KEGG   PATHWAY: ko00900
Entry
ko00900                     Pathway                                
Name
Terpenoid backbone biosynthesis
Description
Terpenoids, also known as isoprenoids, are a large class of natural products consisting of isoprene (C5) units. There are two biosynthetic pathways, the mevalonate pathway [MD:M00095] and the non-mevalonate pathway or the MEP/DOXP pathway [MD:M00096], for the terpenoid building blocks: isopentenyl diphosphate (IPP) and dimethylallyl diphosphate (DMAPP). The action of prenyltransferases then generates higher-order building blocks: geranyl diphosphate (GPP), farsenyl diphosphate (FPP), and geranylgeranyl diphosphate (GGPP), which are the precursors of monoterpenoids (C10), sesquiterpenoids (C15), and diterpenoids (C20), respectively. Condensation of these building blocks gives rise to the precursors of sterols (C30) and carotenoids (C40). The MEP/DOXP pathway is absent in higher animals and fungi, but in green plants the MEP/DOXP and mevalonate pathways co-exist in separate cellular compartments. The MEP/DOXP pathway, operating in the plastids, is responsible for the formation of essential oil monoterpenes and linalyl acetate, some sesquiterpenes, diterpenes, and carotenoids and phytol. The mevalonate pathway, operating in the cytosol, gives rise to triterpenes, sterols, and most sesquiterpenes.
Class
Metabolism; Metabolism of terpenoids and polyketides
Pathway map
ko00900  Terpenoid backbone biosynthesis
ko00900

Module
M00095  C5 isoprenoid biosynthesis, mevalonate pathway [PATH:ko00900]
M00096  C5 isoprenoid biosynthesis, non-mevalonate pathway [PATH:ko00900]
M00364  C10-C20 isoprenoid biosynthesis, bacteria [PATH:ko00900]
M00365  C10-C20 isoprenoid biosynthesis, archaea [PATH:ko00900]
M00366  C10-C20 isoprenoid biosynthesis, plants [PATH:ko00900]
M00367  C10-C20 isoprenoid biosynthesis, non-plant eukaryotes [PATH:ko00900]
M00849  C5 isoprenoid biosynthesis, mevalonate pathway, archaea [PATH:ko00900]
Other DBs
GO: 0009240 0016091
Orthology
K00021  HMGCR; hydroxymethylglutaryl-CoA reductase (NADPH) [EC:1.1.1.34]
K00054  mvaA; hydroxymethylglutaryl-CoA reductase [EC:1.1.1.88]
K00099  dxr; 1-deoxy-D-xylulose-5-phosphate reductoisomerase [EC:1.1.1.267]
K00587  ICMT, STE14; protein-S-isoprenylcysteine O-methyltransferase [EC:2.1.1.100]
K00626  ACAT, atoB; acetyl-CoA C-acetyltransferase [EC:2.3.1.9]
K00787  FDPS; farnesyl diphosphate synthase [EC:2.5.1.1 2.5.1.10]
K00795  ispA; farnesyl diphosphate synthase [EC:2.5.1.1 2.5.1.10]
K00804  GGPS1; geranylgeranyl diphosphate synthase, type III [EC:2.5.1.1 2.5.1.10 2.5.1.29]
K00805  hepS; heptaprenyl diphosphate synthase component 1 [EC:2.5.1.30]
K00806  uppS; undecaprenyl diphosphate synthase [EC:2.5.1.31]
K00869  MVK, mvaK1; mevalonate kinase [EC:2.7.1.36]
K00919  ispE; 4-diphosphocytidyl-2-C-methyl-D-erythritol kinase [EC:2.7.1.148]
K00938  E2.7.4.2, mvaK2; phosphomevalonate kinase [EC:2.7.4.2]
K00991  ispD; 2-C-methyl-D-erythritol 4-phosphate cytidylyltransferase [EC:2.7.7.60]
K01597  MVD, mvaD; diphosphomevalonate decarboxylase [EC:4.1.1.33]
K01641  HMGCS; hydroxymethylglutaryl-CoA synthase [EC:2.3.3.10]
K01662  dxs; 1-deoxy-D-xylulose-5-phosphate synthase [EC:2.2.1.7]
K01770  ispF; 2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase [EC:4.6.1.12]
K01823  idi; isopentenyl-diphosphate Delta-isomerase [EC:5.3.3.2]
