N-acetyl-beta-neuraminic acid

Three steps

• CHEBI:17895Reach from here →
  1. N-Acetylneuraminate pyruvate-lyase (N-acetyl-D-mannosamine-forming)
  2. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase
  3. transport of alanine and tyrosine (cytosol to extracellular)

  Catalysed by NPL, AGXT2, SLC7A5cytosol, mitochondrial matrix, extracellular spaceOne of 8 routes

• all-trans-retinalReach from here →
  1. N-Acetylneuraminate pyruvate-lyase (N-acetyl-D-mannosamine-forming)
  2. transport of pyruvate and retinoate (cytosol to extracellular)
  3. retinoate reduction

  Catalysed by NPL, SLC16A4, SLC16A5, SLC16A3 and 3 morecytosol, extracellular space

• a beta-D-Gal-(1->4)-beta-D-Glc-(1<->1)-Cer(d18:1(4E))Reach from here →
  1. CTP:N-acetylneuraminate cytidylyltransferase
  2. ST3 beta-galactoside alpha-2,3-sialyltransferase (CMP-N-acetylneuraminate)
  3. exo-alpha-sialidase (GM3)

  Catalysed by CMAS, ST3GAL5, NEU4, NEU1 and 2 morenucleus, cytosolOne of 3 routes

• 3-phenylpyruvateReach from here →
  1. N-Acetylneuraminate pyruvate-lyase (N-acetyl-D-mannosamine-forming)
  2. L-Glutamine:pyruvate aminotransferase
  3. 3-phenylpyruvate + L-glutamine = 2-oxoglutaramate + L-phenylalanine

  Catalysed by NPL, KYAT1cytosol

• fumaric acidReach from here →
  1. N-Acetylneuraminate pyruvate-lyase (N-acetyl-D-mannosamine-forming)
  2. (S)-malate + NAD(+) = pyruvate + CO2 + NADH
  3. (S)-malate hydro-lyase (fumarate-forming)

  Catalysed by NPL, ME2, FHcytosolOne of 6 routes

• CHEBI:18019Reach from here →
  1. N-Acetylneuraminate pyruvate-lyase (N-acetyl-D-mannosamine-forming)
  2. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase
  3. transport of alanine and lysine (cytosol to extracellular)

  Catalysed by NPL, AGXT2, SLC7A6cytosol, mitochondrial matrix, extracellular spaceOne of 4 routes

• thiocyanateReach from here →
  1. N-Acetylneuraminate pyruvate-lyase (N-acetyl-D-mannosamine-forming)
  2. 2-oxo-3-sulfanylpropanoate + [thioredoxin]-dithiol = [thioredoxin]-disulfide + hydrogen sulfide + pyruvate + H(+)
  3. 3-mercaptopyruvate sulfurtransferase (hydrogen-cyanide)

  Catalysed by NPL, MPST, TSTcytosol

• 4-fumarylacetoacetateReach from here →
  1. N-Acetylneuraminate pyruvate-lyase (N-acetyl-D-mannosamine-forming)
  2. transport of acetoacetate and pyruvate (cytosol to mitochondria)
  3. 4-fumarylacetoacetate + H2O = acetoacetate + fumarate + H(+)

  Catalysed by NPL, FAHcytosol, mitochondrial matrix

• L-glutamineReach from here →
  1. N-Acetylneuraminate pyruvate-lyase (N-acetyl-D-mannosamine-forming)
  2. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase
  3. transport of alanine and glutamine (cytosol to extracellular)

  Catalysed by NPL, AGXT2, SLC3A2, SLC7A5 and 1 morecytosol, mitochondrial matrix, extracellular spaceOne of 17 routes

• dTTPReach from here →
  1. N-Acetylneuraminate pyruvate-lyase (N-acetyl-D-mannosamine-forming)
  2. pyruvate kinase (dTDP)
  3. DTTP Nucleotidohydrolase

