ENTRY       sly00900                    Pathway
NAME        Terpenoid backbone biosynthesis - Solanum lycopersicum (tomato)
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 sly00900  Terpenoid backbone biosynthesis
MODULE      sly_M00095  C5 isoprenoid biosynthesis, mevalonate pathway [PATH:sly00900]
            sly_M00096  C5 isoprenoid biosynthesis, non-mevalonate pathway [PATH:sly00900]
            sly_M00366  C10-C20 isoprenoid biosynthesis, plants [PATH:sly00900]
DBLINKS     GO: 0009240 0016091
ORGANISM    Solanum lycopersicum (tomato) [GN:sly]
GENE        101251053  dxs2; 1-deoxy-D-xylulose 5-phosphate synthase 2 [KO:K01662] [EC:2.2.1.7]
            544220  DXS; 1-D-deoxyxylulose 5-phosphate synthase [KO:K01662] [EC:2.2.1.7]
            101260957  probable 1-deoxy-D-xylulose-5-phosphate synthase, chloroplastic [KO:K01662] [EC:2.2.1.7]
            543682  DXR; 1-deoxy-D-xylulose-5-phosphate reductoisomerase [KO:K00099] [EC:1.1.1.267]
            101251334  2-C-methyl-D-erythritol 4-phosphate cytidylyltransferase, chloroplastic isoform X1 [KO:K00991] [EC:2.7.7.60]
            543658  ispE; 4-diphosphocytidyl-2-C-methyl-D-erythritol kinase, chloroplastic/chromoplastic [KO:K00919] [EC:2.7.1.148]
            101246365  2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase, chloroplastic [KO:K01770] [EC:4.6.1.12]
            543704  HDS; 4-hydroxy-3-methylbut-2-en-1-yl diphosphate synthase [KO:K03526] [EC:1.17.7.1 1.17.7.3]
            100316901  HDR; 4-hydroxy-3-methylbut-2-enyl diphosphate reductase [KO:K03527] [EC:1.17.7.4]
            101256172  probable acetyl-CoA acetyltransferase, cytosolic 2 [KO:K00626] [EC:2.3.1.9]
            101260435  acetyl-CoA acetyltransferase, cytosolic 1 [KO:K00626] [EC:2.3.1.9]
            101262830  acetyl-CoA acetyltransferase, cytosolic 1 [KO:K00626] [EC:2.3.1.9]
            101260619  hydroxymethylglutaryl-CoA synthase-like [KO:K01641] [EC:2.3.3.10]
            100134904  HMGS; 3-hydroxy-3-methylglutaryl coenzyme A synthase [KO:K01641] [EC:2.3.3.10]
            101249394  hydroxymethylglutaryl-CoA synthase [KO:K01641] [EC:2.3.3.10]
            101266490  3-hydroxy-3-methylglutaryl-coenzyme A reductase 3 [KO:K00021] [EC:1.1.1.34]
            101266800  3-hydroxy-3-methylglutaryl-coenzyme A reductase 3 [KO:K00021] [EC:1.1.1.34]
            101265292  HMG2; 3-hydroxy-3-methylglutaryl-coenzyme A reductase 2 [KO:K00021] [EC:1.1.1.34]
            543702  HMGR; 3-hydroxy-3-methylglutaryl-coenzyme A reductase 1 [KO:K00021] [EC:1.1.1.34]
            101261961  mevalonate kinase [KO:K00869] [EC:2.7.1.36]
            101256682  phosphomevalonate kinase, peroxisomal-like [KO:K00938] [EC:2.7.4.2]
            101252616  phosphomevalonate kinase, peroxisomal isoform X2 [KO:K00938] [EC:2.7.4.2]
            101254587  diphosphomevalonate decarboxylase MVD2, peroxisomal-like [KO:K01597] [EC:4.1.1.33]
            100134900  MDC; mevalonate disphosphate decarboxylase [KO:K01597] [EC:4.1.1.33]
            101250107  isopentenyl phosphate kinase isoform X1 [KO:K06981] [EC:2.7.4.26]
            101255683  IDI1; isopentenyl diphosphate isomerase [KO:K01823] [EC:5.3.3.2]
            100134905  IPI; isopentenyl diphosphate isomerase [KO:K01823] [EC:5.3.3.2]
            101259377  farnesyl pyrophosphate synthase 1-like isoform X1 [KO:K00787] [EC:2.5.1.1 2.5.1.10]
            543552  FPPS1; farnesyl pyrophosphate synthase [KO:K00787] [EC:2.5.1.1 2.5.1.10]
