KEGG   PATHWAY: pop00940
Entry
pop00940                    Pathway                                
Name
Phenylpropanoid biosynthesis - Populus trichocarpa (black cottonwood)
Description
Phenylpropanoids are a group of plant secondary metabolites derived from phenylalanine and having a wide variety of functions both as structural and signaling molecules. Phenylalanine is first converted to cinnamic acid by deamination. It is followed by hydroxylation and frequent methylation to generate coumaric acid and other acids with a phenylpropane (C6-C3) unit. Reduction of the CoA-activated carboxyl groups of these acids results in the corresponding aldehydes and alcohols. The alcohols are called monolignols, the starting compounds for biosynthesis of lignin.
Class
Metabolism; Biosynthesis of other secondary metabolites
Pathway map
pop00940  Phenylpropanoid biosynthesis
pop00940

Module
pop_M00039  Monolignol biosynthesis, phenylalanine/tyrosine => monolignol [PATH:pop00940]
pop_M00137  Flavanone biosynthesis, phenylalanine => naringenin [PATH:pop00940]
Other DBs
GO: 0009699
Organism
Populus trichocarpa (black cottonwood) [GN:pop]
Gene
7463441  phenylalanine ammonia-lyase G2B isoform X1 [KO:K10775] [EC:4.3.1.24]
7479878  phenylalanine ammonia-lyase G4 [KO:K10775] [EC:4.3.1.24]
18100180  phenylalanine ammonia-lyase-like [KO:K10775] [EC:4.3.1.24]
7486485  phenylalanine ammonia-lyase-like [KO:K10775] [EC:4.3.1.24]
7464737  trans-cinnamate 4-monooxygenase [KO:K00487] [EC:1.14.14.91]
7498118  trans-cinnamate 4-monooxygenase [KO:K00487] [EC:1.14.14.91]
112325022  cytochrome P450 CYP73A100 [KO:K00487] [EC:1.14.14.91]
7469843  4-coumarate--CoA ligase 2 [KO:K01904] [EC:6.2.1.12]
7494541  probable CoA ligase CCL7 [KO:K01904] [EC:6.2.1.12]
18103805  4-coumarate--CoA ligase-like 9 [KO:K01904] [EC:6.2.1.12]
7454537  4-coumarate--CoA ligase-like 9 [KO:K01904] [EC:6.2.1.12]
7488981  4-coumarate--CoA ligase 2 [KO:K01904] [EC:6.2.1.12]
7462820  4-coumarate--CoA ligase 1 [KO:K01904] [EC:6.2.1.12]
7455782  4-coumarate--CoA ligase 1 [KO:K01904] [EC:6.2.1.12]
7460544  4-coumarate--CoA ligase-like 1 [KO:K01904] [EC:6.2.1.12]
18107395  probable CoA ligase CCL7 [KO:K01904] [EC:6.2.1.12]
7454694  4-coumarate--CoA ligase-like 9 [KO:K01904] [EC:6.2.1.12]
7491889  4-coumarate--CoA ligase-like 6 [KO:K01904] [EC:6.2.1.12]
18100511  4-coumarate--CoA ligase CCL1 [KO:K01904] [EC:6.2.1.12]
18108773  4-coumarate--CoA ligase-like 9 isoform X1 [KO:K01904] [EC:6.2.1.12]
7454535  4-coumarate--CoA ligase-like 9 [KO:K01904] [EC:6.2.1.12]
7477039  4-coumarate--CoA ligase-like 9 [KO:K01904] [EC:6.2.1.12]
7458540  acetyl-CoA-benzylalcohol acetyltransferase [KO:K13065] [EC:2.3.1.133]
7463669  stemmadenine O-acetyltransferase [KO:K13065] [EC:2.3.1.133]
7462355  stemmadenine O-acetyltransferase isoform X10 [KO:K13065] [EC:2.3.1.133]
