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CHEBI:16015 ChEBI Vanylglycol 1.14.18.1 false 1.14.18.1 2 5,6-Dihydroxyindole-2-carboxylic acid + Oxygen → Melanin + Water LEFT_TO_RIGHT Reaction1130 false Indole-5,6-quinone → Melanin LEFT_TO_RIGHT 5.3.3.12 false 5.3.3.12 L-Dopachrome → 5,6-Dihydroxyindole-2-carboxylic acid LEFT_TO_RIGHT Amiloride-sensitive amine oxidase [copper-containing] 439153 PubChem-compound ReactionCatalysis825 ACTIVATION ReactionCatalysis826 ACTIVATION ReactionCatalysis823 ACTIVATION ReactionCatalysis824 ACTIVATION 2.1.1.6 false 2.1.1.6 3,4-Dihydroxybenzeneacetic acid + Guaiacol → Homovanillic acid + Pyrocatechol LEFT_TO_RIGHT 50 ChemSpider ReactionCatalysis822 ACTIVATION 56-DIHYDROXYINDOLE-2-CARBOXYLATE BioCyc OXALACETIC_ACID BioCyc 775-01-9 CAS Indole-5,6-quinone 1.0 1.4.3.22 false 1.4.3.22 Oxygen + Tyramine + Water → Ammonia + Homovanillin + Hydrogen peroxide LEFT_TO_RIGHT Phenylethanolamine N-methyltransferase 1.4.3.4 false 1.4.3.4 Oxygen + Tyramine + Water → Ammonia + Homovanillin + Hydrogen peroxide LEFT_TO_RIGHT 4.1.1.28 false 4.1.1.28 L-Tyrosine → Carbon dioxide + Tyramine LEFT_TO_RIGHT P21964 UniProt ReactionCatalysis818 ACTIVATION CHEBI:846276 ChEBI ReactionCatalysis819 ACTIVATION ReactionCatalysis816 ACTIVATION ReactionCatalysis817 ACTIVATION ReactionCatalysis814 ACTIVATION 1.14.18.1 false 1.14.18.1 5,6-Dihydroxyindole + Oxygen → Indole-5,6-quinone + Water LEFT_TO_RIGHT ReactionCatalysis815 ACTIVATION ReactionCatalysis812 ACTIVATION Reaction1127 false Leucodopachrome → L-Dopachrome LEFT_TO_RIGHT 1.14.18.1 false 1.14.18.1 L-Dopachrome + Oxygen → 5,6-Dihydroxyindole + Water LEFT_TO_RIGHT Reaction1126 false Dopaquinone → Leucodopachrome LEFT_TO_RIGHT 1.2.1.5 false 1.2.1.5 Homovanillin + NADP + Water → NADPH + p-Hydroxyphenylacetic acid LEFT_TO_RIGHT 1.14.18.1 false 1.14.18.1 Oxygen + Tyramine → Dopamine + Water LEFT_TO_RIGHT C00218 KEGG Compound ReactionCatalysis850 ACTIVATION ReactionCatalysis851 ACTIVATION 5745 ChemSpider CHEBI:44747 ChEBI NADH L-ASPARTATE BioCyc CHEBI:16474 ChEBI 736172 PubChem-compound Aspartate aminotransferase, cytoplasmic HMDB0006779 HMDB Amine oxidase [flavin-containing] A ReactionCatalysis847 ACTIVATION SMILES COC1=CC=CC=C1O ReactionCatalysis848 ACTIVATION 2.1.1.6 false 2.1.1.6 3,4-Dihydroxymandelic acid + Guaiacol → Pyrocatechol + Vanillylmandelic acid LEFT_TO_RIGHT 1.2.1.5 false 1.2.1.5 3-Methoxy-4-hydroxyphenylglycolaldehyde + NADP + Water → NADPH + Vanillylmandelic acid LEFT_TO_RIGHT 1.4.3.4 false 1.4.3.4 Normetanephrine + Oxygen + Water → 3-Methoxy-4-hydroxyphenylglycolaldehyde + Ammonia + Hydrogen peroxide LEFT_TO_RIGHT 1.4.3.4 false 1.4.3.4 Metanephrine + Oxygen + Water → 3-Methoxy-4-hydroxyphenylglycolaldehyde + Ammonia + Hydrogen peroxide LEFT_TO_RIGHT CHEBI:16240 ChEBI O43708 UniProt 119219 PubChem-compound 979-92-0 CAS 1.0 Reaction392 false 4-Hydroxyphenylpyruvic acid → 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid LEFT_TO_RIGHT 1.4.3.4 false 1.4.3.4 Dopamine + Oxygen + Water → 3,4-Dihydroxyphenylacetaldehyde + Ammonia + Hydrogen peroxide LEFT_TO_RIGHT Maleylacetoacetic acid 1.4.3.4 false 1.4.3.4 3-Methoxytyramine + Oxygen + Water → Ammonia + Homovanillin + Hydrogen peroxide LEFT_TO_RIGHT 1.4.3.4 false 1.4.3.4 Epinephrine + Oxygen + Water → 3,4-Dihydroxymandelaldehyde + Hydrogen peroxide + Methylamine LEFT_TO_RIGHT 94 ChemSpider ReactionCatalysis866 ACTIVATION 1.0 1.4.3.4 false 1.4.3.4 Norepinephrine + Oxygen + Water → 3,4-Dihydroxymandelaldehyde + Ammonia + Hydrogen peroxide LEFT_TO_RIGHT ReactionCatalysis863 ACTIVATION ReactionCatalysis861 ACTIVATION 388447 ChemSpider C00007 KEGG Compound C00006 KEGG Compound ReactionCatalysis860 ACTIVATION C03758 KEGG Compound CHEBI:18009 ChEBI Hydrogen Ion 17592-23-3 CAS C00001 KEGG Compound 50-81-7 CAS C00483 KEGG Compound 1.0 C00005 KEGG Compound 82648 ChemSpider C00004 KEGG Compound NADPH CHEBI:18243 ChEBI C00003 KEGG Compound C8H8O3 3,4-Dihydroxyphenylacetaldehyde 152.04735 Homovanillin 2.1.1.6 false 2.1.1.6 Dopamine + Guaiacol → 3-Methoxytyramine + Pyrocatechol LEFT_TO_RIGHT 2.1.1.6 false 2.1.1.6 Epinephrine + Guaiacol → Metanephrine + Pyrocatechol LEFT_TO_RIGHT 1.1.1.1 false 1.1.1.1 3,4-Dihydroxymandelaldehyde + NAD → 3,4-Dihydroxyphenylglycol + NADH LEFT_TO_RIGHT 1.14.18.1 false 1.14.18.1 Oxygen + Tyramine → L-Dopa + Water LEFT_TO_RIGHT 2.1.1.6 false 2.1.1.6 3,4-Dihydroxyphenylglycol + Guaiacol → Pyrocatechol + Vanylglycol LEFT_TO_RIGHT 1.0 2.1.1.6 false 2.1.1.6 Guaiacol + Norepinephrine → Normetanephrine + Pyrocatechol LEFT_TO_RIGHT 182283 ChemSpider ReactionCatalysis858 ACTIVATION ReactionCatalysis859 ACTIVATION ReactionCatalysis856 ACTIVATION ReactionCatalysis857 ACTIVATION ReactionCatalysis854 ACTIVATION 8049-97-6 CAS 1.0 ReactionCatalysis852 ACTIVATION Leucodopachrome ReactionCatalysis853 ACTIVATION C00019 KEGG Compound C00011 KEGG Compound C00014 KEGG Compound P14174 UniProt 1.0 1.0 Fumarylacetoacetase H Hydrogen Ion 1.007825 1.0 1.0 C00021 KEGG Compound 53-84-9 CAS L-Glutamic acid C00027 KEGG Compound C00026 KEGG Compound