KEGG   PATHWAY: ko00999
Entry
ko00999                     Pathway                                
Name
Biosynthesis of various plant secondary metabolites
  Including
Crocin biosynthesis, Ginsenoside biosynthesis, Saponin adjuvant biosynthesis, Cannabidiol biosynthesis, Mugineic acid biosynthesis, Pentagalloylglucose biosynthesis, Benzoxazinoid biosynthesis, Gramine biosynthesis, Coumarin biosynthesis, Furanocoumarin biosynthesis, Hordatine biosynthesis, Podophyllotoxin biosynthesis
Class
Metabolism; Biosynthesis of other secondary metabolites
Pathway map
ko00999  Biosynthesis of various plant secondary metabolites
ko00999

Module
M00894  Cannabidiol biosynthesis, malonyl-CoA => cannabidiol/dronabinol [PATH:ko00999]
M00900  Crocin biosynthesis, crocetin => crocin [PATH:ko00999]
M00902  Podophyllotoxin biosynthesis, coniferyl alcohol => podophyllotoxin [PATH:ko00999]
M00952  Benzoxazinoid biosynthesis, indoleglycerol phosphate => DIMBOA-glucoside [PATH:ko00999]
M00953  Mugineic acid biosynthesis, methionine => 3-epihydroxymugineic acid [PATH:ko00999]
M00971  QS-7 biosynthesis, 2,3-epoxysqualene => QS-7 [PATH:ko00999]
Orthology
K00014  aroE; shikimate dehydrogenase [EC:1.1.1.25]
K00789  metK, MAT; S-adenosylmethionine synthetase [EC:2.5.1.6]
K01188  E3.2.1.21; beta-glucosidase [EC:3.2.1.21]
K05349  bglX; beta-glucosidase [EC:3.2.1.21]
K05350  bglB; beta-glucosidase [EC:3.2.1.21]
K05953  NAS; nicotianamine synthase [EC:2.5.1.43]
K06892  F6H; feruloyl-CoA 6-hydroxylase [EC:1.14.11.61]
K13222  BX1, IGL; indole-3-glycerol-phosphate lyase [EC:4.1.2.8]
K13223  BX2, CYP71C4, CYP71C9; indole-2-monooxygenase [EC:1.14.14.153]
K13224  BX3, CYP71C2, CYP71C7; indolin-2-one monooxygenase [EC:1.14.14.157]
K13225  BX4, CYP71C1, CYP71C6; 3-hydroxyindolin-2-one monooxygenase [EC:1.14.14.109]
K13226  BX5, CYP71C3, CYP71C8; 2-hydroxy-1,4-benzoxazin-3-one monooxygenase [EC:1.14.14.110]
K13227  BX8_9; UDP-glucosyltransferase BX8/BX9 [EC:2.4.1.202]
K13229  BX6; 2,4-dihydroxy-1,4-benzoxazin-3-one-glucoside dioxygenase [EC:1.14.11.59]
K13230  BX7; 2,4,7-trihydroxy-1,4-benzoxazin-3-one-glucoside 7-O-methyltransferase [EC:2.1.1.241]
K13830  ARO1; pentafunctional AROM polypeptide [EC:4.2.3.4 4.2.1.10 1.1.1.25 2.7.1.71 2.5.1.19]
K13832  aroDE, DHQ-SDH; 3-dehydroquinate dehydratase / shikimate dehydrogenase [EC:4.2.1.10 1.1.1.25]
K14271  NAAT; nicotianamine aminotransferase [EC:2.6.1.80]
K14329  ACT; agmatine coumaroyltransferase [EC:2.3.1.64 2.3.1.-]
K15813  LUP4; beta-amyrin synthase [EC:5.4.99.39]
K15817  DDS; dammarenediol II synthase [EC:4.2.1.125]
K18054  IDS3_2; 2'-deoxymugineic-acid 2'-dioxygenase / mugineic-acid 3-dioxygenase [EC:1.14.11.24 1.14.11.25]
K19650  SDH; secoisolariciresinol dehydrogenase [EC:1.1.1.331]
K20501  THCAS; tetrahydrocannabinolic acid synthase [EC:1.21.3.7]
K20502  CBDAS; cannabidiolic acid synthase [EC:1.21.3.8]
K20503  OLS; 3,5,7-trioxododecanoyl-CoA synthase [EC:2.3.1.206]
