Tryptophan metabolism (Homo sapiens)

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(Z)-5-Oxohex-2-enedioate3-HydroxykynurenamineGlucobrassicin5-HydroxyindolepyruvateOxaloacetateL-Tryptophanyl-tRNA3-Hydroxy-L-kynurenine2-Amino-3-carboxymuconate2-Aminomuconate2-AminomuconateKynurenate5-HydroxykynurenamineCinnavalininate3-Methyldioxyindole3-MethylindolepyruvateIndole-3-ethanol5-Hydroxyindoleacetylglycine2-FormaminobenzoylacetateIndole-3-acetaldoxime4-(2-Amino-5-hydroxyphenyl)-2,4-dioxobutanoate2-FormylaminobenzaldehydeIsophenoxazine5-(3'-Carboxy-3'-oxopropyl) -4,6-dihydroxypicolinateIndolepyruvate7,8-DihydroxykynurenateFormylanthranilate5-(3'-Carboxy-3'-oxopropenyl)-4,6-dihydroxypicolin3-Methoxyanthranilate8-MethoxykynurenateIndole-3-acetaldehydeQuinolinateIndole-3-acetate3-IndoleglycolaldehydeAnthranilate3-(2-Aminoethyl)-1H-indol-5-olIndolelactateC01144N-Acetylindoxyl5-MethoxyindoleacetateFormyl-N-acetyl-5-methoxykynurenamineBenzoate degradation via hydroxylation2-OxoglutarateAnthranilate6-Hydroxykynurenate4-(2-Aminophenyl)-2,4-dioxobutanoate3-Hydroxyanthranilate5-(2'-Formylethyl)-4,6-dihydroxypicolinate5-Hydroxyindoleacetate2,3-Dihydroxyindole7,8-Dihydro-7,8-dihydroxykynurenate6-HydroxyindolelactateFormyl-5-hydroxykynurenamine4,8-Dihydroxyquinoline2-OxoadipateCYP2J2GCDHDHCR241.13.12.3Nicotinate and nicotinamide metabolismACAT1N-MethyltryptamineCyp2d2CYP2C184,6-DihydroxyquinolineCyp2b151.2.1.32WARSAADAT2-AminophenolTryptamineAANATHADH2AFMID2.6.1.271.3.1.185-HydroxykynurenineHRMT1L24.1.99.13.5.99.5CATCYP2A131.13.99.3N-MethylserotoninKYNUHRMT1L2HADHSCDDCALDH3A21.13.11.231.13.11.173.2.1.1471.14.99.24.1.1.43ECHS1ASMTCYP19A13.5.1.91.4.3.21.14.16.3Cyp2a26-HydroxymelatoninKYNUIndoleCYP3A41.14.16.-Aldh1a4HAAO1.5.1.-Cyp2c395-MethoxytryptamineGlutaryl-CoAASMT2.6.1.27AADAT4.2.1.84L-Tryptophan2.1.1.47Cyp2a1ALDH1A1Phenylalanine, Tyrosine and Tryptophan metabolismALDH2Indole-3-acetamide1.13.11.-L-Kynurenine5-Hydroxy-L-tryptophanINMT1.1.1.1911.1.1.110N-AcetylserotoninACMSDN-AcetylisatinDDCMelatoninCyp2c121.7.3.2CYP1A1Aldh1a42.1.1.49Crotonoyl-CoA3-IndoleacetonitrileABP1Acetoacetyl-CoACYP1B13.5.1.4TPH15-Hydroxy-N-formylkynurenineCYP2F1MAOBGCDHCYP7B1DDC5-Hydroxyindoleacetaldehyde2.6.1.27MAOBGlycolysis/Gluconeogenesis1.2.3.71.13.11.10Benzoate degradation via hydroxylationMAOBFormylkynurenineOGDH4.1.1.-INDOINDOTDO2ALDH9A1Xanthurenic acidALDH1A2ALDH21.2.1.-4-(2-Amino-3-hydroxyphenyl)-2,4-dioxobutanoateKYNU1.1.1.190CYP4F12ALDH1A23.5.1.49ALDH3A2CYP2E1Acetyl-CoA5-(2'-Carboxyethyl)-4,6-Dihydroxypicolinate1.10.3.4CYP1A2ALDH9A13.5.5.11.14.13.9HRMT1L2MAOBINDOALDH1A1AOX16.3.2.-


Description

Converted from rat to human using ortholog information. Originally adapted from: KEGG.

