S-methyl-5'-thioadenosine

Three steps

• (9Z,12Z)-octadecadienoyl-CoAReach from here →
  1. S-adenosyl 3-(methylsulfanyl)propylamine + putrescine = S-methyl-5'-thioadenosine + spermidine + H(+)
  2. acetyl-CoA:putrescine N-acetyltransferase
  3. long-chain-fatty-acid-CoA ligase ((6Z,9Z)-octadecadienoic acid)

  Catalysed by SRM, SAT1, SAT2, SLC27A2 and 7 morecytosolOne of 13 routes

• tetradecanoyl-CoAReach from here →
  1. S-adenosyl 3-(methylsulfanyl)propylamine + putrescine = S-methyl-5'-thioadenosine + spermidine + H(+)
  2. acetyl-CoA:putrescine N-acetyltransferase
  3. long-chain-fatty-acid-CoA ligase (myristic acid)

  Catalysed by SRM, SAT1, SAT2, SLC27A2 and 7 morecytosolOne of 11 routes

• octanoyl-CoAReach from here →
  1. S-adenosyl 3-(methylsulfanyl)propylamine + putrescine = S-methyl-5'-thioadenosine + spermidine + H(+)
  2. acetyl-CoA:putrescine N-acetyltransferase
  3. Octanoyl-CoA:L-carnitine O-octanoyltransferase

  Catalysed by SRM, SAT1, SAT2, CROTcytosol, mitochondrial matrixOne of 20 routes

• phytanoyl-CoAReach from here →
  1. S-adenosyl 3-(methylsulfanyl)propylamine + putrescine = S-methyl-5'-thioadenosine + spermidine + H(+)
  2. acetyl-CoA:putrescine N-acetyltransferase
  3. phytanate-CoA ligase

  Catalysed by SRM, SAT1, SAT2cytosolOne of 5 routes

• octadecanoyl-CoAReach from here →
  1. S-adenosyl 3-(methylsulfanyl)propylamine + putrescine = S-methyl-5'-thioadenosine + spermidine + H(+)
  2. acetyl-CoA:putrescine N-acetyltransferase
  3. long-chain-fatty-acid-CoA ligase (stearate)

  Catalysed by SRM, SAT1, SAT2, SLC27A2 and 6 morecytosolOne of 15 routes

• 2-(N(omega)-L-arginino)succinateReach from here →
  1. S-adenosyl 3-(methylsulfanyl)propylamine + putrescine = S-methyl-5'-thioadenosine + spermidine + H(+)
  2. Putrescine Export via Putrescine/Arginine Antiporter
  3. 2-(Nomega-L-arginino)succinate arginine-lyase (fumarate-forming)

  Catalysed by SRM, SLC3A2, SLC7A7, ASLextracellular space, cytosolOne of 2 routes

• propane-1,3-diamineReach from here →
  1. S-adenosyl 3-(methylsulfanyl)propylamine + putrescine = S-methyl-5'-thioadenosine + spermidine + H(+)
  2. S-adenosylmethioninamine:putrescine 3-aminopropyltransferase
  3. [eIF5A protein]-L-lysine + spermidine = [eIF5A protein]-deoxyhypusine + propane-1,3-diamine

  Catalysed by SRM, DHPScytosol

• 4-guanidinobutanoateReach from here →
  1. S-adenosyl 3-(methylsulfanyl)propylamine + putrescine = S-methyl-5'-thioadenosine + spermidine + H(+)
  2. Putrescine Export via Putrescine/Arginine Antiporter
  3. 4-aminobutanoate + L-arginine = 4-guanidinobutanoate + L-ornithine

  Catalysed by SRM, SLC3A2, SLC7A7, GATMextracellular space, cytosol

• 3-guanidinopropanoateReach from here →
  1. S-adenosyl 3-(methylsulfanyl)propylamine + putrescine = S-methyl-5'-thioadenosine + spermidine + H(+)
  2. Putrescine Export via Putrescine/Arginine Antiporter
  3. beta-alanine + L-arginine = 3-guanidinopropanoate + L-ornithine