K02523  ispB; octaprenyl-diphosphate synthase [EC:2.5.1.90]
K03186  ubiX, bsdB, PAD1; flavin prenyltransferase [EC:2.5.1.129]
K03526  gcpE, ispG; (E)-4-hydroxy-3-methylbut-2-enyl-diphosphate synthase [EC:1.17.7.1 1.17.7.3]
K03527  ispH, lytB; 4-hydroxy-3-methylbut-2-en-1-yl diphosphate reductase [EC:1.17.7.4]
K05355  hexPS, COQ1; hexaprenyl diphosphate synthase [EC:2.5.1.82 2.5.1.83]
K05356  SPS, sds; all-trans-nonaprenyl-diphosphate synthase [EC:2.5.1.84 2.5.1.85]
K05906  PCYOX1, FCLY; prenylcysteine oxidase / farnesylcysteine lyase [EC:1.8.3.5 1.8.3.6]
K05954  FNTB; protein farnesyltransferase subunit beta [EC:2.5.1.58]
K05955  FNTA; protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha [EC:2.5.1.58 2.5.1.59]
K06013  STE24; STE24 endopeptidase [EC:3.4.24.84]
K06981  ipk; isopentenyl phosphate kinase [EC:2.7.4.26]
K08658  RCE1, FACE2; intramembrane prenyl-peptidase [EC:3.4.26.1]
K09128  acnX2; phosphomecalonate degydratase small subunit [EC:4.2.1.182]
K10960  chlP, bchP; geranylgeranyl diphosphate/geranylgeranyl-bacteriochlorophyllide a reductase [EC:1.3.1.83 1.3.1.111]
K11778  DHDDS, RER2, SRT1; ditrans,polycis-polyprenyl diphosphate synthase [EC:2.5.1.87]
K12503  uppS; short-chain Z-isoprenyl diphosphate synthase [EC:2.5.1.68]
K12504  PDSS1; decaprenyl-diphosphate synthase subunit 1 [EC:2.5.1.91]
K12505  PDSS2; decaprenyl-diphosphate synthase subunit 2 [EC:2.5.1.91]
K12506  ispDF; 2-C-methyl-D-erythritol 4-phosphate cytidylyltransferase / 2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase [EC:2.7.7.60 4.6.1.12]
K12742  ispS; isoprene synthase [EC:4.2.3.27]
K13273  PMVK; phosphomevalonate kinase [EC:2.7.4.2]
K13787  idsA; geranylgeranyl diphosphate synthase, type I [EC:2.5.1.1 2.5.1.10 2.5.1.29]
K13789  GGPS; geranylgeranyl diphosphate synthase, type II [EC:2.5.1.1 2.5.1.10 2.5.1.29]
K14066  GPS; geranyl diphosphate synthase [EC:2.5.1.1]
K14215  E2.5.1.86; trans,polycis-decaprenyl diphosphate synthase [EC:2.5.1.86]
K15793  K15793; acyclic sesquiterpene synthase [EC:4.2.3.49 4.2.3.47 3.1.7.6]
K15887  ZFPS; (2Z,6Z)-farnesyl diphosphate synthase [EC:2.5.1.92]
K15888  uppS, cpdS; tritrans,polycis-undecaprenyl-diphosphate synthase [geranylgeranyl-diphosphate specific] [EC:2.5.1.89]
K15889  PCME; prenylcysteine alpha-carboxyl methylesterase [EC:3.1.1.-]
K15890  FOHSDR; NADP+-dependent farnesol dehydrogenase [EC:1.1.1.216]
K15891  FLDH; NAD+-dependent farnesol dehydrogenase [EC:1.1.1.354]
K15892  FOLK; farnesol kinase [EC:2.7.1.216]
K17942  pmd; phosphomevalonate decarboxylase [EC:4.1.1.99]
K18689  E2.7.1.185; mevalonate-3-kinase [EC:2.7.1.185]
K18690  E2.7.1.186; mevalonate-3-phosphate-5-kinase [EC:2.7.1.186]
K19177  NUS1; dehydrodolichyl diphosphate syntase complex subunit NUS1 [EC:2.5.1.87]
K21268  gdS-2; hexaprenyl diphosphate synthase [EC:2.5.1.82]
K21273  E2.5.1.88; trans,polycis-polyprenyl diphosphate synthase [EC:2.5.1.88]
K21274  hexs-a; hexaprenyl diphosphate synthase small subunit [EC:2.5.1.83]
K21275  hexs-b; hexaprenyl diphosphate synthase large subunit [EC:2.5.1.83]
K22813  E4.1.1.110; bisphosphomevalonate decarboxylase [EC:4.1.1.110]
K24873  hepT; heptaprenyl diphosphate synthase component 2
K25517  acnX1; phosphomecalonate degydratase large subunit
K25518  E4.1.1.126; anhydromevalonate phosphate decarboxylase
K28131  fgs; geranylfarnesyl diphosphate synthase
Compound
C00022  Pyruvate
C00024  Acetyl-CoA
C00118  D-Glyceraldehyde 3-phosphate