  Catalysed by NPL, PKM, PKLR, ENTPD3 and 2 morecytosol, extracellular spaceOne of 11 routes

• CHEBI:18095Reach from here →
  1. N-Acetylneuraminate pyruvate-lyase (N-acetyl-D-mannosamine-forming)
  2. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase
  3. Transport of Hydroxy-Proline

  Catalysed by NPL, AGXT2, SLC1A4cytosol, mitochondrial matrix, extracellular space

• S-methylmercury-L-cysteineReach from here →
  1. N-Acetylneuraminate pyruvate-lyase (N-acetyl-D-mannosamine-forming)
  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 NPL, TYW1B, TYW1, SLC7A8cytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• 2-(alpha-Hydroxypropyl)thiamine diphosphateReach from here →
  1. N-Acetylneuraminate pyruvate-lyase (N-acetyl-D-mannosamine-forming)
  2. 2-oxobutanoate + L-alanine = (2S)-2-aminobutanoate + pyruvate
  3. branched chain keto acid dehydrogenase E1 (2-oxobutyrate)

  Catalysed by NPL, AGXT2, BCKDHA, BCKDHBcytosol, mitochondrial matrix

• 2-aminoisobutanoateReach from here →
  1. N-Acetylneuraminate pyruvate-lyase (N-acetyl-D-mannosamine-forming)
  2. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase
  3. 2-aminoisobutanoate(out) + L-alanine(in) = 2-aminoisobutanoate(in) + L-alanine(out)

  Catalysed by NPL, AGXT2, SLC7A10cytosol, mitochondrial matrix, inner side of the membrane, outer side of the membraneOne of 2 routes

• D-isoleucineReach from here →
  1. N-Acetylneuraminate pyruvate-lyase (N-acetyl-D-mannosamine-forming)
  2. D-serine = pyruvate + NH4(+)
  3. D-isoleucine(out) + D-serine(in) = D-isoleucine(in) + D-serine(out)

  Catalysed by NPL, SRR, SLC7A10cytosol, inner side of the membrane, outer side of the membrane

• an 8-O-sulfo-ganglioside GM1bReach from here →
  1. CTP:N-acetylneuraminate cytidylyltransferase
  2. a ganglioside GA1 + CMP-N-acetyl-beta-neuraminate = a ganglioside GM1b + CMP + H(+)
  3. a ganglioside GM1b + 3'-phosphoadenylyl sulfate = an 8-O-sulfo-ganglioside GM1b + adenosine 3',5'-bisphosphate + H(+)

  Catalysed by CMAS, ST3GAL1, ST3GAL2, WSCD1nucleus

• N(omega),N('omega)-dimethyl-L-arginineReach from here →
  1. N-Acetylneuraminate pyruvate-lyase (N-acetyl-D-mannosamine-forming)
  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 NPL, AGXT2cytosol, mitochondrial matrixOne of 3 routes

• a ganglioside Ac-O-7-GD3(d18:1(4E))Reach from here →
  1. CTP:N-acetylneuraminate cytidylyltransferase
  2. ST8 alpha-N-acetyl-neuraminide alpha-2,8-sialyltransferase (CMP-N-acetylneuraminate)
  3. a ganglioside GD3 (d18:1(4E)) + acetyl-CoA = a ganglioside Ac-O-7-GD3(d18:1(4E)) + CoA

  Catalysed by CMAS, ST8SIA1, CASD1nucleus, cytosol

• (S)-lactoyl-AMPReach from here →
  1. N-Acetylneuraminate pyruvate-lyase (N-acetyl-D-mannosamine-forming)
  2. (S)-lactate + NAD(+) = pyruvate + NADH + H(+)
  3. (S)-lactate + ATP + H(+) = (S)-lactoyl-AMP + diphosphate

