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 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] M00921 Cyclooctatin biosynthesis, dimethylallyl-PP + isopentenyl-PP => cyclooctatin [PATH:ko00900] DBLINKS GO: 0009240 0016091 ORTHOLOGY K01662 1-deoxy-D-xylulose-5-phosphate synthase [EC:2.2.1.7] K00099 1-deoxy-D-xylulose-5-phosphate reductoisomerase [EC:1.1.1.267] K00991 2-C-methyl-D-erythritol 4-phosphate cytidylyltransferase [EC:2.7.7.60] K12506 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] K00919 4-diphosphocytidyl-2-C-methyl-D-erythritol kinase [EC:2.7.1.148] K01770 2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase [EC:4.6.1.12] K03526 (E)-4-hydroxy-3-methylbut-2-enyl-diphosphate synthase [EC:1.17.7.1 1.17.7.3] K03527 4-hydroxy-3-methylbut-2-en-1-yl diphosphate reductase [EC:1.17.7.4] K00626 acetyl-CoA C-acetyltransferase [EC:2.3.1.9] K01641 hydroxymethylglutaryl-CoA synthase [EC:2.3.3.10] K00021 hydroxymethylglutaryl-CoA reductase (NADPH) [EC:1.1.1.34] K00054 hydroxymethylglutaryl-CoA reductase [EC:1.1.1.88] K00869 mevalonate kinase [EC:2.7.1.36] K00938 phosphomevalonate kinase [EC:2.7.4.2] K13273 phosphomevalonate kinase [EC:2.7.4.2] K01597 diphosphomevalonate decarboxylase [EC:4.1.1.33] K17942 phosphomevalonate decarboxylase [EC:4.1.1.99] K06981 isopentenyl phosphate kinase [EC:2.7.4.26] K25517 phosphomecalonate degydratase large subunit [EC:4.2.1.182] K09128 phosphomecalonate degydratase small subunit [EC:4.2.1.182] K25518 anhydromevalonate phosphate decarboxylase [EC:4.1.1.126] K03186 flavin prenyltransferase [EC:2.5.1.129] K18689 mevalonate-3-kinase [EC:2.7.1.185] K18690 mevalonate-3-phosphate-5-kinase [EC:2.7.1.186] K22813 bisphosphomevalonate decarboxylase [EC:4.1.1.110] K01823 isopentenyl-diphosphate Delta-isomerase [EC:5.3.3.2] K00787 farnesyl diphosphate synthase [EC:2.5.1.1 2.5.1.10] K00795 farnesyl diphosphate synthase [EC:2.5.1.1 2.5.1.10] K14066 geranyl diphosphate synthase [EC:2.5.1.1] K00804 geranylgeranyl diphosphate synthase, type III [EC:2.5.1.1 2.5.1.10 2.5.1.29] K13789 geranylgeranyl diphosphate synthase, type II [EC:2.5.1.1 2.5.1.10 2.5.1.29] K13787 geranylgeranyl diphosphate synthase, type I [EC:2.5.1.1 2.5.1.10 2.5.1.29] K12503 short-chain Z-isoprenyl diphosphate synthase [EC:2.5.1.68] K15887 (2Z,6Z)-farnesyl diphosphate synthase [EC:2.5.1.92] K14215 trans,polycis-decaprenyl diphosphate synthase [EC:2.5.1.86] K21273 trans,polycis-polyprenyl diphosphate synthase [EC:2.5.1.88] K05355 hexaprenyl diphosphate synthase [EC:2.5.1.82 2.5.1.83] K21268 hexaprenyl diphosphate synthase [EC:2.5.1.82] K21274 hexaprenyl diphosphate synthase small subunit [EC:2.5.1.83] K21275 hexaprenyl diphosphate synthase large subunit [EC:2.5.1.83] K00805 heptaprenyl diphosphate synthase component 1 [EC:2.5.1.30] K24873 heptaprenyl diphosphate synthase component 2 [EC:2.5.1.30] K02523 octaprenyl-diphosphate synthase [EC:2.5.1.90] K05356 all-trans-nonaprenyl-diphosphate synthase [EC:2.5.1.84 2.5.1.85] K12504 decaprenyl-diphosphate synthase subunit 1 [EC:2.5.1.91] K12505 decaprenyl-diphosphate synthase subunit 2 [EC:2.5.1.91] K00806 undecaprenyl diphosphate synthase [EC:2.5.1.31] K11778 ditrans,polycis-polyprenyl diphosphate synthase [EC:2.5.1.87] K19177 dehydrodolichyl diphosphate syntase complex subunit NUS1 [EC:2.5.1.87] K15888 tritrans,polycis-undecaprenyl-diphosphate synthase [geranylgeranyl-diphosphate specific] [EC:2.5.1.89] K10960 geranylgeranyl diphosphate/geranylgeranyl-bacteriochlorophyllide a reductase [EC:1.3.1.83 1.3.1.111] K12742 isoprene synthase [EC:4.2.3.27] K05955 protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha [EC:2.5.1.58 2.5.1.59] K05954 protein farnesyltransferase subunit beta [EC:2.5.1.58] K08658 intramembrane prenyl-peptidase [EC:3.4.26.1] K06013 STE24 endopeptidase [EC:3.4.24.84] K00587 protein-S-isoprenylcysteine O-methyltransferase [EC:2.1.1.100] K15889 prenylcysteine alpha-carboxyl methylesterase [EC:3.1.1.-] K05906 prenylcysteine oxidase / farnesylcysteine lyase [EC:1.8.3.5 1.8.3.6] K15890 NADP+-dependent farnesol dehydrogenase [EC:1.1.1.216] K15891 NAD+-dependent farnesol dehydrogenase [EC:1.1.1.354] K15892 farnesol kinase [EC:2.7.1.216] K15793 acyclic sesquiterpene synthase [EC:4.2.3.49 4.2.3.47 3.1.7.6] 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 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 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 ///