C00025 KEGG Compound 3-Methoxy-4-hydroxyphenylglycolaldehyde C00272 KEGG Compound L-Dopachrome 54670067 PubChem-compound NADP Oxygen 4a-Hydroxytetrahydrobiopterin BiologicalState24 Homo sapiens, Adrenal Medulla Homogentisate 1,2-dioxygenase 4-HYDROXYPHENYLACETATE BioCyc C00036 KEGG Compound Dopamine beta-hydroxylase HMDB0000134 HMDB HMDB0006915 HMDB P19801 UniProt TETRA-H-BIOPTERIN BioCyc HMDB0001229 HMDB C15522 KEGG Compound Tyrosinase 3,4-Dihydroxyphenylacetaldehyde P11086 UniProt HMDB0000130 HMDB 1.0 SMILES OC(=O)CC1=CC(O)=C(O)C=C1 Water C00049 KEGG Compound P30838 UniProt Epinephrine 1.0 1.0 HMDB0000148 HMDB 59-92-7 CAS 784 PubChem-compound 51-61-6 CAS 547 PubChem-compound FUM BioCyc SMILES OC(=O)CC(=O)C(O)=O 780 PubChem-compound CHEBI:18012 ChEBI HMDB0001487 HMDB 4-Hydroxyphenylpyruvic acid HMDB0000158 HMDB SMILES OC(C(O)=O)C1=CC=C(O)C(O)=C1 SMP0000716 SMPDB DOPAMINE BioCyc C9H13NO3 Normetanephrine 183.08954 3,4-Dihydroxyphenylglycol 21100 PubChem-compound 661 ChemSpider C00072 KEGG Compound C01161 KEGG Compound HMDB0001490 HMDB Amiloride-sensitive amine oxidase [copper-containing] HMDB0001253 HMDB HMDB0000164 HMDB 962 PubChem-compound 31983 ChemSpider 5703-24-2 CAS 17528-72-2 CAS 114908 ChemSpider CO2 Carbon dioxide 43.98983 C00080 KEGG Compound 306-08-1 CAS SMILES O=O 1738 PubChem-compound HMDB0001268 HMDB SMILES OC(=O)C(\O)=C\C1=CC=C(O)C=C1 C9H10O3 Homovanillin 166.06299 C00082 KEGG Compound 102-32-9 CAS HMDB0002111 HMDB HMDB0001264 HMDB 1.0 Macrophage migration inhibitory factor C01179 KEGG Compound 636708 PubChem-compound C00090 KEGG Compound HMDB0000181 HMDB 1.0 Homogentisic acid Acetoacetic acid 156-39-8 CAS 133725 ChemSpider 1.0 SMILES COC1=C(O)C=CC(=C1)[C@H](O)C(O)=O Maleylacetoacetate isomerase H2O2 Hydrogen peroxide 34.005478 C9H15N5O4 4a-Hydroxytetrahydrobiopterin 257.1124 HMDB0000191 HMDB C8H11NO Tyramine 137.08406 NADH BioCyc 1.0 977 PubChem-compound 970 PubChem-compound 1.0 1.0 55-10-7 CAS C8H10O4 3,4-Dihydroxyphenylglycol 170.0579 979 PubChem-compound 19844 ChemSpider 127 PubChem-compound 30572 ChemSpider 1.0 17215925 ChemSpider 90-05-1 CAS 3,4-Dihydroxyphenylacetaldehyde 91528 PubChem-compound 3131-52-0 CAS 1.0 21883788 PubChem-compound SMILES NCCC1=CC=C(O)C=C1 SMILES OO SMILES CC(O)C(O)C1CNC2=NC(N)=NC(=O)C2(O)N1 HMDB0001866 HMDB H3N Ammonia 17.026548 C6H8O6 Ascorbic acid 176.03209 1.0 1.0 C05579 KEGG Compound 1125 PubChem-compound C05576 KEGG Compound C05578 KEGG Compound C05577 KEGG Compound C05583 KEGG Compound C05582 KEGG Compound C05584 KEGG Compound 51 