  Catalysed by NPL, LDHA, LDHB, LDHC and 4 morecytosol

• (S)-lactoyl-CoAReach from here →
  1. N-Acetylneuraminate pyruvate-lyase (N-acetyl-D-mannosamine-forming)
  2. (S)-lactate + NAD(+) = pyruvate + NADH + H(+)
  3. (S)-lactate + ATP + CoA = (S)-lactoyl-CoA + AMP + diphosphate

  Catalysed by NPL, LDHA, LDHB, LDHC and 3 morecytosol

• N-acetylneuraminate 9-phosphateReach from here →
  1. N-Acetylneuraminate pyruvate-lyase (N-acetyl-D-mannosamine-forming)
  2. ATP:N-acyl-D-mannosamine 6-phosphotransferase
  3. N-acetylneuraminate synthase

  Catalysed by NPL, GNE, NANScytosolOne of 3 routes

• a quinolReach from here →
  1. N-Acetylneuraminate pyruvate-lyase (N-acetyl-D-mannosamine-forming)
  2. (S)-malate + NAD(+) = pyruvate + CO2 + NADH
  3. (S)-malate + a quinone = enol-oxaloacetate + a quinol

  Catalysed by NPL, ME2, SDHB, SDHAcytosol

• selenomethionineReach from here →
  1. N-Acetylneuraminate pyruvate-lyase (N-acetyl-D-mannosamine-forming)
  2. 2-oxobutanoate + L-alanine = (2S)-2-aminobutanoate + pyruvate
  3. Selenomethionine methanethiol-lyase (deaminating)

  Catalysed by NPL, AGXT2, CTHcytosol

• a ganglioside GA2 (d18:1(4E))Reach from here →
  1. CTP:N-acetylneuraminate cytidylyltransferase
  2. lactosylceramide alpha-2,3-sialyltransferase (CMP-N-acetylneuraminate)
  3. exo-alpha-sialidase (GM2)

  Catalysed by CMAS, ST6GALNAC2, ST3GAL5, NEU4 and 3 morenucleus, cytosolOne of 2 routes

• CHEBI:27760Reach from here →
  1. N-Acetylneuraminate pyruvate-lyase (N-acetyl-D-mannosamine-forming)
  2. 2-oxobutanoate + L-alanine = (2S)-2-aminobutanoate + pyruvate
  3. Selenocystathionine Lysteine-lyase (deaminating)

  Catalysed by NPL, AGXT2, CTHcytosol

• a ganglioside GA1 (d18:1(4E))Reach from here →
  1. CTP:N-acetylneuraminate cytidylyltransferase
  2. ST3 beta-galactoside alpha-2,3-sialyltransferase (CMP-N-acetylneuraminate)
  3. a ganglioside GM1 (d18:1(4E)) + H2O = a ganglioside GA1 (d18:1(4E)) + N-acetylneuraminate

  Catalysed by CMAS, ST3GAL5, NEU3nucleus, cytosol

• alpha-D-galactoseReach from here →
  1. CTP:N-acetylneuraminate cytidylyltransferase
  2. ST3 beta-galactoside alpha-2,3-sialyltransferase (CMP-N-acetylneuraminate)
  3. beta-galactosidase (GM1)

  Catalysed by CMAS, ST3GAL5, LCT, GLB1 and 2 morenucleus, cytosolOne of 5 routes

• N-acetyl-beta-D-galactosamineReach from here →
  1. CTP:N-acetylneuraminate cytidylyltransferase
  2. lactosylceramide alpha-2,3-sialyltransferase (CMP-N-acetylneuraminate)
  3. a ganglioside GM2 (d18:1(4E)) + H2O = a ganglioside GM3 (d18:1(4E)) + N-acetyl-beta-D-galactosamine

