Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2006-02-21 08:10:09 UTC |
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Update Date | 2023-02-21 17:15:50 UTC |
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HMDB ID | HMDB0001855 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 5-Hydroxytryptophol |
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Description | 5-Hydroxytryptophol is a relatively minor metabolite of serotonin that is excreted primarily as the glucuronide conjugate in human urine. 5-Hydroxytryptophol becomes more important quantitatively during alcohol intoxication, when a shift in the metabolism of serotonin occurs from 5-hydroxyindole acetic acid toward increased (15-fold higher) formation of 5-hydroxytryptophol due to the inhibition of aldehyde dehydrogenase by ethanol-derived acetaldehyde. Urinary excretion of 5-hydroxytryptophol has also been shown to be markedly increased for several hours following intake of foods rich in serotonin, such as bananas. Wide interspecies variation has been reported in the metabolism serotonin to 5-hydroxytryptophol; 5-Hydroxytryptophol makes up 35% of the excreted serotonin metabolites in the rat on average and 10 to 20% in several other species. Human UDP-glucuronosyltransferase 1A6 (UGT1A6) plays a predominant role in the glucuronidation of 5-hydroxytryptophol by human liver microsomes. (PMID 15258112 ). |
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Structure | InChI=1S/C10H11NO2/c12-4-3-7-6-11-10-2-1-8(13)5-9(7)10/h1-2,5-6,11-13H,3-4H2 |
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Synonyms | Value | Source |
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5-HTOL | HMDB | 5-Hydroxy-1H-indole-3-ethanol | HMDB | 5-Hydroxy-1H-indole-3-ethanol(9ci) | HMDB | 5-Hydroxy-3-indole | HMDB | 5-Hydroxy-3-indoleacetic acid | HMDB | 5-Hydroxy-indole-acetic acid | HMDB | 5-Hydroxyindoacetic acid | HMDB | 5-Hydroxyindol | HMDB | 5-Hydroxyindolacetate | HMDB | 5-Hydroxyindolacetic acid | HMDB | 5-Hydroxyindole-3-ethanol | HMDB | 5-Hydroxyindole-acetic acid | HMDB | Hydroxyindoleacetic acid | HMDB | Hydroxytryptophol | HMDB, MeSH |
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Chemical Formula | C10H11NO2 |
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Average Molecular Weight | 177.1998 |
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Monoisotopic Molecular Weight | 177.078978601 |
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IUPAC Name | 3-(2-hydroxyethyl)-1H-indol-5-ol |
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Traditional Name | hydroxytryptophol |
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CAS Registry Number | 154-02-9 |
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SMILES | OCCC1=CNC2=CC=C(O)C=C12 |
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InChI Identifier | InChI=1S/C10H11NO2/c12-4-3-7-6-11-10-2-1-8(13)5-9(7)10/h1-2,5-6,11-13H,3-4H2 |
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InChI Key | KQROHCSYOGBQGJ-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as hydroxyindoles. These are organic compounds containing an indole moiety that carries a hydroxyl group. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Indoles and derivatives |
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Sub Class | Hydroxyindoles |
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Direct Parent | Hydroxyindoles |
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Alternative Parents | |
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Substituents | - 3-alkylindole
- Hydroxyindole
- Indole
- 1-hydroxy-2-unsubstituted benzenoid
- Substituted pyrrole
- Benzenoid
- Heteroaromatic compound
- Pyrrole
- Azacycle
- Organic oxygen compound
- Alcohol
- Primary alcohol
- Organooxygen compound
- Organonitrogen compound
- Organic nitrogen compound
- Hydrocarbon derivative
- Organopnictogen compound
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Ontology |
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Not Available | Not Available |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Experimental Collision Cross Sections |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Retention Times UnderivatizedChromatographic Method | Retention Time | Reference |
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Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022. | 2.83 minutes | 32390414 | Predicted by Siyang on May 30, 2022 | 9.4801 minutes | 33406817 | Predicted by Siyang using ReTip algorithm on June 8, 2022 | 1.5 minutes | 32390414 | AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid | 29.2 seconds | 40023050 | Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid | 1255.3 seconds | 40023050 | Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid | 301.8 seconds | 40023050 | Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid | 96.1 seconds | 40023050 | Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid | 163.3 seconds | 40023050 | RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 204.3 seconds | 40023050 | Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid | 299.5 seconds | 40023050 | BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid | 260.8 seconds | 40023050 | HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate) | 139.6 seconds | 40023050 | UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid | 640.3 seconds | 40023050 | BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid | 264.1 seconds | 40023050 | UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid | 996.4 seconds | 40023050 | SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 272.2 seconds | 40023050 | RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 225.3 seconds | 40023050 | MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate | 530.6 seconds | 40023050 | KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA | 255.9 seconds | 40023050 | Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water | 181.7 seconds | 40023050 |
Predicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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5-Hydroxytryptophol,1TMS,isomer #1 | C[Si](C)(C)OCCC1=C[NH]C2=CC=C(O)C=C12 | 2096.0 | Semi standard non polar | 33892256 | 5-Hydroxytryptophol,1TMS,isomer #2 | C[Si](C)(C)OC1=CC=C2[NH]C=C(CCO)C2=C1 | 2026.3 | Semi standard non polar | 33892256 | 5-Hydroxytryptophol,1TMS,isomer #3 | C[Si](C)(C)N1C=C(CCO)C2=CC(O)=CC=C21 | 2087.7 | Semi standard non polar | 33892256 | 5-Hydroxytryptophol,2TMS,isomer #1 | C[Si](C)(C)OCCC1=C[NH]C2=CC=C(O[Si](C)(C)C)C=C12 | 2063.7 | Semi standard non polar | 33892256 | 5-Hydroxytryptophol,2TMS,isomer #2 | C[Si](C)(C)OCCC1=CN([Si](C)(C)C)C2=CC=C(O)C=C12 | 2112.9 | Semi standard non polar | 33892256 | 5-Hydroxytryptophol,2TMS,isomer #3 | C[Si](C)(C)OC1=CC=C2C(=C1)C(CCO)=CN2[Si](C)(C)C | 2070.4 | Semi standard non polar | 33892256 | 5-Hydroxytryptophol,3TMS,isomer #1 | C[Si](C)(C)OCCC1=CN([Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C12 | 2099.5 | Semi standard non polar | 33892256 | 5-Hydroxytryptophol,3TMS,isomer #1 | C[Si](C)(C)OCCC1=CN([Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C12 | 2173.8 | Standard non polar | 33892256 | 5-Hydroxytryptophol,3TMS,isomer #1 | C[Si](C)(C)OCCC1=CN([Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C12 | 2147.5 | Standard polar | 33892256 | 5-Hydroxytryptophol,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OCCC1=C[NH]C2=CC=C(O)C=C12 | 2366.6 | Semi standard non polar | 33892256 | 5-Hydroxytryptophol,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC1=CC=C2[NH]C=C(CCO)C2=C1 | 2313.5 | Semi standard non polar | 33892256 | 5-Hydroxytryptophol,1TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)N1C=C(CCO)C2=CC(O)=CC=C21 | 2354.7 | Semi standard non polar | 33892256 | 5-Hydroxytryptophol,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OCCC1=C[NH]C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12 | 2585.6 | Semi standard non polar | 33892256 | 5-Hydroxytryptophol,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OCCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O)C=C12 | 2599.2 | Semi standard non polar | 33892256 | 5-Hydroxytryptophol,2TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)C(CCO)=CN2[Si](C)(C)C(C)(C)C | 2583.4 | Semi standard non polar | 33892256 | 5-Hydroxytryptophol,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OCCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12 | 2801.7 | Semi standard non polar | 33892256 | 5-Hydroxytryptophol,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OCCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12 | 2796.0 | Standard non polar | 33892256 | 5-Hydroxytryptophol,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OCCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12 | 2478.9 | Standard polar | 33892256 |
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Disease References | Leukemia |
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- Curtius HC, Wolfensberger M, Redweik U, Leimbacher W, Maibach RA, Isler W: Mass fragmentography of 5-hydroxytryptophol and 5-methoxytryptophol in human cerebrospinal fluid. J Chromatogr. 1975 Oct 29;112:523-31. [PubMed:1184685 ]
| Schizophrenia |
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- Harnryd C, Bjerkenstedt L, Grimm VE, Sedvall G: Reduction of MOPEG levels in cerebrospinal fluid of psychotic women after electroconvulsive treatment. Psychopharmacology (Berl). 1979 Aug 8;64(2):131-4. [PubMed:115032 ]
| Parkinson's disease |
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- Dizdar N, Kagedal B, Lindvall B: Treatment of Parkinson's disease with NADH. Acta Neurol Scand. 1994 Nov;90(5):345-7. [PubMed:7887134 ]
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General References | - Curtius HC, Wolfensberger M, Redweik U, Leimbacher W, Maibach RA, Isler W: Mass fragmentography of 5-hydroxytryptophol and 5-methoxytryptophol in human cerebrospinal fluid. J Chromatogr. 1975 Oct 29;112:523-31. [PubMed:1184685 ]
- Krishnaswamy S, Hao Q, Von Moltke LL, Greenblatt DJ, Court MH: Evaluation of 5-hydroxytryptophol and other endogenous serotonin (5-hydroxytryptamine) analogs as substrates for UDP-glucuronosyltransferase 1A6. Drug Metab Dispos. 2004 Aug;32(8):862-9. [PubMed:15258112 ]
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