Spermine (BioCAD00000017898)

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Metabolite Card

Formula: C10H26N4 (202.2157)
SMILES: NCCCNCCCCNCCCN

Synonyms [en]

spermine; N,N'-Bis(3-aminopropyl)-1,4-butanediamine; musculamine; gerontine; neuridine; Diaminopropyltetramethylenediamine

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

Spermine. 数据之源，洞见之始. SMRUCC genomics institute, a synthetic life researcher from China. https://biocad_registry.innovation.ac.cn/s/(-)-arctiin (retrieved 2026-01-03) (CAD Registry RN: BioCAD00000017898). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

Spermine, 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. The resultin N-carbamoylputrescine is acted on by a hydrolase to split off urea group, leaving putrescine. The precursor for synthesis of spermine is the amino acid ornithine. The intermediate is spermidine. Spermine is a drug. Spermine exists in all living species, ranging from bacteria to humans. 5'-methylthioadenosine and spermine can be biosynthesized from S-adenosylmethioninamine and spermidine through its interaction with the enzyme spermine synthase. Another pathway in plants starts with decarboxylation of L-arginine to produce agmatine. In humans, spermine is involved in spermidine and spermine biosynthesis. Outside of the human body, spermine is found, on average, in the highest concentration in oats. Spermine has also been detected, but not quantified in several different foods, such as sapodilla, mexican groundcherries, cloves, sourdocks, and sunflowers. This could make spermine a potential biomarker for the consumption of these foods. This decarboxylation gives putrescine. The name spermin was first used by the German chemists Ladenburg and Abel in 1888, and the correct structure of spermine was not finally established until 1926, simultaneously in England (by Dudley, Rosenheim, and Starling) and Germany (by Wrede et al.). In one pathway L-glutamine is the precursor to L-ornithine, after which the synthesis of spermine from L-ornithine follows the same pathway as in animals. Spermine is a potentially toxic compound.

