13-cis-retinal

Three steps

• ferrocytochrome cReach from here →
  1. retinal dehydrogenase (13-cis-retinal)
  2. transport of L-lactate and retinoate (cytosol to extracellular)
  3. (S)-Lactate:ferricytochrome-c 2-oxidoreductase

  Catalysed by ALDH1A2, ALDH1A1, SLC16A4, SLC16A5 and 5 moreendoplasmic reticulum, extracellular space, cytosol, mitochondrial matrix

• 3-hydroxypyruvateReach from here →
  1. retinal dehydrogenase (13-cis-retinal)
  2. transport of pyruvate and retinoate (cytosol to extracellular)
  3. L-serine + pyruvate = 3-hydroxypyruvate + L-alanine

  Catalysed by ALDH1A2, ALDH1A1, SLC16A4, SLC16A5 and 5 moreendoplasmic reticulum, extracellular space, cytosol

• 17alpha-hydroxyprogesteroneReach from here →
  1. retinal dehydrogenase (13-cis-retinal)
  2. transport of acetate and retinoate (cytosol to extracellular)
  3. cytochrome P450 (17alpha-hydroxyprogesterone)

  Catalysed by ALDH1A2, ALDH1A1, SLC16A4, SLC16A5 and 2 moreendoplasmic reticulum, extracellular space, cytosol

• aceneuramateReach from here →
  1. retinal dehydrogenase (13-cis-retinal)
  2. transport of pyruvate and retinoate (cytosol to extracellular)
  3. aceneuramate = aldehydo-N-acetyl-D-mannosamine + pyruvate

  Catalysed by ALDH1A2, ALDH1A1, SLC16A4, SLC16A5 and 5 moreendoplasmic reticulum, extracellular space, cytosol

• 5'-deoxyadenosineReach from here →
  1. retinal dehydrogenase (13-cis-retinal)
  2. transport of pyruvate and retinoate (cytosol to extracellular)
  3. N(1)-methylguanosine(37) in tRNA(Phe) + pyruvate + S-adenosyl-L-methionine = 4-demethylwyosine(37) in tRNA(Phe) + 5'-deoxyadenosine + L-methionine + CO2 + H2O

  Catalysed by ALDH1A2, ALDH1A1, SLC16A4, SLC16A5 and 6 moreendoplasmic reticulum, extracellular space, cytosol

• 1-O-acyl-sn-glycero-3-phosphocholine(1+)Reach from here →
  1. 13-cis-retinal to retinal conversion
  2. all-trans-retinol + NADP(+) = all-trans-retinal + NADPH + H(+)
  3. Lecithin Retinol Acyltransferase

  Catalysed by AKR1B15, AKR1B10, DHRS3, AKR1B1 and 8 morecytosol

• all-trans-retinyl hexadecanoateReach from here →
  1. 13-cis-retinal to retinal conversion
  2. all-trans-retinol + NADP(+) = all-trans-retinal + NADPH + H(+)
  3. all-trans-retinol + hexadecanoyl-CoA = all-trans-retinyl hexadecanoate + CoA

  Catalysed by AKR1B15, AKR1B10, DHRS3, AKR1B1 and 12 morecytosolOne of 2 routes

• 4-methylumbelliferyl acetateReach from here →
  1. retinal dehydrogenase (13-cis-retinal)
  2. transport of acetate and retinoate (cytosol to extracellular)
  3. 4-methylumbelliferyl acetate + H2O = 4-methylumbelliferone + acetate + H(+)

  Catalysed by ALDH1A2, ALDH1A1, SLC16A4, SLC16A5 and 4 moreendoplasmic reticulum, extracellular space, cytosol

• urateReach from here →
  1. retinal dehydrogenase (13-cis-retinal)
  2. transport of L-lactate and retinoate (cytosol to extracellular)
  3. transport of L-lactate and urate (cytosol to extracellular)

  Catalysed by ALDH1A2, ALDH1A1, SLC16A4, SLC16A5 and 5 moreendoplasmic reticulum, extracellular space, cytosol

• 4-fumarylacetoacetateReach from here →
  1. retinal dehydrogenase (13-cis-retinal)
  2. transport of acetoacetate and retinoate (cytosol to extracellular)
  3. 4-fumarylacetoacetate + H2O = acetoacetate + fumarate + H(+)

