ENTRY       mtr00900                    Pathway
NAME        Terpenoid backbone biosynthesis - Medicago truncatula (barrel medic)
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 mtr00900  Terpenoid backbone biosynthesis
MODULE      mtr_M00095  C5 isoprenoid biosynthesis, mevalonate pathway [PATH:mtr00900]
            mtr_M00096  C5 isoprenoid biosynthesis, non-mevalonate pathway [PATH:mtr00900]
            mtr_M00366  C10-C20 isoprenoid biosynthesis, plants [PATH:mtr00900]
DBLINKS     GO: 0009240 0016091
ORGANISM    Medicago truncatula (barrel medic) [GN:mtr]
GENE        11438335  probable 1-deoxy-D-xylulose-5-phosphate synthase, chloroplastic [KO:K01662] [EC:2.2.1.7]
            11441515  probable 1-deoxy-D-xylulose-5-phosphate synthase 2, chloroplastic [KO:K01662] [EC:2.2.1.7]
            25501402  probable 1-deoxy-D-xylulose-5-phosphate synthase 2, chloroplastic [KO:K01662] [EC:2.2.1.7]
            11432476  probable 1-deoxy-D-xylulose-5-phosphate synthase, chloroplastic [KO:K01662] [EC:2.2.1.7]
            11405342  probable 1-deoxy-D-xylulose-5-phosphate synthase, chloroplastic [KO:K01662] [EC:2.2.1.7]
            25500270  1-deoxy-D-xylulose 5-phosphate reductoisomerase, chloroplastic [KO:K00099] [EC:1.1.1.267]
            11438073  1-deoxy-D-xylulose 5-phosphate reductoisomerase, chloroplastic [KO:K00099] [EC:1.1.1.267]
            25494363  2-C-methyl-D-erythritol 4-phosphate cytidylyltransferase, chloroplastic isoform X1 [KO:K00991] [EC:2.7.7.60]
            25490472  4-diphosphocytidyl-2-C-methyl-D-erythritol kinase, chloroplastic/chromoplastic [KO:K00919] [EC:2.7.1.148]
            11443066  2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase, chloroplastic [KO:K01770] [EC:4.6.1.12]
            11413255  4-hydroxy-3-methylbut-2-en-1-yl diphosphate synthase (ferredoxin), chloroplastic [KO:K03526] [EC:1.17.7.1 1.17.7.3]
            25492711  4-hydroxy-3-methylbut-2-enyl diphosphate reductase, chloroplastic [KO:K03527] [EC:1.17.7.4]
            25492714  4-hydroxy-3-methylbut-2-enyl diphosphate reductase, chloroplastic [KO:K03527] [EC:1.17.7.4]
            25481093  acetyl-CoA acetyltransferase, cytosolic 1 [KO:K00626] [EC:2.3.1.9]
            25494326  LOW QUALITY PROTEIN: acetyl-CoA acetyltransferase, cytosolic 1 [KO:K00626] [EC:2.3.1.9]
            11424070  acetyl-CoA acetyltransferase, cytosolic 1 [KO:K00626] [EC:2.3.1.9]
            11429131  hydroxymethylglutaryl-CoA synthase [KO:K01641] [EC:2.3.3.10]
            11438999  hydroxymethylglutaryl-CoA synthase [KO:K01641] [EC:2.3.3.10]
            11441531  3-hydroxy-3-methylglutaryl-coenzyme A reductase 1 [KO:K00021] [EC:1.1.1.34]
            120580464  3-hydroxy-3-methylglutaryl-coenzyme A reductase 1-like [KO:K00021] [EC:1.1.1.34]
            120580466  3-hydroxy-3-methylglutaryl-coenzyme A reductase 1-like [KO:K00021] [EC:1.1.1.34]
            11416526  3-hydroxy-3-methylglutaryl coenzyme A reductase 2-A [KO:K00021] [EC:1.1.1.34]
            11416581  3-hydroxy-3-methylglutaryl-coenzyme A reductase 1 [KO:K00021] [EC:1.1.1.34]
            11410653  3-hydroxy-3-methylglutaryl-coenzyme A reductase 1 [KO:K00021] [EC:1.1.1.34]
            11415590  3-hydroxy-3-methylglutaryl-coenzyme A reductase 1 [KO:K00021] [EC:1.1.1.34]
            11407896  3-hydroxy-3-methylglutaryl-coenzyme A reductase 1 [KO:K00021] [EC:1.1.1.34]
            11409457  3-hydroxy-3-methylglutaryl-coenzyme A reductase 1 [KO:K00021] [EC:1.1.1.34]
            11432311  3-hydroxy-3-methylglutaryl-coenzyme A reductase 1 [KO:K00021] [EC:1.1.1.34]
            11435433  3-hydroxy-3-methylglutaryl-coenzyme A reductase 1 [KO:K00021] [EC:1.1.1.34]
            11429779  mevalonate kinase [KO:K00869] [EC:2.7.1.36]
            11425190  phosphomevalonate kinase, peroxisomal [KO:K00938] [EC:2.7.4.2]