  Catalysed by CMAS, ST6GALNAC2, ST3GAL5, HEXA and 1 morenucleus, cytosol

• 3-mercaptolactic acidReach from here →
  1. N-Acetylneuraminate pyruvate-lyase (N-acetyl-D-mannosamine-forming)
  2. 2-oxo-3-sulfanylpropanoate + [thioredoxin]-dithiol = [thioredoxin]-disulfide + hydrogen sulfide + pyruvate + H(+)
  3. 3-Mercaptolactate:NAD+ oxidoreductase

  Catalysed by NPL, MPST, LDHB, LDHC and 2 morecytosol

• 2-oxopentanoateReach from here →
  1. N-Acetylneuraminate pyruvate-lyase (N-acetyl-D-mannosamine-forming)
  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 NPL, AGXT2cytosol

• 17alpha-hydroxypregnenoloneReach from here →
  1. N-Acetylneuraminate pyruvate-lyase (N-acetyl-D-mannosamine-forming)
  2. transport of acetate and pyruvate (cytosol to extracellular)
  3. cytochrome P450 (17alpha-hydroxypregnenolone)

  Catalysed by NPL, SLC16A4, SLC16A5, SLC16A3 and 3 morecytosol, extracellular space, endoplasmic reticulum

• pyridoxine 5'-phosphateReach from here →
  1. N-Acetylneuraminate pyruvate-lyase (N-acetyl-D-mannosamine-forming)
  2. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase
  3. L-selenocysteine selenide-lyase (L-alanine-forming)

  Catalysed by NPL, AGXT2, SCLYcytosol, mitochondrial matrix

• a carboxylateReach from here →
  1. N-Acetylneuraminate pyruvate-lyase (N-acetyl-D-mannosamine-forming)
  2. a 3-acylpyruvate + H2O = a carboxylate + pyruvate + H(+)
  3. a 3-acylpyruvate + H2O = a carboxylate + pyruvate + H(+)

  Catalysed by NPL, FAHD1cytosol

• chlorine(.)Reach from here →
  1. N-Acetylneuraminate pyruvate-lyase (N-acetyl-D-mannosamine-forming)
  2. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase
  3. transport of alanine and chloride (cytosol to extracellular)

  Catalysed by NPL, AGXT2, SLC6A14cytosol, mitochondrial matrix, extracellular spaceOne of 6 routes

• hydrogen sulfideReach from here →
  1. N-Acetylneuraminate pyruvate-lyase (N-acetyl-D-mannosamine-forming)
  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 NPL, MPSTcytosol

• L-aspartateReach from here →
  1. N-Acetylneuraminate pyruvate-lyase (N-acetyl-D-mannosamine-forming)
  2. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase
  3. oxaloacetate + L-alanine = L-aspartate + pyruvate

  Catalysed by NPL, AGXT2cytosol, mitochondrial matrixOne of 8 routes

• citric acidReach from here →
  1. N-Acetylneuraminate pyruvate-lyase (N-acetyl-D-mannosamine-forming)
  2. Pyruvate:carbon-dioxide ligase (ADP-forming)
  3. acetyl-CoA:oxaloacetate C-acetyltransferase (thioester-hydrolysing)

  Catalysed by NPL, PC, CScytosol, mitochondrial matrixOne of 9 routes

• isocitric acidReach from here →
  1. N-Acetylneuraminate pyruvate-lyase (N-acetyl-D-mannosamine-forming)
  2. pyruvate kinase (dTDP)
  3. transport of isocitrate and PEP (cytosol to mitochondria)

  Catalysed by NPL, PKM, PKLR, SLC25A1cytosol, mitochondrial matrixOne of 5 routes

• 4-hydroxy-2-oxoglutaric acidReach from here →
  1. N-Acetylneuraminate pyruvate-lyase (N-acetyl-D-mannosamine-forming)
  2. Pyruvate:carbon-dioxide ligase (ADP-forming)
  3. D-aspartate:2-oxoglutarate aminotransferase