  Catalysed by ALDH1A2, ALDH1A1, SLC16A4, SLC16A5 and 1 moreendoplasmic reticulum, extracellular space, cytosol

• a diacylglycerolReach from here →
  1. 13-cis-retinal to retinal conversion
  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

• dTDPReach from here →
  1. retinal dehydrogenase (13-cis-retinal)
  2. transport of pyruvate and retinoate (cytosol to extracellular)
  3. pyruvate kinase (dTDP)

  Catalysed by ALDH1A2, ALDH1A1, SLC16A4, SLC16A5 and 6 moreendoplasmic reticulum, extracellular space, cytosol

• 5-(3,3-dimethylguanidino)-2-oxopentanoateReach from here →
  1. retinal dehydrogenase (13-cis-retinal)
  2. transport of pyruvate and retinoate (cytosol to extracellular)
  3. N(omega),N(omega)-dimethyl-L-arginine + pyruvate = 5-(3,3-dimethylguanidino)-2-oxopentanoate + L-alanine

  Catalysed by ALDH1A2, ALDH1A1, SLC16A4, SLC16A5 and 5 moreendoplasmic reticulum, extracellular space, cytosol

• 5-(3,3'-dimethylguanidino)-2-oxopentanoateReach from here →
  1. retinal dehydrogenase (13-cis-retinal)
  2. transport of pyruvate and retinoate (cytosol to extracellular)
  3. N(omega),N('omega)-dimethyl-L-arginine + pyruvate = 5-(3,3'-dimethylguanidino)-2-oxopentanoate + L-alanine

  Catalysed by ALDH1A2, ALDH1A1, SLC16A4, SLC16A5 and 5 moreendoplasmic reticulum, extracellular space, cytosol

• 5-(3-methylguanidino)-2-oxopentanoateReach from here →
  1. retinal dehydrogenase (13-cis-retinal)
  2. transport of pyruvate and retinoate (cytosol to extracellular)
  3. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine

  Catalysed by ALDH1A2, ALDH1A1, SLC16A4, SLC16A5 and 5 moreendoplasmic reticulum, extracellular space, cytosol

• 17alpha-hydroxypregnenoloneReach from here →
  1. retinal dehydrogenase (13-cis-retinal)
  2. transport of acetate and retinoate (cytosol to extracellular)
  3. cytochrome P450 (17alpha-hydroxypregnenolone)

  Catalysed by ALDH1A2, ALDH1A1, SLC16A4, SLC16A5 and 2 moreendoplasmic reticulum, extracellular space, cytosol

• chlorine(.)Reach from here →
  1. retinal dehydrogenase (13-cis-retinal)
  2. transport of formate and retinoate (cytosol to extracellular)
  3. transport of chloride and formate (cytosol to extracellular)

  Catalysed by ALDH1A2, ALDH1A1, SLC16A4, SLC16A5 and 1 moreendoplasmic reticulum, extracellular space, cytosolOne of 2 routes

• 3-hydroxypyruvic acidReach from here →
  1. retinal dehydrogenase (13-cis-retinal)
  2. transport of pyruvate and retinoate (cytosol to extracellular)
  3. L-Serine:pyruvate aminotransferase

  Catalysed by ALDH1A2, ALDH1A1, SLC16A4, SLC16A5 and 5 moreendoplasmic reticulum, extracellular space, cytosolOne of 2 routes

• 3-oxopropanoateReach from here →
  1. retinal dehydrogenase (13-cis-retinal)
  2. transport of pyruvate and retinoate (cytosol to extracellular)
  3. 3-oxopropanoate + L-alanine = beta-alanine + pyruvate

  Catalysed by ALDH1A2, ALDH1A1, SLC16A4, SLC16A5 and 5 moreendoplasmic reticulum, extracellular space, cytosol

• D-serineReach from here →
  1. retinal dehydrogenase (13-cis-retinal)
  2. transport of pyruvate and retinoate (cytosol to extracellular)
  3. D-serine = pyruvate + NH4(+)

  Catalysed by ALDH1A2, ALDH1A1, SLC16A4, SLC16A5 and 5 moreendoplasmic reticulum, extracellular space, cytosol

