Table 2 KEGG pathway modules and hierarchical bin structure for MapMan style representation of compounds identified in Table 1, matched with rice reference pathways (osa) using KEGG Mapper

From: A large-scale metabolomics study to harness chemical diversity and explore biochemical mechanisms in ryegrass

Bin code

Name

Module

Reaction

Compound

KEGG ID

1

Metabolic pathways

     

1.1

Nucleotide and amino acid metabolism

     

1.1.1

Cysteine and methionine metabolism

     

1.1.1.1

Methionine degradation

M00035

S-Adenosyl-l-Methionine → l-Homocysteine

S-Adenosyl-l-Homocysteine

C00021

1.1.1.2

Methionine degradation

M00035

l-Serine → l-Cystathionine

l-Serine

C00065

1.1.1.3

Cysteine biosynthesis

M00609

Methionine → Cysteine

S-Adenosyl-l-Homocysteine

C00021

1.1.1.4

Cysteine biosynthesis

M00021

Serine → Cysteine

l-Serine

C00065

1.1.1.5

Cysteine biosynthesis

M00338

Homocysteine + Serine → Cysteine

l-Serine

C00065

1.1.2

Serine and threonine metabolism

     

1.1.2.1

Serine biosynthesis

M00020

Glycerate-3P → Serine

l-Serine

C00065

1.1.3

Cofactor and vitamin biosynthesis

     

1.1.3.1

Ascorbate degradation

M00550

Ascorbate → d-Xylulose 5-Phosphate

d-Xylulose 5-Phosphate

C00231

1.1.3.2

Pantothenate biosynthesis

M00119

Valine/l-Aspartate → Pantothenate

2-Dehydropantoate

C00966

1.1.3.3

Biotin biosynthesis

M00123

Pimeloyl-ACP/CoA → Biotin

8-Amino-7-Oxononanoate

C01092

1.1.3.4

Biotin biosynthesis, BioI pathway

M00573

Long-chain-acyl-ACP → Pimeloyl-ACP → Biotin

8-Amino-7-Oxononanoate

C01092

1.1.3.5

Biotin biosynthesis, BioW pathway

M00577

Pimelate → Pimeloyl-CoA → Biotin

8-Amino-7-Oxononanoate

C01092

1.1.3.6

Ascorbate biosynthesis

M00114

Glucose 6-Phosphate → Ascorbate

l-Galactose

C01825

1.1.3.7

Riboflavin biosynthesis

M00125

GTP → Riboflavin/FMN/FAD

6,7-Dimethyl-8-(d-Ribityl)Lumazine

C04332

1.1.4

Arginine and proline metabolism

     

1.1.4.1

Urea cycle

M00029

 

l-Citrulline

C00327

1.1.5

Branched-chain amino acid metabolism

     

1.1.5.1

Valine/Isoleucine biosynthesis

M00019

Pyruvate → Valine/2-Oxobutanoate → Isoleucine

(S)-2-Aceto-2-Hydroxybutanoate

C06006

1.1.5.2

Isoleucine biosynthesis

M00570

Threonine → 2-Oxobutanoate → Isoleucine

(S)-2-Aceto-2-Hydroxybutanoate

C06006

1.2

Carbohydrate and lipid metabolism

     

1.2.1

Lipid metabolism

     

1.2.1.1

Ceramide biosynthesis

M00094

 

l-Serine

C00065

1.2.1.2

Inositol phosphate metabolism

M00131

Ins(1,3,4,5)P4 → Ins(1,3,4)P3 → Myo-inositol

Myo-Inositol

C00137

1.2.2

Other carbohydrate metabolism

     