K20508  OAC; olivetolic acid cyclase [EC:4.4.1.26]
K20545  CYP716A47, PPDS; dammarenediol 12-hydroxylase [EC:1.14.14.120]
K20546  CYP716A53; protopanaxadiol 6-hydroxylase [EC:1.14.14.121]
K20667  CYP716A; beta-amyrin 28-monooxygenase [EC:1.14.14.126]
K21202  2-ODD; (-)-deoxypodophyllotoxin synthase [EC:1.14.20.8]
K21203  OMT3; (-)-pluviatolide 4-O-methyltransferase [EC:2.1.1.323]
K21204  OMT1; 5'-demethylyatein 5'-O-methyltransferase [EC:2.1.1.330]
K21205  CYP71CU1; bursehernin 5'-monooxygenase [EC:1.14.14.131]
K21207  CYP719A23_24; (-)-pluviatolide synthase [EC:1.14.19.72]
K21354  UGT94E5; beta-D-glucosyl crocetin beta-1,6-glucosyltransferase [EC:2.4.1.330]
K21371  UGT75L6, UGTCs2; crocetin glucosyltransferase [EC:2.4.1.271]
K21550  BMT; 5-hydroxyfuranocoumarin 5-O-methyltransferase [EC:2.1.1.69]
K21568  PLR; pinoresinol/lariciresinol reductase [EC:1.23.1.1 1.23.1.2 1.23.1.3 1.23.1.4]
K21588  PT; umbelliferone 6-dimethylallyltransferase [EC:2.5.1.139]
K21714  CYP71AJ1; psoralen synthase [EC:1.14.14.141]
K21715  CYP71AJ4; angelicin synthase [EC:1.14.14.148]
K21937  NMT; 3-aminomethylindole N-methyltransferase [EC:2.1.1.340]
K22374  DMAS1; 3''-deamino-3''-oxonicotianamine reductase [EC:1.1.1.285]
K22458  CCD2; crocetin dialdehyde synthase [EC:1.13.11.84]
K23136  CYP82C4; fraxetin 5-hydroxylase
K23137  CYP82C2; indole-3-carbonyl nitrile 4-hydroxylase
K23145  S8H; scopoletin 8-hydroxylase
K23260  TOGT1; scopoletin glucosyltransferase
K23279  UGT84A13; gallate 1-beta-glucosyltransferase
K23378  DIOX4, IB2; feruloyl-CoA 6-hydroxylase / trans-4-coumaroyl-CoA 2-hydroxylase
K23520  UGTPg1; ginsenoside 20-O-glucosyltransferase
K23521  UGT74AE2; protopanaxadiol-type ginsenoside 3-O-glucosyltransferase
K23522  UGT94Q2; protopanaxadiol-type ginsenoside-3-O-glucoside 2''-O-glucosyltransferase
K23523  UGTPg101; ginsenoside F1 6-O-glucosyltransferase
K23524  UGTPg100; ginsenoside 6-O-glucosyltransferase
K25522  CYP76F112; marmesin synthase
K25523  CYP71AZ; cytochrome P450 family 71 subfamily AZ
K26481  CYP716A297; oleanolic acid C16alpha-oxidase
K26482  CYP714E52; echinocystic acid C23-oxidase
K26483  CSLM; quillaic acid 3-O-glucuronosyltransferase
K26484  UGT73CU3; quillaic acid 3-O-GlcA beta-1,2-galactosyltransferase
K26485  UGT73CX1; quillaic acid 3-O-Gal-1,2-GlcA beta-1,3-xylosyltransferase
K26486  UGT73CX2; quillaic acid 3-O-Gal-1,2-GlcA alpha-1,3-rhamnosyltransferase
K26487  UGT74BX1; quillaic acid 3-O-Xyl/L-Rha-1,3-(Gal-1,2)-GlcA 28-O-glycosyltransferase
K26488  FucSyn; 4-keto-6-deoxyglucose 4-dehydrogenase
K26489  UGT91AR1; quillaic acid 3-O-Xyl/L-Rha-1,3-(Gal-1,2)-GlcA-28-O-Fuc alpha-1,2-rhamnosyltransferase
K26490  UGT91AQ1; quillaic acid 3-O-Xyl/L-Rha-1,3-(Gal-1,2)-GlcA-28-O-L-Rha-1,2-Fuc beta-1,4-xylosyltransferase
K26491  UGT73CY2; quillaic acid 3-O-Xyl/L-Rha-1,3-(Gal-1,2)-GlcA-28-O-Xyl-1,4-L-Rha-1,2-Fuc beta-1,3-apiosyltransferase
K26492  UGT73CY3; quillaic acid 3-O-Xyl/L-Rha-1,3-(Gal-1,2)-GlcA-28-O-Xyl-1,4-L-Rha-1,2-Fuc beta-1,3-xylosyltransferase
