KEGG PATHWAY: rn00900

PATHWAY: rn00900

Entry

rn00900                     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

rn00900

Terpenoid backbone biosynthesis

Module

M00095

C5 isoprenoid biosynthesis, mevalonate pathway [PATH:rn00900]

M00096

C5 isoprenoid biosynthesis, non-mevalonate pathway [PATH:rn00900]

M00364

C10-C20 isoprenoid biosynthesis, bacteria [PATH:rn00900]

M00365

C10-C20 isoprenoid biosynthesis, archaea [PATH:rn00900]

M00366

C10-C20 isoprenoid biosynthesis, plants [PATH:rn00900]

M00367

C10-C20 isoprenoid biosynthesis, non-plant eukaryotes [PATH:rn00900]

M00849

C5 isoprenoid biosynthesis, mevalonate pathway, archaea [PATH:rn00900]

Other DBs

GO:	0009240 0016091

Reaction

R00238

acetyl-CoA:acetyl-CoA C-acetyltransferase

R01121

ATP:(R)-5-diphosphomevalonate carboxy-lyase (adding ATP; isopentenyl-diphosphate-forming); ATP:(R)-5-diphosphomevalonate carboxy-lyase (dehydrating)

R01123

isopentenyl-diphosphate Delta3-Delta2-isomerase

R01658

dimethylallyl-diphosphate:isopentenyl-diphosphate dimethylallyltranstransferase

R01978

acetyl-CoA:acetoacetyl-CoA C-acetyltransferase (thioester-hydrolysing, carboxymethyl-forming)

R02003

geranyl-diphosphate:isopentenyl-diphosphate geranyltrans-transferase

R02061

trans,trans-farnesyl-diphosphate:isopentenyl-diphosphate farnesyltranstransferase

R02063

geranylgeranyl reductase

R02081

(R)-mevalonate:NAD+ oxidoreductase (CoA-acetylating)

R02082

(R)-mevalonate:NADP+ oxidoreductase (CoA acylating)

R02245

ATP:(R)-mevalonate 5-phosphotransferase

R03245

ATP:(R)-5-phosphomevalonate phosphotransferase

R03264

2-trans,6-trans-farnesol:NADP+ 1-oxidoreductase

R03917

poly-cis-polyprenyl-diphosphate:isopentenyl-diphosphate polyprenylcistransferase

R04496

S-adenosyl-L-methionine:protein-C-terminal-S-farnesyl-L-cysteine O-methyltransferase

R05556

(2E,6E)-farnesyl-diphosphate:isopentenyl-diphosphate cistransferase (adding 10-55 isopentenyl units)

R05633

CTP: 2-C-methyl-D-erythritol 4-phosphate cytidylyltransferase

R05634

ATP:4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol 2-phosphotransferase

R05636

1-deoxy-D-xylulose-5-phosphate pyruvate-lyase (carboxylating)

R05637

2-phospho-4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol CMP-lyase (cyclizing)

R05688

1-deoxy-D-xylulose-5-phosphate isomeroreductase

R05884

isopentenyl-diphosphate:ferredoxin oxidoreductase

R06447

(2E,6E)-farnesyl-diphosphate:isopentenyl-diphosphate cistransferase (adding 8 isopentenyl units)

R07475

geranylgeranyl-diphosphate:isopentenyl-diphosphate transtransferase

R08199

dimethylallyl-diphosphate diphosphate-lyase (isoprene-forming)

R08210

dimethylallyl diphosphate:ferredoxin oxidoreductase

R08528

Z-farnesyl diphosphate synthase

R08689

(E)-4-hydroxy-3-methylbut-2-en-1-yl-diphosphate:oxidized ferredoxin oxidoreductase (hydrating)

R08697

trans,trans-farnesyl-diphosphate diphosphohydrolase; (2E,6E)-farnesyl-diphosphate diphosphohydrolase

R09244

(2Z,6E)-farnesyl-diphosphate:isopentenyl-diphosphate farnesylcistransferase (adding 7 isopentenyl units)

R09245

(2E,6E)-farnesyl-diphosphate:isopentenyl-diphosphate farnesyltranstransferase (adding 3 isopentenyl units)

R09246

geranylgeranyl-diphosphate:isopentenyl-diphosphate transferase (adding 2 isopentenyl units)

R09247

(2E,6E)-farnesyl-diphosphate:isopentenyl-diphosphate farnesyltranstransferase (adding 4 isopentenyl units)

R09248

(2E,6E)-farnesyl-diphosphate:isopentenyl-diphosphate farnesyltranstransferase (adding 5 isopentenyl units)

R09249

(2E,6E)-farnesyl-diphosphate:isopentenyl-diphosphate farnesyltranstransferase (adding 7 isopentenyl units)

R09250

geranyl-diphosphate:isopentenyl-diphosphate transtransferase (adding 7 isopentenyl units)

R09251

geranylgeranyl-diphosphate:isopentenyl-diphosphate transtransferase (adding 5 isopentenyl units)

R09562

S-(2E,6E)-farnesyl-L-cysteine oxidase

R09633

dimethylallyl-diphosphate:isopentenyl-diphosphate cistransferase (adding 2 isopentenyl units)

R09730

geranylgeranyl-diphosphate:isopentenyl-diphosphate cistransferase (adding 7 isopentenyl units)

R09731

(2Z,6E)-farnesyl-diphosphate:isopentenyl-diphosphate cistransferase (adding 9-11 isopentenyl units)

R09844

farnesyl-diphosphate:protein-cysteine farnesyltransferase

R09845

CAAX protease

R09846

prenylcycteine methylesterase

R09847

R09849

CTP:2-trans,6-trans-farnesol O-phosphotransferase

R09850

CTP:farnesyl-phosphate phosphotransferase

R10093

ATP:isopentenyl phosphate phosphotransferase

R10412

(2E,6E)-farnesol:NAD+ 1-oxidoreductase

R10561

ATP:phosphomevalonate carboxy-lyase (adding ATP; isopentenyl-phosphate-forming)

R10779

ATP:(R)-mevalonate 3-phosphotransferase

R10780

ATP:(R)-3-phosphomevalonate 5-phosphotransferase

R10781

(R)-3,5-bisphosphomevalonate carboxy-lyase (isopentenyl-phosphate-forming)

R10859

(E)-4-hydroxy-3-methylbut-2-en-1-yl-diphosphate:oxidized flavodoxin oxidoreductase

R12894

(R)-5-phosphomevalonate hydro-lyase

R12895

trans-anhydromevalonate 5-phosphate carboxy-lyase; (2E)-3-methyl-5-phosphooxypent-2-enoate carboxy-lyase

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

Related
pathway

rn00010

Glycolysis / Gluconeogenesis

rn00100

Steroid biosynthesis

rn00130

Ubiquinone and other terpenoid-quinone biosynthesis

rn00270

Cysteine and methionine metabolism

rn00403