• (R)-lactic acidReach from here →
  1. retinal dehydrogenase (13-cis-retinal)
  2. transport of pyruvate and retinoate (cytosol to extracellular)
  3. (R)-Lactate:NAD+ oxidoreductase

  Catalysed by ALDH1A2, ALDH1A1, SLC16A4, SLC16A5 and 5 moreendoplasmic reticulum, extracellular space, cytosol

• (3S)-3-hydroxy-3-methylglutaryl-CoAReach from here →
  1. retinal dehydrogenase (13-cis-retinal)
  2. transport of acetoacetate and retinoate (cytosol to extracellular)
  3. (3S)-3-hydroxy-3-methylglutaryl-CoA = acetoacetate + acetyl-CoA

  Catalysed by ALDH1A2, ALDH1A1, SLC16A4, SLC16A5 and 2 moreendoplasmic reticulum, extracellular space, cytosol

• 2-iminopropanoateReach from here →
  1. retinal dehydrogenase (13-cis-retinal)
  2. transport of pyruvate and retinoate (cytosol to extracellular)
  3. 2-iminopropanoate + H2O = pyruvate + NH4(+)

  Catalysed by ALDH1A2, ALDH1A1, SLC16A4, SLC16A5 and 5 moreendoplasmic reticulum, extracellular space, cytosol

• all-trans-4-oxoretinolReach from here →
  1. 13-cis-retinal to retinal conversion
  2. all-trans-retinol + NADP(+) = all-trans-retinal + NADPH + H(+)
  3. cytochrome P450 (retinol)

  Catalysed by AKR1B15, AKR1B10, DHRS3, AKR1B1 and 8 morecytosol

• phosphoenolpyruvic acidReach from here →
  1. retinal dehydrogenase (13-cis-retinal)
  2. transport of pyruvate and retinoate (cytosol to extracellular)
  3. pyruvate kinase (dTDP)

  Catalysed by ALDH1A2, ALDH1A1, SLC16A4, SLC16A5 and 6 moreendoplasmic reticulum, extracellular space, cytosol

• N-acetyl-beta-neuraminic acidReach from here →
  1. retinal dehydrogenase (13-cis-retinal)
  2. transport of pyruvate and retinoate (cytosol to extracellular)
  3. N-Acetylneuraminate pyruvate-lyase (N-acetyl-D-mannosamine-forming)

  Catalysed by ALDH1A2, ALDH1A1, SLC16A4, SLC16A5 and 5 moreendoplasmic reticulum, extracellular space, cytosol

• N-(acetyl)-sphing-4-enineReach from here →
  1. retinal dehydrogenase (13-cis-retinal)
  2. transport of acetate and retinoate (cytosol to extracellular)
  3. N-(acetyl)-sphing-4-enine + H2O = sphing-4-enine + acetate

  Catalysed by ALDH1A2, ALDH1A1, SLC16A4, SLC16A5 and 2 moreendoplasmic reticulum, extracellular space, cytosol

• all-trans-13,14-dihydroretinolReach from here →
  1. 13-cis-retinal to retinal conversion
  2. all-trans-retinol + NADP(+) = all-trans-retinal + NADPH + H(+)
  3. all-trans-13,14-dihydroretinol + A = all-trans-retinol + AH2

  Catalysed by AKR1B15, AKR1B10, DHRS3, AKR1B1 and 8 morecytosol

• a 3-acylpyruvateReach from here →
  1. retinal dehydrogenase (13-cis-retinal)
  2. transport of pyruvate and retinoate (cytosol to extracellular)
  3. a 3-acylpyruvate + H2O = a carboxylate + pyruvate + H(+)

  Catalysed by ALDH1A2, ALDH1A1, SLC16A4, SLC16A5 and 5 moreendoplasmic reticulum, extracellular space, cytosol

• acetoacetyl-CoAReach from here →
  1. retinal dehydrogenase (13-cis-retinal)
  2. transport of acetoacetate and retinoate (cytosol to extracellular)
  3. acetoacetate + ATP + CoA = acetoacetyl-CoA + AMP + diphosphate