  Catalysed by SRM, SLC3A2, SLC7A7, GATMextracellular space, cytosol

• L-histidineReach from here →
  1. S-adenosyl 3-(methylsulfanyl)propylamine + putrescine = S-methyl-5'-thioadenosine + spermidine + H(+)
  2. Putrescine Export via Putrescine/Arginine Antiporter
  3. L-histidine(out) + L-arginine(in) + Na(+)(out) = L-histidine(in) + L-arginine(out) + Na(+)(in)

  Catalysed by SRM, SLC3A2, SLC7A7, SLC7A6extracellular space, cytosol, inner side of the membrane, outer side of the membraneOne of 5 routes

• D-ornithineReach from here →
  1. S-adenosyl 3-(methylsulfanyl)propylamine + putrescine = S-methyl-5'-thioadenosine + spermidine + H(+)
  2. L-ornithine + H(+) = putrescine + CO2
  3. D-ornithine(in) + L-ornithine(out) = D-ornithine(out) + L-ornithine(in)

  Catalysed by SRM, ODC1, SLC25A2inner side of the membrane, outer side of the membraneOne of 2 routes

• alpha-D-ribose 1-phosphateReach from here →
  1. S-methyl-5'-thioadenosine:phosphate S-methyl-5-thio-alpha-D-ribosyl-transferase
  2. adenosine:phosphate alpha-D-ribosyltransferase
  3. adenosine + phosphate = alpha-D-ribose 1-phosphate + adenine

  Catalysed by MTAP, PNP, LACC1cytosol

• guanidinoacetateReach from here →
  1. S-adenosyl 3-(methylsulfanyl)propylamine + putrescine = S-methyl-5'-thioadenosine + spermidine + H(+)
  2. Putrescine Export via Putrescine/Arginine Antiporter
  3. L-Arginine:glycine amidinotransferase

  Catalysed by SRM, SLC3A2, SLC7A7, GATMextracellular space, cytosolOne of 2 routes

• sphing-4-enineReach from here →
  1. S-adenosyl 3-(methylsulfanyl)propylamine + putrescine = S-methyl-5'-thioadenosine + spermidine + H(+)
  2. acetyl-CoA:putrescine N-acetyltransferase
  3. acyl-CoA:sphingosine N-acyltransferase

  Catalysed by SRM, SAT1, SAT2, ASAH1 and 3 morecytosol, Golgi apparatusOne of 2 routes

• L-methionineReach from here →
  1. S-adenosyl 3-(methylsulfanyl)propylamine + putrescine = S-methyl-5'-thioadenosine + spermidine + H(+)
  2. acetyl-CoA:putrescine N-acetyltransferase
  3. N-acetylglutamate synthase (N-acetylmethionine)

  Catalysed by SRM, SAT1, SAT2, NAGScytosol, mitochondrial matrixOne of 8 routes

• L-tryptophanReach from here →
  1. S-adenosyl 3-(methylsulfanyl)propylamine + putrescine = S-methyl-5'-thioadenosine + spermidine + H(+)
  2. Putrescine Export via Putrescine/Arginine Antiporter
  3. transport of arginine and tryptophan (cytosol to extracellular)

  Catalysed by SRM, SLC3A2, SLC7A7, SLC7A6extracellular space, cytosolOne of 4 routes

• L-alanineReach from here →
  1. S-adenosyl 3-(methylsulfanyl)propylamine + putrescine = S-methyl-5'-thioadenosine + spermidine + H(+)
  2. acetyl-CoA:putrescine N-acetyltransferase
  3. amino-acid N-acetyltransferase (N-acetyl-L-alanine)