K26493  ACT1; O-acetyltransferase
K26494  UGT73B44; alpha-1,3-rhamnosyltransferase
K26495  UGT91AP1; beta-1,3-glucosyltransferase
K27602  PT4; geranyl-pyrophosphate---olivetolic acid geranyltransferase
Compound
C00019  S-Adenosyl-L-methionine
C00024  Acetyl-CoA
C00036  Oxaloacetate
C00049  L-Aspartate
C00073  L-Methionine
C00074  Phosphoenolpyruvate
C00078  L-Tryptophan
C00079  L-Phenylalanine
C00082  L-Tyrosine
C00083  Malonyl-CoA
C00108  Anthranilate
C00179  Agmatine
C00223  p-Coumaroyl-CoA
C00251  Chorismate
C00254  Prephenate
C00323  Caffeoyl-CoA
C00353  Geranylgeranyl diphosphate
C00406  Feruloyl-CoA
C00423  trans-Cinnamate
C00448  trans,trans-Farnesyl diphosphate
C00463  Indole
C00493  Shikimate
C00590  Coniferyl alcohol
C00751  Squalene
C00758  Bergaptol
C00841  Xanthotoxol
C01054  (S)-2,3-Epoxysqualene
C01158  1-O-Galloyl-beta-D-glucose
C01198  3-(2-Hydroxyphenyl)propanoate
C01424  Gallate
C01527  Scopolin
C01557  Bergapten
C01752  Scopoletin
C01772  trans-2-Hydroxycinnamate
C01864  Xanthotoxin
C02162  Isopimpinellin
C02274  Dihydrocoumarin
C02637  3-Dehydroshikimate
C02951  5-Hydroxyxanthotoxin
C03506  Indoleglycerol phosphate
C04498  p-Coumaroylagmatine
C04576  Pentagalloylglucose
C04831  DIMBOA-glucoside
C05158  trans-beta-D-Glucosyl-2-hydroxycinnamate
C05324  Nicotianamine
C05366  (+)-Pinoresinol
C05838  cis-2-Hydroxycinnamate
C05839  cis-beta-D-Glucosyl-2-hydroxycinnamate
C05851  Coumarin
C06098  Zeaxanthin
C06972  Dronabinol
C07578  Cannabidiol
C08304  Gramine
C08307  Hordatine A
C08308  Hordatine B
C08588  Crocetin
C08589  Crocin
C08616  beta-Amyrin
C08942  Echinocystic acid
C08946  Ginsenoside Rg1
C08972  Quillaic acid
C09060  Angelicin
C09263  Esculetin
C09265  Fraxetin
C09276  Marmesin
C09305  Psoralen
C09311  Scoparone
C09315  Umbelliferone
C10556  Deoxypodophyllotoxin
C10557  Dihydroanhydropodorhizol
C10646  Lariciresinol
C10682  Matairesinol
C10784  Cannabidiolic acid
C10874  Podophyllotoxin
C11130  3-Hydroxyindolin-2-one
C12312  Indolin-2-one
C15485  2'-Deoxymugineic acid
C15486  3''-Deamino-3''-oxonicotianamine
C15500  Mugineic acid
C15501  3-Epihydroxymugineic acid
C15502  3-Epihydroxy-2'-deoxymugineic acid
C15769  HBOA
C15770  DIBOA
C15772  DIBOA-glucoside
C17055  Picrocrocin
C17062  Safranal
C17148  Oleanolic acid
C17513  trans-Crocetin (beta-D-glucosyl) (beta-D-gentibiosyl) ester
C18062  TRIBOA-glucoside
C18079  Isoscopoletin
C18080  Osthenol
C18083  Demethylsuberosin
C18167  Secoisolariciresinol
C18325  Feruloylagmatine
C19707  (+)-Columbianetin
C19730  Crocetin dialdehyde
C19731  (3S)-3-Hydroxycyclocitral
C19829  Dammarenediol-II
C19867  beta-D-Glucosyl crocetin
C19868  Bis(beta-D-glucosyl) crocetin
C19869  beta-D-Gentiobiosyl crocetin
C20406  Cannabigerolate
C20413  3,5,7-Trioxododecanoyl-CoA
C20417  2,4-Dihydroxy-6-pentylbenzoate
C20454  (-)-Lariciresinol
C20455  (-)-Pinoresinol
C20456  (+)-Secoisolariciresinol
