all-trans-retinoic acid

Three steps

• 2-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. transport of acetate and retinoate (cytosol to extracellular)
  2. N-(acetyl)-sphing-4-enine + H2O = sphing-4-enine + acetate
  3. 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphoethanolamine + N-(acetyl)-sphing-4-enine = 2-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphoethanolamine + 1-hexadecanoyl-N-(acetyl)-sphing-4-enine

  Catalysed by SLC16A4, SLC16A5, SLC16A7, ASAH1 and 1 moreextracellular space, cytosol

• 2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. transport of acetate and retinoate (cytosol to extracellular)
  2. N-(acetyl)-sphing-4-enine + H2O = sphing-4-enine + acetate
  3. 1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamine + N-(acetyl)-sphing-4-enine = 2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphoethanolamine + 1-hexadecanoyl-N-(acetyl)-sphing-4-enine

  Catalysed by SLC16A4, SLC16A5, SLC16A7, ASAH1 and 1 moreextracellular space, cytosol

• 16alpha,17alpha-dihydroxyprogesteroneReach from here →
  1. transport of acetate and retinoate (cytosol to extracellular)
  2. cytochrome P450 (17alpha-hydroxyprogesterone)
  3. 17alpha-hydroxyprogesterone + reduced [NADPH--hemoprotein reductase] + O2 = 16alpha,17alpha-dihydroxyprogesterone + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by SLC16A4, SLC16A5, SLC16A7, CYP17A1extracellular space, cytosol, endoplasmic reticulum

• 2-acyl-sn-glycero-3-phospho-(1'-sn-glycerol)Reach from here →
  1. transport of acetate and retinoate (cytosol to extracellular)
  2. N-(acetyl)-sphing-4-enine + H2O = sphing-4-enine + acetate
  3. a 1,2-diacyl-sn-glycero-3-phospho-(1'-sn-glycerol) + N-(acetyl)-sphing-4-enine = 2-acyl-sn-glycero-3-phospho-(1'-sn-glycerol) + 1-O-acyl-N-(acetyl)-sphing-4-enine

  Catalysed by SLC16A4, SLC16A5, SLC16A7, ASAH1 and 1 moreextracellular space, cytosol

• 2-iminobutanoateReach from here →
  1. transport of 2-hydroxybutyrate and retinoate (cytosol to extracellular)
  2. 2-hydroxybutyrate:NAD+ oxidoreductase
  3. 2-iminobutanoate + H2O = 2-oxobutanoate + NH4(+)

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

• 2-aminoprop-2-enoateReach from here →
  1. transport of pyruvate and retinoate (cytosol to extracellular)
  2. D-serine = pyruvate + NH4(+)
  3. D-serine = 2-aminoprop-2-enoate + H2O

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

• 2-(9Z-octadecenoyl)-sn-glycero-3-phospho-L-serineReach from here →
  1. transport of acetate and retinoate (cytosol to extracellular)
  2. N-(acetyl)-sphing-4-enine + H2O = sphing-4-enine + acetate
  3. 1-octadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phospho-L-serine + N-(acetyl)-sphing-4-enine = 1-octadecanoyl-N-(acetyl)-sphing-4-enine + 2-(9Z-octadecenoyl)-sn-glycero-3-phospho-L-serine

  Catalysed by SLC16A4, SLC16A5, SLC16A7, ASAH1 and 1 moreextracellular space, cytosol

• 9-cis-retinolReach from here →
  1. retinoate reduction
  2. retinol binding protein (retinal)
  3. 9-cis-retinol:NAD+ oxidoreductase

  Catalysed by RBP1, RBP2, HSD17B6, RDH16 and 7 morecytosol, endoplasmic reticulumOne of 4 routes

• 1-octadecanoyl-sn-glycero-3-phosphoserineReach from here →
  1. transport of acetate and retinoate (cytosol to extracellular)
  2. N-(acetyl)-sphing-4-enine + H2O = sphing-4-enine + acetate
  3. 1-octadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phospho-L-serine + N-(acetyl)-sphing-4-enine = 1-octadecanoyl-sn-glycero-3-phosphoserine + 1-(9Z-octadecenoyl)-N-(acetyl)-sphing-4-enine

  Catalysed by SLC16A4, SLC16A5, SLC16A7, ASAH1 and 1 moreextracellular space, cytosol

• 1-O-acyl-N-(acetyl)-sphing-4-enineReach from here →
  1. transport of acetate and retinoate (cytosol to extracellular)
  2. N-(acetyl)-sphing-4-enine + H2O = sphing-4-enine + acetate
  3. N-(acetyl)-sphing-4-enine + a 1,2-diacyl-sn-glycero-3-phosphocholine = 1-O-acyl-N-(acetyl)-sphing-4-enine + a 1-acyl-sn-glycero-3-phosphocholine

  Catalysed by SLC16A4, SLC16A5, SLC16A7, ASAH1 and 1 moreextracellular space, cytosolOne of 8 routes

• O-3-oxobutanoyl-(R)-carnitineReach from here →
  1. transport of acetoacetate and retinoate (cytosol to extracellular)
  2. acetoacetate + ATP + CoA = acetoacetyl-CoA + AMP + diphosphate
  3. acetoacetyl-CoA + (R)-carnitine = O-3-oxobutanoyl-(R)-carnitine + CoA

  Catalysed by SLC16A4, SLC16A5, AACS, CRATextracellular space, cytosol

• N-(acetyl)-sphing-4-enine-1-phosphateReach from here →
  1. transport of acetate and retinoate (cytosol to extracellular)
  2. N-(acetyl)-sphing-4-enine + H2O = sphing-4-enine + acetate
  3. N-(acetyl)-sphing-4-enine + ATP = N-(acetyl)-sphing-4-enine-1-phosphate + ADP + H(+)

  Catalysed by SLC16A4, SLC16A5, SLC16A7, ASAH1 and 1 moreextracellular space, cytosol

• thromboxane B2Reach from here →
  1. transport of pyruvate and retinoate (cytosol to extracellular)
  2. (S)-lactate + NAD(+) = pyruvate + NADH + H(+)
  3. thromboxane B2(out) + 2 (S)-lactate(in) = thromboxane B2(in) + 2 (S)-lactate(out)

  Catalysed by SLC16A4, SLC16A5, SLC16A3, SLC16A7 and 8 moreextracellular space, cytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• thiamine(1+) diphosphateReach from here →
  1. transport of pyruvate and retinoate (cytosol to extracellular)
  2. pyruvate:thiamin diphosphate acetaldehydetransferase (decarboxylating)
  3. 2-(alpha-hydroxyethyl)thiamine-diphosphate[m] + lipoamide[m] = S-acetyldihydrolipoamide[m] + thiamin-PP[m]

  Catalysed by SLC16A4, SLC16A5, SLC16A3, SLC16A7 and 6 moreextracellular space, cytosol, mitochondrial matrix