PubChem-compound C8H8O6 Maleylacetoacetic acid 200.03209 3,4-Dihydroxybenzeneacetic acid C05581 KEGG Compound SMILES OCC(O)C1=CC(O)=C(O)C=C1 C05580 KEGG Compound C4H6O3 Acetoacetic acid 102.03169 2.0 440729 PubChem-compound 440728 PubChem-compound HMDB0000306 HMDB C05587 KEGG Compound C05589 KEGG Compound C05588 KEGG Compound C05594 KEGG Compound Tyramine C05350 KEGG Compound 274 ChemSpider C8H8O3 p-Hydroxyphenylacetic acid 152.04735 1.0 C9H15N5O3 Tetrahydrobiopterin 241.1175 CPD-400 BioCyc C9H13NO2 3-Methoxytyramine 167.09464 485-80-3 CAS HMDB0000318 HMDB C9H7NO4 L-Dopachrome 193.0375 114683 PubChem-compound C8H8O4 3,4-Dihydroxymandelaldehyde 168.04225 18766-67-1 CAS 1.14.18.1 false 1.14.18.1 2 L-Dopa + Oxygen → 2 Dopaquinone + 2 Water LEFT_TO_RIGHT Tyramine NADPH BioCyc CHEBI:16852 ChEBI Fumaric acid CHEBI:15765 ChEBI GO:0033162 GENE ONTOLOGY Carbon dioxide CPD-6641 BioCyc CHEBI:15760 ChEBI 217 ChemSpider 58-68-4 CAS C04043 KEGG Compound 1.0 1.0 SMILES COC1=C(O)C=CC(CCN)=C1 SMILES OC(=O)CC1=CC=C(O)C=C1 5,6-Dihydroxyindole-2-carboxylic acid CHEBI:30915 ChEBI 1.0 Vanillylmandelic acid C9H10O4 Homovanillic acid 182.0579 CHEBI:15772 ChEBI CHEBI:144308 ChEBI SMILES CC(O)C(O)C1CNC2=C(N1)C(=O)N=C(N)N2 SMILES OC(=O)[C@@H]1CC2=CC(=O)C(=O)C=C2N1 161255 PubChem-compound 447 ChemSpider 13837760 ChemSpider SMILES OC(C=O)C1=CC(O)=C(O)C=C1 C4H4O4 Fumaric acid 116.010956 CHEBI:30907 ChEBI HMDB0001430 HMDB C8H8O4 Homogentisic acid 168.04225 Oxoglutaric acid CHEBI:16830 ChEBI C9H13NO3 Epinephrine 183.08954 SMILES O=C=O SMILES COC1=C(O)C=CC(CC=O)=C1 C21H29N7O14P2 NADH 665.12476 P21397 UniProt HMDB0000118 HMDB CHEBI:1387 ChEBI C9H12O4 Vanylglycol 184.07356 CHEBI:27978 ChEBI C8H11NO2 Dopamine 153.07898 3-hydroxyanthranilate 3,4-dioxygenase CHEBI:15999 ChEBI 1.0 CHEBI:2003 ChEBI 133331 ChemSpider Norepinephrine 106648 ChemSpider SMP0000008 SMPDB 3-KETOBUTYRATE BioCyc Maleylacetoacetate isomerase 5682 ChemSpider 10805 PubChem-compound 439316 PubChem-compound 1.0 HMDB0004058 HMDB PW000693 PathWhiz HMDB0004061 HMDB 5675 ChemSpider HMDB0000939 HMDB 1.0 3343-19-9 CAS 2.0 1.2.1.5 false 1.2.1.5 Homovanillin + NAD + Water → Homovanillic acid + Hydrogen Ion + NADH LEFT_TO_RIGHT HMDB0004063 HMDB SMP0000494 SMPDB 1.13.11.6 false 1.13.11.6 3,4-Dihydroxyphenylacetaldehyde + NAD + Water → 3,4-Dihydroxybenzeneacetic acid + Hydrogen Ion + NADH LEFT_TO_RIGHT HMDB0006242 HMDB 1.2.1.5 false 1.2.1.5 3,4-Dihydroxymandelaldehyde + NAD + Water → 3,4-Dihydroxymandelic acid + Hydrogen Ion + NADH LEFT_TO_RIGHT HMDB0004068 HMDB