1.2.2.1

Photorespiration

M00532

 

l-Serine

C00065

1.2.2.2

Nucleotide sugar biosynthesis

M00554

Galactose → UDP-Galactose

d-Galactose

C00124

1.2.2.3

Galactose degradation, Leloir pathway

M00632

Galactose → Alpha-D-Glucose 1-Phosphate

d-Galactose

C00124

1.2.2.4

Glucuronate pathway, Uronate pathway

M00014

 

d-Xylulose 5-Phosphate

C00231

1.2.2.5

Nucleotide sugar biosynthesis

M00549

Glucose → UDP-Glucose

Alpha-d-Glucose

C00267

1.2.2.6

Trehalose biosynthesis

M00565

D-Glucose 1-Phosphate → Trehalose

alpha,alpha-Trehalose

C01083

1.2.3

Central carbohydrate metabolism

     

1.2.3.1

Glycolysis (Embden–Meyerhof pathway)

M00001

Glucose → Pyruvate

Glycerone Phosphate

C00111

1.2.3.2

Glycolysis, core module involving three-carbon compounds

M00002

 

Glycerone Phosphate

C00111

1.2.3.3

Gluconeogenesis

M00003

Oxaloacetate → Fructose 6-Phosphate

Glycerone Phosphate

C00111

1.2.3.4

Pentose phosphate pathway (pentose phosphate cycle)

M00004

 

d-Ribose 5-Phosphate

C00117

1.2.3.5

PRPP biosynthesis

M00005

Ribose 5-Phosphate → PRPP

d-Ribose 5-Phosphate

C00117

1.2.3.6

Pentose phosphate pathway, non-oxidative phase

M00007

Fructose 6-Phosphate → Ribose 5-Phosphate

d-Ribose 5-Phosphate

C00117

1.2.3.7

Pentose phosphate pathway, archaea

M00580

Fructose 6-Phosphate → Ribose 5-Phosphate

d-Ribose 5-Phosphate

C00117

1.2.3.8

Pentose phosphate pathway (pentose phosphate cycle)

M00004

 

d-Xylulose 5-Phosphate

C00231

1.2.3.9

Pentose phosphate pathway, non-oxidative phase

M00007

Fructose 6-Phosphate → Ribose 5-Phosphate

d-Xylulose 5-Phosphate

C00231

1.2.3.10

Glycolysis (Embden–Meyerhof pathway)

M00001

Glucose → Pyruvate

Alpha-d-Glucose

C00267

1.2.4

Lipopolysaccharide metabolism

     

1.2.4.1

CMP-KDO biosynthesis

M00063

 

d-Arabinose 5-Phosphate

C01112

1.3

Energy metabolism

     

1.3.1

Carbon fixation

     

1.3.1.1

Reductive pentose phosphate cycle (Calvin cycle)

M00165

 

d-Ribose 5-Phosphate

C00117

1.3.1.2

Reductive pentose phosphate cycle

M00167

Glyceraldehyde 3-Phosphate → Ribulose 5-Phosphate

d-Ribose 5-Phosphate

C00117

1.4

Secondary metabolism

     

1.4.1

Biosynthesis of secondary metabolites

     

1.4.1.1

Monolignol biosynthesis

M00039

Phenylalanine/Tyrosine → Monolignol

Coniferyl Aldehyde

C02666

1.4.1.2

Monolignol biosynthesis

M00039

Phenylalanine/Tyrosine → Monolignol

Sinapoyl Aldehyde

C05610

1.5

Others

     

1.5.1

Amino acid

  

l-Asparagine

C00152

1.5.2

Oligosaccharides

  

Maltose

C00208

1.5.3

Glycolysis/Gluconeogenesis

  

Beta-d-Glucose

C00221

1.5.4

Arginine and proline metabolism

  

4-Aminobutyraldehyde

C00555

1.5.5

Cysteine and methionine metabolism

  

O-Acetyl-l-Homoserine

C01077

1.5.6

Lipopolysaccharide biosynthesis

  

d-Arabinose 5-Phosphate

C01112

1.5.7

Biosynthesis of secondary metabolites

  

1-Aminocyclopropane-1-Carboxylate

C01234

1.5.8

Biosynthesis of phenylpropanoids

  

