CHEBI:17927

Three steps

• L-tyrosineReach from here →
  1. N1,N8-diacetylspermidine to N1-acetylspermidine conversion
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. L-tyrosine + glyoxylate = 3-(4-hydroxyphenyl)pyruvate + glycine

  Catalysed by GLYAT, GLYATL2, GLYATL1, AADATcytosol, mitochondrial matrixOne of 2 routes

• 3-aminopropanalReach from here →
  1. diamine N-acetyltransferase (N1-acetylspermidine)
  2. S-adenosylmethioninamine:spermidine 3-aminopropyltransferase
  3. spermidine:oxygen oxidoreductase (spermidine-forming)

  Catalysed by SAT1, SAT2, SRM, SMS and 1 morecytosolOne of 3 routes

• trans-4-hydroxy-L-prolineReach from here →
  1. N1,N8-diacetylspermidine to N1-acetylspermidine conversion
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. trans-4-hydroxy-L-proline(out) + L-alanine(in) + Na(+)(out) = trans-4-hydroxy-L-proline(in) + L-alanine(out) + Na(+)(in)

  Catalysed by SLC1A4cytosol, mitochondrial matrix, inner side of the membrane, outer side of the membraneOne of 2 routes

• histamineReach from here →
  1. Transport by Y+Lat-2 into Extracellular Space
  2. transport of arginine and histidine (cytosol to extracellular)
  3. L-histidine carboxy-lyase (histamine-forming)

  Catalysed by SLC3A2, SLC7A6, SLC7A5, HDCextracellular space, cytosolOne of 2 routes

• L-2-aminopentanoateReach from here →
  1. Transport by Y+Lat-2 into Extracellular Space
  2. N(omega),N(omega)-dimethyl-L-arginine(in) + L-arginine(out) = N(omega),N(omega)-dimethyl-L-arginine(out) + L-arginine(in)
  3. 2-oxopentanoate + N(omega),N(omega)-dimethyl-L-arginine = 5-(3,3-dimethylguanidino)-2-oxopentanoate + L-2-aminopentanoate

  Catalysed by SLC3A2, SLC7A6, SLC25A2, AGXT2extracellular space, cytosol, inner side of the membrane, outer side of the membrane

• L-2-aminohexanoateReach from here →
  1. Transport by Y+Lat-2 into Extracellular Space
  2. N(omega),N(omega)-dimethyl-L-arginine(in) + L-arginine(out) = N(omega),N(omega)-dimethyl-L-arginine(out) + L-arginine(in)
  3. 2-oxohexanoate + N(omega),N(omega)-dimethyl-L-arginine = L-2-aminohexanoate + 5-(3,3-dimethylguanidino)-2-oxopentanoate

  Catalysed by SLC3A2, SLC7A6, SLC25A2, AGXT2extracellular space, cytosol, inner side of the membrane, outer side of the membrane

• 5-(methylsulfanyl)-alpha-D-ribose 1-phosphateReach from here →
  1. diamine N-acetyltransferase (N1-acetylspermidine)
  2. S-adenosylmethioninamine:spermidine 3-aminopropyltransferase
  3. S-methyl-5'-thioadenosine:phosphate S-methyl-5-thio-alpha-D-ribosyl-transferase

  Catalysed by SAT1, SAT2, SRM, SMS and 1 morecytosolOne of 2 routes

• (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoateReach from here →
  1. N1,N8-diacetylspermidine to N1-acetylspermidine conversion
  2. long-chain-fatty-acid-CoA ligase (EPA)
  3. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 2 routes

• S-sulfanyl-L-cysteineReach from here →
  1. N1,N8-diacetylspermidine to N1-acetylspermidine conversion
  2. N-acetylglutamate synthase (N-acetyl-L-cysteine)
  3. 2 L-cysteine = S-sulfanyl-L-cysteine + L-alanine

  Catalysed by NAGS, CARS2cytosol, mitochondrial matrix

• a 1,2-diacyl-sn-glycero-3-phosphateReach from here →
  1. N1,N8-diacetylspermidine to N1-acetylspermidine conversion
  2. acyl-CoA:sphingosine N-acyltransferase
  3. a 1-acyl-sn-glycero-3-phosphate + an acyl-CoA = a 1,2-diacyl-sn-glycero-3-phosphate + CoA

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 13 morecytosol, Golgi apparatus

• N-formyl-L-kynurenineReach from here →
  1. Transport by Y+Lat-2 into Extracellular Space
  2. transport of arginine and tryptophan (cytosol to extracellular)
  3. L-tryptophan + O2 = N-formyl-L-kynurenine

  Catalysed by SLC3A2, SLC7A6, IDO1, TDO2 and 1 moreextracellular space, cytosol

• (3S)-citramalyl-CoAReach from here →
  1. N1,N8-diacetylspermidine to N1-acetylspermidine conversion
  2. Itaconate:CoA ligase (GDP-forming)
  3. (3S)-citramalyl-CoA = itaconyl-CoA + H2O

  Catalysed by SUCLG1, SUCLG2, SUCLA2, AUHcytosol, mitochondrial matrix

• 5-phospho-beta-D-ribosylamineReach from here →
  1. Transport by Y+Lat-2 into Extracellular Space
  2. transport of arginine and glutamine (cytosol to extracellular)
  3. phosphoribosyl pyrophosphate amidotransferase (glutamine)

  Catalysed by SLC3A2, SLC7A6, PPATextracellular space, cytosolOne of 2 routes

• phosphoenolpyruvateReach from here →
  1. N1,N8-diacetylspermidine to N1-acetylspermidine conversion
  2. ATP citrate lyase (citrate)
  3. oxaloacetate + GTP = phosphoenolpyruvate + GDP + CO2

  Catalysed by ACLY, PCK1, PCK2cytosol

• D-glucosamine 6-phosphateReach from here →
  1. Transport by Y+Lat-2 into Extracellular Space
  2. transport of arginine and glutamine (cytosol to extracellular)
  3. D-fructose 6-phosphate + L-glutamine = D-glucosamine 6-phosphate + L-glutamate

  Catalysed by SLC3A2, SLC7A6, GFPT2, GFPT1extracellular space, cytosol

• L-methionine (S)-S-oxideReach from here →
  1. N1,N8-diacetylspermidine to N1-acetylspermidine conversion
  2. N-acetylglutamate synthase (N-acetylmethionine)
  3. [thioredoxin]-disulfide + L-methionine + H2O = L-methionine (S)-S-oxide + [thioredoxin]-dithiol

  Catalysed by NAGS, MSRAcytosol, mitochondrial matrix

• L-methionine (R)-S-oxideReach from here →
  1. N1,N8-diacetylspermidine to N1-acetylspermidine conversion
  2. N-acetylglutamate synthase (N-acetylmethionine)
  3. [thioredoxin]-disulfide + L-methionine + H2O = L-methionine (R)-S-oxide + [thioredoxin]-dithiol

  Catalysed by NAGS, MSRB3, MSRB1, MSRB2cytosol, mitochondrial matrix

• 5-amino-2-oxopentanoateReach from here →
  1. N1-acetylspermidine:oxygen oxidoreductase (3-acetamidopropanal-forming)
  2. L-ornithine + H(+) = putrescine + CO2
  3. L-ornithine + pyruvate = 5-amino-2-oxopentanoate + L-alanine

  Catalysed by PAOX, SMOX, ODC1, AGXT2cytosolOne of 2 routes

• N-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-glycineReach from here →
  1. N1,N8-diacetylspermidine to N1-acetylspermidine conversion
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + glycine = N-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-glycine + CoA + H(+)

  Catalysed by GLYAT, GLYATL2, GLYATL1cytosol, mitochondrial matrixOne of 2 routes

• methylamineReach from here →
  1. Transport by Y+Lat-2 into Extracellular Space
  2. N(omega)-methyl-L-arginine(in) + L-arginine(out) = N(omega)-methyl-L-arginine(out) + L-arginine(in)
  3. N(omega)-methyl-L-arginine + H2O = L-citrulline + methylamine

  Catalysed by SLC3A2, SLC7A6, SLC25A29, DDAH1extracellular space, cytosol, inner side of the membrane, outer side of the membrane

• N-[(R)-4-phosphopantothenoyl]-L-cysteineReach from here →
  1. N1,N8-diacetylspermidine to N1-acetylspermidine conversion
  2. N-acetylglutamate synthase (N-acetyl-L-cysteine)
  3. (R)-4'-phosphopantothenate:L-cysteine ligase

  Catalysed by NAGS, PPCScytosol, mitochondrial matrixOne of 4 routes

• 4-aminobutanoateReach from here →
  1. diamine N-acetyltransferase (N1-acetylspermidine)
  2. spermidine:(acceptor) oxidoreductase
  3. 4-Aminobutyraldehyde:NAD+ oxidoreductase

  Catalysed by SAT1, SAT2, ALDH2, ALDH1B1 and 3 morecytosol, mitochondrial matrixOne of 9 routes

• 3-iodo-L-tyrosineReach from here →
  1. Transport by Y+Lat-2 into Extracellular Space
  2. transport of arginine and tyrosine (cytosol to extracellular)
  3. thyroid peroxidase (iodine)

