| 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 |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
|
| 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 puriss
- 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 |
|
| Direct Parent |
Polyamines |
| Ontology |
| Status |
Detected and Quantified |
| Origin |
|
| Biofunction |
- Component of Arginine and proline metabolism
- Component of beta-Alanine metabolism
|
| Application |
Not Available |
| Cellular locations |
|
| 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 |
|
| 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 |
|
| 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 |
|
| Blood |
Detected and Quantified |
|
9.97 +/- 3.26 uM |
Adult (>18 years old) |
Male |
Normal |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.14 +/- 0.01 uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Saliva |
Detected and Quantified |
|
0.04 uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
0.08 (0.01-0.28) umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and not Quantified |
|
Not Applicable |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
0.019 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
0.13 +/- 0.065 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
Not Available |
|
| Abnormal Concentrations |
|
| Urine |
Detected and not Quantified |
|
Not Applicable |
Adult (>18 years old) |
Both |
Leukemia |
Not Available |
|
| Associated Disorders and Diseases |
| Disease References |
None |
| Associated OMIM IDs |
None |
| External Links |
| DrugBank ID |
DB00127  |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB003225 |
| KNApSAcK ID |
C00001432  |
| Chemspider ID |
1072  |
| KEGG Compound ID |
C00750  |
| BioCyc ID |
SPERMINE  |
| BiGG ID |
35875  |
| Wikipedia Link |
Spermine  |
| NuGOwiki Link |
HMDB01256  |
| Metagene Link |
HMDB01256  |
| METLIN ID |
255  |
| PubChem Compound |
1103  |
| PDB ID |
SPM  |
| ChEBI ID |
15746  |
| 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 |
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
|
| Enzymes |
|
|
|
|
|
|
|
|
|
|
| Name: |
Spermine synthase
|
| Reactions: |
- S-adenosylmethioninamine + spermidine = S-methyl-5'-thioadenosine + spermine [RN:R02869]
|
| Gene Name: |
SMS |
| Uniprot ID: |
P52788  |
| 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  |
| 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  |
| 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  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
|
|
|
|
|
|
|
|
|
|
|
|
|