Taxifolin

C01617

1.5.9

Ascorbate and aldarate metabolism

  

l-Galactose

C01825

1.5.10

Amino sugar and nucleotide sugar metabolism

  

Beta-l-Arabinose 1-Phosphate

C03906

1.5.11

Biosynthesis of secondary metabolites

  

(2S)-2-Isopropyl-3-Oxosuccinate

C04236

1.5.12

Biosynthesis of secondary metabolites

  

Pelargonidin 3-O-Glucoside

C12137

2

Biosynthesis of secondary metabolites

     

2.1

Nucleotide and amino acid metabolism

     

2.1.1

Cysteine and methionine metabolism

     

2.1.1.1

Cysteine biosynthesis

M00021

Serine → Cysteine

l-Serine

C00065

2.1.1.2

Ethylene biosynthesis

M00368

Methionine → Ethylene

1-Aminocyclopropane-1-Carboxylate

C01234

2.1.2

Cofactor and vitamin biosynthesis

     

2.1.2.1

Pantothenate biosynthesis

M00119

Valine/l-Aspartate → Pantothenate

2-Dehydropantoate

C00966

2.1.2.2

Ascorbate biosynthesis

M00114

Glucose 6-Phosphate → Ascorbate

l-Galactose

C01825

2.1.2.3

Riboflavin biosynthesis

M00125

GTP → Riboflavin/FMN/FAD

6,7-Dimethyl-8-(d-Ribityl)Lumazine

C04332

2.1.3

Branched-chain amino acid metabolism

     

2.1.3.1

Valine/Isoleucine biosynthesis

M00019

Pyruvate → Valine/2-Oxobutanoate → Isoleucine

(S)−2-Aceto-2-Hydroxybutanoate

C06006

2.2

Carbohydrate and lipid metabolism

     

2.2.1

Other carbohydrate metabolism

     

2.2.1.1

Photorespiration

M00532

 

l-Serine

C00065

2.2.1.2

Trehalose biosynthesis

M00565

D-Glucose 1-Phosphate → Trehalose

alpha,alpha-Trehalose

C01083

2.3

Secondary metabolism

     

2.3.1

Biosynthesis of secondary metabolites

     

2.3.1.1

Monolignol biosynthesis

M00039

Phenylalanine/Tyrosine → Monolignol

Coniferyl Aldehyde

C02666

2.3.1.2

Monolignol biosynthesis

M00039

Phenylalanine/Tyrosine → Monolignol

Sinapoyl Aldehyde

C05610

2.4

Others

     

2.4.1

Flavonoid biosynthesis

  

Eriodictyol

C05631

2.4.2

Flavonoid biosynthesis

  

Leucodelphinidin

C05909

2.4.3

Biosynthesis of phenylpropanoids

  

Umbelliferone

C09315

2.4.4

Biosynthesis of secondary metabolites

  

Pelargonidin 3-O-Glucoside

C12137

2.4.5

Biosynthesis of phenylpropanoids

  

Taxifolin

C01617

2.4.6

Biosynthesis of secondary metabolites

  

2-Isopropylmaleate

C02631

2.4.7

Biosynthesis of secondary metabolites

  

(2S)-2-Isopropyl-3-Oxosuccinate

C04236

3

Biosynthesis of amino acids

     

3.1

Nucleotide and amino acid metabolism

     

3.1.1

Cysteine and methionine metabolism

     

3.1.1.1

Cysteine biosynthesis

M00609

Methionine → Cysteine

S-Adenosyl-l-Homocysteine

C00021

3.1.1.2

Cysteine biosynthesis

M00021

Serine → Cysteine

l-Serine

C00065

3.1.1.3

Cysteine biosynthesis

M00338

Homocysteine + Serine → Cysteine

l-Serine

C00065

3.1.2

Serine and threonine metabolism

     

3.1.2.1

Serine biosynthesis

M00020

Glycerate 3-Phosphate → Serine

l-Serine

C00065

3.1.3

Arginine and proline metabolism

     