112324975  shikimate O-hydroxycinnamoyltransferase isoform X2 [KO:K13065] [EC:2.3.1.133]
7481810  acetyl-CoA-benzylalcohol acetyltransferase [KO:K13065] [EC:2.3.1.133]
7489456  spermidine hydroxycinnamoyl transferase [KO:K13065] [EC:2.3.1.133]
18094244  shikimate O-hydroxycinnamoyltransferase [KO:K13065] [EC:2.3.1.133]
7489434  shikimate O-hydroxycinnamoyltransferase [KO:K13065] [EC:2.3.1.133]
7489436  shikimate O-hydroxycinnamoyltransferase [KO:K13065] [EC:2.3.1.133]
18107988  pelargonidin 3-O-(6-caffeoylglucoside) 5-O-(6-O-malonylglucoside) 4'''-malonyltransferase [KO:K13065] [EC:2.3.1.133]
18100471  spermidine hydroxycinnamoyl transferase [KO:K13065] [EC:2.3.1.133]
18101360  stemmadenine O-acetyltransferase [KO:K13065] [EC:2.3.1.133]
18101361  stemmadenine O-acetyltransferase [KO:K13065] [EC:2.3.1.133]
18098695  shikimate O-hydroxycinnamoyltransferase [KO:K13065] [EC:2.3.1.133]
18107990  stemmadenine O-acetyltransferase [KO:K13065] [EC:2.3.1.133]
7478310  shikimate O-hydroxycinnamoyltransferase [KO:K13065] [EC:2.3.1.133]
18100835  minovincinine 19-hydroxy-O-acetyltransferase [KO:K13065] [EC:2.3.1.133]
18101362  LOW QUALITY PROTEIN: stemmadenine O-acetyltransferase [KO:K13065] [EC:2.3.1.133]
112327538  acetyl-CoA-benzylalcohol acetyltransferase [KO:K13065] [EC:2.3.1.133]
7477052  stemmadenine O-acetyltransferase [KO:K13065] [EC:2.3.1.133]
112328871  stemmadenine O-acetyltransferase [KO:K13065] [EC:2.3.1.133]
112328896  stemmadenine O-acetyltransferase [KO:K13065] [EC:2.3.1.133]
7474394  acyltransferase GLAUCE [KO:K13065] [EC:2.3.1.133]
127904043  stemmadenine O-acetyltransferase-like [KO:K13065] [EC:2.3.1.133]
7479864  stemmadenine O-acetyltransferase-like [KO:K13065] [EC:2.3.1.133]
7495679  cytochrome P450 98A2 [KO:K09754] [EC:1.14.14.96]
7458907  cytochrome P450 98A2 [KO:K09754] [EC:1.14.14.96]
18106094  cytochrome P450 98A2-like [KO:K09754] [EC:1.14.14.96]
7486620  caffeoylshikimate esterase [KO:K18368] [EC:3.1.1.-]
7475727  caffeoylshikimate esterase [KO:K18368] [EC:3.1.1.-]
7487784  caffeoylshikimate esterase isoform X1 [KO:K18368] [EC:3.1.1.-]
7469795  caffeoylshikimate esterase [KO:K18368] [EC:3.1.1.-]
18102566  caffeoylshikimate esterase [KO:K18368] [EC:3.1.1.-]
7489601  caffeoylshikimate esterase [KO:K18368] [EC:3.1.1.-]
18105288  caffeoylshikimate esterase [KO:K18368] [EC:3.1.1.-]
18099494  caffeoylshikimate esterase [KO:K18368] [EC:3.1.1.-]
7457542  caffeoyl-CoA O-methyltransferase 1 [KO:K00588] [EC:2.1.1.104]
7492044  caffeoyl-CoA O-methyltransferase 2 [KO:K00588] [EC:2.1.1.104]
18107656  probable caffeoyl-CoA O-methyltransferase At4g26220 isoform X3 [KO:K00588] [EC:2.1.1.104]
7457813  caffeoyl-CoA O-methyltransferase [KO:K00588] [EC:2.1.1.104]
7459098  caffeoyl-CoA O-methyltransferase [KO:K00588] [EC:2.1.1.104]
18094264  cinnamoyl-CoA reductase 1 [KO:K09753] [EC:1.2.1.44]