HMDB0004067 HMDB 1.0 HMDB0000707 HMDB 3-hydroxyanthranilate 3,4-dioxygenase Maleylacetoacetate isomerase ReactionCatalysis447 ACTIVATION ReactionCatalysis445 ACTIVATION C5H9NO4 L-Glutamic acid 147.05316 ReactionCatalysis446 ACTIVATION Water 33032 PubChem-compound 60-18-4 CAS Dehydroascorbic acid 1093 ChemSpider HMDB0000957 HMDB 7782-44-7 CAS C10H15NO3 Metanephrine 197.1052 C9H9NO4 Leucodopachrome 195.05316 C18H10N2O4 Melanin 318.06406 1.0 Leucodopachrome 2.0 HMDB0005175 HMDB Reaction386 false Maleylacetoacetic acid → 4-Fumarylacetoacetic acid LEFT_TO_RIGHT C8H7NO2 5,6-Dihydroxyindole 149.04768 C9H10O4 3-Methoxy-4-hydroxyphenylglycolaldehyde 182.0579 9606 TAXONOMY 2-KETOGLUTARATE BioCyc 388394 ChemSpider 3-Methoxytyramine 1.13.11.5 false 1.13.11.5 Homogentisic acid + Oxygen → Maleylacetoacetic acid LEFT_TO_RIGHT 4790-08-3 CAS CHEBI:15377 ChEBI Cell Membrane CHEBI:15379 ChEBI CHEBI:15378 ChEBI SMILES [H+] SMILES COC1=CC(=CC=C1O)C(O)CN Catechol O-methyltransferase CHEBI:15372 ChEBI CHEBI:15374 ChEBI Dopaquinone Oxygen 97-31-4 CAS CHEBI:30744 ChEBI ReactionCatalysis218 ACTIVATION Reaction320 false 4-Hydroxyphenylpyruvic acid + Oxygen → Carbon dioxide + Homogentisic acid LEFT_TO_RIGHT CHEBI:15344 ChEBI 10348 ChemSpider Normetanephrine Tyrosinase ReactionCatalysis2116 ACTIVATION CHEBI:144365 ChEBI ReactionCatalysis2115 ACTIVATION ReactionCatalysis2117 ACTIVATION 2.0 C00547 KEGG Compound C00788 KEGG Compound 5698-52-2 CAS Macrophage migration inhibitory factor CHEBI:16680 ChEBI C00544 KEGG Compound 102690 ChemSpider PW000470 PathWhiz SMILES OC1=C(O)C=C(CC=O)C=C1 ASCORBATE BioCyc 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid Dopamine Aromatic-L-amino-acid decarboxylase 2.0 7722-84-1 CAS 937 ChemSpider CHEBI:16134 ChEBI Catechol O-methyltransferase HMDB0003125 HMDB 1.0 110-17-8 CAS L-Tyrosine SubPathwayInput HMDB0001185 HMDB 1.0 1.0 C9H9NO4 Dopaquinone 195.05316 Thyroid Hormone Synthesis SubPathway 5833 ChemSpider 554-52-9 CAS Melanosome Membrane Aspartate aminotransferase, cytoplasmic Aromatic-L-amino-acid decarboxylase Aspartate aminotransferase, cytoplasmic CHEBI:28591 ChEBI HMDB0002281 HMDB 4-Fumarylacetoacetic acid L-DOPA BioCyc CHEBI:28111 ChEBI C15H23N6O5S S-Adenosylmethionine 399.14505 P07327 UniProt 534-82-7 CAS Dopaquinone 1.0 PW000042 PathWhiz 954 ChemSpider 6047 PubChem-compound 952 ChemSpider Aldehyde dehydrogenase, dimeric NADP-preferring HMDB0002052 HMDB TYR BioCyc CHEBI:47904 ChEBI 5611 ChemSpider 945 ChemSpider 1010 ChemSpider P40126 UniProt 1.0 Dopamine