3.1.3.1

Urea cycle

M00029

 

l-Citrulline

C00327

3.1.3.2

Arginine biosynthesis

M00844

Ornithine → Arginine

l-Citrulline

C00327

3.1.3.3

Arginine biosynthesis

M00845

Glutamate → Acetylcitrulline → Arginine

l-Citrulline

C00327

3.1.4

Branched-chain amino acid metabolism

     

3.1.4.1

Valine/Isoleucine biosynthesis

M00019

Pyruvate → Valine/2-Oxobutanoate → Isoleucine

(S)-2-Aceto-2-Hydroxybutanoate

C06006

3.1.4.2

Isoleucine biosynthesis

M00570

Threonine → 2-Oxobutanoate → Isoleucine

(S)-2-Aceto-2-Hydroxybutanoate

C06006

3.2

Carbohydrate and lipid metabolism

     

3.2.1

Central carbohydrate metabolism

     

3.2.1.1

Glycolysis, core module involving three-carbon compounds

M00002

 

Glycerone Phosphate

C00111

3.2.1.2

PRPP biosynthesis

M00005

Ribose 5-Phosphate → PRPP

d-Ribose 5-Phosphate

C00117

3.2.1.3

Pentose phosphate pathway, non-oxidative phase

M00007

Fructose 6-Phosphate → Ribose 5-Phosphate

d-Ribose 5-Phosphate

C00117

3.2.1.4

Pentose phosphate pathway, archaea

M00580

Fructose 6-Phosphate → Ribose 5-Phosphate

d-Ribose 5-Phosphate

C00117

3.2.1.5

Pentose phosphate pathway, non-oxidative phase

M00007

Fructose 6-Phosphate → Ribose 5-Phosphate

d-Xylulose 5-Phosphate

C00231

3.3

Others

     

3.3.1

Amino acid

  

l-Asparagine

C00152

4

Carbon metabolism

     

4.1

Nucleotide and amino acid metabolism

     

4.1.1

Serine and threonine metabolism

     

4.1.1.1

Serine biosynthesis

M00020

Glycerate 3-Phosphate → Serine

l-Serine

C00065

4.1.2

Cysteine and methionine metabolism

     

4.1.2.1

Cysteine biosynthesis

M00021

Serine → Cysteine

l-Serine

C00065

4.2

Energy metabolism

     

4.2.1

Methane metabolism

     

4.2.1.1

Formaldehyde assimilation, serine pathway

M00346

 

l-Serine

C00065

4.2.1.2

Formaldehyde assimilation, xylulose monophosphate pathway

M00344

 

Glycerone Phosphate

C00111

4.2.1.3

Formaldehyde assimilation, ribulose monophosphate pathway

M00345

 

Glycerone Phosphate

C00111

4.2.2

Carbon fixation

     

4.2.2.1

Reductive pentose phosphate cycle (Calvin cycle)

M00165

 

d-Ribose 5-Phosphate

C00117

4.2.2.2

Reductive pentose phosphate cycle

M00167

Glyceraldehyde 3-Phosphate → Ribulose 5-Phosphate

d-Ribose 5-Phosphate

C00117

4.3

Carbohydrate and lipid metabolism

     

4.3.1

Central carbohydrate metabolism

     

4.3.1.1

Glycolysis (Embden-Meyerhof pathway)

M00001

Glucose → Pyruvate

Glycerone Phosphate

C00111

4.3.1.2

Glycolysis, core module involving three-carbon compounds

M00002

 

Glycerone Phosphate

C00111

4.3.1.3

Pentose phosphate pathway (Pentose phosphate cycle)

