all-trans-retinoic acid

Three steps

• CHEBI:17895Reach from here →
  1. transport of pyruvate and retinoate (cytosol to extracellular)
  2. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase
  3. transport of alanine and tyrosine (cytosol to extracellular)

  Catalysed by SLC16A4, SLC16A5, SLC16A3, SLC16A7 and 4 moreextracellular space, cytosol, mitochondrial matrixOne of 10 routes

• butanoateReach from here →
  1. transport of butyrate and retinoate (cytosol to extracellular)
  2. Butanoate:CoA ligase (AMP-forming)
  3. butanoyl-CoA + H2O = butanoate + CoA + H(+)

  Catalysed by SLC16A4, SLC16A5, ACSM4, ACSM1 and 10 moreextracellular space, cytosol

• 3-phenylpyruvateReach from here →
  1. transport of pyruvate and retinoate (cytosol to extracellular)
  2. L-Glutamine:pyruvate aminotransferase
  3. 3-phenylpyruvate + L-glutamine = 2-oxoglutaramate + L-phenylalanine

  Catalysed by SLC16A4, SLC16A5, SLC16A3, SLC16A7 and 3 moreextracellular space, cytosol

• fumaric acidReach from here →
  1. transport of acetoacetate and retinoate (cytosol to extracellular)
  2. 4-fumarylacetoacetate + H2O = acetoacetate + fumarate + H(+)
  3. 4-fumarylacetoacetate fumarylhydrolase

  Catalysed by SLC16A4, SLC16A5, FAHextracellular space, cytosolOne of 8 routes

• CHEBI:18019Reach from here →
  1. transport of pyruvate and retinoate (cytosol to extracellular)
  2. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase
  3. transport of alanine and lysine (cytosol to extracellular)

  Catalysed by SLC16A4, SLC16A5, SLC16A3, SLC16A7 and 4 moreextracellular space, cytosol, mitochondrial matrixOne of 5 routes

• thiocyanateReach from here →
  1. transport of pyruvate and retinoate (cytosol to extracellular)
  2. 2-oxo-3-sulfanylpropanoate + [thioredoxin]-dithiol = [thioredoxin]-disulfide + hydrogen sulfide + pyruvate + H(+)
  3. 3-mercaptopyruvate sulfurtransferase (hydrogen-cyanide)

  Catalysed by SLC16A4, SLC16A5, SLC16A3, SLC16A7 and 4 moreextracellular space, cytosol

• a diacylglycerolReach from here →
  1. retinoate reduction
  2. all-trans-retinol + NADP(+) = all-trans-retinal + NADPH + H(+)
  3. a triacylglycerol + all-trans-retinol = an all-trans-retinyl ester + a diacylglycerol

  Catalysed by AKR1B15, AKR1B10, DHRS3, AKR1B1 and 9 morecytosol

• L-glutamineReach from here →
  1. transport of pyruvate and retinoate (cytosol to extracellular)
  2. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase
  3. transport of alanine and glutamine (cytosol to extracellular)

  Catalysed by SLC16A4, SLC16A5, SLC16A3, SLC16A7 and 6 moreextracellular space, cytosol, mitochondrial matrixOne of 18 routes

• 5-hydroxyisourateReach from here →
  1. transport of L-lactate and retinoate (cytosol to extracellular)
  2. transport of L-lactate and urate (cytosol to extracellular)
  3. urate:oxygen oxidoreductase

  Catalysed by SLC16A4, SLC16A5, SLC16A3, SLC16A7 and 3 moreextracellular space, cytosol

• dTTPReach from here →
  1. transport of pyruvate and retinoate (cytosol to extracellular)
  2. pyruvate kinase (dTDP)
  3. DTTP Nucleotidohydrolase

  Catalysed by SLC16A4, SLC16A5, SLC16A3, SLC16A7 and 7 moreextracellular space, cytosolOne of 11 routes

• CHEBI:18095Reach from here →
  1. transport of pyruvate and retinoate (cytosol to extracellular)
  2. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase
  3. Transport of Hydroxy-Proline

  Catalysed by SLC16A4, SLC16A5, SLC16A3, SLC16A7 and 4 moreextracellular space, cytosol, mitochondrial matrixOne of 2 routes

