Compound

S-methyl-5'-thioadenosine

A guanine-derived antineoplastic agent that functions as a nucleic acid synthesis inhibitor through its binding to, and inhibition of, thymidylate synthase.

Definition from MeSH (D000068437), National Library of Medicine, read 2026-09-23. NLM revises MeSH; this copy may not reflect its current record.

CHEBI:17509ChEBI

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Structure

2D depiction · 3D model shown

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A generated conformer of S-methyl-5'-thioadenosine — one low-energy arrangement PubChem computed, not a measured structure. Hydrogens are not drawn; the formula counts them.

Class: Organic compound
Formula: C11H15N5O3S
Mass: 297.34 g/mol
Charge: 0
InChIKey: WUUGFSXJNOTRMR-IOSLPCCCSA-N
SMILES: CSC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O
Look it up: ChEBI PubChem By InChIKey

Identity from ChEBI, geometry from PubChem. Not evidence.

What it touches on the way

Mechanistic reach

4 entities

4 entities reached.

0 reported hops4 assembled from the scaffold

What the reference databases state

Chemical structure

S-methyl-5'-thioadenosine has the functional parent adenosineCompoundChEBI CHEBI:17509Inferred only

Statements

8 statements

8 statements · 2 reference databases · Subject: S-methyl-5'-thioadenosine · Sources: Human-GEM, Rhea

Order

S-methyl-5'-thioadenosine is a substrate of DPH1ProteinRhea RHEA:36783Inferred only
S-methyl-5'-thioadenosine is a substrate of DTWD1ProteinRhea RHEA:62432Inferred only
S-methyl-5'-thioadenosine is a substrate of DTWD2ProteinRhea RHEA:62432Inferred only
S-methyl-5'-thioadenosine is a substrate of LACC1ProteinRhea RHEA:11852Inferred only
S-methyl-5'-thioadenosine is a substrate of MTAPProteinHuman-GEM MAR05384Inferred only
S-methyl-5'-thioadenosine is a substrate of MTAPProteinRhea RHEA:11852Inferred only
S-methyl-5'-thioadenosine is a substrate of SRMProteinRhea RHEA:12721Inferred only
S-methyl-5'-thioadenosine is a substrate of TYW2ProteinRhea RHEA:36355Inferred only

Reactions

40 reactions

putrescine+S-adenosylmethioninamineS-methyl-5'-thioadenosine+proton+spermidine
Catalysed by SRM
Reaction pageLeft to rightBalancedEC 2.5.1.16cytosol
Human-GEM MAR04075CC BY 4.0Reference data
S-adenosylmethioninamine+spermidineS-methyl-5'-thioadenosine+proton+CHEBI:15746
Catalysed by SMS or SRM
Reaction pageLeft to rightBalancedEC 2.5.1.16, 2.5.1.22cytosol
Human-GEM MAR04077CC BY 4.0Reference data
S-methyl-5'-thioadenosine+phosphate(3-)adenine+5-(methylsulfanyl)-alpha-D-ribose 1-phosphate
Catalysed by MTAP
Reaction pageLeft to rightBalancedEC 2.4.2.28cytosol
Human-GEM MAR05384CC BY 4.0Reference data
S-methyl-5'-thioadenosineS-methyl-5'-thioadenosine
Reaction pageReversibleBalancedextracellular space, cytosol
Human-GEM MAR09004CC BY 4.0Reference data
S-methyl-5'-thioadenosine
Reaction pageReversibleBalance undeterminableextracellular space
Human-GEM MAR09021CC BY 4.0Reference data
a fatty acyl-[ACP]+S-adenosyl-L-methionineCHEBI:55474+S-methyl-5'-thioadenosine+holo-[ACP]+hydron
Reaction pageDirection not assertedBalance undeterminable
Rhea RHEA:10096CC BY 4.0Reference data
S-methyl-5'-thioadenosine+hydrogenphosphate5-(methylsulfanyl)-alpha-D-ribose 1-phosphate+adenine
Catalysed by MTAP or LACC1
Reaction pageLeft to rightBalanced
Rhea RHEA:11852CC BY 4.0Reference data
uridine(47) in tRNA(Phe)+S-adenosyl-L-methionine3-[(3S)-3-amino-3-carboxypropyl]uridine(47) in tRNA(Phe)+S-methyl-5'-thioadenosine+hydron
Reaction pageDirection not assertedBalance undeterminable
Rhea RHEA:12300CC BY 4.0Reference data
S-adenosyl 3-(methylsulfanyl)propylamine+putrescineS-methyl-5'-thioadenosine+spermidine+hydron
Catalysed by SRM
Reaction pageDirection not assertedBalanced
Rhea RHEA:12721CC BY 4.0Reference data
S-methyl-5'-thioadenosine+waterCHEBI:78440+adenine
Reaction pageDirection not assertedBalanced
Rhea RHEA:13617CC BY 4.0Reference data
3S-adenosyl-L-methionineCHEBI:58249+3S-methyl-5'-thioadenosine+3hydron
Reaction pageDirection not assertedBalanced
Rhea RHEA:16481CC BY 4.0Reference data
CHEBI:17660+S-adenosyl-L-methionineCHEBI:57585+S-methyl-5'-thioadenosine+hydron
Reaction pageDirection not assertedBalanced
Rhea RHEA:19581CC BY 4.0Reference data

Show the remaining 28

Other names

9 names

Resolves to: S-methyl-5'-thioadenosine

Also called: 5-Methylthioadenosine5'-Deoxy-5'-(methylthio)adenosine5'-Methylthioadenosine9-(5-S-methyl-5-thio-beta-D-ribofuranosyl)-9H-purin-6-amine9-(5-S-methyl-5-thio-β-D-ribofuranosyl)-9H-purin-6-amineMethylthioadenosineMTAThiomethyladenosine
Systematic name: 5'-deoxy-5'-(methylsulfanyl)adenosine