            25485588  diphosphomevalonate decarboxylase MVD2, peroxisomal [KO:K01597] [EC:4.1.1.33]
            11417595  isopentenyl phosphate kinase isoform X2 [KO:K06981] [EC:2.7.4.26]
            11415814  isopentenyl-diphosphate Delta-isomerase I [KO:K01823] [EC:5.3.3.2]
            11410760  farnesyl pyrophosphate synthase 1 [KO:K00787] [EC:2.5.1.1 2.5.1.10]
            25493517  solanesyl diphosphate synthase 3, chloroplastic/mitochondrial [KO:K14066] [EC:2.5.1.1]
            11406646  geranylgeranyl pyrophosphate synthase, chloroplastic [KO:K13789] [EC:2.5.1.1 2.5.1.10 2.5.1.29]
            11407094  geranylgeranyl pyrophosphate synthase 7, chloroplastic [KO:K13789] [EC:2.5.1.1 2.5.1.10 2.5.1.29]
            11423374  heterodimeric geranylgeranyl pyrophosphate synthase small subunit, chloroplastic [KO:K13789] [EC:2.5.1.1 2.5.1.10 2.5.1.29]
            120577316  heterodimeric geranylgeranyl pyrophosphate synthase small subunit, chloroplastic isoform X1 [KO:K13789] [EC:2.5.1.1 2.5.1.10 2.5.1.29]
            25487134  solanesyl diphosphate synthase 1, chloroplastic [KO:K05356] [EC:2.5.1.84 2.5.1.85]
            11445331  dehydrodolichyl diphosphate synthase CPT3 [KO:K11778] [EC:2.5.1.87]
            11407863  dehydrodolichyl diphosphate synthase 2 isoform X1 [KO:K11778] [EC:2.5.1.87]
            11439929  dehydrodolichyl diphosphate synthase complex subunit NUS1 [KO:K11778] [EC:2.5.1.87]
            11410618  dehydrodolichyl diphosphate synthase 2 [KO:K11778] [EC:2.5.1.87]
            11418409  dehydrodolichyl diphosphate synthase CPT3 [KO:K11778] [EC:2.5.1.87]
            120580108  geranylgeranyl diphosphate reductase, chloroplastic [KO:K10960] [EC:1.3.1.83 1.3.1.111]
            11429848  geranylgeranyl diphosphate reductase, chloroplastic [KO:K10960] [EC:1.3.1.83 1.3.1.111]
            25492046  TPS4; tricyclene synthase TPS4, chloroplastic [KO:K12742] [EC:4.2.3.27]
            11424569  protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha [KO:K05955] [EC:2.5.1.58 2.5.1.59]
            25495171  protein farnesyltransferase subunit beta [KO:K05954] [EC:2.5.1.58]
            25483841  CAAX prenyl protease 2 [KO:K08658] [EC:3.4.22.-]
            11408152  CAAX prenyl protease 1 homolog [KO:K06013] [EC:3.4.24.84]
            25496684  protein-S-isoprenylcysteine O-methyltransferase A [KO:K00587] [EC:2.1.1.100]
            25501513  probable isoprenylcysteine alpha-carbonyl methylesterase ICMEL1 isoform X1 [KO:K15889] [EC:3.1.1.-]
            25495574  probable isoprenylcysteine alpha-carbonyl methylesterase ICMEL2 [KO:K15889] [EC:3.1.1.-]
            25489862  farnesylcysteine lyase isoform X1 [KO:K05906] [EC:1.8.3.5 1.8.3.6]
            11431375  putative dihydroflavonol 4-reductase [KO:K15891] [EC:1.1.1.354]
            25491456  probable phytol kinase 3, chloroplastic [KO:K15892] [EC:2.7.1.216]
            25491458  probable phytol kinase 3, chloroplastic [KO:K15892] [EC:2.7.1.216]
            25490962  probable phytol kinase 3, chloroplastic isoform X1 [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 phosphate
REFERENCE   PMID:12777052
  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   PMID:16262699
  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   PMID:24375100
  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
REL_PATHWAY mtr00010  Glycolysis / Gluconeogenesis
            mtr00100  Steroid biosynthesis
            mtr00130  Ubiquinone and other terpenoid-quinone biosynthesis
            mtr00270  Cysteine and methionine metabolism
            mtr00510  N-Glycan biosynthesis
            mtr00904  Diterpenoid biosynthesis
            mtr00906  Carotenoid biosynthesis
            mtr00908  Zeatin biosynthesis
            mtr00909  Sesquiterpenoid and triterpenoid biosynthesis
KO_PATHWAY  ko00900
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