SubPathwayInteraction163 SubPathway163Reaction SubPathwayReaction CHEBI:18357 ChEBI 5408 ChemSpider 1.0 SMILES C[S+](CC[C@H](N)C(O)=O)C[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N Cytosol C00355 KEGG Compound C8H5NO2 Indole-5,6-quinone 147.03203 C14H20N6O5S S-Adenosylhomocysteine 384.12158 Alcohol dehydrogenase 1A 1.0 Tyramine 451-13-8 CAS C00122 KEGG Compound DOPAQUINONE BioCyc C01693 KEGG Compound 1.0 CATECHOL BioCyc P20711 UniProt Tetrahydrobiopterin C9H7NO4 5,6-Dihydroxyindole-2-carboxylic acid 193.0375 85782 PubChem-compound C21H28N7O14P2 NAD 664.11694 44367445 PubChem-compound 1.0 HMDB0000902 HMDB Dopamine beta-hydroxylase CHEBI:17242 ChEBI NAD(P) BioCyc 552441 ChemSpider C6H6O6 Dehydroascorbic acid 174.01643 388301 ChemSpider 2.0 6325610 PubChem-compound CHEBI:18101 ChEBI C8H8O6 4-Fumarylacetoacetic acid 200.03209 Tyrosinase 3,4-Dihydroxymandelaldehyde 389601 ChemSpider 389600 ChemSpider C05606 KEGG Compound C05604 KEGG Compound 141655 ChemSpider 328-50-7 CAS 2.0 MELANIN BioCyc SMILES NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](CO[P@](O)(=O)O[P@](O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1O 532 ChemSpider SMILES NCCC1=CC(O)=C(O)C=C1 Oxalacetic acid SMILES COC1=CC(=CC=C1O)C(O)CO HYDROGEN-PEROXIDE BioCyc p-Hydroxyphenylacetic acid C9H8O4 4-Hydroxyphenylpyruvic acid 180.04225 Water SubPathwayInteraction787 SubPathwayReaction SubPathway787Reaction 1.0 L-Dopa C00164 KEGG Compound Fumarylacetoacetase 6089 ChemSpider 763 ChemSpider HMDB0000027 HMDB HMDB0000020 HMDB HMDB0000022 HMDB 1.0 10197150 ChemSpider C6H6O2 Pyrocatechol 110.03678 7732-18-5 CAS CHEBI:18135 ChEBI L-dopachrome tautomerase SMILES [H][C@@]1(OC(=O)C(O)=C1O)[C@@H](O)CO AMMONIA BioCyc SMILES N 56-86-0 CAS 13023-73-9 CAS 1.0 Macrophage migration inhibitory factor NOREPINEPHRINE BioCyc 151276 PubChem-compound NAD L-dopachrome tautomerase 1.0 CHEBI:17053 ChEBI 4444081 ChemSpider C01036 KEGG Compound HMDB0001377 HMDB 1.0 S-Adenosylhomocysteine SMILES CC(=O)CC(O)=O 1.0 SMILES CNC[C@H](O)C1=CC(O)=C(O)C=C1 SMILES OC(=O)CC(=O)CC(=O)\C=C/C(O)=O 1669 PubChem-compound HMDB0003791 HMDB Amine oxidase [flavin-containing] A HMDB0000044 HMDB Guaiacol CH5N Methylamine 31.0422 643307 ChemSpider 1200 ChemSpider 156-38-7 CAS C9H11NO3 L-Tyrosine 181.0739 Hydrogen peroxide P14679 UniProt Phenylethanolamine N-methyltransferase HMDB0000291 HMDB HMDB0000051 HMDB SMILES N[C@@H](CCC(O)=O)C(O)=O 6057 PubChem-compound Norepinephrine C9H11NO4 L-Dopa 197.0688 5,6-Dihydroxyindole 1675 ChemSpider L-EPINEPHRINE BioCyc 