMRSDOHW-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aliphatic Acyclic Compounds
Class Alkylamines
Sub Class Polyamines
Other Descriptors
  • Alkylamines
  • polyazaalkane(ChEBI)
  • tetraamine(ChEBI)
Substituents
  • N/A
Direct Parent Polyamines
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Arginine and proline metabolism
  • Component of beta-Alanine metabolism
Application Not Available
Cellular locations
  • Cytoplasm
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 29 °C Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
LogP -0.66 ALOGPS
LogP -1.5 ChemAxon
LogS -1.97 ALOGPS
pKa (strongest basic) 11.1 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 4 ChemAxon
Polar Surface Area 76.1 A2 ChemAxon
Rotatable Bond Count 11 ChemAxon
Refractivity 62.56 ChemAxon
Polarizability 26.4 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 4 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40
[1H,1H] 2D NMR Spectrum
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Saliva
  • Urine
Tissue Location
  • Muscle
  • Fibroblasts
  • Intestine
  • Neuron
  • Pancreas
  • Testes
  • Erythrocyte
  • Liver
  • Brain
  • Prostate
  • Skin
  • Platelet
Pathways
Name SMPDB Link KEGG Link
Spermidine and Spermine Biosynthesis SMP00445 Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
9.97 +/- 3.26 uM Adult (>18 years old) Male Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
0.14 +/- 0.01 uM Adult (>18 years old) Both Normal Not Available
Saliva Detected and Quantified
Article_icon
0.04 uM Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
Article_icon
0.08 (0.01-0.28) umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and not Quantified
Article_icon
Not Applicable Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
Article_icon
0.019 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
Article_icon
0.13 +/- 0.065 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Urine Detected and not Quantified
Article_icon
Not Applicable Adult (>18 years old) Both Leukemia Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID DB00127 Link_out
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB003225
KNApSAcK ID C00001432 Link_out
Chemspider ID 1072 Link_out
KEGG Compound ID C00750 Link_out
BioCyc ID SPERMINE Link_out
BiGG ID 35875 Link_out
Wikipedia Link Spermine Link_out
NuGOwiki Link HMDB01256 Link_out
Metagene Link HMDB01256 Link_out
METLIN ID 255 Link_out
PubChem Compound 1103 Link_out
PDB ID SPM Link_out
ChEBI ID 15746 Link_out
References
Synthesis Reference Wrede, Fritz; Strack, Erich; Hettche, Otto. Spermine. VII. Z. physiol. Chem. (1928), 173 61-8.
Material Safety Data Sheet (MSDS) Download (PDF)
General References
  1. 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 Link_out
  2. 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 Link_out
  3. 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 Link_out
  4. 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 Link_out
  5. 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 Link_out
  6. 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 Link_out
  7. 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 Link_out
  8. 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 Link_out
  9. 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 Link_out
  10. 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 Link_out
  11. 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 Link_out
  12. 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 Link_out
Enzymes
Name: Diamine acetyltransferase 2
Reactions:
  • acetyl-CoA + an alkane-alpha,omega-diamine = CoA + an N-acetyldiamine [RN:R03910]
Gene Name: SAT2
Uniprot ID: Q96F10 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Diamine acetyltransferase 1
Reactions:
  • acetyl-CoA + an alkane-alpha,omega-diamine = CoA + an N-acetyldiamine [RN:R03910]
Gene Name: SAT1
Uniprot ID: P21673 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Xanthine dehydrogenase/oxidase
Reactions:
  • xanthine + H2O + O2 = urate + H2O2 [RN:R02107]
Gene Name: XDH
Uniprot ID: P47989 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Choline dehydrogenase, mitochondrial
Reactions:
  • choline + acceptor = betaine aldehyde + reduced acceptor [RN:R01025]
Gene Name: CHDH
Uniprot ID: Q8NE62 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Dimethylglycine dehydrogenase, mitochondrial
Reactions:
  • N,N-dimethylglycine + acceptor + H2O = sarcosine + formaldehyde + reduced acceptor [RN:R01565]