• N-carbamoyl-beta-alanineReach from here →
  1. transport of formate and retinoate (cytosol to extracellular)
  2. transport of chloride and formate (cytosol to extracellular)
  3. Transport of 3-Ureidopropionate

  Catalysed by SLC16A4, SLC16A5, SLC26A4extracellular space, cytosolOne of 2 routes

• N(2)-formyl-N(1)-(5-phospho-D-ribosyl)glycinamideReach from here →
  1. transport of formate and retinoate (cytosol to extracellular)
  2. Formate:tetrahydrofolate ligase (ADP-forming)
  3. 10-formyltetrahydrofolate:5'-phosphoribosylglycinamide formyltransferase

  Catalysed by SLC16A4, SLC16A5, MTHFD1, GARTextracellular space, cytosol

• CHEBI:18381Reach from here →
  1. transport of formate and retinoate (cytosol to extracellular)
  2. Formate:tetrahydrofolate ligase (ADP-forming)
  3. phosphoribosylaminoimidazolecarboxamide formyltransferase (10-formyl-THF)

  Catalysed by SLC16A4, SLC16A5, MTHFD1, ATICextracellular space, cytosol

• S-methylmercury-L-cysteineReach from here →
  1. transport of pyruvate and retinoate (cytosol to extracellular)
  2. N(1)-methylguanosine(37) in tRNA(Phe) + pyruvate + S-adenosyl-L-methionine = 4-demethylwyosine(37) in tRNA(Phe) + 5'-deoxyadenosine + L-methionine + CO2 + H2O
  3. S-methylmercury-L-cysteine(out) + L-methionine(in) = S-methylmercury-L-cysteine(in) + L-methionine(out)

  Catalysed by SLC16A4, SLC16A5, SLC16A3, SLC16A7 and 5 moreextracellular space, cytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• 2-(alpha-Hydroxypropyl)thiamine diphosphateReach from here →
  1. transport of 2-hydroxybutyrate and retinoate (cytosol to extracellular)
  2. 2-hydroxybutyrate:NAD+ oxidoreductase
  3. branched chain keto acid dehydrogenase E1 (2-oxobutyrate)

  Catalysed by SLC16A4, SLC16A5, SLC16A8, SLC16A1 and 6 moreextracellular space, cytosol, mitochondrial matrix

• 2-aminoisobutanoateReach from here →
  1. transport of pyruvate and retinoate (cytosol to extracellular)
  2. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase
  3. 2-aminoisobutanoate(out) + L-alanine(in) = 2-aminoisobutanoate(in) + L-alanine(out)

  Catalysed by SLC16A4, SLC16A5, SLC16A3, SLC16A7 and 4 moreextracellular space, cytosol, mitochondrial matrix, inner side of the membrane, outer side of the membraneOne of 2 routes

• D-isoleucineReach from here →
  1. transport of pyruvate and retinoate (cytosol to extracellular)
  2. D-serine = pyruvate + NH4(+)
  3. D-isoleucine(out) + D-serine(in) = D-isoleucine(in) + D-serine(out)

  Catalysed by SLC16A4, SLC16A5, SLC16A3, SLC16A7 and 4 moreextracellular space, cytosol, inner side of the membrane, outer side of the membrane

• 13-cis-retinyl esterReach from here →
  1. retinal dehydrogenase (13-cis-retinal)
  2. retinol dehydrogenase (13-cis-retinal)
  3. 13-cis-retinol + a fatty acyl-CoA = 13-cis-retinyl ester + CoA

  Catalysed by ALDH1A2, ALDH1A1, RDH5, AWAT2endoplasmic reticulum, cytosol

• N(omega),N('omega)-dimethyl-L-arginineReach from here →
  1. transport of pyruvate and retinoate (cytosol to extracellular)
  2. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase
  3. N(omega),N('omega)-dimethyl-L-arginine + pyruvate = 5-(3,3'-dimethylguanidino)-2-oxopentanoate + L-alanine

  Catalysed by SLC16A4, SLC16A5, SLC16A3, SLC16A7 and 3 moreextracellular space, cytosol, mitochondrial matrixOne of 3 routes