5280393 PubChem-compound Q93099 UniProt HMDB0000068 HMDB HMDB0001398 HMDB 5280398 PubChem-compound SMILES CNCC(O)C1=CC(OC)=C(O)C=C1 490-83-5 CAS SMILES OC(=O)[C@@H]1CC2=CC(O)=C(O)C=C2N1 SMILES CC1=C2NC=C3C2=C(C2=CNC4=C(C)C(=O)C(=O)C3=C24)C(=O)C1=O C01061 KEGG Compound HMDB0000060 HMDB C4H7NO4 L-Aspartic acid 133.0375 SMILES OC1=C(O)C=C2C=CNC2=C1 96 PubChem-compound SMILES COC1=C(O)C=CC(=C1)C(O)C=O 28613-33-4 CAS 5824 ChemSpider CPD-4521 BioCyc CHEBI:29073 ChEBI 4884931 ChemSpider 759 ChemSpider L-Aspartic acid 22833512 PubChem-compound 25246222 PubChem-compound L-Dopa SMILES COC1=CC(CC(O)=O)=CC=C1O H2O Water 18.010565 Alcohol dehydrogenase 1A HMDB0000073 HMDB NAD BioCyc HMDB0059597 HMDB 1.0 56-84-8 CAS SMILES OC(=O)\C=C\C(O)=O Melanin SMILES OC(=O)CC1=C(O)C=CC(O)=C1 1.0 51-41-2 CAS C4H4O5 Oxalacetic acid 132.00587 1.14.17.1 false 1.14.17.1 Ascorbic acid + Dopamine + Oxygen → Dehydroascorbic acid + Norepinephrine + Water LEFT_TO_RIGHT 1.0 CPD-7650 BioCyc CHEBI:28918 ChEBI 5610 PubChem-compound P-HYDROXY-PHENYLPYRUVATE BioCyc 1.0 C8H8O5 3,4-Dihydroxymandelic acid 184.03717 Tyrosinase P16930 UniProt SMILES O 1.0 4.1.1.28 false 4.1.1.28 L-Dopa + Oxygen + Tetrahydrobiopterin → 4a-Hydroxytetrahydrobiopterin + Dopamine LEFT_TO_RIGHT 4573572 ChemSpider CPD-782 BioCyc 1.0 P09172 UniProt 124 ChemSpider 328-42-7 CAS SMILES N[C@@H](CC1=CC=C(O)C=C1)C(O)=O CHEBI:15846 ChEBI 1.0 53-59-8 CAS Alcohol dehydrogenase 1A 1038 PubChem-compound GO:0005829 GENE ONTOLOGY 10189562 ChemSpider C5H6O5 Oxoglutaric acid 146.02153 CHEBI:16908 ChEBI Ammonia 4430-97-1 25520-73-4 CAS ADENOSYL-HOMO-CYS BioCyc SMILES OC(=O)C(=O)CC1=CC=C(O)C=C1 C21H30N7O17P3 NADPH 745.0911 Aldehyde dehydrogenase, dimeric NADP-preferring C21H29N7O17P3 NADP 744.08325 C8H11NO3 Norepinephrine 169.0739 4444078 ChemSpider 1.0 51-43-4 CAS HMDB0000208 HMDB 681 PubChem-compound CHEBI:742324 ChEBI Reaction80 false L-Tyrosine + Oxoglutaric acid ↔ 4-Hydroxyphenylpyruvic acid + L-Glutamic acid REVERSIBLE 5816 PubChem-compound SMILES OC(=O)CCC(=O)C(O)=O HMDB0000217 HMDB HMDB0000216 HMDB CHEBI:27637 ChEBI GO:0005886 GENE ONTOLOGY 124-38-9 CAS C9H10O5 Vanillylmandelic acid 198.05283 Fumarylacetoacetase 1606 ChemSpider CHEBI:15414 ChEBI 1.0 SMILES NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](CO[P@](O)(=O)O[P@](O)(=O)OC[C@H]2O[C@H]([C@H](OP(O)(O)=O)[C@@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1O HMDB0000221 HMDB SMILES NC[C@H](O)C1=CC(O)=C(O)C=C1 4-FUMARYL-ACETOACETATE BioCyc HMDB0000223 HMDB SMILES