Gene Name: DMGDH
Uniprot ID: Q9UI17 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Spermine synthase
Reactions:
  • S-adenosylmethioninamine + spermidine = S-methyl-5'-thioadenosine + spermine [RN:R02869]
Gene Name: SMS
Uniprot ID: P52788 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Spermidine synthase
Reactions:
  • S-adenosylmethioninamine + putrescine = 5'-S-methyl-5'-thioadenosine + spermidine [RN:R01920]
Gene Name: SRM
Uniprot ID: P19623 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 4-trimethylaminobutyraldehyde dehydrogenase
Reactions:
  • 4-trimethylammoniobutanal + NAD+ + H2O = 4-trimethylammoniobutanoate + NADH + 2 H+ [RN:R03283]
Gene Name: ALDH9A1
Uniprot ID: P49189 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Gamma-butyrobetaine dioxygenase
Reactions:
  • 4-trimethylammoniobutanoate + 2-oxoglutarate + O2 = 3-hydroxy-4-trimethylammoniobutanoate + succinate + CO2 [RN:R02397]
Gene Name: BBOX1
Uniprot ID: O75936 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Amiloride-sensitive amine oxidase [copper-containing]
Reactions:
  • histamine + H2O + O2 = (imidazol-4-yl)acetaldehyde + NH3 + H2O2 [RN:R02150]
Gene Name: ABP1
Uniprot ID: P19801 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: S-methyl-5'-thioadenosine phosphorylase
Reactions:
  • S-methyl-5'-thioadenosine + phosphate = adenine + S-methyl-5-thio-alpha-D-ribose 1-phosphate [RN:R01402]
Gene Name: MTAP
Uniprot ID: Q13126 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: S-adenosylmethionine decarboxylase proenzyme
Reactions:
  • S-adenosyl-L-methionine = (5-deoxy-5-adenosyl)(3-aminopropyl)methylsulfonium salt + CO2 [RN:R00178]
Gene Name: AMD1
Uniprot ID: P17707 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glycine amidinotransferase, mitochondrial
Reactions:
  • L-arginine + glycine = L-ornithine + guanidinoacetate [RN:R00565]
Gene Name: GATM
Uniprot ID: P50440 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Betaine--homocysteine S-methyltransferase 1
Reactions:
  • trimethylammonioacetate + L-homocysteine = dimethylglycine + L-methionine [RN:R02821]
Gene Name: BHMT
Uniprot ID: Q93088 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Sarcosine dehydrogenase, mitochondrial
Reactions:
  • sarcosine + acceptor + H2O = glycine + formaldehyde + reduced acceptor [RN:R00611]
Gene Name: SARDH
Uniprot ID: Q9UL12 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Histidine decarboxylase
Reactions:
  • L-histidine = histamine + CO2 [RN:R01167]
Gene Name: HDC
Uniprot ID: P19113 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Ornithine decarboxylase
Reactions:
  • L-ornithine = putrescine + CO2 [RN:R00670]
Gene Name: ODC1
Uniprot ID: P11926 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Spermine oxidase
Reactions:
  • spermine + O2 + H2O = spermidine + 3-aminopropanal + H2O2 [RN:R09076]
Gene Name: SMOX
Uniprot ID: Q9NWM0 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Agmatinase, mitochondrial
Reactions:
  • agmatine + H2O = putrescine + urea [RN:R01157]
Gene Name: AGMAT
Uniprot ID: Q9BSE5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Trimethyllysine dioxygenase, mitochondrial
Reactions:
  • N6,N6,N6-trimethyl-L-lysine + 2-oxoglutarate + O2 = 3-hydroxy-N6,N6,N6-trimethyl-L-lysine + succinate + CO2 [RN:R03451]
Gene Name: TMLHE
Uniprot ID: Q9NVH6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Betaine--homocysteine S-methyltransferase 2
Reactions:
  • trimethylammonioacetate + L-homocysteine = dimethylglycine + L-methionine [RN:R02821]
Gene Name: BHMT2
Uniprot ID: Q9H2M3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Pyruvate dehydrogenase phosphatase regulatory subunit, mitochondrial
Reactions:
    Gene Name: PDPR
    Uniprot ID: Q8NCN5 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Ornithine decarboxylase antizyme 1
    Reactions:
      Gene Name: OAZ1
      Uniprot ID: P54368 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Polyamine-modulated factor 1
      Reactions:
        Gene Name: PMF1
        Uniprot ID: Q6P1K2 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Transporters
        Name: Solute carrier family 22 member 4
        Reactions:
        • --- []
        Gene Name: SLC22A4
        Uniprot ID: Q9H015 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Solute carrier family 22 member 1
        Reactions:
        • --- []
        Gene Name: SLC22A1
        Uniprot ID: O15245 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA