Common NameSpermidine
DescriptionSpermidine, also known as SPD, 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. Abnormal bleeding, such as bleeding spontaneously or profusely from a very minor injury can also occur. Spermidine exists in all living species, ranging from bacteria to humans. Within humans, spermidine participates in a number of enzymatic reactions. In particular, 5'-methylthioadenosine and spermidine can be biosynthesized from S-adenosylmethioninamine and putrescine by the enzyme spermidine synthase. In addition, S-adenosylmethioninamine and spermidine can be converted into 5'-methylthioadenosine and spermine through the action of the enzyme spermine synthase. In humans, spermidine is involved in spermidine and spermine biosynthesis. Outside of the human body, spermidine is found, on average, in the highest concentration within cow milk and oats. Spermidine has also been detected, but not quantified in several different foods, such as common chokecherries, watercress, agars, strawberry guava, and bog bilberries. This could make spermidine a potential biomarker for the consumption of these foods. Spermidine is consideres as an uremic toxine. Increased levels of uremic toxins can stimulate the production of reactive oxygen species. Chronic exposure to uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease. As a uremic toxin, this compound can cause uremic syndrome. Uremic toxins such as spermidine are actively transported into the kidneys via organic ion transporters (especially OAT3).
Structure
Molecular FormulaC7H19N3
Average Mass145.24590
Monoisotopic Mass145.15790
IUPAC Name(4-aminobutyl)(3-aminopropyl)amine
Traditional NameSpermidine
CAS Registry Number124-20-9
SMILES[NH3+]CCCC[NH2+]CCC[NH3+]
InChI IdentifierInChI=1S/C7H19N3/c8-4-1-2-6-10-7-3-5-9/h10H,1-9H2
InChI KeyATHGHQPFGPMSJY-UHFFFAOYSA-N
CHEBI IDCHEBI:57834
HMDB IDHMDB0001257
Pathways
NameSMPDB/PathBank
Methionine Metabolism
Cystathionine Beta-Synthase Deficiency
S-Adenosylhomocysteine (SAH) Hydrolase Deficiency
Methionine Adenosyltransferase Deficiency
Glycine N-methyltransferase Deficiency
Methylenetetrahydrofolate Reductase Deficiency (MTHFRD)
Hypermethioninemia
Spermidine and Spermine Biosynthesis
Homocystinuria-megaloblastic anemia due to defect in cobalamin metabolism, cblG complementation type
StateSolid
Water Solubility3.27e+01 g/l
logP-0.62
logS-0.65
pKa (Strongest Acidic)Not Available
pKa (Strongest Basic)10.90
Hydrogen Acceptor Count3
Hydrogen Donor Count3
Polar Surface Area64.07 Ų
Rotatable Bond Count7
Physiological Charge3
Formal Charge0
Refractivity44.97 m³·mol⁻¹
Polarizability18.80

We require the use of cookies for essential features like storing your previously submitted BASys2 queries. Rejecting the usage of cookies will result in certain features being disabled. By clicking ACCEPT or continuing to use the website you are agreeing to our use of cookies.

ACCEPT