NC(=O)C1=CN(C=CC1)[C@H]1O[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2O[C@@H]([C@@H](OP(O)(O)=O)[C@H]2O)N2C=NC3=C(N)N=CN=C23)[C@H](O)[C@@H]1O 2.0 GLT BioCyc 7664-41-7 CAS Phenylalanine and Tyrosine Metabolism SubPathway 53-57-6 CAS 1.0 51-67-2 CAS Homovanillic acid S-ADENOSYLMETHIONINE BioCyc 460 PubChem-compound CHEBI:1127735 ChEBI 222 PubChem-compound SMILES CN C04185 KEGG Compound Tyrosinemia, Transient, of the Newborn CHEBI:27852 ChEBI 1237 PubChem-compound 1.0 BTO:0000049 BRENDA TISSUE ONTOLOGY C00822 KEGG Compound SMILES N[C@@H](CC1=CC(O)=C(O)C=C1)C(O)=O C8H8O4 3,4-Dihydroxybenzeneacetic acid 168.04225 5001-33-2 CAS Amiloride-sensitive amine oxidase [copper-containing] Ascorbic acid HMDB0001336 HMDB SMILES N[C@@H](CC(O)=O)C(O)=O Pyrocatechol CHEBI:60872 ChEBI 74-89-5 CAS 5707-55-1 CAS SMILES NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1O SMILES OC(=O)C1=CC2=C(N1)C=C(O)C(O)=C2 119405 PubChem-compound 210328 PubChem-compound 2.0 C7H8O2 Guaiacol 124.05243 5459802 PubChem-compound 2.0 S-Adenosylmethionine HMDB0000819 HMDB SMILES [H][C@@]1(OC(=O)C(=O)C1=O)[C@H](O)CO 77371 ChemSpider SMILES OC(=O)CC(=O)CC(=O)\C=C\C(O)=O 1.0 120-80-9 CAS 106504 ChemSpider Homo sapiens 6329 PubChem-compound 388299 ChemSpider O2 Oxygen 31.98983 Adrenal Medulla 151725 PubChem-compound 1.0 CHEBI:16526 ChEBI 129803 PubChem-compound C9H8O4 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid 180.04225 SMILES N[C@@H](CC1=CC(=O)C(=O)C=C1)C(O)=O CHEBI:27404 ChEBI CHEBI:27406 ChEBI Metanephrine 1.0 3.7.1.2 false 3.7.1.2 4-Fumarylacetoacetic acid + Water → Acetoacetic acid + Fumaric acid LEFT_TO_RIGHT 89762-39-0 CAS 289 PubChem-compound 1.0 70110-58-6 CAS SMILES OC1=CC=CC=C1O 1.0 5893 PubChem-compound P46952 UniProt Oxygen CHEBI:41941 ChEBI 5886 PubChem-compound C00642 KEGG Compound L-DEHYDRO-ASCORBATE BioCyc Methylamine 280 PubChem-compound 1.0 C01502 KEGG Compound CHEBI:545959 ChEBI 439260 PubChem-compound SMILES O=C1C=C2NC=CC2=CC1=O SMILES N[C@@H](CCSC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N)C(O)=O 2.0 3,4-Dihydroxymandelic acid Reaction1118 false L-Aspartic acid + Oxoglutaric acid → L-Glutamic acid + Oxalacetic acid LEFT_TO_RIGHT 541-50-4 CAS CHEBI:17895 ChEBI C00425 KEGG Compound 1.0 HMDB0001967 HMDB 24762165 PubChem-compound 1.0 1.0 2.1.1.28 false 2.1.1.28 Norepinephrine + S-Adenosylmethionine → Epinephrine + S-Adenosylhomocysteine LEFT_TO_RIGHT P17174 UniProt ReactionCatalysis117 ACTIVATION ReactionCatalysis118 ACTIVATION CHEBI:27683 ChEBI Homogentisate 1,2-dioxygenase 4-MALEYL-ACETOACETATE BioCyc