  Catalysed by SLC3A2, SLC7A6, TPOextracellular space, cytosolOne of 2 routes

• 1-acyl-2-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphocholineReach from here →
  1. N1,N8-diacetylspermidine to N1-acetylspermidine conversion
  2. long-chain-fatty-acid-CoA ligase ((6Z,9Z)-octadecadienoic acid)
  3. (9Z,12Z)-octadecadienoyl-CoA + a 1-acyl-sn-glycero-3-phosphocholine = 1-acyl-2-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphocholine + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 5 morecytosol

• L-prolineReach from here →
  1. N1,N8-diacetylspermidine to N1-acetylspermidine conversion
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. L-proline(out) + L-alanine(in) + Na(+)(out) = L-proline(in) + L-alanine(out) + Na(+)(in)

  Catalysed by SLC1A4cytosol, mitochondrial matrix, inner side of the membrane, outer side of the membraneOne of 2 routes

• sphing-4-enine 1-phosphateReach from here →
  1. N1,N8-diacetylspermidine to N1-acetylspermidine conversion
  2. acyl-CoA:sphingosine N-acyltransferase
  3. sphing-4-enine + ATP = sphing-4-enine 1-phosphate + ADP + H(+)

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 2 morecytosol, Golgi apparatus

• N-benzoylglycineReach from here →
  1. N1,N8-diacetylspermidine to N1-acetylspermidine conversion
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. Hippurate (Benzoylglycinate) Formation

  Catalysed by GLYAT, GLYATL2, GLYATL1cytosol, mitochondrial matrixOne of 2 routes

• 3-sulfino-L-alanineReach from here →
  1. N1,N8-diacetylspermidine to N1-acetylspermidine conversion
  2. N-acetylglutamate synthase (N-acetyl-L-cysteine)
  3. L-Cysteine:oxygen oxidoreductase

  Catalysed by NAGS, CDO1cytosol, mitochondrial matrixOne of 2 routes

• (2E)-tetradecenoyl-CoAReach from here →
  1. N1,N8-diacetylspermidine to N1-acetylspermidine conversion
  2. long-chain-fatty-acid-CoA ligase (myristic acid)
  3. trans-tetradec-2-enoyl-CoA reductase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 5 morecytosol, mitochondrial matrixOne of 5 routes

• (2E)-decenoyl-CoAReach from here →
  1. N1,N8-diacetylspermidine to N1-acetylspermidine conversion
  2. medium-chain acyl-CoA ligase (decanoic acid)
  3. trans-dec-2-enoyl-CoA reductase

  Catalysed by ACSM4, ACSM1, ACSM2A, ACSM3 and 3 morecytosol, mitochondrial matrixOne of 8 routes

• L-cysteinylglycineReach from here →
  1. N1,N8-diacetylspermidine to N1-acetylspermidine conversion
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. gamma-glutamyltransferase (alanine)

  Catalysed by GGTLC3, GGT1, GGT5, GGTLC2 and 2 morecytosol, mitochondrial matrixOne of 2 routes

• (2E)-hexenoyl-CoAReach from here →
  1. N1,N8-diacetylspermidine to N1-acetylspermidine conversion
  2. medium-chain acyl-CoA ligase (hexanoic acid)
  3. trans-hex-2-enoyl-CoA reductase

  Catalysed by ACSM4, ACSM1, ACSM2A, ACSM3 and 3 morecytosol, mitochondrial matrixOne of 3 routes

• a cardiolipinReach from here →
  1. N1,N8-diacetylspermidine to N1-acetylspermidine conversion
  2. acyl-CoA:sphingosine N-acyltransferase
  3. 1'-[1,2-diacyl-sn-glycero-3-phospho],3'-[1-acyl-sn-glycero-3-phospho]-glycerol + an acyl-CoA = a cardiolipin + CoA

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 1 morecytosol, Golgi apparatus

• (2E)-octenoyl-CoAReach from here →
  1. N1,N8-diacetylspermidine to N1-acetylspermidine conversion
  2. Octanoyl-CoA:L-carnitine O-octanoyltransferase
  3. trans-oct-2-enoyl-CoA reductase

  Catalysed by CROT, MECRcytosol, mitochondrial matrixOne of 5 routes

• 3-oxotetradecanoyl-CoAReach from here →
  1. N1,N8-diacetylspermidine to N1-acetylspermidine conversion
  2. long-chain-fatty-acid-CoA ligase (lauric acid)
  3. dodecanoyl-CoA + malonyl-CoA + H(+) = 3-oxotetradecanoyl-CoA + CO2 + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 5 morecytosol

• an all-trans-retinyl esterReach from here →
  1. N1,N8-diacetylspermidine to N1-acetylspermidine conversion
  2. acyl-CoA:sphingosine N-acyltransferase
  3. all-trans-retinol + an acyl-CoA = an all-trans-retinyl ester + CoA

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 4 morecytosol, Golgi apparatusOne of 4 routes