  Catalysed by SRM, SAT1, SAT2cytosol, mitochondrial matrixOne of 7 routes

• L-asparagineReach from here →
  1. S-adenosyl 3-(methylsulfanyl)propylamine + putrescine = S-methyl-5'-thioadenosine + spermidine + H(+)
  2. acetyl-CoA:putrescine N-acetyltransferase
  3. N-acetylglutamate synthase (N-acetyl-L-asparagine)

  Catalysed by SRM, SAT1, SAT2, NAGScytosol, mitochondrial matrixOne of 5 routes

• IMPReach from here →
  1. S-methyl-5'-thioadenosine:phosphate S-methyl-5-thio-alpha-D-ribosyl-transferase
  2. Adenine aminohydrolase
  3. IMP + diphosphate = hypoxanthine + 5-phospho-alpha-D-ribose 1-diphosphate

  Catalysed by MTAP, HPRT1cytosol

• taurocyamineReach from here →
  1. S-adenosyl 3-(methylsulfanyl)propylamine + putrescine = S-methyl-5'-thioadenosine + spermidine + H(+)
  2. Putrescine Export via Putrescine/Arginine Antiporter
  3. taurine + L-arginine = taurocyamine + L-ornithine

  Catalysed by SRM, SLC3A2, SLC7A7, GATMextracellular space, cytosol

• L-glutamate 5-semialdehydeReach from here →
  1. S-adenosyl 3-(methylsulfanyl)propylamine + putrescine = S-methyl-5'-thioadenosine + spermidine + H(+)
  2. L-ornithine + H(+) = putrescine + CO2
  3. L-ornithine + 2-oxoglutarate = L-glutamate 5-semialdehyde + L-glutamate

  Catalysed by SRM, ODC1, OAT

• L-phenylalanineReach from here →
  1. S-adenosyl 3-(methylsulfanyl)propylamine + putrescine = S-methyl-5'-thioadenosine + spermidine + H(+)
  2. Putrescine Export via Putrescine/Arginine Antiporter
  3. transport of arginine and phenylalanine (cytosol to extracellular)

  Catalysed by SRM, SLC3A2, SLC7A7, SLC7A6extracellular space, cytosolOne of 6 routes

• N(1)-acetylspermineReach from here →
  1. S-adenosyl 3-(methylsulfanyl)propylamine + putrescine = S-methyl-5'-thioadenosine + spermidine + H(+)
  2. S-adenosylmethioninamine:putrescine 3-aminopropyltransferase
  3. N(1)-acetylspermine + O2 + H2O = 3-acetamidopropanal + spermidine + H2O2

  Catalysed by SRM, PAOXcytosolOne of 2 routes

• L,L-cystathionineReach from here →
  1. S-adenosyl 3-(methylsulfanyl)propylamine + putrescine = S-methyl-5'-thioadenosine + spermidine + H(+)
  2. acetyl-CoA:putrescine N-acetyltransferase
  3. N-acetylglutamate synthase (N-acetyl-L-cystathionine)

  Catalysed by SRM, SAT1, SAT2, NAGScytosol, mitochondrial matrix

• N(omega),N(omega)-dimethyl-L-arginineReach from here →
  1. S-adenosyl 3-(methylsulfanyl)propylamine + putrescine = S-methyl-5'-thioadenosine + spermidine + H(+)
  2. Putrescine Export via Putrescine/Arginine Antiporter
  3. N(omega),N(omega)-dimethyl-L-arginine(in) + L-arginine(out) = N(omega),N(omega)-dimethyl-L-arginine(out) + L-arginine(in)

  Catalysed by SRM, SLC3A2, SLC7A7, SLC25A2extracellular space, cytosol, inner side of the membrane, outer side of the membraneOne of 4 routes

• an acyl-CoAReach from here →
  1. S-adenosyl 3-(methylsulfanyl)propylamine + putrescine = S-methyl-5'-thioadenosine + spermidine + H(+)
  2. acetyl-CoA:putrescine N-acetyltransferase
  3. acyl-CoA:sphingosine N-acyltransferase