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Quality Tags

Ontology Terms

 

Bibliography

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  1. Qian Han, Tao Cai, Danilo A. Tagle, Jianyong Li; ''Structure, expression, and function of kynurenine aminotransferases in human and rodent brains''; Cell Mol Life Sci., 2010 PubMed Europe PMC Scholia
  2. Jessica M Yano, Kristie Yu, Gregory P Donaldson, Gauri G Shastri, Phoebe Ann, Liang Ma, Cathryn R Nagler, Rustem F Ismagilov, Sarkis K Mazmanian, Elaine Y Hsiao; ''Indigenous bacteria from the gut microbiota regulate host serotonin biosynthesis''; Cell, 2015 PubMed Europe PMC Scholia
  3. Allison Agus, Julien Planchais, Harry Sokol 2; ''Gut Microbiota Regulation of Tryptophan Metabolism in Health and Disease''; Cell Host Microbe, 2018 PubMed Europe PMC Scholia
  4. ''''; https://www.genome.jp/dbget-bin/www_bget?pathway+rno00380,
  5. Kan Gao, Chun-Long Mu, Aitak Farzi, Wei-Yun Zhu; ''Tryptophan Metabolism: A Link Between the Gut Microbiota and Brain''; Adv Nutr ., 2020 PubMed Europe PMC Scholia
  6. Mona Dehhaghi, Hamed Kazemi Shariat Panahi, Gilles J Guillemin; ''Microorganisms, Tryptophan Metabolism, and Kynurenine Pathway: A Complex Interconnected Loop Influencing Human Health Status''; Int J Tryptophan Res., 2019 PubMed Europe PMC Scholia
  7. Gary M Mawe, Jill M Hoffman; ''Serotonin signalling in the gut--functions, dysfunctions and therapeutic targets''; Nat Rev Gastroenterol Hepatol., 2013 PubMed Europe PMC Scholia
  8. Jing Gao, Kang Xu, Hongnan Liu, Gang Liu, Miaomiao Bai, Can Peng, Tiejun Li, Yulong Yin; ''''; , PubMed Europe PMC Scholia
  9. Camille Martin-Gallausiaux, Pierre Larraufie, Anne Jarry, Fabienne Béguet-Crespe, Ludovica Marinelli, Florence Ledue, Frank Reimann, Hervé M Blottière, Nicolas Lapaque; ''Butyrate Produced by Commensal Bacteria Down-Regulates Indolamine 2,3-Dioxygenase 1 ( IDO-1) Expression via a Dual Mechanism in Human Intestinal Epithelial Cells''; Front Immunol., 2018 PubMed Europe PMC Scholia
  10. G Clarke, S Grenham, P Scully, P Fitzgerald, R D Moloney, F Shanahan, T G Dinan, J F Cryan; ''The microbiome-gut-brain axis during early life regulates the hippocampal serotonergic system in a sex-dependent manner''; Mol Psychiatry, 2013 PubMed Europe PMC Scholia
  11. Denisse Bravo, Anilei Hoare, Cristopher Soto, Manuel A Valenzuela, Andrew Fg Quest; ''Helicobacter pylori in human health and disease: Mechanisms for local gastric and systemic effects''; World J Gastroenterol., 2018 PubMed Europe PMC Scholia