7493223  cinnamoyl-CoA reductase 1 [KO:K09753] [EC:1.2.1.44]
112325957  cinnamoyl-CoA reductase 1 isoform X1 [KO:K09753] [EC:1.2.1.44]
7458755  aldehyde dehydrogenase family 2 member C4 [KO:K12355] [EC:1.2.1.68]
7480159  cytochrome P450 84A1 [KO:K09755] [EC:1.14.-.-]
7494301  cytochrome P450 84A1 [KO:K09755] [EC:1.14.-.-]
18099227  cytochrome P450 84A1 [KO:K09755] [EC:1.14.-.-]
7464476  caffeic acid 3-O-methyltransferase 3 [KO:K13066] [EC:2.1.1.68 2.1.1.4]
7493466  caffeic acid 3-O-methyltransferase 1 [KO:K13066] [EC:2.1.1.68 2.1.1.4]
7491420  caffeic acid 3-O-methyltransferase 1 [KO:K13066] [EC:2.1.1.68 2.1.1.4]
7487746  caffeic acid 3-O-methyltransferase isoform X9 [KO:K13066] [EC:2.1.1.68 2.1.1.4]
7489078  caffeic acid 3-O-methyltransferase 1 [KO:K13066] [EC:2.1.1.68 2.1.1.4]
7486809  caffeic acid 3-O-methyltransferase [KO:K13066] [EC:2.1.1.68 2.1.1.4]
112326165  caffeic acid 3-O-methyltransferase-like [KO:K13066] [EC:2.1.1.68 2.1.1.4]
7455369  caffeic acid 3-O-methyltransferase [KO:K13066] [EC:2.1.1.68 2.1.1.4]
7465014  probable cinnamyl alcohol dehydrogenase 9 [KO:K00083] [EC:1.1.1.195]
7490064  probable cinnamyl alcohol dehydrogenase [KO:K00083] [EC:1.1.1.195]
18103450  probable cinnamyl alcohol dehydrogenase 1 [KO:K00083] [EC:1.1.1.195]
7496910  probable cinnamyl alcohol dehydrogenase 6 [KO:K00083] [EC:1.1.1.195]
18103449  probable cinnamyl alcohol dehydrogenase 1 [KO:K00083] [EC:1.1.1.195]
7495648  probable cinnamyl alcohol dehydrogenase 1 [KO:K00083] [EC:1.1.1.195]
7453739  probable cinnamyl alcohol dehydrogenase 1 [KO:K00083] [EC:1.1.1.195]
18099784  probable cinnamyl alcohol dehydrogenase 1 isoform X1 [KO:K00083] [EC:1.1.1.195]
7455876  probable cinnamyl alcohol dehydrogenase 1 [KO:K00083] [EC:1.1.1.195]
7460239  probable cinnamyl alcohol dehydrogenase 1 [KO:K00083] [EC:1.1.1.195]
7480403  berberine bridge enzyme-like 15 [KO:K22395] [EC:1.1.1.195]
7489117  berberine bridge enzyme-like 15 [KO:K22395] [EC:1.1.1.195]
7480406  berberine bridge enzyme-like 15 [KO:K22395] [EC:1.1.1.195]
7480409  berberine bridge enzyme-like 15 [KO:K22395] [EC:1.1.1.195]
7480410  berberine bridge enzyme-like 15 [KO:K22395] [EC:1.1.1.195]
7485205  berberine bridge enzyme-like 15 [KO:K22395] [EC:1.1.1.195]
18109453  berberine bridge enzyme-like 13 [KO:K22395] [EC:1.1.1.195]
7484482  berberine bridge enzyme-like 15 [KO:K22395] [EC:1.1.1.195]
112323330  berberine bridge enzyme-like 13 [KO:K22395] [EC:1.1.1.195]
112323320  berberine bridge enzyme-like 15 [KO:K22395] [EC:1.1.1.195]
18103481  berberine bridge enzyme-like 13 [KO:K22395] [EC:1.1.1.195]
18105648  berberine bridge enzyme-like 15 [KO:K22395] [EC:1.1.1.195]
18103480  berberine bridge enzyme-like 13 [KO:K22395] [EC:1.1.1.195]
18103482  berberine bridge enzyme-like 13 [KO:K22395] [EC:1.1.1.195]
18103495  berberine bridge enzyme-like 13 [KO:K22395] [EC:1.1.1.195]