  Catalysed by ALDH1A2, ALDH1A1, SLC16A4, SLC16A5 and 1 moreendoplasmic reticulum, extracellular space, cytosolOne of 2 routes

• butanoyl-CoAReach from here →
  1. retinal dehydrogenase (13-cis-retinal)
  2. transport of butyrate and retinoate (cytosol to extracellular)
  3. Butanoate:CoA ligase (AMP-forming)

  Catalysed by ALDH1A2, ALDH1A1, SLC16A4, SLC16A5 and 6 moreendoplasmic reticulum, extracellular space, cytosolOne of 2 routes

• N-acetyl-D-glucosamine 6-phosphateReach from here →
  1. retinal dehydrogenase (13-cis-retinal)
  2. transport of acetate and retinoate (cytosol to extracellular)
  3. N-acetyl-D-glucosamine 6-phosphate + H2O = D-glucosamine 6-phosphate + acetate

  Catalysed by ALDH1A2, ALDH1A1, SLC16A4, SLC16A5 and 2 moreendoplasmic reticulum, extracellular space, cytosol

• 2-oxo-3-sulfanylpropanoateReach from here →
  1. retinal dehydrogenase (13-cis-retinal)
  2. transport of pyruvate and retinoate (cytosol to extracellular)
  3. 2-oxo-3-sulfanylpropanoate + [thioredoxin]-dithiol = [thioredoxin]-disulfide + hydrogen sulfide + pyruvate + H(+)

  Catalysed by ALDH1A2, ALDH1A1, SLC16A4, SLC16A5 and 5 moreendoplasmic reticulum, extracellular space, cytosol

• 2-methyl-3-oxopropanoateReach from here →
  1. retinal dehydrogenase (13-cis-retinal)
  2. transport of pyruvate and retinoate (cytosol to extracellular)
  3. (R)-3-amino-2-methylpropanoate + pyruvate = 2-methyl-3-oxopropanoate + L-alanine

  Catalysed by ALDH1A2, ALDH1A1, SLC16A4, SLC16A5 and 5 moreendoplasmic reticulum, extracellular space, cytosol

• L-methionineReach from here →
  1. retinal dehydrogenase (13-cis-retinal)
  2. transport of pyruvate and retinoate (cytosol to extracellular)
  3. N(1)-methylguanosine(37) in tRNA(Phe) + pyruvate + S-adenosyl-L-methionine = 4-demethylwyosine(37) in tRNA(Phe) + 5'-deoxyadenosine + L-methionine + CO2 + H2O

  Catalysed by ALDH1A2, ALDH1A1, SLC16A4, SLC16A5 and 6 moreendoplasmic reticulum, extracellular space, cytosol

• L-alanineReach from here →
  1. retinal dehydrogenase (13-cis-retinal)
  2. transport of pyruvate and retinoate (cytosol to extracellular)
  3. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase

  Catalysed by ALDH1A2, ALDH1A1, SLC16A4, SLC16A5 and 5 moreendoplasmic reticulum, extracellular space, cytosol, mitochondrial matrixOne of 18 routes

• N-acetylputrescineReach from here →
  1. retinal dehydrogenase (13-cis-retinal)
  2. transport of acetate and retinoate (cytosol to extracellular)
  3. N-acetylputrescine + H2O = putrescine + acetate

  Catalysed by ALDH1A2, ALDH1A1, SLC16A4, SLC16A5 and 2 moreendoplasmic reticulum, extracellular space, cytosol

• N(8)-acetylspermidineReach from here →
  1. retinal dehydrogenase (13-cis-retinal)
  2. transport of acetate and retinoate (cytosol to extracellular)
  3. N(8)-acetylspermidine + H2O = spermidine + acetate

  Catalysed by ALDH1A2, ALDH1A1, SLC16A4, SLC16A5 and 2 moreendoplasmic reticulum, extracellular space, cytosol

• (3S)-citramalyl-CoAReach from here →
  1. retinal dehydrogenase (13-cis-retinal)
  2. transport of pyruvate and retinoate (cytosol to extracellular)
  3. (3S)-citramalyl-CoA = pyruvate + acetyl-CoA

  Catalysed by ALDH1A2, ALDH1A1, SLC16A4, SLC16A5 and 5 moreendoplasmic reticulum, extracellular space, cytosol