History

View all...
CompareRevisionActionTimeUserComment
122957view14:15, 3 June 2022DeSlOntology Term : 'indoleamine and related compounds metabolic pathway' added !
122956view14:14, 3 June 2022DeSlOntology Term : 'indoleamine and related compounds biosynthetic pathway' added !
122955view14:13, 3 June 2022DeSlOntology Term : 'type EC enteroendocrine cell' added !
122954view14:13, 3 June 2022DeSlOntology Term : 'enterochromaffin-like cell' added !
122953view14:13, 3 June 2022DeSlOntology Term : 'regulatory pathway' added !
122952view14:12, 3 June 2022DeSlOntology Term : 'signaling pathway' added !
122951view14:12, 3 June 2022DeSlOntology Term : 'classic metabolic pathway' added !
122950view14:12, 3 June 2022DeSlOntology Term : 'aryl hydrocarbon receptor signaling pathway' added !
122949view14:12, 3 June 2022DeSlOntology Term : 'serotonin secreting cell' added !
122948view14:12, 3 June 2022DeSlOntology Term : 'kynurenine metabolic pathway' added !
122947view14:11, 3 June 2022DeSlOntology Term : 'tryptophan degradation pathway' added !
122946view14:11, 3 June 2022DeSlOntology Term : 'tryptophan biosynthetic pathway' added !
122945view14:10, 3 June 2022DeSlRemoved unconnected interaction
122944view14:05, 3 June 2022DeSlAdded serotonin stimuli
122943view13:54, 3 June 2022DeSlAdded HDAC regulation of IDO info.
122942view13:43, 3 June 2022DeSlAdded influence of butyrate to kynurenic PW
122941view13:20, 3 June 2022DeSlAdded details from Fig. 1 PMID:31825083
122940view13:09, 3 June 2022DeSlAdded more details from PMID: 31258331, Fig. 3
122939view12:48, 3 June 2022DeSlAdded more details on kynurenine PW
122938view12:30, 3 June 2022DeSlAdded more details from Agus et al to description.
122937view12:27, 3 June 2022DeSlAdded last step of Fig.2
122936view12:19, 3 June 2022DeSlFinalized annotation of INDOLE microbial genes/proteins
122935view11:48, 3 June 2022DeSlAdded more details for legend
122934view11:43, 3 June 2022DeSlAdded more microbial interactions to PW
122933view11:32, 3 June 2022DeSlAdded first microbial pathway interactions
122932view11:11, 3 June 2022DeSlAdded refs to PW
122931view11:06, 3 June 2022DeSlAdded more lit. refs to description
122928view10:07, 3 June 2022DeSlConnected unconnected line
122927view10:06, 3 June 2022DeSlAdded latest missing metabolite IDs.
122926view10:02, 3 June 2022DeSlUpdated last section of PW
122924view09:29, 3 June 2022DeSlChecked bottom part
122922view08:48, 3 June 2022DeSlChecked left middle section
122919view08:18, 3 June 2022DeSlStarting to remove elements not relevant for species.
119262view07:46, 23 June 2021Finterlyadded KEGG pathway info to publicationXref
113999view21:46, 16 December 2020EgonwAnother pathway clickable
106518view23:30, 5 September 2019Khanspersadded reference
106203view12:09, 16 August 2019MaintBotHMDB identifier normalization
105847view23:14, 15 August 2019KhanspersModified description
104898view15:43, 23 June 2019EgonwReplaced secondary ChEBI identifiers with a primary identifiers.
104829view14:28, 19 June 2019Fehrhartadded some more metabolite IDs
104828view14:20, 19 June 2019Fehrhartadded metabolite IDs
104821view12:57, 19 June 2019FehrhartModified description
103977view02:10, 20 April 2019AlexanderPicoFixed EC6.3.2.-
102311view21:09, 17 December 2018KhanspersModified description
102310view21:08, 17 December 2018Khanspersremoved GenMAPP comment
94086view12:40, 18 August 2017DeSlModified description
93713view12:41, 11 August 2017DeSlModified description
85055view10:47, 10 April 2016EgonwReplaced a Wikipedia ID with a ChEBI ID.
79226view18:51, 15 March 2015EgonwAdded a number of missing metabolite Chemspider identifiers (based on IUPAC names).
77387view12:04, 4 September 2014EgonwAdded a number of missing metabolite Chemspider identifiers (based on IUPAC names).

