Structure via PubChem · Public domain (PubChem)
S-adenosylmethioninamine
Sign in to saveAlso known as S-Adenosyl-3-methylthiopropylamine, [1-(adenin-9-yl)-1,5-dideoxy-beta-D-ribofuranos-5-yl](3-aminopropyl)(methyl)sulfonium, (5-Deoxy-5-adenosyl)(3-aminopropyl)methylsulfonium, S-Adenosyl-(5')-3-methylthiopropylamine, (5-Deoxy-5-adenosyl)(3-aminopropyl)methylsulfonium cation, (5-deoxy-5-adenosyl)(3-aminopropyl) methylsulfonium salt, Decarboxylated S-adenosylmethionine, DAdoMet
'''S-Adenosylmethioninamine' is a substrate that is required for the biosynthesis of polyamines including spermidine, spermine, and thermospermine. It is produced by decarboxylation of S''-adenosyl methionine.
Chemical data
- Formula
- C14H23N6O3S+
- Molecular weight
- 355.44 g/mol
- IUPAC name
- 3-aminopropyl-[[(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl]-methylsulfanium
- SMILES
- C[S+](CCCN)C[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=NC3=C(N=CN=C32)N)O)O
- InChIKey
- ZUNBITIXDCPNSD-LSRJEVITSA-N
- XLogP
- -0.8
- Polar surface area
- 146 Ų
- H-bond donors
- 4
- H-bond acceptors
- 8
- Formal charge
- 1
via PubChem
Wikidata facts
- Subclass of
- primary metabolite
- Mass
- 355.155235
Show 4 more facts
- canonical SMILES
- C[S+](CCCN)CC1C(C(C(O1)N2C=NC3=C2N=CN=C3N)O)O
- isomeric SMILES
- C[S+](CCCN)C[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=NC3=C2N=CN=C3N)O)O
- found in taxon
- Escherichia coli
- chemical formula
- C₁₄H₂₃N₆O₃S⁺
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- See also
- References
{{Chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 418104160 | Name=S-Adenosylmethioninamine | ImageFile = S-adenosyl-3-methylthiopropylamine.svg | IUPACName = S-(3-Aminopropyl)-S-methyl-5′-thioadenosin-5′-ium | SystematicName = (3-Aminopropyl){[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}methylsulfanium | OtherNames = S-Adenosyl-(5′)-3-methylthiopropylaminedecarboxylated S-adenosyl methioninedecarboxy-S-adenosyl methionine(5-Deoxy-5-adenosyl)(3-aminopropyl)methylsulfonium cation | Section1 = | Section2 = }}'''S-Adenosylmethioninamine' is a substrate that is required for the biosynthesis of polyamines including spermidine, spermine, and thermospermine. It is produced by decarboxylation of S''-adenosyl methionine.
This reaction is catalyzed by S-adenosylmethionine decarboxylase. The enzyme binds to S-adenosyl methionine (SAM) and removes the carboxyl group from the methionine. Once formed, S-adenosylmethioninamine donates its aminopropyl group to synthesize polyamines. Polyamines are important for DNA stability, RNA function, and cell growth.
Excerpted from Wikipedia’s “S-adenosylmethioninamine” article, available under the CC BY-SA 4.0 licence.