KEGG   PATHWAY: msyl00900
Entry
msyl00900                   Pathway                                
Name
Terpenoid backbone biosynthesis - Malus sylvestris (European crab apple)
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
msyl00900  Terpenoid backbone biosynthesis
msyl00900

Module
msyl_M00095  C5 isoprenoid biosynthesis, mevalonate pathway [PATH:msyl00900]
msyl_M00096  C5 isoprenoid biosynthesis, non-mevalonate pathway [PATH:msyl00900]
msyl_M00366  C10-C20 isoprenoid biosynthesis, plants [PATH:msyl00900]
Other DBs
GO: 0009240 0016091
Organism
Malus sylvestris (European crab apple) [GN:msyl]
Gene
126597174  probable 1-deoxy-D-xylulose-5-phosphate synthase, chloroplastic [KO:K01662] [EC:2.2.1.7]
126628211  probable 1-deoxy-D-xylulose-5-phosphate synthase 2, chloroplastic [KO:K01662] [EC:2.2.1.7]
126603764  probable 1-deoxy-D-xylulose-5-phosphate synthase 2, chloroplastic [KO:K01662] [EC:2.2.1.7]
126633286  probable 1-deoxy-D-xylulose-5-phosphate synthase, chloroplastic isoform X1 [KO:K01662] [EC:2.2.1.7]
126605765  probable 1-deoxy-D-xylulose-5-phosphate synthase, chloroplastic [KO:K01662] [EC:2.2.1.7]
126606903  probable 1-deoxy-D-xylulose-5-phosphate synthase, chloroplastic [KO:K01662] [EC:2.2.1.7]
126626187  1-deoxy-D-xylulose 5-phosphate reductoisomerase, chloroplastic-like [KO:K00099] [EC:1.1.1.267]
126600287  1-deoxy-D-xylulose 5-phosphate reductoisomerase, chloroplastic [KO:K00099] [EC:1.1.1.267]
126601509  2-C-methyl-D-erythritol 4-phosphate cytidylyltransferase, chloroplastic-like isoform X1 [KO:K00991] [EC:2.7.7.60]
126633453  2-C-methyl-D-erythritol 4-phosphate cytidylyltransferase, chloroplastic-like isoform X1 [KO:K00991] [EC:2.7.7.60]
126615822  4-diphosphocytidyl-2-C-methyl-D-erythritol kinase, chloroplastic [KO:K00919] [EC:2.7.1.148]
126598905  2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase, chloroplastic-like [KO:K01770] [EC:4.6.1.12]
126625018  2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase, chloroplastic-like [KO:K01770] [EC:4.6.1.12]
126615240  4-hydroxy-3-methylbut-2-en-1-yl diphosphate synthase (ferredoxin), chloroplastic-like [KO:K03526] [EC:1.17.7.1 1.17.7.3]
126590742  4-hydroxy-3-methylbut-2-en-1-yl diphosphate synthase (ferredoxin), chloroplastic [KO:K03526] [EC:1.17.7.1 1.17.7.3]
126586439  4-hydroxy-3-methylbut-2-enyl diphosphate reductase, chloroplastic [KO:K03527] [EC:1.17.7.4]
126624468  4-hydroxy-3-methylbut-2-enyl diphosphate reductase, chloroplastic-like [KO:K03527] [EC:1.17.7.4]
126610892  acetyl-CoA acetyltransferase, cytosolic 1-like [KO:K00626] [EC:2.3.1.9]
126586120  acetyl-CoA acetyltransferase, cytosolic 1 isoform X1 [KO:K00626] [EC:2.3.1.9]
126634327  acetyl-CoA acetyltransferase, cytosolic 1 [KO:K00626] [EC:2.3.1.9]
126619119  hydroxymethylglutaryl-CoA synthase-like [KO:K01641] [EC:2.3.3.10]
126625112  hydroxymethylglutaryl-CoA synthase-like [KO:K01641] [EC:2.3.3.10]