External references

DataNodes

View all...
NameTypeDatabase referenceComment
(Z)-5-Oxohex-2-enedioateMetabolite(Z)-5-Oxohex-2-enedioate
1.1.1.110GeneProduct1.1.1.110 (Enzyme Nomenclature)
1.1.1.190GeneProduct1.1.1.190 (Enzyme Nomenclature)
1.1.1.191GeneProduct1.1.1.191 (Enzyme Nomenclature)
1.10.3.4GeneProduct1.10.3.4 (Enzyme Nomenclature)
1.13.11.-GeneProduct1.13.11.- (Enzyme Nomenclature)
1.13.11.10GeneProduct1.13.11.10 (Enzyme Nomenclature)
1.13.11.17GeneProduct1.13.11.17 (Enzyme Nomenclature)
1.13.11.23GeneProduct1.13.11.23 (Enzyme Nomenclature)
1.13.12.3GeneProduct1.13.12.3 (Enzyme Nomenclature)
1.13.99.3GeneProduct1.13.99.3 (Enzyme Nomenclature)
1.14.13.9GeneProduct1.14.13.9 (Enzyme Nomenclature)
1.14.16.-GeneProduct1.14.16.- (Enzyme Nomenclature)
1.14.16.3GeneProduct1.14.16.3 (Enzyme Nomenclature)
1.14.99.2GeneProduct1.14.99.2 (Enzyme Nomenclature)
1.2.1.-GeneProduct1.2.1.- (Enzyme Nomenclature)
1.2.1.32GeneProduct1.2.1.32 (Enzyme Nomenclature)
1.2.3.7GeneProduct1.2.3.7 (Enzyme Nomenclature)
1.3.1.18GeneProduct1.3.1.18 (Enzyme Nomenclature)
1.4.3.2GeneProduct1.4.3.2 (Enzyme Nomenclature)
1.5.1.-GeneProduct1.5.1.- (Enzyme Nomenclature)
1.7.3.2GeneProduct1.7.3.2 (Enzyme Nomenclature)
2,3-DihydroxyindoleMetabolite20546 (Chemspider)
2-Amino-3-carboxymuconateMetabolite2-Amino-3-carboxymuconate
2-AminomuconateMetabolite2-Aminomuconate
2-AminophenolMetabolite95-55-6 (CAS) 2-Aminophenol
2-Formamino benzoylacetateMetabolite2-Formaminobenzoylacetate
2-FormylaminobenzaldehydeMetabolite389 (Chemspider)
2-OxoadipateMetabolite19951093 (Chemspider) 2-Oxoadipate
2-OxoglutarateMetabolite144236 (Chemspider) 2-Oxoglutarate
2.1.1.47GeneProduct2.1.1.47 (Enzyme Nomenclature)
2.1.1.49GeneProduct2.1.1.49 (Enzyme Nomenclature)
2.6.1.27GeneProduct2.6.1.27 (Enzyme Nomenclature)
3-(2-Aminoethyl) -1H-indol-5-olMetabolite5013 (Chemspider) 3-(2-Aminoethyl)-1H-indol-5-ol
3-Hydroxy- L-kynurenineMetabolite3-Hydroxy-L-kynurenine
3-HydroxyanthranilateMetabolite7822291 (Chemspider) 3-Hydroxyanthranilate
3-HydroxykynurenamineMetabolite3-Hydroxykynurenamine
3-IndoleacetonitrileMetabolite771-51-7 (CAS) 3-Indoleacetonitrile
3-IndoleglycolaldehydeMetabolite388979 (Chemspider)
3-MethoxyanthranilateMetabolite7827589 (Chemspider) 3-Methoxyanthranilate
3-MethyldioxyindoleMetabolite
3-MethylindolepyruvateMetabolite3-Methylindolepyruvate
3.2.1.147GeneProduct3.2.1.147 (Enzyme Nomenclature)
3.5.1.4GeneProduct3.5.1.4 (Enzyme Nomenclature)
3.5.1.49GeneProduct3.5.1.49 (Enzyme Nomenclature)
3.5.1.9GeneProduct3.5.1.9 (Enzyme Nomenclature)
3.5.5.1GeneProduct3.5.5.1 (Enzyme Nomenclature)
3.5.99.5GeneProduct3.5.99.5 (Enzyme Nomenclature)
4,6-DihydroxyquinolineMetaboliteHMDB04077 (HMDB)
4,8-DihydroxyquinolineMetabolite389608 (Chemspider) 4,8-Dihydroxyquinoline
