Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:07:02 UTC |
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Update date | 2019-11-26 03:01:01 UTC |
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Primary ID | FDB006231 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | 5-Hydroxy-L-tryptophan |
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Description | 5-Hydroxy-L-tryptophan, also known as 5-HTP or levothym, belongs to the class of organic compounds known as serotonins. Serotonins are compounds containing a serotonin moiety, which consists of an indole that bears an aminoethyl a position 2 and a hydroxyl group at position 5. 5-Hydroxy-L-tryptophan exists in all living organisms, ranging from bacteria to humans. 5-Hydroxy-L-tryptophan has been detected, but not quantified in, several different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), domestic pigs (Sus scrofa domestica), french plantains (Musa X paradisiaca), and milk (cow). This could make 5-hydroxy-L-tryptophan a potential biomarker for the consumption of these foods. 5-Hydroxy-L-tryptophan, with regard to humans, has been found to be associated with several diseases such as ulcerative colitis, colorectal cancer, and crohn's disease; 5-hydroxy-L-tryptophan has also been linked to the inborn metabolic disorder aromatic l-amino acid decarboxylase deficiency. Based on a literature review a significant number of articles have been published on 5-Hydroxy-L-tryptophan. |
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CAS Number | 4350-09-8 |
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Structure | |
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Synonyms | |
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Predicted Properties | |
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Chemical Formula | C11H12N2O3 |
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IUPAC name | (2S)-2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoic acid |
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InChI Identifier | InChI=1S/C11H12N2O3/c12-9(11(15)16)3-6-5-13-10-2-1-7(14)4-8(6)10/h1-2,4-5,9,13-14H,3,12H2,(H,15,16)/t9-/m0/s1 |
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InChI Key | LDCYZAJDBXYCGN-VIFPVBQESA-N |
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Isomeric SMILES | N[C@@H](CC1=CNC2=C1C=C(O)C=C2)C(O)=O |
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Average Molecular Weight | 220.2246 |
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Monoisotopic Molecular Weight | 220.08479226 |
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Classification |
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Description | Belongs to the class of organic compounds known as serotonins. Serotonins are compounds containing a serotonin moiety, which consists of an indole that bears an aminoethyl a position 2 and a hydroxyl group at position 5. |
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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 | Tryptamines and derivatives |
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Direct Parent | Serotonins |
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Alternative Parents | |
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Substituents | - Serotonin
- Indolyl carboxylic acid derivative
- Alpha-amino acid
- Alpha-amino acid or derivatives
- 3-alkylindole
- L-alpha-amino acid
- Hydroxyindole
- Indole
- Aralkylamine
- 1-hydroxy-2-unsubstituted benzenoid
- Benzenoid
- Substituted pyrrole
- Heteroaromatic compound
- Pyrrole
- Amino acid
- Amino acid or derivatives
- Azacycle
- Carboxylic acid derivative
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Hydrocarbon derivative
- Organonitrogen compound
- Primary aliphatic amine
- Organic oxygen compound
- Organic nitrogen compound
- Organooxygen compound
- Primary amine
- Carbonyl group
- Organopnictogen compound
- Amine
- Organic oxide
- 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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Physiological effect | Health effect: |
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Disposition | Route of exposure: Source: Biological location: |
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Role | Indirect biological role: Industrial application: |
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Physico-Chemical Properties |
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Physico-Chemical Properties - Experimental | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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GC-MS | 5-Hydroxy-L-tryptophan, 4 TMS, GC-MS Spectrum | splash10-0006-0390000000-d4e36a90b7591787e67b | Spectrum | GC-MS | 5-Hydroxy-L-tryptophan, 3 TMS, GC-MS Spectrum | splash10-0006-1390000000-b0af49def87c0211653c | Spectrum | GC-MS | 5-Hydroxy-L-tryptophan, 3 TMS, GC-MS Spectrum | splash10-014i-0390000000-8b7f6cc8f51c032dd86d | Spectrum | GC-MS | 5-Hydroxy-L-tryptophan, non-derivatized, GC-MS Spectrum | splash10-014i-0390000000-88191cf8140abf0f3205 | Spectrum | GC-MS | 5-Hydroxy-L-tryptophan, non-derivatized, GC-MS Spectrum | splash10-0006-0290000000-a30ea02ff8d4d14ba7a4 | Spectrum | GC-MS | 5-Hydroxy-L-tryptophan, non-derivatized, GC-MS Spectrum | splash10-0006-0390000000-d4e36a90b7591787e67b | Spectrum | GC-MS | 5-Hydroxy-L-tryptophan, non-derivatized, GC-MS Spectrum | splash10-0006-1390000000-b0af49def87c0211653c | Spectrum | GC-MS | 5-Hydroxy-L-tryptophan, non-derivatized, GC-MS