126584724  3-hydroxy-3-methylglutaryl-coenzyme A reductase 1-like [KO:K00021] [EC:1.1.1.34]
126603659  3-hydroxy-3-methylglutaryl coenzyme A reductase 2-B-like [KO:K00021] [EC:1.1.1.34]
126621351  3-hydroxy-3-methylglutaryl-coenzyme A reductase 1-like [KO:K00021] [EC:1.1.1.34]
126621687  3-hydroxy-3-methylglutaryl-coenzyme A reductase 2-like [KO:K00021] [EC:1.1.1.34]
126608760  3-hydroxy-3-methylglutaryl-coenzyme A reductase 1-like [KO:K00021] [EC:1.1.1.34]
126608765  3-hydroxy-3-methylglutaryl coenzyme A reductase 2-B-like [KO:K00021] [EC:1.1.1.34]
126619049  mevalonate kinase-like [KO:K00869] [EC:2.7.1.36]
126593342  mevalonate kinase [KO:K00869] [EC:2.7.1.36]
126610975  phosphomevalonate kinase, peroxisomal-like [KO:K00938] [EC:2.7.4.2]
126582056  phosphomevalonate kinase, peroxisomal-like isoform X1 [KO:K00938] [EC:2.7.4.2]
126629743  diphosphomevalonate decarboxylase 2-like [KO:K01597] [EC:4.1.1.33]
126591769  diphosphomevalonate decarboxylase 2-like [KO:K01597] [EC:4.1.1.33]
126595038  isopentenyl phosphate kinase isoform X1 [KO:K06981] [EC:2.7.4.26]
126592075  isopentenyl-diphosphate Delta-isomerase I-like [KO:K01823] [EC:5.3.3.2]
126619835  isopentenyl-diphosphate Delta-isomerase I [KO:K01823] [EC:5.3.3.2]
126585791  farnesyl pyrophosphate synthase [KO:K00787] [EC:2.5.1.1 2.5.1.10]
126615738  farnesyl pyrophosphate synthase-like isoform X1 [KO:K00787] [EC:2.5.1.1 2.5.1.10]
126590148  farnesyl pyrophosphate synthase-like [KO:K00787] [EC:2.5.1.1 2.5.1.10]
126623343  farnesyl pyrophosphate synthase-like isoform X1 [KO:K00787] [EC:2.5.1.1 2.5.1.10]
126585612  solanesyl diphosphate synthase 3, chloroplastic/mitochondrial-like [KO:K14066] [EC:2.5.1.1]
126623431  solanesyl diphosphate synthase 3, chloroplastic/mitochondrial-like isoform X1 [KO:K14066] [EC:2.5.1.1]
126623432  solanesyl diphosphate synthase 3, chloroplastic/mitochondrial-like [KO:K14066] [EC:2.5.1.1]
126582430  geranylgeranyl pyrophosphate synthase 7, chloroplastic-like [KO:K13789] [EC:2.5.1.1 2.5.1.10 2.5.1.29]
126611010  geranylgeranyl pyrophosphate synthase, chloroplastic/chromoplastic-like [KO:K13789] [EC:2.5.1.1 2.5.1.10 2.5.1.29]
126602815  geranylgeranyl pyrophosphate synthase, chloroplastic-like [KO:K13789] [EC:2.5.1.1 2.5.1.10 2.5.1.29]
126604373  geranylgeranyl pyrophosphate synthase, chloroplastic-like [KO:K13789] [EC:2.5.1.1 2.5.1.10 2.5.1.29]
126623599  heterodimeric geranylgeranyl pyrophosphate synthase small subunit, chloroplastic [KO:K13789] [EC:2.5.1.1 2.5.1.10 2.5.1.29]
126616763  solanesyl diphosphate synthase 2, chloroplastic-like [KO:K05356] [EC:2.5.1.84 2.5.1.85]
126590530  solanesyl diphosphate synthase 1, chloroplastic-like [KO:K05356] [EC:2.5.1.84 2.5.1.85]
126587545  uncharacterized protein LOC126587545 [KO:K11778] [EC:2.5.1.87]
126615339  cis-prenyltransferase 4, chloroplastic-like [KO:K11778] [EC:2.5.1.87]