• 1-butanoyl-2-(9Z-octadecenoyl)-glycerolReach from here →
  1. transport of butyrate and retinoate (cytosol to extracellular)
  2. Butanoate:CoA ligase (AMP-forming)
  3. 2-(9Z-octadecenoyl)-glycerol + butanoyl-CoA = 1-butanoyl-2-(9Z-octadecenoyl)-glycerol + CoA

  Catalysed by SLC16A4, SLC16A5, ACSM4, ACSM1 and 6 moreextracellular space, cytosol

• 5,6,7,8-tetrahydrofolic acidReach from here →
  1. transport of formate and retinoate (cytosol to extracellular)
  2. Formate:tetrahydrofolate ligase (ADP-forming)
  3. 10-formyltetrahydrofolate:NADP+ oxidoreductase

  Catalysed by SLC16A4, SLC16A5, MTHFD1, ALDH1L1 and 1 moreextracellular space, cytosolOne of 4 routes

• O-butanoyl-(R)-carnitineReach from here →
  1. transport of butyrate and retinoate (cytosol to extracellular)
  2. Butanoate:CoA ligase (AMP-forming)
  3. butanoyl-CoA + (R)-carnitine = O-butanoyl-(R)-carnitine + CoA

  Catalysed by SLC16A4, SLC16A5, ACSM4, ACSM1 and 5 moreextracellular space, cytosol

• (S)-lactoyl-AMPReach from here →
  1. transport of pyruvate and retinoate (cytosol to extracellular)
  2. (S)-lactate + NAD(+) = pyruvate + NADH + H(+)
  3. (S)-lactate + ATP + H(+) = (S)-lactoyl-AMP + diphosphate

  Catalysed by SLC16A4, SLC16A5, SLC16A3, SLC16A7 and 9 moreextracellular space, cytosol

• (S)-lactoyl-CoAReach from here →
  1. transport of pyruvate and retinoate (cytosol to extracellular)
  2. (S)-lactate + NAD(+) = pyruvate + NADH + H(+)
  3. (S)-lactate + ATP + CoA = (S)-lactoyl-CoA + AMP + diphosphate

  Catalysed by SLC16A4, SLC16A5, SLC16A3, SLC16A7 and 8 moreextracellular space, cytosol

• N-acetylneuraminate 9-phosphateReach from here →
  1. transport of pyruvate and retinoate (cytosol to extracellular)
  2. pyruvate kinase (dTDP)
  3. N-acetylneuraminate synthase

  Catalysed by SLC16A4, SLC16A5, SLC16A3, SLC16A7 and 5 moreextracellular space, cytosol

• CHEBI:240943Reach from here →
  1. transport of formate and retinoate (cytosol to extracellular)
  2. transport of chloride and formate (cytosol to extracellular)
  3. 2-Methylbutyrylglycine Transport, Extracellular

  Catalysed by SLC16A4, SLC16A5, SLC26A4, SLC6A5extracellular space, cytosolOne of 2 routes

• a quinolReach from here →
  1. transport of pyruvate and retinoate (cytosol to extracellular)
  2. (S)-malate + NAD(+) = pyruvate + CO2 + NADH
  3. (S)-malate + a quinone = enol-oxaloacetate + a quinol

  Catalysed by SLC16A4, SLC16A5, SLC16A3, SLC16A7 and 5 moreextracellular space, cytosol

• hypochlorous acidReach from here →
  1. transport of formate and retinoate (cytosol to extracellular)
  2. transport of chloride and formate (cytosol to extracellular)
  3. Peroxidase

  Catalysed by SLC16A4, SLC16A5, SLC26A4, LPOextracellular space, cytosolOne of 4 routes

• potassium atomReach from here →
  1. transport of formate and retinoate (cytosol to extracellular)
  2. transport of chloride and formate (cytosol to extracellular)
  3. transport of chloride (cytosol to extracellular)

  Catalysed by SLC16A4, SLC16A5, SLC26A4, SLC12A2 and 1 moreextracellular space, cytosolOne of 2 routes

• selenomethionineReach from here →
  1. transport of 2-hydroxybutyrate and retinoate (cytosol to extracellular)
  2. 2-hydroxybutyrate:NAD+ oxidoreductase
  3. Selenomethionine methanethiol-lyase (deaminating)