4-(2-Amino-3-hydroxyphenyl)-2,4-dioxobutanoateMetaboliteHMDB04083 (HMDB)
4-(2-Amino-5-hydroxyphenyl) -2,4-dioxobutanoateMetabolite389617 (Chemspider) 4-(2-Amino-5-hydroxyphenyl)-2,4-dioxobutanoate
4-(2-Aminophenyl)-2,4-dioxobutanoateMetabolite19951260 (Chemspider) 4-(2-Aminophenyl)-2,4-dioxobutanoate
4.1.1.-GeneProduct4.1.1.- (Enzyme Nomenclature)
4.1.1.43GeneProduct4.1.1.43 (Enzyme Nomenclature)
4.1.99.1GeneProduct4.1.99.1 (Enzyme Nomenclature)
4.2.1.84GeneProduct4.2.1.84 (Enzyme Nomenclature)
5-(2'-Carboxyethyl)-4,6-DihydroxypicolinateMetaboliteHMDB06794 (HMDB)
5-(2'-Formylethyl)-4,6-dihydroxypicolinateMetabolite30791294 (Chemspider) 5-(2'-Formylethyl)-4,6-dihydroxypicolinate
5-(3'-Carboxy-3'-oxopropenyl)-4,6-dihydroxypicolinMetabolite5-(3'-Carboxy-3'-oxopropenyl)-4,6-dihydroxypicolinate
5-(3'-Carboxy-3'-oxopropyl) -4,6-dihydroxypicolinateMetabolite30791292 (Chemspider) 5-(3'-Carboxy-3'-oxopropyl)-4,6-dihydroxypicolinate
5-Hydroxy-L-tryptophanMetaboliteHMDB00472 (HMDB)
5-Hydroxy-N-formylkynurenineMetaboliteHMDB04086 (HMDB)
5-HydroxyindoleacetaldehydeMetaboliteHMDB04073 (HMDB)
5-HydroxyindoleacetateMetabolite10637170 (Chemspider) 5-Hydroxyindoleacetate
5-HydroxyindoleacetylglycineMetabolite
5-HydroxyindolepyruvateMetabolite
5-HydroxykynurenamineMetabolite5-Hydroxykynurenamine
5-HydroxykynurenineMetabolite484-78-6 (CAS)
5-MethoxyindoleacetateMetabolite14533147 (Chemspider) 5-Methoxyindoleacetate
5-MethoxytryptamineMetabolite608-07-1 (CAS)
6-HydroxyindolelactateMetabolite6-Hydroxyindolelactate
6-HydroxykynurenateMetabolite6-Hydroxykynurenate
6-HydroxymelatoninMetabolite2208-41-5 (CAS)
6.3.2.-GeneProduct6.3.2.- (Enzyme Nomenclature)
7,8-Dihydro-7,8-dihydroxykynurenateMetabolite7,8-Dihydro-7,8-dihydroxykynurenate
7,8-DihydroxykynurenateMetabolite7,8-Dihydroxykynurenate
8-MethoxykynurenateMetabolite8-Methoxykynurenate
AADATGeneProduct51166 (Entrez Gene)
AANATGeneProduct15 (Entrez Gene)
ABP1GeneProduct26 (Entrez Gene)
ACAT1GeneProduct38 (Entrez Gene)
ACMSDGeneProduct130013 (Entrez Gene)
AFMIDGeneProduct125061 (Entrez Gene)
ALDH1A1GeneProduct216 (Entrez Gene)
ALDH1A2GeneProduct8854 (Entrez Gene)
ALDH2GeneProduct217 (Entrez Gene)
ALDH3A2GeneProduct224 (Entrez Gene)
ALDH9A1GeneProduct223 (Entrez Gene)
AOX1GeneProduct316 (Entrez Gene)
ASMTGeneProduct438 (Entrez Gene)
Acetoacetyl-CoAMetaboliteC00332 (KEGG Compound)
Acetyl-CoAMetabolite72-89-9 (CAS) Acetyl-CoA
Aldh1a4GeneProduct
AnthranilateMetabolite4573598 (Chemspider) Anthranilate
Benzoate degradation via hydroxylationPathway
C01144Metabolite(S)-3-Hydroxybutanoyl-CoA
CATGeneProduct847 (Entrez Gene)
CYP19A1GeneProduct1588 (Entrez Gene)
CYP1A1GeneProduct1543 (Entrez Gene)
CYP1A2GeneProduct1544 (Entrez Gene)
CYP1B1GeneProduct1545 (Entrez Gene)