126615340  dehydrodolichyl diphosphate synthase 2-like isoform X1 [KO:K11778] [EC:2.5.1.87]
126615341  dehydrodolichyl diphosphate synthase 2-like [KO:K11778] [EC:2.5.1.87]
126603550  dehydrodolichyl diphosphate synthase 6-like [KO:K11778] [EC:2.5.1.87]
126620977  dehydrodolichyl diphosphate synthase CPT3-like [KO:K11778] [EC:2.5.1.87]
126581999  dehydrodolichyl diphosphate synthase CPT3-like [KO:K11778] [EC:2.5.1.87]
126625843  geranylgeranyl diphosphate reductase, chloroplastic-like [KO:K10960] [EC:1.3.1.83 1.3.1.111]
126598918  geranylgeranyl diphosphate reductase, chloroplastic-like [KO:K10960] [EC:1.3.1.83 1.3.1.111]
126591304  geranylgeranyl diphosphate reductase, chloroplastic-like [KO:K10960] [EC:1.3.1.83 1.3.1.111]
126611736  tricyclene synthase EBOS, chloroplastic-like [KO:K12742] [EC:4.2.3.27]
126612183  tricyclene synthase EBOS, chloroplastic-like isoform X1 [KO:K12742] [EC:4.2.3.27]
126619293  protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha [KO:K05955] [EC:2.5.1.58 2.5.1.59]
126583550  protein farnesyltransferase subunit beta-like isoform X1 [KO:K05954] [EC:2.5.1.58]
126610578  protein farnesyltransferase subunit beta-like [KO:K05954] [EC:2.5.1.58]
126599691  CAAX prenyl protease 2-like isoform X1 [KO:K08658] [EC:3.4.26.1]
126593231  CAAX prenyl protease 2-like [KO:K08658] [EC:3.4.26.1]
126618613  CAAX prenyl protease 1 homolog [KO:K06013] [EC:3.4.24.84]
126597500  protein-S-isoprenylcysteine O-methyltransferase A-like isoform X1 [KO:K00587] [EC:2.1.1.100]
126607109  protein-S-isoprenylcysteine O-methyltransferase A-like isoform X1 [KO:K00587] [EC:2.1.1.100]
126583018  isoprenylcysteine alpha-carbonyl methylesterase ICME-like [KO:K15889] [EC:3.1.1.-]
126611318  probable isoprenylcysteine alpha-carbonyl methylesterase ICMEL2 [KO:K15889] [EC:3.1.1.-]
126594881  probable isoprenylcysteine alpha-carbonyl methylesterase ICMEL1 [KO:K15889] [EC:3.1.1.-]
126607495  probable isoprenylcysteine alpha-carbonyl methylesterase ICMEL1 isoform X1 [KO:K15889] [EC:3.1.1.-]
126601919  farnesylcysteine lyase [KO:K05906] [EC:1.8.3.5 1.8.3.6]
126633132  uncharacterized protein LOC126633132 [KO:K15891] [EC:1.1.1.354]
126615528  probable phytol kinase 3, chloroplastic [KO:K15892] [EC:2.7.1.216]
126591118  farnesol kinase, chloroplastic-like [KO:K15892] [EC:2.7.1.216]
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 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
msyl00010  Glycolysis / Gluconeogenesis
msyl00100  Steroid biosynthesis
msyl00130  Ubiquinone and other terpenoid-quinone biosynthesis
msyl00270  Cysteine and methionine metabolism
msyl00510  N-Glycan biosynthesis
msyl00902  Monoterpenoid biosynthesis
msyl00904  Diterpenoid biosynthesis
msyl00906  Carotenoid biosynthesis
msyl00908  Zeatin biosynthesis
msyl00909  Sesquiterpenoid and triterpenoid biosynthesis
KO pathway
ko00900   
LinkDB

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