Spectrum | splash10-014i-0390000000-8b7f6cc8f51c032dd86d | Spectrum | Predicted GC-MS | 5-Hydroxy-L-tryptophan, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-00bd-4920000000-c1f07beecfc6ada179c1 | Spectrum | Predicted GC-MS | 5-Hydroxy-L-tryptophan, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-00di-9044000000-9dc0e361e3885451d81f | Spectrum | Predicted GC-MS | 5-Hydroxy-L-tryptophan, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 5-Hydroxy-L-tryptophan, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 5-Hydroxy-L-tryptophan, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 5-Hydroxy-L-tryptophan, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 5-Hydroxy-L-tryptophan, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 5-Hydroxy-L-tryptophan, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 5-Hydroxy-L-tryptophan, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 5-Hydroxy-L-tryptophan, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 5-Hydroxy-L-tryptophan, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 5-Hydroxy-L-tryptophan, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 5-Hydroxy-L-tryptophan, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 5-Hydroxy-L-tryptophan, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 5-Hydroxy-L-tryptophan, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 5-Hydroxy-L-tryptophan, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 5-Hydroxy-L-tryptophan, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-0udi-0790000000-a699ed429ebd1609f995 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-03e9-0900000000-bbd302f8ff188f6cf93d | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-053r-0900000000-6cc3ba396b1cfa8db1e6 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - , positive | splash10-053r-2900000000-90a465428eacaced71e2 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-0udi-0390000000-8d1a103c7fb1b7dfa685 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Positive | splash10-03di-0900000000-25de1fda6182de338d15 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 30V, Positive | splash10-053r-0900000000-e8cfeeeea0f83c87c0a3 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-0w29-0790000000-61308573c0d4d1caee8a | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 0V, Positive | splash10-0w90-0590000000-9c6aa4b5a920add9f8ea | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-03di-0930000000-074911d5bc17a486cbb0 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 0V, Positive | splash10-0uk9-0190000000-9d6cad9671c04310ac0c | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 30V, Positive | splash10-05ox-2900000000-08b2a2c24032d96597db | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Negative | splash10-000x-1900000000-9c83828dc6df75a0e798 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 30V, Negative | splash10-001l-1900000000-dc720fc8e93906bb0c67 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-014l-1970000000-6deb0cc19e89586090e6 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Negative | splash10-001l-0900000000-cab77201c86bda083dd0 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-053r-1900000000-b1c220623de477b387ee | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 30V, Positive | splash10-053r-0900000000-f7c54dfcc55add0c83d6 | 2021-09-20 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00b9-0950000000-e3f9fbda111b2109f630 | 2017-07-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-004i-0900000000-b21f3fecc8ae15c125de | 2017-07-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0002-0900000000-817e4d468ea1bf1a3bc3 | 2017-07-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014i-2190000000-65b1ee730ae09a2cd6a5 | 2017-07-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00di-9650000000-68d73bfc7c9dd0f880e1 | 2017-07-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00di-9600000000-c58badf19c5cbb2f4347 | 2017-07-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001i-1950000000-5df9078df2a62ba2dc7e | 2021-09-24 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 141 |
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ChEMBL ID | CHEMBL162789 |
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KEGG Compound ID | C01017 |
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Pubchem Compound ID | 144 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 17780 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | DB02959 |
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HMDB ID | HMDB00472 |
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CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
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EAFUS ID | Not Available |
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Dr. Duke ID | 5-HYDROXY-L-TRYPTOPHAN |
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BIGG ID | 36630 |
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KNApSAcK ID | C00001371 |
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HET ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | 5-HTP |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Not Available |
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Enzymes | |
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Pathways | |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | show |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
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