KEGG   PATHWAY: rn00900
Entry
rn00900                     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
rn00900  Terpenoid backbone biosynthesis
rn00900

Module
M00095  C5 isoprenoid biosynthesis, mevalonate pathway [PATH:rn00900]
M00096  C5 isoprenoid biosynthesis, non-mevalonate pathway [PATH:rn00900]
M00364  C10-C20 isoprenoid biosynthesis, bacteria [PATH:rn00900]
M00365  C10-C20 isoprenoid biosynthesis, archaea [PATH:rn00900]
M00366  C10-C20 isoprenoid biosynthesis, plants [PATH:rn00900]
M00367  C10-C20 isoprenoid biosynthesis, non-plant eukaryotes [PATH:rn00900]
M00849  C5 isoprenoid biosynthesis, mevalonate pathway, archaea [PATH:rn00900]
M00921  Cyclooctatin biosynthesis, dimethylallyl-PP + isopentenyl-PP => cyclooctatin [PATH:rn00900]
Other DBs
GO: 0009240 0016091
Reaction
R00238  acetyl-CoA:acetyl-CoA C-acetyltransferase
R01121  ATP:(R)-5-diphosphomevalonate carboxy-lyase (adding ATP; isopentenyl-diphosphate-forming)
R01123  isopentenyl-diphosphate Delta3-Delta2-isomerase
R01658  Dimethylallyl-diphosphate:isopentenyl-diphosphate dimethylallyltranstransferase
R01978  acetyl-CoA:acetoacetyl-CoA C-acetyltransferase (thioester-hydrolysing, carboxymethyl-forming)
R02003  Geranyl-diphosphate:isopentenyl-diphosphate geranyltrans-transferase
R02061  trans,trans-Farnesyl-diphosphate:isopentenyl-diphosphate farnesyltranstransferase
R02063  geranylgeranyl reductase
R02081  (R)-Mevalonate:NAD+ oxidoreductase (CoA-acetylating)
R02082  (R)-Mevalonate:NADP+ oxidoreductase (CoA acylating)
R02245  ATP:(R)-mevalonate 5-phosphotransferase
R03245  ATP:(R)-5-phosphomevalonate phosphotransferase
R03264  2-trans,6-trans-farnesol:NADP+ 1-oxidoreductase
R03917  poly-cis-Polyprenyl-diphosphate:isopentenyl-diphosphate polyprenylcistransferase
R04496  S-Adenosyl-L-methionine:protein-C-terminal-S-farnesyl-L-cysteine O-methyltransferase
R05556  (2E,6E)-farnesyl-diphosphate:isopentenyl-diphosphate cistransferase (adding 10-55 isopentenyl units)
R05633  CTP: 2-C-Methyl-D-erythritol 4-phosphate cytidylyltransferase
R05634  ATP:4-(Cytidine 5'-diphospho)-2-C-methyl-D-erythritol 2-phosphotransferase
R05636  1-Deoxy-D-xylulose-5-phosphate pyruvate-lyase (carboxylating)
R05637  2-Phospho-4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol CMP-lyase (cyclizing)
R05688  1-Deoxy-D-xylulose-5-phosphate isomeroreductase
R05884  isopentenyl-diphosphate:ferredoxin oxidoreductase
R06447  (2E,6E)-farnesyl-diphosphate:isopentenyl-diphosphate cistransferase (adding 8 isopentenyl units)
R08199  dimethylallyl-diphosphate diphosphate-lyase (isoprene-forming)
R08210  dimethylallyl diphosphate:ferredoxin oxidoreductase
R08528  Z-farnesyl diphosphate synthase
R08689  (E)-4-hydroxy-3-methylbut-2-en-1-yl-diphosphate:oxidized ferredoxin oxidoreductase (hydrating)
R08697  trans,trans-Farnesyl-diphosphate diphosphohydrolase
R09244  (2Z,6E)-farnesyl-diphosphate:isopentenyl-diphosphate farnesylcistransferase (adding 7 isopentenyl units)
R09245  (2E,6E)-farnesyl-diphosphate:isopentenyl-diphosphate farnesyltranstransferase (adding 3 isopentenyl units)
R09246  geranylgeranyl-diphosphate:isopentenyl-diphosphate transferase (adding 2 isopentenyl units)
R09247  (2E,6E)-farnesyl-diphosphate:isopentenyl-diphosphate farnesyltranstransferase (adding 4 isopentenyl units)
R09248  (2E,6E)-farnesyl-diphosphate:isopentenyl-diphosphate farnesyltranstransferase (adding 5 isopentenyl units)
R09249  (2E,6E)-farnesyl-diphosphate:isopentenyl-diphosphate farnesyltranstransferase (adding 7 isopentenyl units)
R09250  geranyl-diphosphate:isopentenyl-diphosphate transtransferase (adding 7 isopentenyl units)
R09251  geranylgeranyl-diphosphate:isopentenyl-diphosphate transtransferase (adding 5 isopentenyl units)
R09562  S-(2E,6E)-farnesyl-L-cysteine oxidase
R09633  dimethylallyl-diphosphate:isopentenyl-diphosphate cistransferase (adding 2 isopentenyl units)
R09730  geranylgeranyl-diphosphate:isopentenyl-diphosphate cistransferase (adding 7 isopentenyl units)
R09731  (2Z,6E)-farnesyl-diphosphate:isopentenyl-diphosphate cistransferase (adding 9-11 isopentenyl units)
R09844  farnesyl-diphosphate:protein-cysteine farnesyltransferase
R09845  CAAX protease
R09846  prenylcycteine methylesterase
R09847   
R09849  CTP:2-trans,6-trans-farnesol O-phosphotransferase
R09850  CTP:farnesyl-phosphate phosphotransferase
R10093  ATP:isopentenyl phosphate phosphotransferase
R10412  (2E,6E)-farnesol:NAD+ 1-oxidoreductase
R10561  ATP:phosphomevalonate carboxy-lyase (adding ATP; isopentenyl-phosphate-forming)
R10779  ATP:(R)-mevalonate 3-phosphotransferase
R10780  ATP:(R)-3-phosphomevalonate 5-phosphotransferase
R10781  (R)-3,5-bisphosphomevalonate carboxy-lyase (isopentenyl-phosphate-forming)
R10859  (E)-4-hydroxy-3-methylbut-2-en-1-yl-diphosphate:oxidized flavodoxin oxidoreductase
R12894   
R12895   
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
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 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
rn00010  Glycolysis / Gluconeogenesis
rn00100  Steroid biosynthesis
rn00130  Ubiquinone and other terpenoid-quinone biosynthesis
rn00270  Cysteine and methionine metabolism
rn00403  Indole diterpene alkaloid biosynthesis
rn00510  N-Glycan biosynthesis
rn00902  Monoterpenoid biosynthesis
rn00904  Diterpenoid biosynthesis
rn00906  Carotenoid biosynthesis
rn00908  Zeatin biosynthesis
rn00909  Sesquiterpenoid and triterpenoid biosynthesis
KO pathway
ko00900   
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