M00004

 

d-Ribose 5-Phosphate

C00117

4.3.1.4

PRPP biosynthesis

M00005

Ribose 5-Phosphate → PRPP

d-Ribose 5-Phosphate

C00117

4.3.1.5

Pentose phosphate pathway, non-oxidative phase

M00007

Fructose 6-Phosphate → Ribose 5-Phosphate

d-Ribose 5-Phosphate

C00117

4.3.1.6

Pentose phosphate pathway, archaea

M00580

Fructose 6-Phosphate → Ribose 5-Phosphate

d-Ribose 5-Phosphate

C00117

4.3.1.7

Pentose phosphate pathway (Pentose phosphate cycle)

M00004

 

d-Xylulose 5-Phosphate

C00231

4.3.1.8

Pentose phosphate pathway, non-oxidative phase

M00007

Fructose 6-Phosphate → Ribose 5-Phosphate

d-Xylulose 5-Phosphate

C00231

4.3.1.9

Glycolysis (Embden-Meyerhof pathway)

M00001

Glucose → Pyruvate

Alpha-d-Glucose

C00267

4.3.2

Other carbohydrate metabolism

     

4.3.2.1

Photorespiration

M00532

 

l-Serine

C00065

4.4

Others

     

4.4.1

Glycolysis/Gluconeogenesis

  

Beta-d-Glucose

C00221

5

Galactose metabolism

     

5.1

Glycolysis, core module involving three-carbon compounds

  

Glycerone Phosphate

C00111

5.2

Galactose degradation

  

d-Galactose

C00124

5.3

Inositol phosphate metabolism

  

Myo-Inositol

C00137

5.4

Glycolysis (Embden–Meyerhof pathway)

  

Alpha-d-Glucose

C00267

5.5

Galactose metabolism

  

Galactinol

C01235

6

ABC transporters

     

6.1

Phosphate and amino acid transporters

  

l-Serine

C00065

6.2

Monosaccharide transporters

  

Myo-Inositol

C00137

6.3

Oligosaccharide, polyol, and lipid transporters

  

Maltose

C00208

6.4

Oligosaccharide, polyol, and lipid transporters

  

alpha,alpha-trehalose

C01083

7

Cysteine and methionine metabolism

     

7.1

Methionine degradation

M00035

 

S-Adenosyl-l-Homocysteine

C00021

7.2

Glycine, serine and threonine metabolism

  

l-Serine

C00065

7.3

Aspartate metabolism

  

O-Acetyl-l-Homoserine

C01077

7.4

Propanoate metabolism

  

1-Aminocyclopropane-1-Carboxylate

C01234

8

Flavonoid biosynthesis

     

8.1

Flavone and flavonol biosynthesis

  

Vitexin

C01460

8.2

Flavone and flavonol biosynthesis

  

Taxifolin

C01617

8.3

Flavanone biosynthesis

  

Eriodictyol

C05631

8.4

Flavan 3,4-diols biosynthesis

  

Leucodelphinidin

C05909

9

Glycerophospholipid metabolism

     

9.1

Ether lipid metabolism

  

Glycerone Phosphate

C00111

9.2

Phosphocholine biosynthesis

  

N-Methylethanolamine Phosphate

C01210

9.3

Phosphocholine biosynthesis

  

Phosphodimethylethanolamine

C13482

10

Glycolysis/gluconeogenesis

     

10.1

Core module involving three-carbon compounds

  

Glycerone Phosphate

C00111

10.2

Starch and sucrose metabolism

  

Beta-d-Glucose

C00221

10.3

Starch and sucrose metabolism

  

Alpha-d-Glucose

C00267

11

Amino sugar and nucleotide sugar metabolism

     

11.1

Uridine diphosphate sugar metabolism

  

Alpha-d-Glucose

C00267

11.2

Uridine diphosphate sugar metabolism

  

Beta-d-Fructose

C02336

11.3

Uridine diphosphate sugar metabolism

  

Beta-l-Arabinose 1-Phosphate

C03906

12

Carbon fixation in photosynthetic organisms

     

12.1

Glycolysis

  