            101258792  farnesyl pyrophosphate synthase 2 isoform X3 [KO:K00787] [EC:2.5.1.1 2.5.1.10]
            778311  GPS; geranyl pyrophosphate synthase [KO:K14066] [EC:2.5.1.1]
            778360  GGPS2; geranylgeranyl pyrophosphate synthase 2 [KO:K13789] [EC:2.5.1.1 2.5.1.10 2.5.1.29]
            101246371  heterodimeric geranylgeranyl pyrophosphate synthase small subunit, chloroplastic [KO:K13789] [EC:2.5.1.1 2.5.1.10 2.5.1.29]
            778310  GGPS1; geranylgeranyl pyrophosphate synthase 1 [KO:K13789] [EC:2.5.1.1 2.5.1.10 2.5.1.29]
            100037490  geranylgeranyl pyrophosphate synthetase-like protein [KO:K13789] [EC:2.5.1.1 2.5.1.10 2.5.1.29]
            101249319  geranylgeranyl pyrophosphate synthase, chloroplastic-like [KO:K13789] [EC:2.5.1.1 2.5.1.10 2.5.1.29]
            112940944  geranylgeranyl pyrophosphate synthase, chloroplastic-like [KO:K13789] [EC:2.5.1.1 2.5.1.10 2.5.1.29]
            101266434  heterodimeric geranylgeranyl pyrophosphate synthase small subunit, chloroplastic-like [KO:K13789] [EC:2.5.1.1 2.5.1.10 2.5.1.29]
            101253007  SppS; solanesyl diphosphate synthase [KO:K05356] [EC:2.5.1.84 2.5.1.85]
            101256886  CPT7; cis-prenyltransferase 7, chloroplastic [KO:K11778] [EC:2.5.1.87]
            104644439  dehydrodolichyl diphosphate synthase 2 [KO:K11778] [EC:2.5.1.87]
            101250227  CPT-binding protein [KO:K11778] [EC:2.5.1.87]
            101253666  CPT3; dehydrodolichyl diphosphate synthase CPT3 [KO:K11778] [EC:2.5.1.87]
            101244138  CPT4; cis-prenyltransferase 4, chloroplastic [KO:K11778] [EC:2.5.1.87]
            101267417  dimethylallylcistransferase, chloroplastic-like [KO:K11778] [EC:2.5.1.87]
            101266160  geranylgeranyl diphosphate reductase, chloroplastic-like [KO:K10960] [EC:1.3.1.83 1.3.1.111]
            101262299  geranylgeranyl diphosphate reductase, chloroplastic [KO:K10960] [EC:1.3.1.83 1.3.1.111]
            544036  FTA; protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha [KO:K05955] [EC:2.5.1.58 2.5.1.59]
            544037  FTB; farnesyl protein transferase subunit B [KO:K05954] [EC:2.5.1.58]
            101259663  CAAX prenyl protease 2 [KO:K08658] [EC:3.4.22.-]
            101247858  CAAX prenyl protease 1 homolog [KO:K06013] [EC:3.4.24.84]
            101267014  protein-S-isoprenylcysteine O-methyltransferase A isoform X1 [KO:K00587] [EC:2.1.1.100]
            101256248  probable isoprenylcysteine alpha-carbonyl methylesterase ICMEL2 [KO:K15889] [EC:3.1.1.-]
            101244664  probable isoprenylcysteine alpha-carbonyl methylesterase ICMEL1 [KO:K15889] [EC:3.1.1.-]
            101250000  farnesylcysteine lyase [KO:K05906] [EC:1.8.3.5 1.8.3.6]
            101264803  uncharacterized protein LOC101264803 isoform X1 [KO:K15891] [EC:1.1.1.354]
            101252619  probable phytol kinase 3, chloroplastic [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 sly00010  Glycolysis / Gluconeogenesis
            sly00100  Steroid biosynthesis
            sly00130  Ubiquinone and other terpenoid-quinone biosynthesis
            sly00270  Cysteine and methionine metabolism
            sly00510  N-Glycan biosynthesis
            sly00902  Monoterpenoid biosynthesis
            sly00904  Diterpenoid biosynthesis
            sly00906  Carotenoid biosynthesis
            sly00908  Zeatin biosynthesis
            sly00909  Sesquiterpenoid and triterpenoid biosynthesis
KO_PATHWAY  ko00900
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