(R)-3-hydroxybutyric acid

Three steps

• S-methylmercury-L-cysteineReach from here →
  1. transport of (R)-3-hydroxybutanoate and pyruvate (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 (R)-3-hydroxybutanoate and pyruvate (cytosol to extracellular)
  2. 2-oxobutanoate + L-alanine = (2S)-2-aminobutanoate + pyruvate
  3. branched chain keto acid dehydrogenase E1 (2-oxobutyrate)

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

• 2-aminoisobutanoateReach from here →
  1. transport of (R)-3-hydroxybutanoate and pyruvate (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 (R)-3-hydroxybutanoate and pyruvate (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

• N(omega),N('omega)-dimethyl-L-arginineReach from here →
  1. transport of (R)-3-hydroxybutanoate and pyruvate (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 (R)-3-hydroxybutanoate and butyrate (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, SLC16A3, SLC16A7 and 8 moreextracellular space, cytosol

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

  Catalysed by SLC16A4, SLC16A5, SLC16A7, SLC16A1 and 3 moreextracellular space, cytosolOne of 4 routes

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

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

• (S)-lactoyl-AMPReach from here →
  1. transport of (R)-3-hydroxybutanoate and pyruvate (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 (R)-3-hydroxybutanoate and pyruvate (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 (R)-3-hydroxybutanoate and pyruvate (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 (R)-3-hydroxybutanoate and formate (cytosol to extracellular)
  2. transport of chloride and formate (cytosol to extracellular)
  3. 2-Methylbutyrylglycine Transport, Extracellular

  Catalysed by SLC16A4, SLC16A5, SLC16A7, SLC16A1 and 2 moreextracellular space, cytosolOne of 2 routes

• a quinolReach from here →
  1. transport of (R)-3-hydroxybutanoate and pyruvate (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 (R)-3-hydroxybutanoate and formate (cytosol to extracellular)
  2. transport of chloride and formate (cytosol to extracellular)
  3. Peroxidase

  Catalysed by SLC16A4, SLC16A5, SLC16A7, SLC16A1 and 2 moreextracellular space, cytosolOne of 4 routes

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

  Catalysed by SLC16A4, SLC16A5, SLC16A7, SLC16A1 and 3 moreextracellular space, cytosolOne of 2 routes

• selenomethionineReach from here →
  1. transport of (R)-3-hydroxybutanoate and pyruvate (cytosol to extracellular)
  2. 2-oxobutanoate + L-alanine = (2S)-2-aminobutanoate + pyruvate
  3. Selenomethionine methanethiol-lyase (deaminating)

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

• CHEBI:27760Reach from here →
  1. transport of (R)-3-hydroxybutanoate and pyruvate (cytosol to extracellular)
  2. 2-oxobutanoate + L-alanine = (2S)-2-aminobutanoate + pyruvate
  3. Selenocystathionine Lysteine-lyase (deaminating)

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

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

  Catalysed by SLC16A4, SLC16A5, SLC16A7, SLC16A1 and 2 moreextracellular space, cytosol, endoplasmic reticulum

• hydroxyacetoneReach from here →
  1. (R)-3-Hydroxybutanoate:NAD+ oxidoreductase
  2. Acetoacetate carboxy-lyase (acetone-forming)
  3. cytochrome P450 (acetone)

  Catalysed by BDH1, BDH2, CYP2E1mitochondrial matrix, cytosol

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

  Catalysed by SLC16A4, SLC16A5, SLC16A7, SLC16A1 and 2 moreextracellular space, cytosol, endoplasmic reticulumOne of 3 routes

• 3-mercaptolactic acidReach from here →
  1. transport of (R)-3-hydroxybutanoate and pyruvate (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 (R)-3-hydroxybutanoate and acetate (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, SLC16A1 and 2 moreextracellular space, cytosolOne of 3 routes

• 2-oxopentanoateReach from here →
  1. transport of (R)-3-hydroxybutanoate and pyruvate (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 (R)-3-hydroxybutanoate and acetate (cytosol to extracellular)
  2. cytochrome P450 (17alpha-hydroxypregnenolone)
  3. cytochrome P450 (17alpha-hydroxypregnenolone)

  Catalysed by SLC16A4, SLC16A5, SLC16A7, SLC16A1 and 1 moreextracellular space, cytosol, endoplasmic reticulumOne of 6 routes

• pyridoxine 5'-phosphateReach from here →
  1. transport of (R)-3-hydroxybutanoate and pyruvate (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 (R)-3-hydroxybutanoate and L-lactate (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, SLC16A7, SLC16A8 and 3 moreextracellular space, cytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• N-glycoloylneuraminateReach from here →
  1. transport of (R)-3-hydroxybutanoate and pyruvate (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 (R)-3-hydroxybutanoate and pyruvate (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 (R)-3-hydroxybutanoate and pyruvate (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 (R)-3-hydroxybutanoate and pyruvate (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 (R)-3-hydroxybutanoate and pyruvate (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 (R)-3-hydroxybutanoate and formate (cytosol to extracellular)
  2. transport of chloride and formate (cytosol to extracellular)
  3. Malonate Transport, Antiport with Chloride

  Catalysed by SLC16A4, SLC16A5, SLC16A7, SLC16A1 and 1 moreextracellular space, cytosolOne of 2 routes