  Catalysed by SLC16A4, SLC16A5, SLC16A8, SLC16A1 and 5 moreextracellular space, cytosol

• CHEBI:27760Reach from here →
  1. transport of 2-hydroxybutyrate and retinoate (cytosol to extracellular)
  2. 2-hydroxybutyrate:NAD+ oxidoreductase
  3. Selenocystathionine Lysteine-lyase (deaminating)

  Catalysed by SLC16A4, SLC16A5, SLC16A8, SLC16A1 and 5 moreextracellular space, cytosol

• 17alpha,21-dihydroxypregnenoloneReach from here →
  1. transport of acetate and retinoate (cytosol to extracellular)
  2. cytochrome P450 (17alpha-hydroxypregnenolone)
  3. cytochrome P450

  Catalysed by SLC16A4, SLC16A5, SLC16A7, CYP17A1 and 1 moreextracellular space, cytosol, endoplasmic reticulum

• hydroxyacetoneReach from here →
  1. transport of acetoacetate and retinoate (cytosol to extracellular)
  2. Acetoacetate carboxy-lyase (acetone-forming)
  3. cytochrome P450 (acetone)

  Catalysed by SLC16A4, SLC16A5, CYP2E1extracellular space, cytosol, mitochondrial matrix

• 11-deoxycortisolReach from here →
  1. transport of acetate and retinoate (cytosol to extracellular)
  2. cytochrome P450 (17alpha-hydroxyprogesterone)
  3. cytochrome P450 (17alpha-hydroxyprogesterone)

  Catalysed by SLC16A4, SLC16A5, SLC16A7, CYP17A1 and 1 moreextracellular space, cytosol, endoplasmic reticulumOne of 3 routes

• 3-mercaptolactic acidReach from here →
  1. transport of pyruvate and retinoate (cytosol to extracellular)
  2. 2-oxo-3-sulfanylpropanoate + [thioredoxin]-dithiol = [thioredoxin]-disulfide + hydrogen sulfide + pyruvate + H(+)
  3. 3-Mercaptolactate:NAD+ oxidoreductase

  Catalysed by SLC16A4, SLC16A5, SLC16A3, SLC16A7 and 7 moreextracellular space, cytosol

• 1-(9Z-octadecenoyl)-sn-glycero-3-phosphocholineReach from here →
  1. transport of acetate and retinoate (cytosol to extracellular)
  2. N-(acetyl)-sphing-4-enine + H2O = sphing-4-enine + acetate
  3. 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine = 1-(9Z-octadecenoyl)-N-(acetyl)-sphing-4-enine + 1-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine

  Catalysed by SLC16A4, SLC16A5, SLC16A7, ASAH1 and 1 moreextracellular space, cytosolOne of 3 routes

• 2-oxopentanoateReach from here →
  1. transport of pyruvate and retinoate (cytosol to extracellular)
  2. N(omega),N(omega)-dimethyl-L-arginine + pyruvate = 5-(3,3-dimethylguanidino)-2-oxopentanoate + L-alanine
  3. 2-oxopentanoate + N(omega),N(omega)-dimethyl-L-arginine = 5-(3,3-dimethylguanidino)-2-oxopentanoate + L-2-aminopentanoate

  Catalysed by SLC16A4, SLC16A5, SLC16A3, SLC16A7 and 3 moreextracellular space, cytosol

• 3beta-hydroxyandrost-5-en-17-oneReach from here →
  1. transport of acetate and retinoate (cytosol to extracellular)
  2. cytochrome P450 (17alpha-hydroxypregnenolone)
  3. cytochrome P450 (17alpha-hydroxypregnenolone)

  Catalysed by SLC16A4, SLC16A5, SLC16A7, CYP17A1extracellular space, cytosol, endoplasmic reticulumOne of 6 routes

• pyridoxine 5'-phosphateReach from here →
  1. transport of pyruvate and retinoate (cytosol to extracellular)
  2. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase
  3. L-selenocysteine selenide-lyase (L-alanine-forming)

  Catalysed by SLC16A4, SLC16A5, SLC16A3, SLC16A7 and 4 moreextracellular space, cytosol, mitochondrial matrix

