Ubiquinone and other terpenoid-quinone biosynthesis - Homo sapiens (human)

Curator(s): Joe Strothman

Ubiquinone (UQ), also called coenzyme Q, and plastoquinone (PQ) are electron carriers in oxidative phosphorylation and photosynthesis, respectively. The quinoid nucleus of ubiquinone is derived from the shikimate pathway; 4-hydroxybenzoate is directly formed from chorismate in bacteria, while it can be formed from either chorismate or tyrosine in yeast. The following biosynthesis of terpenoid moiety involves reactions of prenylation, decarboxylation, and three hydroxylations alternating with three methylations. The order of these reactions are somewhat different between bacteria and yeast. Phylloquinone (vitamin K1), menaquinone (vitamin K2), and tocopherol (vitamin E) are fat-soluble vitamins. Phylloquinone is a compound present in all photosynthetic plants serving as a cofactor for photosystem I-mediated electron transport. Menaquinone is an obligatory component of the electron-transfer pathway in bacteria.    
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Ubiquinone and other terpenoid-quinone biosynthesis - Homo sapiens (human) cluster_node109 3-Polyprenyl-4-hydroxybenzoate cluster_node32 Polyprenyl-PP cluster_UbiA UbiA cluster_node110 3-Polyprenyl-4-hydroxy-5-methoxybenzoate cluster_node111 2-Polyprenol-6-methoxyphenol cluster_node112 3-Polyprenyl-4;5-dihydroxy-benzoate cluster_node57 2-Polyprenylphenol cluster_node113 2-Polyprenyl-6-hydroxyphenol cluster_node114 2-Polyprenyl-6-methoxy-1;4-benzoquinone cluster_UbiG UbiG cluster_node115 2-Polyprenyl-3-methyl-6-methoxyl-1;4-benzoquinone cluster_node116 2-Polyprenyl-3-methyl-5-hydroxy-6-methoxyl-1;4-benzoquinone cluster_node117 Ubiquinone-n node1 4-Hydroxy -phenyllactate node14 4-Coumerate node1->node14 node2 node2->node1 node3 4-Hydroxyphenyl -pyruvate node2->node3 node4 node3->node4 Homogentisate node4->Homogentisate HST Homogentisate->HST hypoparathyroidism HPT Homogentisate->HPT VTE3 node5 Plastoquinone-9 VTE3->node5 node11 2,3 -Dimethyl -5-phytylquinol VTE3->node11 node6 Solanesyl-PP node6->HST Terpinoid backbone biosynthesis Terpinoid backbone biosynthesis->node6 node7 Phytyl-PP Terpinoid backbone biosynthesis->node7 GPP Terpinoid backbone biosynthesis->GPP node37 1 Terpinoid backbone biosynthesis->node37 node34 Octaprenyl-PP Terpinoid backbone biosynthesis->node34 node7->HPT node106 node7->node106 node8 2-Methyl -6-phytylquinol HPT->node8 node8->VTE3 VTE1 node8->VTE1 node9 delta-Tocopherol VTE1->node9 node12 gamma-Tocopherol VTE1->node12 node10 G-TMT node9->node10 node13 alpha-Tocopherol (Vit. E) node10->node13 node23 beta-Tocopherol node10->node23 node11->VTE1 node12->node10 node15 node14->node15 node16 4-Coumaroyl -CoA node15->node16 node17 4-Hydroxy -benzoyl-CoA node16->node17 node18 node17->node18 node22 4-Hydroxybenzoate node18->node22 node19 node19->node3 node20 L-Tyrosine node20->node19 Chorismate node86 4.1.99.- Chorismate->node86 node21 node21->Chorismate node21->node22 node25 node22->node25 LEPGT node22->LEPGT node23->node13 node24 Phenylalanine, tyrosine and tryptophan biosynthesis node24->node20 node24->Chorismate node26 4-Hydroxybenzoate -O-glucoside node25->node26 node27 3.2.1.- node26->node27 node27->node22 node28 Geranyl-hydroxybenzoate LEPGT->node28 node29 Geranyl-hydroquinone node28->node29 node30 Dihydro-shikonofuran node29->node30 node84 1.14.13.- node29->node84 node31 Dihydro-echinofuran node30->node31 GPP->LEPGT node39 node44 3 node39->node44 node48 node82 13 node48->node82 node50 3-Hexaprenyl -4-hydroxy -5-methoxybenzoate node48->node50 node49 3-Polyprenyl -4-hydroxy -5-methoxybenzoate node48->node49 node56 4.1.1.