18103496  berberine bridge enzyme-like 15 [KO:K22395] [EC:1.1.1.195]
18103497  berberine bridge enzyme-like 15 [KO:K22395] [EC:1.1.1.195]
7480408  berberine bridge enzyme-like 13 [KO:K22395] [EC:1.1.1.195]
18103478  LOW QUALITY PROTEIN: berberine bridge enzyme-like 26 [KO:K22395] [EC:1.1.1.195]
18100202  berberine bridge enzyme-like 13 [KO:K22395] [EC:1.1.1.195]
7489118  berberine bridge enzyme-like 13 [KO:K22395] [EC:1.1.1.195]
7498229  1-Cys peroxiredoxin [KO:K11188] [EC:1.11.1.7 1.11.1.27 3.1.1.-]
7458526  peroxidase 42 [KO:K00430] [EC:1.11.1.7]
7479718  peroxidase 9 [KO:K00430] [EC:1.11.1.7]
7456237  peroxidase 51 [KO:K00430] [EC:1.11.1.7]
7483269  peroxidase A2 [KO:K00430] [EC:1.11.1.7]
7455755  peroxidase A2 isoform X1 [KO:K00430] [EC:1.11.1.7]
7455766  peroxidase E5 isoform X3 [KO:K00430] [EC:1.11.1.7]
7455194  peroxidase 17 [KO:K00430] [EC:1.11.1.7]
7495509  peroxidase 72 [KO:K00430] [EC:1.11.1.7]
7491786  peroxidase 3 [KO:K00430] [EC:1.11.1.7]
7491729  probable peroxidase 26 [KO:K00430] [EC:1.11.1.7]
7481610  peroxidase 7 [KO:K00430] [EC:1.11.1.7]
7485540  peroxidase 27 [KO:K00430] [EC:1.11.1.7]
7461382  peroxidase 15 [KO:K00430] [EC:1.11.1.7]
7458552  peroxidase 27 [KO:K00430] [EC:1.11.1.7]
7479099  peroxidase 27 [KO:K00430] [EC:1.11.1.7]
7472588  peroxidase 47 [KO:K00430] [EC:1.11.1.7]
7461573  peroxidase 45 [KO:K00430] [EC:1.11.1.7]
7466794  peroxidase 17 [KO:K00430] [EC:1.11.1.7]
7459899  peroxidase 46 [KO:K00430] [EC:1.11.1.7]
7476360  peroxidase 19 [KO:K00430] [EC:1.11.1.7]
7487356  peroxidase 22.3 [KO:K00430] [EC:1.11.1.7]
7457169  peroxidase 41 [KO:K00430] [EC:1.11.1.7]
7494880  lignin-forming anionic peroxidase [KO:K00430] [EC:1.11.1.7]
18109651  lignin-forming anionic peroxidase [KO:K00430] [EC:1.11.1.7]
7465174  peroxidase P7 [KO:K00430] [EC:1.11.1.7]
7465173  peroxidase 4 [KO:K00430] [EC:1.11.1.7]
7466302  peroxidase P7 [KO:K00430] [EC:1.11.1.7]
18110272  peroxidase A2 [KO:K00430] [EC:1.11.1.7]
18100863  peroxidase 56 [KO:K00430] [EC:1.11.1.7]
18102775  lignin-forming anionic peroxidase [KO:K00430] [EC:1.11.1.7]
18102776  lignin-forming anionic peroxidase-like [KO:K00430] [EC:1.11.1.7]
18099238  peroxidase 72 [KO:K00430] [EC:1.11.1.7]
18106986  peroxidase 3 [KO:K00430] [EC:1.11.1.7]
18106988  peroxidase 3 [KO:K00430] [EC:1.11.1.7]
18094201  peroxidase 20 isoform X1 [KO:K00430] [EC:1.11.1.7]
18101311  lignin-forming anionic peroxidase [KO:K00430] [EC:1.11.1.7]
7482222  peroxidase 22.3 [KO:K00430] [EC:1.11.1.7]
7482570  peroxidase 2 [KO:K00430] [EC:1.11.1.7]
18100214  peroxidase 21 [KO:K00430] [EC:1.11.1.7]
18099141  peroxidase 64 [KO:K00430] [EC:1.11.1.7]
7456673  peroxidase 60 [KO:K00430] [EC:1.11.1.7]
7459894  peroxidase 25 [KO:K00430] [EC:1.11.1.7]
18108361  peroxidase 27 [KO:K00430] [EC:1.11.1.7]
18096017  lignin-forming anionic peroxidase [KO:K00430] [EC:1.11.1.7]