  Catalysed by SRM, SAT1, SAT2, ASAH1 and 3 morecytosol, Golgi apparatusOne of 2 routes

• 3-aminopropanalReach from here →
  1. S-adenosyl 3-(methylsulfanyl)propylamine + putrescine = S-methyl-5'-thioadenosine + spermidine + H(+)
  2. S-adenosyl 3-(methylsulfanyl)propylamine + spermidine = spermine + S-methyl-5'-thioadenosine + H(+)
  3. spermine + O2 + H2O = 3-aminopropanal + spermidine + H2O2

  Catalysed by SRM, SMS, SMOX

• 5-guanidino-2-oxopentanoateReach from here →
  1. S-adenosyl 3-(methylsulfanyl)propylamine + putrescine = S-methyl-5'-thioadenosine + spermidine + H(+)
  2. Putrescine Export via Putrescine/Arginine Antiporter
  3. L-arginine + O2 + H2O = 5-guanidino-2-oxopentanoate + H2O2 + NH4(+)

  Catalysed by SRM, SLC3A2, SLC7A7, IL4I1extracellular space, cytosol

• N(8)-acetylspermidineReach from here →
  1. S-adenosyl 3-(methylsulfanyl)propylamine + putrescine = S-methyl-5'-thioadenosine + spermidine + H(+)
  2. S-adenosylmethioninamine:putrescine 3-aminopropyltransferase
  3. N8-acetylspermidine to spermidine conversion

  Catalysed by SRMcytosolOne of 3 routes

• (3Z)-dodecenoyl-CoAReach from here →
  1. S-adenosyl 3-(methylsulfanyl)propylamine + putrescine = S-methyl-5'-thioadenosine + spermidine + H(+)
  2. acetyl-CoA:putrescine N-acetyltransferase
  3. acetyl-CoA C-acyltransferase (3-oxomyrist-5-enoyl-CoA)

  Catalysed by SRM, SAT1, SAT2, HADHA and 2 morecytosol, mitochondrial matrixOne of 3 routes

• N(1),N(12)-diacetylspermineReach from here →
  1. S-adenosyl 3-(methylsulfanyl)propylamine + putrescine = S-methyl-5'-thioadenosine + spermidine + H(+)
  2. N(1)-acetylspermidine + O2 + H2O = 3-acetamidopropanal + putrescine + H2O2
  3. N(1),N(12)-diacetylspermine + O2 + H2O = 3-acetamidopropanal + N(1)-acetylspermidine + H2O2

  Catalysed by SRM, PAOX

• (25R)-3alpha,7alpha,12alpha-trihydroxy-5beta-cholestan-26-oyl-CoAReach from here →
  1. S-adenosyl 3-(methylsulfanyl)propylamine + putrescine = S-methyl-5'-thioadenosine + spermidine + H(+)
  2. acetyl-CoA:putrescine N-acetyltransferase
  3. 3alpha,7alpha,12alpha-trihydroxy-5beta-cholestanoate:CoA ligase (AMP-forming)

  Catalysed by SRM, SAT1, SAT2, SLC27A2 and 1 morecytosol, endoplasmic reticulumOne of 3 routes

• 5-amino-2-oxopentanoateReach from here →
  1. S-adenosyl 3-(methylsulfanyl)propylamine + putrescine = S-methyl-5'-thioadenosine + spermidine + H(+)
  2. L-ornithine + H(+) = putrescine + CO2
  3. L-ornithine + pyruvate = 5-amino-2-oxopentanoate + L-alanine

  Catalysed by SRM, ODC1, AGXT2One of 2 routes

• deoxycholoyl-CoAReach from here →
  1. S-adenosyl 3-(methylsulfanyl)propylamine + putrescine = S-methyl-5'-thioadenosine + spermidine + H(+)
  2. acetyl-CoA:putrescine N-acetyltransferase
  3. cholate-CoA ligase (3alpha,12alpha-dihydroxy-5beta-cholanate)