  Catalysed by NPL, PC, GOT2cytosol, mitochondrial matrix

• cis-aconitic acidReach from here →
  1. N-Acetylneuraminate pyruvate-lyase (N-acetyl-D-mannosamine-forming)
  2. pyruvate kinase (dTDP)
  3. transport of cis-aconitate and PEP (cytosol to mitochondria)

  Catalysed by NPL, PKM, PKLR, SLC25A1cytosol, mitochondrial matrixOne of 5 routes

• thiosulfateReach from here →
  1. N-Acetylneuraminate pyruvate-lyase (N-acetyl-D-mannosamine-forming)
  2. (S)-malate + NAD(+) = pyruvate + CO2 + NADH
  3. transport of malate and thiosulfate (cytosol to mitochondria)

  Catalysed by NPL, ME2, SLC25A10cytosol, mitochondrial matrixOne of 4 routes

• 4-methylthio-2-oxobutanoic acidReach from here →
  1. N-Acetylneuraminate pyruvate-lyase (N-acetyl-D-mannosamine-forming)
  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 NPL, TYW1B, TYW1, IL4I1cytosol

• 2-oxohexanoateReach from here →
  1. N-Acetylneuraminate pyruvate-lyase (N-acetyl-D-mannosamine-forming)
  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 NPL, AGXT2cytosol

• D-cysteineReach from here →
  1. N-Acetylneuraminate pyruvate-lyase (N-acetyl-D-mannosamine-forming)
  2. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase
  3. D-cysteine(out) + L-alanine(in) = D-cysteine(in) + L-alanine(out)

  Catalysed by NPL, AGXT2, SLC7A10cytosol, mitochondrial matrix, inner side of the membrane, outer side of the membraneOne of 2 routes

• N-acetylneuraminateReach from here →
  1. CTP:N-acetylneuraminate cytidylyltransferase
  2. ST3 beta-galactoside alpha-2,3-sialyltransferase (CMP-N-acetylneuraminate)
  3. a ganglioside GM1 (d18:1(4E)) + H2O = a ganglioside GA1 (d18:1(4E)) + N-acetylneuraminate

  Catalysed by CMAS, ST3GAL5, NEU3nucleus, cytosolOne of 10 routes

• L-alpha-aminobutyric acidReach from here →
  1. N-Acetylneuraminate pyruvate-lyase (N-acetyl-D-mannosamine-forming)
  2. 2-oxobutanoate + L-alanine = (2S)-2-aminobutanoate + pyruvate
  3. glutamic-pyruvic transaminase ((S)-2-aminobutanoate)

  Catalysed by NPL, AGXT2, GPTcytosol

• glyoxylateReach from here →
  1. N-Acetylneuraminate pyruvate-lyase (N-acetyl-D-mannosamine-forming)
  2. (S)-malate + NAD(+) = pyruvate + CO2 + NADH
  3. glyoxylate + acetyl-CoA + H2O = (S)-malate + CoA + H(+)

  Catalysed by NPL, ME2, CLYBLcytosolOne of 8 routes

• (3S)-3-hydroxy-3-methylglutaryl-CoAReach from here →
  1. N-Acetylneuraminate pyruvate-lyase (N-acetyl-D-mannosamine-forming)
  2. transport of acetoacetate and pyruvate (cytosol to mitochondria)
  3. (3S)-3-hydroxy-3-methylglutaryl-CoA = acetoacetate + acetyl-CoA

  Catalysed by NPL, HMGCL, HMGCLL1cytosol, mitochondrial matrix

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

  Catalysed by NPL, SLC16A4, SLC16A5, SLC16A3 and 5 morecytosol, extracellular space, endoplasmic reticulum

• L-ornithineReach from here →
  1. N-Acetylneuraminate pyruvate-lyase (N-acetyl-D-mannosamine-forming)
  2. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase
  3. transport of alanine and ornithine (cytosol to extracellular)

  Catalysed by NPL, AGXT2, SLC7A6cytosol, mitochondrial matrix, extracellular spaceOne of 7 routes