- node58 2-Octaprenylphenol node56->node58 node57 2-Polyprenylphenol node56->node57 UbiB node59 2-Polyprenyl -6-hydroxyphenol UbiB->node59 node60 2-Octaprenyl -6-hydroxyphenol UbiB->node60 coenzyme Q6 homolog,monooxygenase (S. cerevisiae) COQ6 node66 7 COQ6->node66 UbiH UbiH->node66 coenzyme Q5 homolog,methyltransferase (S. cerevisiae) COQ5 node71 9 COQ5->node71 UbiE UbiE->node71 coenzyme Q7 homolog,ubiquinone (yeast) COQ7 node76 11 COQ7->node76 UbiF UbiF->node76 node78 node78->node82 Oxidative phosphorylation node85 3-Hydroxy -geranyl-hydroquinone node84->node85 Deoxyshikonin node85->Deoxyshikonin Shikonin Deoxyshikonin->Shikonin Futasoline node86->Futasoline node87 Futasoline->node87 node88 de-Hypoxanthine futasoline node87->node88 node89 1.21.-.- node88->node89 node90 Cyclic de-hypoxanthine futasoline node89->node90 node91 1.14.-.- node90->node91 node92 1,4 -Dihydroxy -6-naphthoate node91->node92 Manaquinone node92->Manaquinone node93 node93->Chorismate Isochorismate node93->Isochorismate node94 Isochorismate->node94 node95 2-Succunyl -5-enolpyruvyl -6-hydroxy -3-cyclohexene -1-carboxylate node94->node95 node96 node95->node96 node97 (1R,6R) -2 -Succinyl-6 -hydroxy-2,4 -cyclohexadiene-1 -carboxylate node96->node97 node98 node97->node98 node99 2-Succinylbenzoate node98->node99 node100 node99->node100 node101 2-Succinylbenzoyl -CoA node100->node101 Spirodilactone node101->Spirodilactone Spirodilactone->node99 node102 node102->node101 node103 1,4 -Dihydroxy -2-naphthoyl -CoA node102->node103 node104 3.1.2.- node103->node104 node105 1,4 -Dihydroxy -2-naphthoate node104->node105 node105->node106 node107 2-Demethyl -menaquinone node106->node107 node108 2-Phytyl -1,4-naphthoquinone node106->node108 Phylloquinone node61 2.1.1.- node108->node61 node36 Decaprenyl-PP node37->node36 node33 Hexaprenyl-PP node37->node33 node35 Nonaprenyl-PP node37->node35 node37->node34 node32 Polyprenyl-PP node37->node32 node38 2 node36->node38 node33->node38 node35->node38 node34->node106 node34->node38 node32->node38 node72 10 node72->COQ7 node72->UbiF node74 2-Hexaprenyl -3-methyl -5-hydroxy -6-methoxyl -1,4-benzoquinone node76->node74 node75 2-Octaprenyl -3-methyl -5-hydroxy -6-methoxyl -1,4-benzoquinone node76->node75 node73 2-Polyprenyl -3-methyl -5-hydroxy -6-methoxyl -1,4-benzoquinone node76->node73 node77 12 node74->node77 node75->node77 node73->node77 node77->node48 node77->node78 Ubiquinone node82->Ubiquinone node79 Ubiquinone-6 node82->node79 node80 Ubiquinone-8 node82->node80 node81 Ubiquinone-9 node82->node81 node83 14 Ubiquinone->node83 node79->node83 node80->node83 node81->node83 node83->Oxidative phosphorylation node38->node39 node40 2.5.1.- node38->node40 node40->node44 node53 2-Hexaprenol -6-methoxyphenol node55 6 node53->node55 node55->COQ6 node55->UbiH node69 2-Hexaprenyl -3-methyl -6-methoxyl -1,4-benzoquinone node69->node72 node64 2-Hexaprenyl -6-methoxy -1,4-benzoquinone node67 8 node64->node67 node67->COQ5 node67->UbiE node52 2-Octaprenol -6-methoxyphenol node52->node55 node70 2-Octaprenyl -3-methyl -6-methoxyl -1,4-benzoquinone node70->node72 node65 2-Octaprenyl -6-methoxy -1,4-benzoquinone node65->node67 node58->UbiB node61->Phylloquinone node54 5 node61->node54 node51 2-Polyprenol -6-methoxyphenol node51->node55 node68 2-Polyprenyl -3-methyl -6-methoxyl -1,4-benzoquinone node68->node72 node59->node61 node63 2-Polyprenyl -6-methoxy -1,4-benzoquinone node63->node67 node57->UbiB node54->node53 node54->node52 node54->node51 node50->node54 node49->node54 node42 3-Hexaprenyl -4-hydroxybenzoate node44->node42 node43 3-Nonaprenyl -4-hydroxybenzoate node44->node43 node41 3-Octaprenyl -4-hydroxybenzoate node44->node41 node62 4-Hydroxy -3-polyprenylbenzoate node44->node62 node45 4 node42->node45 node43->node45 node41->node45 node62->node45 node45->node56 node46 3-Polyprenyl -4,5-dihydroxy -benzoate 1 node45->node46 node47 3-Polyprenyl -4,5-dihydroxy -benzoate 2 node45->node47 node46->node48 node47->node48 node66->node64 node66->node65 node66->node63 node71->node69 node71->node70 node71->node68 print "