  Catalysed by SRM, SAT1, SAT2, SLC27A2 and 1 morecytosolOne of 4 routes

• 4-aminobutanoateReach from here →
  1. S-adenosyl 3-(methylsulfanyl)propylamine + putrescine = S-methyl-5'-thioadenosine + spermidine + H(+)
  2. Putrescine:oxygen oxidoreductase (deaminating)
  3. 4-Aminobutyraldehyde:NAD+ oxidoreductase

  Catalysed by SRM, AOC2, AOC1, AOC3 and 5 moreextracellular space, mitochondrial matrixOne of 4 routes

• decanoyl-CoAReach from here →
  1. S-adenosyl 3-(methylsulfanyl)propylamine + putrescine = S-methyl-5'-thioadenosine + spermidine + H(+)
  2. acetyl-CoA:putrescine N-acetyltransferase
  3. medium-chain acyl-CoA ligase (decanoic acid)

  Catalysed by SRM, SAT1, SAT2, ACSM4 and 5 morecytosolOne of 7 routes

• (2E)-hexadecenoyl-CoAReach from here →
  1. S-adenosyl 3-(methylsulfanyl)propylamine + putrescine = S-methyl-5'-thioadenosine + spermidine + H(+)
  2. acetyl-CoA:putrescine N-acetyltransferase
  3. Carnitine O-Palmitoyltransferase

  Catalysed by SRM, SAT1, SAT2, CPT1A and 2 morecytosolOne of 4 routes

• (9Z)-hexadecenoyl-CoAReach from here →
  1. S-adenosyl 3-(methylsulfanyl)propylamine + putrescine = S-methyl-5'-thioadenosine + spermidine + H(+)
  2. acetyl-CoA:putrescine N-acetyltransferase
  3. long-chain-fatty-acid-CoA ligase (palmitolate)

  Catalysed by SRM, SAT1, SAT2, SLC27A2 and 7 morecytosolOne of 11 routes

• 3-hydroxyisovaleryl-CoAReach from here →
  1. S-adenosyl 3-(methylsulfanyl)propylamine + putrescine = S-methyl-5'-thioadenosine + spermidine + H(+)
  2. acetyl-CoA:putrescine N-acetyltransferase
  3. (3-Hydroxyisovalerylcoa->3-Hydroxyisovalerylcarnitine)

  Catalysed by SRM, SAT1, SAT2, CPT1A and 1 morecytosol

• CHEBI:63544Reach from here →
  1. S-adenosyl 3-(methylsulfanyl)propylamine + putrescine = S-methyl-5'-thioadenosine + spermidine + H(+)
  2. acetyl-CoA:putrescine N-acetyltransferase
  3. long-chain-fatty-acid-CoA ligase (adrenic acid)

  Catalysed by SRM, SAT1, SAT2, SLC27A2 and 7 morecytosolOne of 7 routes

• hexacosanoyl-CoAReach from here →
  1. S-adenosyl 3-(methylsulfanyl)propylamine + putrescine = S-methyl-5'-thioadenosine + spermidine + H(+)
  2. acetyl-CoA:putrescine N-acetyltransferase
  3. long-chain-fatty-acid-CoA ligase (cerotic acid)

  Catalysed by SRM, SAT1, SAT2, SLC27A2 and 7 morecytosolOne of 5 routes

• tetracosanoyl-CoAReach from here →
  1. S-adenosyl 3-(methylsulfanyl)propylamine + putrescine = S-methyl-5'-thioadenosine + spermidine + H(+)
  2. acetyl-CoA:putrescine N-acetyltransferase
  3. long-chain-fatty-acid-CoA ligase (lignocerate)