7496459  peroxidase 5 [KO:K00430] [EC:1.11.1.7]
7464478  peroxidase 5 [KO:K00430] [EC:1.11.1.7]
7464930  cationic peroxidase 1 [KO:K00430] [EC:1.11.1.7]
7470553  putative Peroxidase 48 [KO:K00430] [EC:1.11.1.7]
18097825  peroxidase 10 [KO:K00430] [EC:1.11.1.7]
18109798  peroxidase 60 [KO:K00430] [EC:1.11.1.7]
18109421  peroxidase 47 [KO:K00430] [EC:1.11.1.7]
18094923  peroxidase 60 [KO:K00430] [EC:1.11.1.7]
112328411  lignin-forming anionic peroxidase [KO:K00430] [EC:1.11.1.7]
7456333  putative Peroxidase 48 [KO:K00430] [EC:1.11.1.7]
7486040  peroxidase 56-like [KO:K00430] [EC:1.11.1.7]
7485888  peroxidase 40 [KO:K00430] [EC:1.11.1.7]
18109018  lignin-forming anionic peroxidase isoform X2 [KO:K00430] [EC:1.11.1.7]
18109653  lignin-forming anionic peroxidase [KO:K00430] [EC:1.11.1.7]
18097339  peroxidase 29 [KO:K00430] [EC:1.11.1.7]
18108883  peroxidase 56-like [KO:K00430] [EC:1.11.1.7]
18103107  peroxidase 19 [KO:K00430] [EC:1.11.1.7]
7485929  peroxidase 11 [KO:K00430] [EC:1.11.1.7]
7490007  peroxidase 10 [KO:K00430] [EC:1.11.1.7]
7455756  peroxidase 15 [KO:K00430] [EC:1.11.1.7]
7474697  peroxidase 25 [KO:K00430] [EC:1.11.1.7]
7458438  peroxidase 46 [KO:K00430] [EC:1.11.1.7]
7485174  peroxidase 3 [KO:K00430] [EC:1.11.1.7]
7463603  peroxidase A2 [KO:K00430] [EC:1.11.1.7]
7483472  peroxidase 41 [KO:K00430] [EC:1.11.1.7]
7461384  peroxidase N [KO:K00430] [EC:1.11.1.7]
18097241  peroxidase A2 [KO:K00430] [EC:1.11.1.7]
18107209  peroxidase 55 [KO:K00430] [EC:1.11.1.7]
7488716  peroxidase N1 [KO:K00430] [EC:1.11.1.7]
7466944  peroxidase 11 [KO:K00430] [EC:1.11.1.7]
18102364  peroxidase 6 [KO:K00430] [EC:1.11.1.7]
7489720  peroxidase 10 [KO:K00430] [EC:1.11.1.7]
18104215  peroxidase 4 [KO:K00430] [EC:1.11.1.7]
7496907  peroxidase 64 [KO:K00430] [EC:1.11.1.7]
7490751  lignin-forming anionic peroxidase [KO:K00430] [EC:1.11.1.7]
7464730  peroxidase 4 [KO:K00430] [EC:1.11.1.7]
7497549  peroxidase 7 [KO:K00430] [EC:1.11.1.7]
7489705  peroxidase 44 [KO:K00430] [EC:1.11.1.7]
18105479  peroxidase 5 [KO:K00430] [EC:1.11.1.7]
7487842  peroxidase 31 [KO:K00430] [EC:1.11.1.7]
18101129  peroxidase 73 [KO:K00430] [EC:1.11.1.7]
127903903  lignin-forming anionic peroxidase-like [KO:K00430] [EC:1.11.1.7]
127905566  peroxidase 56-like [KO:K00430] [EC:1.11.1.7]
127905567  peroxidase 56-like [KO:K00430] [EC:1.11.1.7]
127905568  peroxidase 56-like [KO:K00430] [EC:1.11.1.7]
127905569  peroxidase 56-like [KO:K00430] [EC:1.11.1.7]
7461381  peroxidase A2-like [KO:K00430] [EC:1.11.1.7]
7484101  peroxidase 47-like [KO:K00430] [EC:1.11.1.7]
7488771  cationic peroxidase 1-like [KO:K00430] [EC:1.11.1.7]
7473148  anthocyanidin 3-O-glucosyltransferase 5 [KO:K12356] [EC:2.4.1.111]
7473149  anthocyanidin 3-O-glucosyltransferase 5 [KO:K12356] [EC:2.4.1.111]
18109550  anthocyanidin 3-O-glucosyltransferase 5 [KO:K12356] [EC:2.4.1.111]