• an N-acetyl-L-cysteine-S-conjugateReach from here →
  1. retinal dehydrogenase (13-cis-retinal)
  2. transport of acetate and retinoate (cytosol to extracellular)
  3. an N-acetyl-L-cysteine-S-conjugate + H2O = an S-substituted L-cysteine + acetate

  Catalysed by ALDH1A2, ALDH1A1, SLC16A4, SLC16A5 and 2 moreendoplasmic reticulum, extracellular space, cytosol

• 5-amino-2-oxopentanoateReach from here →
  1. retinal dehydrogenase (13-cis-retinal)
  2. transport of pyruvate and retinoate (cytosol to extracellular)
  3. L-ornithine + pyruvate = 5-amino-2-oxopentanoate + L-alanine

  Catalysed by ALDH1A2, ALDH1A1, SLC16A4, SLC16A5 and 5 moreendoplasmic reticulum, extracellular space, cytosol

• (4R)-4-hydroxy-2-oxoglutarateReach from here →
  1. retinal dehydrogenase (13-cis-retinal)
  2. transport of pyruvate and retinoate (cytosol to extracellular)
  3. (4R)-4-hydroxy-2-oxoglutarate = glyoxylate + pyruvate

  Catalysed by ALDH1A2, ALDH1A1, SLC16A4, SLC16A5 and 5 moreendoplasmic reticulum, extracellular space, cytosol

• an all-trans-retinyl esterReach from here →
  1. 13-cis-retinal to retinal conversion
  2. all-trans-retinol + NADP(+) = all-trans-retinal + NADPH + H(+)
  3. Lecithin Retinol Acyltransferase

  Catalysed by AKR1B15, AKR1B10, DHRS3, AKR1B1 and 8 morecytosolOne of 4 routes

• all-trans-retinyl 9Z-octadecenoateReach from here →
  1. 13-cis-retinal to retinal conversion
  2. all-trans-retinol + NADP(+) = all-trans-retinal + NADPH + H(+)
  3. 1,2,3-tri-(9Z-octadecenoyl)-glycerol + all-trans-retinol = all-trans-retinyl 9Z-octadecenoate + di-(9Z)-octadecenoylglycerol

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

• (4S)-4-hydroxy-2-oxoglutarateReach from here →
  1. retinal dehydrogenase (13-cis-retinal)
  2. transport of pyruvate and retinoate (cytosol to extracellular)
  3. (4S)-4-hydroxy-2-oxoglutarate = glyoxylate + pyruvate

  Catalysed by ALDH1A2, ALDH1A1, SLC16A4, SLC16A5 and 5 moreendoplasmic reticulum, extracellular space, cytosol

• di-(9Z)-octadecenoylglycerolReach from here →
  1. 13-cis-retinal to retinal conversion
  2. all-trans-retinol + NADP(+) = all-trans-retinal + NADPH + H(+)
  3. 1,2,3-tri-(9Z-octadecenoyl)-glycerol + all-trans-retinol = all-trans-retinyl 9Z-octadecenoate + di-(9Z)-octadecenoylglycerol

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

• 2-hexadecanoyl-sn-glycero-3-phosphocholineReach from here →
  1. 13-cis-retinal to retinal conversion
  2. all-trans-retinol + NADP(+) = all-trans-retinal + NADPH + H(+)
  3. all-trans-retinol + 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine = all-trans-retinyl hexadecanoate + 2-hexadecanoyl-sn-glycero-3-phosphocholine

  Catalysed by AKR1B15, AKR1B10, DHRS3, AKR1B1 and 8 morecytosol

• 9-cis-retinolReach from here →
  1. 13-cis-retinal to retinal conversion
  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

• 2-(1-hydroxyethyl)thiamine diphosphateReach from here →
  1. retinal dehydrogenase (13-cis-retinal)
  2. transport of pyruvate and retinoate (cytosol to extracellular)
  3. pyruvate:thiamin diphosphate acetaldehydetransferase (decarboxylating)

  Catalysed by ALDH1A2, ALDH1A1, SLC16A4, SLC16A5 and 7 moreendoplasmic reticulum, extracellular space, cytosol, mitochondrial matrix