C20713  Ginsenoside Rb1
C20715  Protopanaxadiol
C20716  Protopanaxatriol
C20725  Ginsenoside Rd
C20778  Ginsenoside Rg3
C20779  Ginsenoside F2
C20780  Ginsenoside F1
C20894  beta-Citraurin
C21183  Bursehernin
C21184  (-)-5'-Demethylyatein
C21191  Pluviatolide
C21459  6-Hydroxyferuloyl-CoA
C21601  3-(Aminomethyl)indole
C21602  (1H-Indol-3-yl)-N-methylmethanamine
C21903  Delta9-Tetrahydrocannabinolate
C22007  Sideretin
C22070  2,4-Dihydroxycinnamoyl-CoA
C22127  Ginsenoside C-K
C22128  (20S)-Ginsenoside Rh2
C22129  Ginsenoside Rh1
C22152  Bergamottin
C22153  Epoxybergamottin
C22156  6',7'-Dihydroxybergamottin
C22438  3,5-Dehydroshikimate
C22444  5,8-Dihydroxypsoralen
C22445  8-Hydroxybergapten
C22452  6,7,8-Trihydroxycoumarin
C22652  Quillaic acid 3-O-beta-D-glucuronide
C22653  Quillaic acid 3-O-beta-D-galactosyl-1,2-beta-D-glucuronide
C22654  Quillaic acid 3-O-beta-D-xylosyl-1,3-(beta-D-galactosyl-1,2)-beta-D-glucuronide
C22655  Quillaic acid 3-O-alpha-L-rhamnosyl-1,3-(beta-D-galactosyl-1,2)-beta-D-glucuronide
C22656  Quillaic acid 3-O-beta-D-xylosyl-1,3-(beta-D-galactosyl-1,2)-beta-D-glucuronide-28-O-beta-D-fucoside
C22657  Quillaic acid 3-O-alpha-L-rhamnosyl-1,3-(beta-D-galactosyl-1,2)-beta-D-glucuronide-28-O-beta-D-fucoside
C22658  Quillaic acid 3-O-beta-D-xylosyl-1,3-(beta-D-galactosyl-1,2)-beta-D-glucuronide-28-O-alpha-L-rhamnosyl-1,2-beta-D-fucoside
C22659  Quillaic acid 3-O-alpha-L-rhamnosyl-1,3-(beta-D-galactosyl-1,2)-beta-D-glucuronide-28-O-alpha-L-rhamnosyl-1,2-beta-D-fucoside
C22660  Quillaic acid 3-O-beta-D-xylosyl-1,3-(beta-D-galactosyl-1,2)-beta-D-glucuronide-28-O-beta-D-xylosyl-1,4-alpha-L-rhamnosyl-1,2-beta-D-fucoside
C22661  Quillaic acid 3-O-alpha-L-rhamnosyl-1,3-(beta-D-galactosyl-1,2)-beta-D-glucuronide-28-O-beta-D-xylosyl-1,4-alpha-L-rhamnosyl-1,2-beta-D-fucoside
C22662  Quillaic acid 3-O-beta-D-xylosyl-1,3-(beta-D-galactosyl-1,2)-beta-D-glucuronide-28-O-beta-D-xylosyl-1,3-beta-D-xylosyl-1,4-alpha-L-rhamnosyl-1,2-beta-D-fucoside
C22663  Quillaic acid 3-O-alpha-L-rhamnosyl-1,3-(beta-D-galactosyl-1,2)-beta-D-glucuronide-28-O-beta-D-xylosyl-1,3-beta-D-xylosyl-1,4-alpha-L-rhamnosyl-1,2-beta-D-fucoside
C22664  Quillaic acid 3-O-beta-D-xylosyl-1,3-(beta-D-galactosyl-1,2)-beta-D-glucuronide-28-O-beta-D-apiosyl-1,3-beta-D-xylosyl-1,4-alpha-L-rhamnosyl-1,2-beta-D-fucoside
C22665  Quillaic acid 3-O-alpha-L-rhamnosyl-1,3-(beta-D-galactosyl-1,2)-beta-D-glucuronide-28-O-beta-D-apiosyl-1,3-beta-D-xylosyl-1,4-alpha-L-rhamnosyl-1,2-beta-D-fucoside
C22666  Quillaic acid 3-O-beta-D-xylosyl-1,3-(beta-D-galactosyl-1,2)-beta-D-glucuronide 28-O-beta-D-apiosyl-1,3-beta-D-xylosyl-1,4-(beta-D-glucosyl-1,3)-alpha-L-rhamnosyl-1,2-(alpha-L-rhamnosyl-1,3)-4-O-acetyl-beta-D-fucoside
Reference
PMID:22569263
  Authors
Nagatoshi M, Terasaka K, Owaki M, Sota M, Inukai T, Nagatsu A, Mizukami H
  Title
UGT75L6 and UGT94E5 mediate sequential glucosylation of crocetin to crocin in Gardenia jasminoides.