CYP2A13GeneProduct1553 (Entrez Gene)
CYP2C18GeneProduct1562 (Entrez Gene)
CYP2E1GeneProduct1571 (Entrez Gene)
CYP2F1GeneProduct1572 (Entrez Gene)
CYP2J2GeneProduct1573 (Entrez Gene)
CYP3A4GeneProduct1576 (Entrez Gene)
CYP4F12GeneProduct66002 (Entrez Gene)
CYP7B1GeneProduct9420 (Entrez Gene)
CinnavalininateMetaboliteCinnavalininate
Crotonoyl-CoAMetaboliteC00877 (KEGG Compound)
Cyp2a1GeneProduct
Cyp2a2GeneProduct
Cyp2b15GeneProduct
Cyp2c12GeneProduct
Cyp2c39GeneProduct
Cyp2d2GeneProduct
DDCGeneProduct1644 (Entrez Gene)
DHCR24GeneProduct1718 (Entrez Gene) predicted
ECHS1GeneProduct1892 (Entrez Gene)
Formyl-5-hydroxykynurenamineMetabolite
Formyl-N-acetyl-5- methoxykynurenamineMetaboliteFormyl-N-acetyl-5-methoxykynurenamine
FormylanthranilateMetaboliteFormylanthranilate
FormylkynurenineMetabolite1022-31-7 (CAS) Formylkynurenine
GCDHGeneProduct2639 (Entrez Gene) predicted
GlucobrassicinMetaboliteGlucobrassicin
Glutaryl-CoAMetaboliteC00527 (KEGG Compound)
Glycolysis/GluconeogenesisPathwayWP534 (WikiPathways)
HAAOGeneProduct23498 (Entrez Gene)
HADH2GeneProduct3028 (Entrez Gene)
HADHSCGeneProduct3033 (Entrez Gene)
HRMT1L2GeneProduct3276 (Entrez Gene)
INDOGeneProduct3620 (Entrez Gene)
INMTGeneProduct11185 (Entrez Gene)
Indole-3-acetaldehydeMetabolite778 (Chemspider) Indole-3-acetaldehyde
Indole-3-acetaldoximeMetabolite388896 (Chemspider) Indole-3-acetaldoxime
Indole-3-acetamideMetabolite879-37-8 (CAS) Indole-3-acetamide
Indole-3-acetateMetabolite779 (Chemspider) Indole-3-acetate
Indole-3-ethanolMetabolite10235 (Chemspider)
IndoleMetabolite120-72-9 (CAS)
IndolelactateMetabolite28571995 (Chemspider) Indolelactate
IndolepyruvateMetabolite24775813 (Chemspider) Indolepyruvate
IsophenoxazineMetaboliteIsophenoxazine
KYNUGeneProduct8942 (Entrez Gene)
KynurenateMetabolite4-Hydroxy-2-quinolinecarboxylic
L-KynurenineMetabolite343-65-7 (CAS) L-Kynurenine
L-TryptophanMetabolite73-22-3 (CAS)
L-Tryptophanyl-tRNAMetabolite
MAOBGeneProduct4129 (Entrez Gene)
MelatoninMetaboliteHMDB01389 (HMDB)
N-AcetylindoxylMetaboliteN-Acetylindoxyl
N-AcetylisatinMetabolite574-17-4 (CAS) N-Acetylisatin
N-AcetylserotoninMetabolite1210-83-9 (CAS) N-Acetylserotonin
N-MethylserotoninMetaboliteHMDB04369 (HMDB)
N-MethyltryptamineMetaboliteCHEBI:28136 (ChEBI)
Nicotinate and nicotinamide metabolismPathway
OGDHGeneProduct4967 (Entrez Gene)
OxaloacetateMetabolite2509917 (Chemspider) Oxaloacetate
Phenylalanine, Tyrosine and Tryptophan metabolismPathway
QuinolinateMetabolite2777129 (Chemspider)
TDO2GeneProduct6999 (Entrez Gene)
TPH1GeneProduct7166 (Entrez Gene)
TryptamineMetabolite61-54-1 (CAS)
WARSGeneProduct7453 (Entrez Gene)
Xanthurenic acidMetaboliteHMDB00881 (HMDB)

Annotated Interactions

No annotated interactions

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