(2S)-naringenin 7-O-beta-D-glucoside

Three steps

• GDP-alpha-D-glucoseReach from here →
  1. (2S)-naringenin + UDP-alpha-D-glucose = (2S)-naringenin 7-O-beta-D-glucoside + UDP + H(+)
  2. alpha-D-galactose 1-phosphate + UDP-alpha-D-glucose = alpha-D-glucose 1-phosphate + UDP-alpha-D-galactose
  3. GDP-alpha-D-glucose + phosphate = alpha-D-glucose 1-phosphate + GDP + H(+)

  Catalysed by UGT3A2, GALT, GDPGP1

• a globoside GalGb4Cer (d18:1(4E))Reach from here →
  1. (2S)-naringenin + UDP-alpha-D-glucose = (2S)-naringenin 7-O-beta-D-glucoside + UDP + H(+)
  2. alpha-D-galactose 1-phosphate + UDP-alpha-D-glucose = alpha-D-glucose 1-phosphate + UDP-alpha-D-galactose
  3. a globoside Gb4Cer (d18:1(4E)) + UDP-alpha-D-galactose = a globoside GalGb4Cer (d18:1(4E)) + UDP + H(+)

  Catalysed by UGT3A2, GALT, B3GALT5

• UDP-N-acetyl-alpha-D-galactosamineReach from here →
  1. (2S)-naringenin + UDP-alpha-D-glucose = (2S)-naringenin 7-O-beta-D-glucoside + UDP + H(+)
  2. alpha-D-galactose 1-phosphate + UDP-alpha-D-glucose = alpha-D-glucose 1-phosphate + UDP-alpha-D-galactose
  3. UDP-N-acetyl-alpha-D-galactosamine(out) + UDP-alpha-D-galactose(in) = UDP-N-acetyl-alpha-D-galactosamine(in) + UDP-alpha-D-galactose(out)

  Catalysed by UGT3A2, GALT, SLC35A2inner side of the membrane, outer side of the membraneOne of 2 routes

• genisteinReach from here →
  1. (2S)-naringenin + UDP-alpha-D-glucose = (2S)-naringenin 7-O-beta-D-glucoside + UDP + H(+)
  2. genistein + UDP-alpha-D-glucose = genistein 7-O-beta-D-glucoside + UDP + H(+)
  3. genistein + UDP-alpha-D-glucose = genistein 7-O-beta-D-glucoside + UDP + H(+)

  Catalysed by UGT3A2, UGT3A1One of 2 routes

• a ganglioside GM1 (d18:1(4E))Reach from here →
  1. (2S)-naringenin + UDP-alpha-D-glucose = (2S)-naringenin 7-O-beta-D-glucoside + UDP + H(+)
  2. alpha-D-galactose 1-phosphate + UDP-alpha-D-glucose = alpha-D-glucose 1-phosphate + UDP-alpha-D-galactose
  3. a ganglioside GM2 (d18:1(4E)) + UDP-alpha-D-galactose = a ganglioside GM1 (d18:1(4E)) + UDP + H(+)

  Catalysed by UGT3A2, GALT, B3GALT4

• daidzeinReach from here →
  1. (2S)-naringenin + UDP-alpha-D-glucose = (2S)-naringenin 7-O-beta-D-glucoside + UDP + H(+)
  2. daidzein + UDP-alpha-D-glucose = daidzein 7-O-beta-D-glucoside + UDP
  3. daidzein + UDP-alpha-D-glucose = daidzein 7-O-beta-D-glucoside + UDP

  Catalysed by UGT3A2One of 2 routes

• a neolactoside IV(3)-beta-[Gal-beta-(1->3)-GlcNAc]-nLc4Cer(d18:1(4E))Reach from here →
  1. (2S)-naringenin + UDP-alpha-D-glucose = (2S)-naringenin 7-O-beta-D-glucoside + UDP + H(+)
  2. alpha-D-galactose 1-phosphate + UDP-alpha-D-glucose = alpha-D-glucose 1-phosphate + UDP-alpha-D-galactose
  3. a neolactoside IV(3)-beta-GlcNAc-nLc4Cer(d18:1(4E)) + UDP-alpha-D-galactose = a neolactoside IV(3)-beta-[Gal-beta-(1->3)-GlcNAc]-nLc4Cer(d18:1(4E)) + UDP + H(+)

  Catalysed by UGT3A2, GALT, B3GALT2

• a beta-D-galactosyl-(1->4)-beta-D-glucosyl-(1<->1)-ceramideReach from here →
  1. (2S)-naringenin + UDP-alpha-D-glucose = (2S)-naringenin 7-O-beta-D-glucoside + UDP + H(+)
  2. alpha-D-galactose 1-phosphate + UDP-alpha-D-glucose = alpha-D-glucose 1-phosphate + UDP-alpha-D-galactose
  3. a beta-D-glucosylceramide + UDP-alpha-D-galactose = a beta-D-galactosyl-(1->4)-beta-D-glucosyl-(1<->1)-ceramide + UDP + H(+)

