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] DBLINKS GO: 0009240 0016091 ORTHOLOGY K00021 HMGCR; hydroxymethylglutaryl-CoA reductase (NADPH) [EC:1.1.1.34] K00054 mvaA; hydroxymethylglutaryl-CoA reductase [EC:1.1.1.88] K00099 dxr; 1-deoxy-D-xylulose-5-phosphate reductoisomerase [EC:1.1.1.267] K00587 ICMT, STE14; protein-S-isoprenylcysteine O-methyltransferase [EC:2.1.1.100] K00626 ACAT, atoB; acetyl-CoA C-acetyltransferase [EC:2.3.1.9] K00787 FDPS; farnesyl diphosphate synthase [EC:2.5.1.1 2.5.1.10] K00795 ispA; farnesyl diphosphate synthase [EC:2.5.1.1 2.5.1.10] K00804 GGPS1; geranylgeranyl diphosphate synthase, type III [EC:2.5.1.1 2.5.1.10 2.5.1.29] K00805 hepS; heptaprenyl diphosphate synthase component 1 [EC:2.5.1.30] K00806 uppS; undecaprenyl diphosphate synthase [EC:2.5.1.31] K00869 MVK, mvaK1; mevalonate kinase [EC:2.7.1.36] K00919 ispE; 4-diphosphocytidyl-2-C-methyl-D-erythritol kinase [EC:2.7.1.148] K00938 E2.7.4.2, mvaK2; phosphomevalonate kinase [EC:2.7.4.2] K00991 ispD; 2-C-methyl-D-erythritol 4-phosphate cytidylyltransferase [EC:2.7.7.60] K01597 MVD, mvaD; diphosphomevalonate decarboxylase [EC:4.1.1.33] K01641 HMGCS; hydroxymethylglutaryl-CoA synthase [EC:2.3.3.10] K01662 dxs; 1-deoxy-D-xylulose-5-phosphate synthase [EC:2.2.1.7] K01770 ispF; 2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase [EC:4.6.1.12] K01823 idi; isopentenyl-diphosphate Delta-isomerase [EC:5.3.3.2] K02523 ispB; octaprenyl-diphosphate synthase [EC:2.5.1.90] K03186 ubiX, bsdB, PAD1; flavin prenyltransferase [EC:2.5.1.129] K03526 gcpE, ispG; (E)-4-hydroxy-3-methylbut-2-enyl-diphosphate synthase [EC:1.17.7.1 1.17.7.3] K03527 ispH, lytB; 4-hydroxy-3-methylbut-2-en-1-yl diphosphate reductase [EC:1.17.7.4] K05355 hexPS, COQ1; hexaprenyl diphosphate synthase [EC:2.5.1.82 2.5.1.83] K05356 SPS, sds; all-trans-nonaprenyl-diphosphate synthase [EC:2.5.1.84 2.5.1.85] K05906 PCYOX1, FCLY; prenylcysteine oxidase / farnesylcysteine lyase [EC:1.8.3.5 1.8.3.6] K05954 FNTB; protein farnesyltransferase subunit beta [EC:2.5.1.58] K05955 FNTA; protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha [EC:2.5.1.58 2.5.1.59] K06013 STE24; STE24 endopeptidase [EC:3.4.24.84] K06981 ipk; isopentenyl phosphate kinase [EC:2.7.4.26] K08658 RCE1, FACE2; intramembrane prenyl-peptidase [EC:3.4.26.1] K09128 acnX2; phosphomecalonate degydratase small subunit [EC:4.2.1.182] K10960 chlP, bchP; geranylgeranyl diphosphate/geranylgeranyl-bacteriochlorophyllide a reductase [EC:1.3.1.83 1.3.1.111] K11778 DHDDS, RER2, SRT1; ditrans,polycis-polyprenyl diphosphate synthase [EC:2.5.1.87] K12503 uppS; short-chain Z-isoprenyl diphosphate synthase [EC:2.5.1.68] K12504 PDSS1; decaprenyl-diphosphate synthase subunit 1 [EC:2.5.1.91] K12505 PDSS2; decaprenyl-diphosphate synthase subunit 2 [EC:2.5.1.91] K12506 ispDF; 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] K12742 ispS; isoprene synthase [EC:4.2.3.27] K13273 PMVK; phosphomevalonate kinase [EC:2.7.4.2] K13787 idsA; geranylgeranyl diphosphate synthase, type I [EC:2.5.1.1 2.5.1.10 2.5.1.29] K13789 GGPS; geranylgeranyl diphosphate synthase, type II [EC:2.5.1.1 2.5.1.10 2.5.1.29] K14066 GPS; geranyl diphosphate synthase [EC:2.5.1.1] K14215 E2.5.1.86; trans,polycis-decaprenyl diphosphate synthase [EC:2.5.1.86] K15793 K15793; acyclic sesquiterpene synthase [EC:4.2.3.49 4.2.3.47 3.1.7.6] K15887 ZFPS; (2Z,6Z)-farnesyl diphosphate synthase [EC:2.5.1.92] K15888 uppS, cpdS; tritrans,polycis-undecaprenyl-diphosphate synthase [geranylgeranyl-diphosphate specific] [EC:2.5.1.89] K15889 PCME; prenylcysteine alpha-carboxyl methylesterase [EC:3.1.1.-] K15890 FOHSDR; NADP+-dependent farnesol dehydrogenase [EC:1.1.1.216] K15891 FLDH; NAD+-dependent farnesol dehydrogenase [EC:1.1.1.354] K15892 FOLK; farnesol kinase [EC:2.7.1.216] K17942 pmd; phosphomevalonate decarboxylase [EC:4.1.1.99] K18689 E2.7.1.185; mevalonate-3-kinase [EC:2.7.1.185] K18690 E2.7.1.186; mevalonate-3-phosphate-5-kinase [EC:2.7.1.186] K19177 NUS1; dehydrodolichyl diphosphate syntase complex subunit NUS1 [EC:2.5.1.87] K21268 gdS-2; hexaprenyl diphosphate synthase [EC:2.5.1.82] K21273 E2.5.1.88; trans,polycis-polyprenyl diphosphate synthase [EC:2.5.1.88] K21274 hexs-a; hexaprenyl diphosphate synthase small subunit [EC:2.5.1.83] K21275 hexs-b; hexaprenyl diphosphate synthase large subunit [EC:2.5.1.83] K22813 E4.1.1.110; bisphosphomevalonate decarboxylase [EC:4.1.1.110] K24873 hepT; heptaprenyl diphosphate synthase component 2 K25517 acnX1; phosphomecalonate degydratase large subunit K25518 E4.1.1.126; anhydromevalonate phosphate decarboxylase K28131 fgs; geranylfarnesyl diphosphate synthase 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 C04217 all-trans-Pentaprenyl 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 ///