Glycerone Phosphate

C00111

12.2

Reductive pentose phosphate cycle

  

d-Ribose 5-Phosphate

C00117

12.3

Reductive pentose phosphate cycle

  

d-Xylulose 5-Phosphate

C00231

13

2-Oxocarboxylic acid metabolism

     

13.1

Pyruvate reductive amination

  

2-Isopropylmaleate

C02631

13.2

Pyruvate reductive amination

  

(2S)−2-Isopropyl-3-Oxosuccinate

C04236

13.3

Pyruvate reductive amination

  

(S)−2-Aceto-2-Hydroxybutanoate

C06006

14

Phenylpropanoid biosynthesis

     

14.1

Sinapate derivatives

  

1-O-Sinapoyl-Beta-d-Glucose

C01175

14.2

Coniferyl alcohol derivatives

  

Coniferyl Aldehyde

C02666

14.3

Sinapate derivatives

  

Sinapoyl Aldehyde

C05610

15

Pentose phosphate pathway

     

15.1

PRPP biosynthesis

 

Ribose 5-Phosphate → PRPP

d-Ribose 5-Phosphate

C00117

15.2

PRPP biosynthesis

  

Beta-d-Glucose

C00221

15.3

PRPP biosynthesis

  

d-Xylulose 5-Phosphate

C00231

16

Anthocyanin biosynthesis

     

16.1

Flavonoids

  

Chrysanthemin

C08604

16.2

Flavonoids

  

Pelargonidin 3-O-Glucoside

C12137

16.3

Flavonoids

  

Cyanidin 5-O-Glucoside

C16298

17

Ascorbate and aldarate metabolism

     

17.1

Sugar alcohols

  

Myo-Inositol

C00137

17.2

Ascorbate degradation

 

Ascorbate → d-Xylulose 5-Phosphate

d-Xylulose 5-Phosphate

C00231

17.3

Aldoses

  

l-Galactose

C01825

18

Valine, leucine and isoleucine biosynthesis

     

18.1

Pyruvate metabolism

  

2-Isopropylmaleate

C02631

18.2

Leucine biosynthesis

  

(2S)-2-Isopropyl-3-Oxosuccinate

C04236

18.3

Isoleucine biosynthesis

  

(S)-2-Aceto-2-Hydroxybutanoate

C06006

19

Glycine, serine and threonine metabolism

     

19.1

Pyruvate, cysteine and tryptophan metabolism

  

l-Serine

C00065

20

Pentose and glucuronate interconversions

     

20.1

Glucuronate interconversion

  

Glycerone Phosphate

C00111

20.2

Pentose interconversion

  

d-Xylulose 5-Phosphate

C00231

21

Fructose and mannose metabolism

     

21.1

Core module involving three-carbon compounds

  

Glycerone Phosphate

C00111

21.2

Fructose biosynthesis

  

Alpha-d-Glucose

C00267

22

Starch and sucrose metabolism

     

22.1

Oligosaccharides

  

Maltose

C00208

22.2

Oligosaccharides

  

alpha,alpha-Trehalose

C01083

23

Inositol phosphate metabolism

     

23.1

Core module involving three-carbon compounds

  

Glycerone Phosphate

C00111

23.2

Inositol phosphate metabolism

 

Ins(1,3,4,5)P4 → Ins(1,3,4)P3 → Myo-Inositol

Myo-Inositol

C00137

24

Flavone and flavonol biosynthesis

     

24.1

Flavones

  

Vitexin

C01460

24.2

Flavones

  

Isovitexin

C01714

25

Phenylalanine, tyrosine and tryptophan biosynthesis

     

25.1

Shikimate pathway

  

Quinate

C00296

  1. KEGG pathways and modules that involve compounds identified in Table 1 were generated by KEGG Mapper75; Bin codes denote the hierarchical structure of KEGG pathways and modules used to generate MapMan77 style representation of the identified compounds (Fig. 4); ↑ refers to a compound with positive t stat value (high- > low-sugar group), whereas ↓ refers to a compound with a  negative t stat value (high- < low-sugar group).