  Catalysed by SRM, SAT1, SAT2, SLC27A2 and 7 morecytosolOne of 10 routes

• docosanoyl-CoAReach from here →
  1. S-adenosyl 3-(methylsulfanyl)propylamine + putrescine = S-methyl-5'-thioadenosine + spermidine + H(+)
  2. acetyl-CoA:putrescine N-acetyltransferase
  3. long-chain-fatty-acid-CoA ligase (behenic acid)

  Catalysed by SRM, SAT1, SAT2, SLC27A2 and 7 morecytosolOne of 9 routes

• N(5)-[(Z)-amino(hydroxyimino)methyl]ornithineReach from here →
  1. S-adenosyl 3-(methylsulfanyl)propylamine + putrescine = S-methyl-5'-thioadenosine + spermidine + H(+)
  2. Putrescine Export via Putrescine/Arginine Antiporter
  3. L-arginine,NADPH:oxygen oxidoreductase (N-(omega)-hydroxyarginine-forming)

  Catalysed by SRM, SLC3A2, SLC7A7, NOS3 and 2 moreextracellular space, cytosol

• (2E)-octadecenoyl-CoAReach from here →
  1. S-adenosyl 3-(methylsulfanyl)propylamine + putrescine = S-methyl-5'-thioadenosine + spermidine + H(+)
  2. acetyl-CoA:putrescine N-acetyltransferase
  3. Carnitine O-Palmitoyltransferase

  Catalysed by SRM, SAT1, SAT2, CPT1A and 2 morecytosolOne of 3 routes

• (6Z,9Z,12Z,15Z)-octadecatetraenoyl-CoAReach from here →
  1. S-adenosyl 3-(methylsulfanyl)propylamine + putrescine = S-methyl-5'-thioadenosine + spermidine + H(+)
  2. acetyl-CoA:putrescine N-acetyltransferase
  3. long-chain-fatty-acid-CoA ligase (stearidonic acid)

  Catalysed by SRM, SAT1, SAT2, SLC27A2 and 7 morecytosolOne of 8 routes

• 4-acetamidobutanalReach from here →
  1. S-adenosyl 3-(methylsulfanyl)propylamine + putrescine = S-methyl-5'-thioadenosine + spermidine + H(+)
  2. acetyl-CoA:putrescine N-acetyltransferase
  3. N-Acetylputrescine:oxygen oxidoreductase(deaminating)(flavin-containing)

  Catalysed by SRM, SAT1, SAT2, AOC2 and 4 morecytosolOne of 2 routes

• (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoAReach from here →
  1. S-adenosyl 3-(methylsulfanyl)propylamine + putrescine = S-methyl-5'-thioadenosine + spermidine + H(+)
  2. acetyl-CoA:putrescine N-acetyltransferase
  3. long-chain-fatty-acid-CoA ligase (EPA)

  Catalysed by SRM, SAT1, SAT2, SLC27A2 and 7 morecytosolOne of 9 routes

• (7Z,10Z,13Z,16Z,19Z)-docosapentaenoyl-CoAReach from here →
  1. S-adenosyl 3-(methylsulfanyl)propylamine + putrescine = S-methyl-5'-thioadenosine + spermidine + H(+)
  2. acetyl-CoA:putrescine N-acetyltransferase
  3. long-chain-fatty-acid-CoA ligase (DPA)

  Catalysed by SRM, SAT1, SAT2, SLC27A2 and 7 morecytosolOne of 6 routes

• (9Z,12Z,15Z)-octadecatrienoyl-CoAReach from here →
  1. S-adenosyl 3-(methylsulfanyl)propylamine + putrescine = S-methyl-5'-thioadenosine + spermidine + H(+)
  2. acetyl-CoA:putrescine N-acetyltransferase
  3. long-chain-fatty-acid-CoA ligase (linolenate)

  Catalysed by SRM, SAT1, SAT2, SLC27A2 and 7 morecytosolOne of 7 routes