Common NameSpermine
DescriptionSpermine, 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.
Structure
Molecular FormulaC10H26N4
Average Mass202.34020
Monoisotopic Mass202.21575
IUPAC Name(3-aminopropyl)({4-[(3-aminopropyl)amino]butyl})amine
Traditional NameSpermine
CAS Registry Number71-44-3
SMILES[NH3+]CCC[NH2+]CCCC[NH2+]CCC[NH3+]
InChI IdentifierInChI=1S/C10H26N4/c11-5-3-9-13-7-1-2-8-14-10-4-6-12/h13-14H,1-12H2
InChI KeyPFNFFQXMRSDOHW-UHFFFAOYSA-N
CHEBI IDCHEBI:45725
HMDB IDHMDB0001256
Pathways
NameSMPDB/PathBank
Spermidine and Spermine Biosynthesis
StateSolid
Water Solubility2.19e+00 g/l
logP-0.66
logS-1.97
pKa (Strongest Acidic)Not Available
pKa (Strongest Basic)11.10
Hydrogen Acceptor Count4
Hydrogen Donor Count4
Polar Surface Area76.1 Ų
Rotatable Bond Count11
Physiological Charge4
Formal Charge0
Refractivity62.56 m³·mol⁻¹
Polarizability26.40

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