  Catalysed by UGT3A2, GALT, B4GALT3, B4GALT1

• a ganglioside GM1Reach from here →
  1. (2S)-naringenin + UDP-alpha-D-glucose = (2S)-naringenin 7-O-beta-D-glucoside + UDP + H(+)
  2. alpha-D-galactose 1-phosphate + UDP-alpha-D-glucose = alpha-D-glucose 1-phosphate + UDP-alpha-D-galactose
  3. a ganglioside GM2 + UDP-alpha-D-galactose = a ganglioside GM1 + UDP + H(+)

  Catalysed by UGT3A2, GALT, B3GALT4

• N-(2-hydroxy-hexanoyl)-beta-D-galactosyl-sphing-4-enineReach from here →
  1. (2S)-naringenin + UDP-alpha-D-glucose = (2S)-naringenin 7-O-beta-D-glucoside + UDP + H(+)
  2. alpha-D-galactose 1-phosphate + UDP-alpha-D-glucose = alpha-D-glucose 1-phosphate + UDP-alpha-D-galactose
  3. N-(2-hydroxy-hexanoyl)-sphing-4-enine + UDP-alpha-D-galactose = N-(2-hydroxy-hexanoyl)-beta-D-galactosyl-sphing-4-enine + UDP + H(+)

  Catalysed by UGT3A2, GALT, UGT8

• N-(2-hydroxyhexanoyl)-beta-D-galactosylsphinganineReach from here →
  1. (2S)-naringenin + UDP-alpha-D-glucose = (2S)-naringenin 7-O-beta-D-glucoside + UDP + H(+)
  2. alpha-D-galactose 1-phosphate + UDP-alpha-D-glucose = alpha-D-glucose 1-phosphate + UDP-alpha-D-galactose
  3. N-(2-hydroxy-hexanoyl)-sphinganine + UDP-alpha-D-galactose = N-(2-hydroxyhexanoyl)-beta-D-galactosylsphinganine + UDP + H(+)

  Catalysed by UGT3A2, GALT, UGT8

• beta-D-glucosyl-(1<->1)-sphing-4-enineReach from here →
  1. (2S)-naringenin + UDP-alpha-D-glucose = (2S)-naringenin 7-O-beta-D-glucoside + UDP + H(+)
  2. an N-acylsphing-4-enine + UDP-alpha-D-glucose = a beta-D-glucosyl-(1<->1')-N-acylsphing-4-enine + UDP + H(+)
  3. a beta-D-glucosyl-(1<->1')-N-acylsphing-4-enine + H2O = beta-D-glucosyl-(1<->1)-sphing-4-enine + a fatty acid

  Catalysed by UGT3A2, UGCG, ASAH1

• a ganglioside GD1b (d18:1(4E))Reach from here →
  1. (2S)-naringenin + UDP-alpha-D-glucose = (2S)-naringenin 7-O-beta-D-glucoside + UDP + H(+)
  2. alpha-D-galactose 1-phosphate + UDP-alpha-D-glucose = alpha-D-glucose 1-phosphate + UDP-alpha-D-galactose
  3. a ganglioside GD2 (d18:1(4E)) + UDP-alpha-D-galactose = a ganglioside GD1b (d18:1(4E)) + UDP + H(+)

  Catalysed by UGT3A2, GALT, B3GALT4

• a globoside Gb3CerReach from here →
  1. (2S)-naringenin + UDP-alpha-D-glucose = (2S)-naringenin 7-O-beta-D-glucoside + UDP + H(+)
  2. alpha-D-galactose 1-phosphate + UDP-alpha-D-glucose = alpha-D-glucose 1-phosphate + UDP-alpha-D-galactose
  3. a beta-D-galactosyl-(1->4)-beta-D-glucosyl-(1<->1)-ceramide + UDP-alpha-D-galactose = a globoside Gb3Cer + UDP + H(+)

  Catalysed by UGT3A2, GALT, A4GALT

• a neolactoside nLc6CerReach from here →
  1. (2S)-naringenin + UDP-alpha-D-glucose = (2S)-naringenin 7-O-beta-D-glucoside + UDP + H(+)
  2. alpha-D-galactose 1-phosphate + UDP-alpha-D-glucose = alpha-D-glucose 1-phosphate + UDP-alpha-D-galactose
  3. a neolactoside IV(3)-beta-GlcNAc-nLc4Cer + UDP-alpha-D-galactose = a neolactoside nLc6Cer + UDP + H(+)

  Catalysed by UGT3A2, GALT, B4GALT3, B4GALT1