• isocitric acidReach from here →
  1. transport of (R)-3-hydroxybutanoate and pyruvate (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 (R)-3-hydroxybutanoate and L-lactate (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, SLC16A7, SLC16A8 and 3 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 (R)-3-hydroxybutanoate and pyruvate (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

• nicotinateReach from here →
  1. transport of (R)-3-hydroxybutanoate and L-lactate (cytosol to extracellular)
  2. transport of L-lactate and urate (cytosol to extracellular)
  3. nicotinate(in) + urate(out) = nicotinate(out) + urate(in)

  Catalysed by SLC16A4, SLC16A5, SLC16A7, SLC16A8 and 3 moreextracellular space, cytosol, inner side of the membrane, outer side of the membrane

• putrescineReach from here →
  1. transport of (R)-3-hydroxybutanoate and acetate (cytosol to extracellular)
  2. N-acetylputrescine + H2O = putrescine + acetate
  3. N-acetylputrescine + H2O = putrescine + acetate

  Catalysed by SLC16A4, SLC16A5, SLC16A7, SLC16A1 and 1 moreextracellular space, cytosol

• cis-aconitic acidReach from here →
  1. transport of (R)-3-hydroxybutanoate and pyruvate (cytosol to extracellular)
  2. pyruvate kinase (dTDP)
  3. transport of cis-aconitate and PEP (cytosol to mitochondria)

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

• thiosulfateReach from here →
  1. transport of (R)-3-hydroxybutanoate and pyruvate (cytosol to extracellular)
  2. (S)-malate + NAD(+) = pyruvate + CO2 + NADH
  3. transport of malate and thiosulfate (cytosol to mitochondria)

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

• 4-methylthio-2-oxobutanoic acidReach from here →
  1. transport of (R)-3-hydroxybutanoate and pyruvate (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. L-Methionine:oxygen oxidoreductase (deaminating)

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

• a phenolReach from here →
  1. transport of (R)-3-hydroxybutanoate and acetate (cytosol to extracellular)
  2. a phenyl acetate + H2O = a phenol + acetate + H(+)
  3. a phenyl acetate + H2O = a phenol + acetate + H(+)

  Catalysed by SLC16A4, SLC16A5, SLC16A7, SLC16A1 and 3 moreextracellular space, cytosol

• 2-oxohexanoateReach from here →
  1. transport of (R)-3-hydroxybutanoate and pyruvate (cytosol to extracellular)
  2. N(omega),N(omega)-dimethyl-L-arginine + pyruvate = 5-(3,3-dimethylguanidino)-2-oxopentanoate + L-alanine
  3. 2-oxohexanoate + N(omega),N(omega)-dimethyl-L-arginine = L-2-aminohexanoate + 5-(3,3-dimethylguanidino)-2-oxopentanoate

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

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

• all-trans-retinoateReach from here →
  1. transport of (R)-3-hydroxybutanoate and retinoate (cytosol to extracellular)
  2. retinoate reduction
  3. all-trans-retinal + NAD(+) + H2O = all-trans-retinoate + NADH + 2 H(+)

  Catalysed by SLC16A4, SLC16A5, SLC16A8, SLC16A1 and 5 moreextracellular space, cytosolOne of 2 routes

• L-alpha-aminobutyric acidReach from here →
  1. transport of (R)-3-hydroxybutanoate and pyruvate (cytosol to extracellular)
  2. 2-oxobutanoate + L-alanine = (2S)-2-aminobutanoate + pyruvate
  3. glutamic-pyruvic transaminase ((S)-2-aminobutanoate)

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

• (R)-mevalonateReach from here →
  1. (R)-3-Hydroxybutanoate:NAD+ oxidoreductase
  2. (3S)-3-hydroxy-3-methylglutaryl-CoA = acetoacetate + acetyl-CoA
  3. (R)-mevalonate + 2 NADP(+) + CoA = (3S)-3-hydroxy-3-methylglutaryl-CoA + 2 NADPH + 2 H(+)

  Catalysed by BDH1, BDH2, HMGCL, HMGCLL1 and 1 moremitochondrial matrix

• glyoxylateReach from here →
  1. transport of (R)-3-hydroxybutanoate and pyruvate (cytosol to extracellular)
  2. (S)-malate + NAD(+) = pyruvate + CO2 + NADH
  3. glyoxylate + acetyl-CoA + H2O = (S)-malate + CoA + H(+)

  Catalysed by SLC16A4, SLC16A5, SLC16A3, SLC16A7 and 4 moreextracellular space, cytosolOne of 8 routes

• 13-cis-retinolReach from here →
  1. transport of (R)-3-hydroxybutanoate and retinoate (cytosol to extracellular)
  2. retinal dehydrogenase (13-cis-retinal)
  3. retinol dehydrogenase (13-cis-retinal)

  Catalysed by SLC16A4, SLC16A5, SLC16A8, SLC16A1 and 3 moreextracellular space, cytosol, endoplasmic reticulumOne of 3 routes

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

  Catalysed by SLC16A4, SLC16A5, SLC16A3, SLC16A7 and 4 moreextracellular space, cytosol, mitochondrial matrixOne of 8 routes

• gamma-Glu-AlaReach from here →
  1. transport of (R)-3-hydroxybutanoate and pyruvate (cytosol to extracellular)
  2. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase
  3. gamma-glutamyltransferase (alanine)

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