Cytoplasm
Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 306-67-2
  • CAS Registry Number: 68956-56-9
  • CAS Registry Number: 71-44-3
  • CAS Registry Number: 71-44-3 (FREE BASE)
  • CAS Registry Number: 71052-31-8
  • PubChem: 1103
  • PubChem: 4012
  • ChEBI: ChEBI:15746
  • HMDB: HMDB0001256
  • KEGG: C00750
  • BioCyc: SPERMINE
  • NCBI MeSH: Spermine
  • Wikipedia: Spermine
  • DrugBank: DB00127
  • RefMet: RM0033343
  • MoNA: BAF_UVA_POS000258
  • MoNA: BAF_UVA_POS000498
  • MoNA: BAF_UVA_POS000499
  • MoNA: BAF_UVA_POS000500
  • MoNA: CCMSLIB00005464388
  • MoNA: CCMSLIB00005720433
  • MoNA: EMBL-MCF_spec351100
  • MoNA: FiehnHILIC000768
  • MoNA: FiehnLib000324
  • MoNA: FiehnLib000325
  • MoNA: FiehnLib000326
  • MoNA: FiehnLib000327
  • MoNA: HMDB0001256_c_ms_2057
  • MoNA: HMDB0001256_c_ms_2082
  • MoNA: HMDB0001256_c_ms_2104
  • MoNA: HMDB0001256_c_ms_2216
  • MoNA: HMDB0001256_ms_ms_1487
  • MoNA: HMDB0001256_ms_ms_1488
  • MoNA: HMDB0001256_ms_ms_1489
  • MoNA: KNA00101
  • MoNA: KNA00102
  • MoNA: KNA00103
  • MoNA: KNA00104
  • MoNA: KNA00463
  • MoNA: KNA00464
  • MoNA: KNA00465
  • MoNA: KNA00466
  • MoNA: KO003977
  • MoNA: KO003978
  • MoNA: KO003979
  • MoNA: KO003980
  • MoNA: KO003981
  • MoNA: KO009230
  • MoNA: KO009231
  • MoNA: KO009232
  • MoNA: KZ000268
  • MoNA: KZ000269
  • MoNA: MoNA001959
  • MoNA: MoNA001960
  • MoNA: MoNA001961
  • MoNA: MoNA032162
  • MoNA: MoNA032163
  • MoNA: MoNA032166
  • MoNA: MoNA032836
  • MoNA: MoNA032837
  • MoNA: MoNA032838
  • MoNA: MoNA036085
  • MoNA: MoNA036086
  • MoNA: MoNA036087
  • MoNA: MoNA036548
  • MoNA: MoNA036553
  • MoNA: MoNA036554
  • MoNA: MoNA037184
  • MoNA: MoNA037402
  • MoNA: MoNA038719
  • MoNA: MoNA_0001268
  • MoNA: MoNA_0001269
  • MoNA: MoNA_0001270
  • MoNA: MoNA_0007695
  • MoNA: MoNA_0007696
  • MoNA: MoNA_0007697
  • MoNA: MoNA_0007698
  • MoNA: MoNA_0007699
  • MoNA: MoNA_0007700
  • MoNA: MoNA_0008019
  • MoNA: MoNA_0008020
  • MoNA: OUF00463
  • MoNA: PB000487
  • MoNA: PB000488
  • MoNA: PB000489
  • MoNA: PB000490
  • MoNA: PR010235
  • MoNA: PR010236
  • MoNA: PS034201
  • MoNA: PS034202
  • MoNA: PS034203
  • MoNA: PS034204
  • MoNA: VF-NPL-LTQ000285
  • MoNA: VF-NPL-LTQ000286
  • MoNA: VF-NPL-LTQ000287
  • MoNA: VF-NPL-LTQ000288
  • MoNA: VF-NPL-LTQ006468
  • MoNA: VF-NPL-QEHF003433
  • MoNA: VF-NPL-QEHF003434
  • MoNA: VF-NPL-QEHF003435
  • MoNA: VF-NPL-QTOF009709
  • MoNA: VF-NPL-QTOF009710
  • MoNA: VF-NPL-QTOF009711
  • Metlin: METLIN_255
  • Coconut NaturalProduct: CNP0224866.0
  • Coconut NaturalProduct: CNP0339469.0
  • Coconut NaturalProduct: CNP0475536.0
  • Coconut NaturalProduct: CNP0579863.0
  • Coconut NaturalProduct: CNP0600892.0

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R02869 2.5.1.22 S-adenosylmethioninamine:spermidine 3-aminopropyltransferase
KEGG:R08352 6.3.1.9 glutathione:spermine ligase (ADP-forming)
KEGG:R09076 1.5.3.16 spermidine:oxygen oxidoreductase (spermidine-forming)
BioCyc:RXN-9015 1.5.3.17 SPERMINE + OXYGEN-MOLECULE + WATER --> SPERMIDINE + CPD-6082 + HYDROGEN-PEROXIDE
BioCyc:SPERMINE-SYNTHASE-RXN 2.5.1.22 SPERMIDINE + S-ADENOSYLMETHIONINAMINE --> PROTON + SPERMINE + 5-METHYLTHIOADENOSINE
BioCyc:RXN-6421 1.5.3.14 SPERMINE + OXYGEN-MOLECULE + WATER --> CPD-6121 + CPD-313 + HYDROGEN-PEROXIDE
BioCyc:RXN-9939 2.3.1.57 ACETYL-COA + SPERMINE --> N1-ACETYLSPERMINE + CO-A + PROTON
View More
Organism Source