C00129  Isopentenyl diphosphate
C00235  Dimethylallyl diphosphate
C00332  Acetoacetyl-CoA
C00341  Geranyl diphosphate
C00353  Geranylgeranyl diphosphate
C00356  (S)-3-Hydroxy-3-methylglutaryl-CoA
C00418  (R)-Mevalonate
C00448  trans,trans-Farnesyl diphosphate
C01107  (R)-5-Phosphomevalonate
C01126  (2E,6E)-Farnesol
C01143  (R)-5-Diphosphomevalonate
C01230  all-trans-Hexaprenyl diphosphate
C02321  cis-1,4-Polyisoprene
C03461  2-trans,6-trans-Farnesal
C04145  all-trans-Nonaprenyl diphosphate
C04146  all-trans-Octaprenyl diphosphate
C04216  all-trans-Heptaprenyl diphosphate
C04217  all-trans-Pentaprenyl diphosphate
C04506  Protein C-terminal S-farnesyl-L-cysteine
C04574  di-trans,poly-cis-Undecaprenyl diphosphate
C04748  Protein C-terminal S-farnesyl-L-cysteine methyl ester
C05427  Phytyl diphosphate
C05859  ditrans,polycis-Polyprenyl diphosphate
C06081  Polyprenol
C11434  2-C-Methyl-D-erythritol 4-phosphate
C11435  4-(Cytidine 5'-diphospho)-2-C-methyl-D-erythritol
C11436  2-Phospho-4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol
C11437  1-Deoxy-D-xylulose 5-phosphate
C11453  2-C-Methyl-D-erythritol 2,4-cyclodiphosphate
C11811  1-Hydroxy-2-methyl-2-butenyl 4-diphosphate
C16521  Isoprene
C16826  2-cis,6-trans-Farnesyl diphosphate
C17432  all-trans-Decaprenyl diphosphate
C18321  trans,octacis-Decaprenyl diphosphate
C19691  Farnesylcysteine
C19760  2-cis,6-cis-Farnesyl diphosphate
C19852  tritrans,heptacis-Undecaprenyl diphosphate
C19853  trans,polycis-Polyprenyl diphosphate
C20120  S-Farnesyl protein
C20121  trans,trans-Farnesyl phosphate
C20345  Isopentenyl phosphate
C20847  (R)-Mevalonate 3-phosphate
C20848  (R)-Mevalonate 3,5-bisphosphate
C22453  trans-Anhydromevalonate 5-phosphate
Reference
  Authors
Lange BM, Ghassemian M.
  Title
Genome organization in Arabidopsis thaliana: a survey for genes involved in isoprenoid and chlorophyll metabolism.
  Journal
Plant Mol Biol 51:925-48 (2003)
DOI:10.1023/A:1023005504702
Reference
  Authors
Saiki R, Nagata A, Kainou T, Matsuda H, Kawamukai M
  Title
Characterization of solanesyl and decaprenyl diphosphate synthases in mice and humans.
  Journal
FEBS J 272:5606-22 (2005)
DOI:10.1111/j.1742-4658.2005.04956.x
Reference
PMID:9858571
  Authors
Sato M, Sato K, Nishikawa S, Hirata A, Kato J, Nakano A
  Title
The yeast RER2 gene, identified by endoplasmic reticulum protein localization mutations, encodes cis-prenyltransferase, a key enzyme in dolichol synthesis.
  Journal
Mol Cell Biol 19:471-83 (1999)
DOI:10.1128/MCB.19.1.471
Reference
  Authors
Vannice JC, Skaff DA, Keightley A, Addo JK, Wyckoff GJ, Miziorko HM
  Title
Identification in Haloferax volcanii of phosphomevalonate decarboxylase and isopentenyl phosphate kinase as catalysts of the terminal enzyme reactions in an  archaeal alternate mevalonate pathway.
  Journal
J Bacteriol 196:1055-63 (2014)
DOI:10.1128/JB.01230-13
Related
pathway
ko00010  Glycolysis / Gluconeogenesis
ko00100  Steroid biosynthesis
ko00130  Ubiquinone and other terpenoid-quinone biosynthesis
ko00270  Cysteine and methionine metabolism
ko00403  Indole diterpene alkaloid biosynthesis
ko00510  N-Glycan biosynthesis
ko00902  Monoterpenoid biosynthesis
ko00904  Diterpenoid biosynthesis
ko00906  Carotenoid biosynthesis
ko00908  Zeatin biosynthesis
ko00909  Sesquiterpenoid and triterpenoid biosynthesis

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