  Journal
FEBS Lett 586:1055-61 (2012)
DOI:10.1016/j.febslet.2012.03.003
Reference
PMID:17544411
  Authors
Taura F, Sirikantaramas S, Shoyama Y, Yoshikai K, Shoyama Y, Morimoto S
  Title
Cannabidiolic-acid synthase, the chemotype-determining enzyme in the fiber-type Cannabis sativa.
  Journal
FEBS Lett 581:2929-34 (2007)
DOI:10.1016/j.febslet.2007.05.043
Reference
PMID:9952442
  Authors
Higuchi K, Suzuki K, Nakanishi H, Yamaguchi H, Nishizawa NK, Mori S
  Title
Cloning of nicotianamine synthase genes, novel genes involved in the biosynthesis of phytosiderophores.
  Journal
Plant Physiol 119:471-80 (1999)
DOI:10.1104/pp.119.2.471
Reference
PMID:7622460
  Authors
Ma JF, Shinada T, Matsuda C, Nomoto K
  Title
Biosynthesis of phytosiderophores, mugineic acids, associated with methionine cycling.
  Journal
J Biol Chem 270:16549-54 (1995)
DOI:10.1074/jbc.270.28.16549
Reference
PMID:33346890
  Authors
Tahara K, Nishiguchi M, Funke E, Miyazawa SI, Miyama T, Milkowski C
  Title
Dehydroquinate dehydratase/shikimate dehydrogenases involved in gallate biosynthesis of the aluminum-tolerant tree species Eucalyptus camaldulensis.
  Journal
Planta 253:3 (2020)
DOI:10.1007/s00425-020-03516-w
Reference
PMID:26558757
  Authors
Dugrand-Judek A, Olry A, Hehn A, Costantino G, Ollitrault P, Froelicher Y, Bourgaud F.
  Title
The Distribution of Coumarins and Furanocoumarins in Citrus Species Closely Matches Citrus Phylogeny and Reflects the Organization of Biosynthetic Pathways.
  Journal
PLoS One 10:e0142757 (2015)
DOI:10.1371/journal.pone.0142757
Reference
PMID:15009205
  Authors
Hehmann M, Lukacin R, Ekiert H, Matern U
  Title
Furanocoumarin biosynthesis in Ammi majus L. Cloning of bergaptol O-methyltransferase.
  Journal
Eur J Biochem 271:932-40 (2004)
DOI:10.1111/j.1432-1033.2004.03995.x
Reference
PMID:26359402
  Authors
Lau W, Sattely ES
  Title
Six enzymes from mayapple that complete the biosynthetic pathway to the etoposide aglycone.
  Journal
Science 349:1224-8 (2015)
DOI:10.1126/science.aac7202
Reference
PMID:36952412
  Authors
Reed J, Orme A, El-Demerdash A, Owen C, Martin LBB, Misra RC, Kikuchi S, Rejzek M, Martin AC, Harkess A, Leebens-Mack J, Louveau T, Stephenson MJ, Osbourn A.
  Title
Elucidation of the pathway for biosynthesis of saponin adjuvants from the soapbark tree.
  Journal
Science 379:1252-1264 (2023)
DOI:10.1126/science.adf3727
Related
pathway
ko00010  Glycolysis / Gluconeogenesis
ko00020  Citrate cycle (TCA cycle)
ko00270  Cysteine and methionine metabolism
ko00400  Phenylalanine, tyrosine and tryptophan biosynthesis
ko00900  Terpenoid backbone biosynthesis
ko00940  Phenylpropanoid biosynthesis

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