Taxonomy Source

  1. Arabidopsis thaliana [ncbi taxid: 3702]
  2. Arachis hypogaea [ncbi taxid: 3818]
  3. Avena sativa [ncbi taxid: 4498]
  4. Canavalia bonariensis [ncbi taxid: 192414]
  5. Canavalia ensiformis [ncbi taxid: 3823]
  6. Capparis masaikai [ncbi taxid: 13395]
  7. Citrullus lanatus [ncbi taxid: 3654]
  8. Cyanidium caldarium [ncbi taxid: 2771]
  9. Daphnia magna [ncbi taxid: 35525]
  10. Helianthus tuberosus [ncbi taxid: 4233]
  11. Homo sapiens [ncbi taxid: 9606]
  12. Hordeum vulgare [ncbi taxid: 4513]
  13. Lablab purpureus [ncbi taxid: 35936]
  14. Lathyrus sativus [ncbi taxid: 3860]
  15. Lyallia kerguelensis [ncbi taxid: 442941]
  16. Mus musculus [ncbi taxid: 10090]
  17. Nectandra pichurim [ncbi taxid: ]
  18. Panax ginseng [ncbi taxid: 4054]
  19. Phaseolus coccineus [ncbi taxid: 3886]
  20. Phaseolus lunatus [ncbi taxid: 3884]
  21. Phaseolus vulgaris [ncbi taxid: 3885]
  22. Pityrogramma tartarea [ncbi taxid: ]
  23. Psophocarpus tetragonolobus [ncbi taxid: 3891]
  24. Saccharomyces cerevisiae [ncbi taxid: 4932]
  25. Trifolium subterraneum [ncbi taxid: 3900]
  26. Vicia faba [ncbi taxid: 3906]
  27. Vicia sativa [ncbi taxid: 3908]
  28. Vigna angularis [ncbi taxid: 3914]
  29. Vigna mungo [ncbi taxid: 3915]
  30. Vigna radiata [ncbi taxid: 157791]
  31. Vigna unguiculata [ncbi taxid: 3917]
  32. Wisteria floribunda [ncbi taxid: 3922]
  33. Avena sativa [ncbi taxid: 4498]
  34. Glycine max [ncbi taxid: 3847]
  35. Helianthus tuberosus [ncbi taxid: 4233]
  36. Hordeum vulgare [ncbi taxid: 4513]
  37. Nicotiana tabacum [ncbi taxid: 4097]
  38. Panax ginseng [ncbi taxid: 4054]
  39. Solanum lycopersicum [ncbi taxid: 4081]

Pathway Synthetic

pathway id name
BioCyc:TRYPANO_ORNSPNANA-PWY spermine biosynthesis II
BioCyc:TRYPANO_POLYAMINSYN3-PWY superpathway of polyamine biosynthesis II
BioCyc:CALBI_POLYAMSYN-YEAST-PWY polyamine biosynthesis
BioCyc:CALBI_POLYAMINE-DEG-PWY polyamine degradation (oxidative deamination pathway)
Plant Reactome:R-OAU-2744345 Metabolism and regulation
Plant Reactome:R-FVE-5096066 Amine and polyamine biosynthesis
Plant Reactome:R-MES-2744345 Metabolism and regulation
Plant Reactome:R-TDI-2744345 Metabolism and regulation
Plant Reactome:R-TDI-5096066 Amine and polyamine biosynthesis
Plant Reactome:R-DRO-2744345 Metabolism and regulation
Plant Reactome:R-DRO-1119317 Spermine biosynthesis
Plant Reactome:R-OGU-5096066 Amine and polyamine biosynthesis
Plant Reactome:R-PTI-2744345 Metabolism and regulation
Plant Reactome:R-GMA-2744345 Metabolism and regulation
Plant Reactome:R-GMA-5096066 Amine and polyamine biosynthesis
Plant Reactome:R-PDA-2744345 Metabolism and regulation
Plant Reactome:R-PVU-2744345 Metabolism and regulation
Plant Reactome:R-PVU-5096066 Amine and polyamine biosynthesis
Plant Reactome:R-BNA-5096066 Amine and polyamine biosynthesis
Plant Reactome:R-BRA-1119317 Spermine biosynthesis
View All Pathways