• a dicarboxylateReach from here →
  1. transport of L-lactate and retinoate (cytosol to extracellular)
  2. transport of L-lactate and urate (cytosol to extracellular)
  3. urate(out) + a dicarboxylate(in) = urate(in) + a dicarboxylate(out)

  Catalysed by SLC16A4, SLC16A5, SLC16A3, SLC16A7 and 4 moreextracellular space, cytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• N-glycoloylneuraminateReach from here →
  1. transport of pyruvate and retinoate (cytosol to extracellular)
  2. N-Acetylneuraminate pyruvate-lyase (N-acetyl-D-mannosamine-forming)
  3. CMP-N-acetylneuraminate monooxygenase (N-acetylneuraminate)

  Catalysed by SLC16A4, SLC16A5, SLC16A3, SLC16A7 and 3 moreextracellular space, cytosol

• a carboxylateReach from here →
  1. transport of pyruvate and retinoate (cytosol to extracellular)
  2. a 3-acylpyruvate + H2O = a carboxylate + pyruvate + H(+)
  3. a 3-acylpyruvate + H2O = a carboxylate + pyruvate + H(+)

  Catalysed by SLC16A4, SLC16A5, SLC16A3, SLC16A7 and 3 moreextracellular space, cytosol

• hydrogen sulfideReach from here →
  1. transport of pyruvate and retinoate (cytosol to extracellular)
  2. 2-oxo-3-sulfanylpropanoate + [thioredoxin]-dithiol = [thioredoxin]-disulfide + hydrogen sulfide + pyruvate + H(+)
  3. 2-oxo-3-sulfanylpropanoate + [thioredoxin]-dithiol = [thioredoxin]-disulfide + hydrogen sulfide + pyruvate + H(+)

  Catalysed by SLC16A4, SLC16A5, SLC16A3, SLC16A7 and 3 moreextracellular space, cytosol

• L-aspartateReach from here →
  1. transport of pyruvate and retinoate (cytosol to extracellular)
  2. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase
  3. oxaloacetate + L-alanine = L-aspartate + pyruvate

  Catalysed by SLC16A4, SLC16A5, SLC16A3, SLC16A7 and 3 moreextracellular space, cytosol, mitochondrial matrixOne of 8 routes

• citric acidReach from here →
  1. transport of pyruvate and retinoate (cytosol to extracellular)
  2. Pyruvate:carbon-dioxide ligase (ADP-forming)
  3. acetyl-CoA:oxaloacetate C-acetyltransferase (thioester-hydrolysing)

  Catalysed by SLC16A4, SLC16A5, SLC16A3, SLC16A7 and 4 moreextracellular space, cytosol, mitochondrial matrixOne of 9 routes

• malonic acidReach from here →
  1. transport of formate and retinoate (cytosol to extracellular)
  2. transport of chloride and formate (cytosol to extracellular)
  3. Malonate Transport, Antiport with Chloride

  Catalysed by SLC16A4, SLC16A5, SLC26A4extracellular space, cytosolOne of 2 routes

• isocitric acidReach from here →
  1. transport of pyruvate and retinoate (cytosol to extracellular)
  2. pyruvate kinase (dTDP)
  3. transport of isocitrate and PEP (cytosol to mitochondria)

  Catalysed by SLC16A4, SLC16A5, SLC16A3, SLC16A7 and 5 moreextracellular space, cytosol, mitochondrial matrixOne of 5 routes

• glutarateReach from here →
  1. transport of L-lactate and retinoate (cytosol to extracellular)
  2. transport of L-lactate and urate (cytosol to extracellular)
  3. urate(in) + glutarate(out) = urate(out) + glutarate(in)

  Catalysed by SLC16A4, SLC16A5, SLC16A3, SLC16A7 and 4 moreextracellular space, cytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• 4-hydroxy-2-oxoglutaric acidReach from here →
  1. transport of pyruvate and retinoate (cytosol to extracellular)
  2. Pyruvate:carbon-dioxide ligase (ADP-forming)
  3. D-aspartate:2-oxoglutarate aminotransferase

  Catalysed by SLC16A4, SLC16A5, SLC16A3, SLC16A7 and 4 moreextracellular space, cytosol, mitochondrial matrix