Structure via PubChem · Public domain (PubChem)
spermine
Sign in to saveAlso known as 4,9-diazadodecane-1,12-diamine, 4,9-diaza-1,12-dodecanediamine, (3-aminopropyl)({4-[(3-aminopropyl)amino]butyl})amine, N1,N4-bis(3-aminopropyl)-1,4-butanediamine, SPM, N,N'-bis(3-aminopropyl)-1,4-tetramethylenediamine, neuridine, 1,5,10,14-tetraazatetradecane
Spermine is a polyamine involved in cellular metabolism that is found in all eukaryotic cells. The precursor for synthesis of spermine is the amino acid ornithine. It is an essential growth factor in some bacteria as well. It is found as a polycation at physiological pH. Spermine is associated with nucleic acids and is thought to stabilize helical structure, particularly in viruses. It functions as an intracellular free radical scavenger to protect DNA from free radical attack. Spermine is the chemical primarily responsible for the characteristic odor of semen.
Chemical data
- Formula
- C10H26N4
- Molecular weight
- 202.34 g/mol
- IUPAC name
- N,N'-bis(3-aminopropyl)butane-1,4-diamine
- SMILES
- C(CCNCCCN)CNCCCN
- InChIKey
- PFNFFQXMRSDOHW-UHFFFAOYSA-N
- XLogP
- -1.1
- Polar surface area
- 76.1 Ų
- H-bond donors
- 4
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Research
12,186 papers- Cellular spermine targets JAK signaling to restrain cytokine-mediated autoimmunity.Immunity · 2024
- Spermidine and spermine delay brain aging by inducing autophagy in SAMP8 mice.Aging · 2020
- The Spermine Oxidase/Spermine Axis Coordinates ATG5-Mediated Autophagy to Orchestrate Renal Senescence and Fibrosis.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024
- Spermine synthase.Cellular and molecular life sciences : CMLS · 2010
- Spermine synthase in Snyder-Robinson syndrome and cancer.Molecular biology reports · 2025
via PubMed
Wikidata facts
- Mass
- 202.216
Show 4 more facts
- chemical formula
- C₁₀H₂₆N₄
- melting point
- 29
- canonical SMILES
- C(CCNCCCN)CNCCCN
- Commons category
- Spermine
via Wikidata · CC0
~3 min read
Article
4 sectionsContents
- Derivative
- Biosynthesis
- References
- Further reading
Spermine is a polyamine involved in cellular metabolism that is found in all eukaryotic cells. The precursor for synthesis of spermine is the amino acid ornithine. It is an essential growth factor in some bacteria as well. It is found as a polycation at physiological pH. Spermine is associated with nucleic acids and is thought to stabilize helical structure, particularly in viruses. It functions as an intracellular free radical scavenger to protect DNA from free radical attack. Spermine is the chemical primarily responsible for the characteristic odor of semen.
Antonie van Leeuwenhoek first described crystals of spermine phosphate in human semen in 1678. The name spermin was first used by the German chemists Ladenburg and Abel in 1888, and the correct structure of spermine was established in the 1920s, independently by Dudley, Rosenheim, and Starling in England and by Wrede et al. in Germany.