• 1-O-hexadecyl-sn-glycero-3-phosphocholineReach from here →
  1. N1,N8-diacetylspermidine to N1-acetylspermidine conversion
  2. acyl-CoA:sphingosine N-acyltransferase
  3. 1-O-hexadecyl-2-acetyl-sn-glycero-3-phosphocholine + sphing-4-enine = 1-O-hexadecyl-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine + H(+)

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 1 morecytosol, Golgi apparatus

• a 1,2-diacyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. N1,N8-diacetylspermidine to N1-acetylspermidine conversion
  2. acyl-CoA:sphingosine N-acyltransferase
  3. a 1-acyl-sn-glycero-3-phosphoethanolamine + an acyl-CoA = a 1,2-diacyl-sn-glycero-3-phosphoethanolamine + CoA

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 4 morecytosol, Golgi apparatus

• a triacyl-sn-glycerolReach from here →
  1. N1,N8-diacetylspermidine to N1-acetylspermidine conversion
  2. acyl-CoA:sphingosine N-acyltransferase
  3. an acyl-CoA + a 1,2-diacyl-sn-glycerol = a triacyl-sn-glycerol + CoA

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 6 morecytosol, Golgi apparatus

• a 1,2-diacyl-sn-glycero-3-phospho-(1'-sn-glycerol)Reach from here →
  1. N1,N8-diacetylspermidine to N1-acetylspermidine conversion
  2. acyl-CoA:sphingosine N-acyltransferase
  3. 1-acyl-sn-glycero-3-phospho-(1'-sn-glycerol) + an acyl-CoA = a 1,2-diacyl-sn-glycero-3-phospho-(1'-sn-glycerol) + CoA

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 3 morecytosol, Golgi apparatus

• 1-octadecanoyl-2-acyl-sn-glycero-3-phospho-1D-myo-inositolReach from here →
  1. N1,N8-diacetylspermidine to N1-acetylspermidine conversion
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. a 2-acyl-sn-glycero-3-phospho-D-myo-inositol + octadecanoyl-CoA = 1-octadecanoyl-2-acyl-sn-glycero-3-phospho-1D-myo-inositol + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 4 morecytosol

• 3-oxoeicosasphinganineReach from here →
  1. N1,N8-diacetylspermidine to N1-acetylspermidine conversion
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. octadecanoyl-CoA + L-serine + H(+) = 3-oxoeicosasphinganine + CO2 + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 morecytosol

• 3-oxoeicosanoyl-CoAReach from here →
  1. N1,N8-diacetylspermidine to N1-acetylspermidine conversion
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. very-long-chain 3-oxoacyl-CoA synthase (malonyl-CoA)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 10 morecytosolOne of 2 routes

• N-docosanoylsphinganineReach from here →
  1. N1,N8-diacetylspermidine to N1-acetylspermidine conversion
  2. long-chain-fatty-acid-CoA ligase (behenic acid)
  3. docosanoyl-CoA + sphinganine = N-docosanoylsphinganine + CoA + H(+)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosol

• N-eicosanoylsphinganineReach from here →
  1. N1,N8-diacetylspermidine to N1-acetylspermidine conversion
  2. long-chain-fatty-acid-CoA ligase (eicosanoate)
  3. eicosanoyl-CoA + sphinganine = N-eicosanoylsphinganine + CoA + H(+)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosol

• N-(octadecanoyl)-sphinganineReach from here →
  1. N1,N8-diacetylspermidine to N1-acetylspermidine conversion
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. sphinganine + octadecanoyl-CoA = N-(octadecanoyl)-sphinganine + CoA + H(+)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosol

• N-(tetradecanoyl)-sphinganineReach from here →
  1. N1,N8-diacetylspermidine to N1-acetylspermidine conversion
  2. long-chain-fatty-acid-CoA ligase (myristic acid)
  3. sphinganine + tetradecanoyl-CoA = N-(tetradecanoyl)-sphinganine + CoA + H(+)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 morecytosol

• 3-oxohexadecasphinganineReach from here →
  1. N1,N8-diacetylspermidine to N1-acetylspermidine conversion
  2. long-chain-fatty-acid-CoA ligase (myristic acid)
  3. tetradecanoyl-CoA + L-serine + H(+) = 3-oxohexadecasphinganine + CO2 + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 morecytosol

• 3-oxotetradecasphinganineReach from here →
  1. N1,N8-diacetylspermidine to N1-acetylspermidine conversion
  2. long-chain-fatty-acid-CoA ligase (lauric acid)
  3. dodecanoyl-CoA + L-serine + H(+) = 3-oxotetradecasphinganine + CO2 + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 morecytosol

• Mo-molybdopterinReach from here →
  1. N1,N8-diacetylspermidine to N1-acetylspermidine conversion
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O

  Catalysed by MOCOScytosol, mitochondrial matrix