7478011  anthocyanidin 3-O-glucosyltransferase 5 [KO:K12356] [EC:2.4.1.111]
Compound
C00079  L-Phenylalanine
C00082  L-Tyrosine
C00223  p-Coumaroyl-CoA
C00315  Spermidine
C00323  Caffeoyl-CoA
C00406  Feruloyl-CoA
C00411  Sinapoyl-CoA
C00423  trans-Cinnamate
C00482  Sinapate
C00540  Cinnamoyl-CoA
C00590  Coniferyl alcohol
C00761  Coniferin
C00811  4-Coumarate
C00852  Chlorogenate
C00903  Cinnamaldehyde
C00933  Sinapine
C01175  1-O-Sinapoyl-beta-D-glucose
C01197  Caffeate
C01494  Ferulate
C01533  Syringin
C02325  Sinapyl alcohol
C02646  4-Coumaryl alcohol
C02666  Coniferyl aldehyde
C02887  Sinapoyl malate
C02947  4-Coumaroylshikimate
C04366  3-(2-Carboxyethenyl)-cis,cis-muconate
C05608  4-Hydroxycinnamyl aldehyde
C05610  Sinapoyl aldehyde
C05619  5-Hydroxyferulic acid
C05627  4-Hydroxystyrene
C05855  4-Hydroxycinnamyl alcohol 4-D-glucoside
C06224  3,4-Dihydroxystyrene
C10428  Anethole
C10434  5-O-Caffeoylshikimic acid
C10452  Estragole
C10453  Eugenol
C10454  Methyleugenol
C10469  Isoeugenol
C10478  Methylisoeugenol
C10945  Caffeic aldehyde
C12203  5-Hydroxyferuloyl-CoA
C12204  5-Hydroxyconiferaldehyde
C12205  5-Hydroxyconiferyl alcohol
C12206  Caffeyl alcohol
C12208  p-Coumaroyl quinic acid
C15804  p-Hydroxyphenyl lignin
C15805  Guaiacyl lignin
C15806  Syringyl lignin
C15807  5-Hydroxy-guaiacyl lignin
C16930  Chavicol
C18069  N1,N5,N10-Tricoumaroyl spermidine
C18070  N1,N5,N10-Tricaffeoyl spermidine
C18071  N1,N5,N10-Triferuloyl spermidine
C18072  N1,N5,N10-Tri(hydroxyferuloyl) spermidine
C18073  N1,N5-Di(hydroxyferuloyl)-N10-sinapoyl spermidine
C20225  Coniferyl acetate
C20464  Isochavicol
C20465  Coumaryl acetate
Reference
  Authors
Nair RB, Bastress KL, Ruegger MO, Denault JW, Chapple C.
  Title
The Arabidopsis thaliana REDUCED EPIDERMAL FLUORESCENCE1 gene encodes an aldehyde dehydrogenase involved in ferulic acid and sinapic acid biosynthesis.
  Journal
Plant Cell 16:544-54 (2004)
DOI:10.1105/tpc.017509
Reference
  Authors
Baucher M, Halpin C, Petit-Conil M, Boerjan W.
  Title
Lignin: genetic engineering and impact on pulping.
  Journal
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Modifications in lignin and accumulation of phenolic glucosides in poplar xylem upon down-regulation of caffeoyl-coenzyme A O-methyltransferase, an enzyme involved in lignin biosynthesis.
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J Biol Chem 275:36899-909 (2000)
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J Biol Chem 275:6537-45 (2000)
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Related
pathway
pop00130  Ubiquinone and other terpenoid-quinone biosynthesis
pop00400  Phenylalanine, tyrosine and tryptophan biosynthesis
pop00941  Flavonoid biosynthesis
pop00945  Stilbenoid, diarylheptanoid and gingerol biosynthesis
KO pathway
ko00940   
LinkDB

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