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Tryptophan | C11H12N2O2 - Pubchem 07.01.2021 Tryptophan | C11H12N2O2 - PubChem COVID-19 is an emerging, rapidly evolving situation. Get the latest public health information from CDC: https://www.coronavirus.gov. Get the latest research from NIH: https://www.nih.gov/coronavirus. COMPOUND SUMMARY Tryptophan PubChem CID 6305 Structure 2D 3D Crystal Find Similar Structures Chemical Safety Laboratory Chemical Safety Summary (LCSS) Datasheet Molecular Formula C11H12N2O2 L-tryptophan 73-22-3 tryptophan Synonyms L-Tryptophane (S)-Tryptophan More... Molecular Weight 204.22 g/mol Modify Create Dates 2021-01-02 2004-09-16 Tryptophan is the least plentiful of all 22 amino acids and an essential amino acid in humans (provided by food), Tryptophan is found in most proteins and a precursor of serotonin. Tryptophan is converted to 5-hydroxy-tryptophan (5-HTP), converted in turn to serotonin, a neurotransmitter essential in regulating appetite, sleep, mood, and pain. Tryptophan is a natural sedative and present in dairy products, meats, brown rice, fish, and soybeans. (NCI04) NCI Thesaurus (NCIt) Source: NCI Thesaurus (NCIt) Record Name: Tryptophan URL: https://ncit.nci.nih.gov/ncitbrowser/ConceptReport.jsp?dictionary=NCI_Thesaurus&ns=NCI_Thesaurus&code=C29603 Description: NCI Thesaurus (NCIt) provides reference terminology for many systems. It covers vocabulary for clinical care, translational and basic research, and public information and administrative activities. License Note: Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source. License URL: https://www.cancer.gov/policies/copyright-reuse L-tryptophan is the L-enantiomer of tryptophan. It has a role as an antidepressant, a nutraceutical, a micronutrient, a plant metabolite, a human metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a mouse metabolite. It is an erythrose 4-phosphate/phosphoenolpyruvate family amino acid, a proteinogenic amino acid, a tryptophan and a L-alpha-amino acid. It is a conjugate base of a L-tryptophanium. It is a conjugate acid of a L-tryptophanate. It is an enantiomer of a D-tryptophan. It is a tautomer of a L-tryptophan zwitterion. ChEBI Source: ChEBI Record Name: L-tryptophan URL: http://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:16828 Description: Chemical Entities of Biological Interest (ChEBI) is a database and ontology of molecular entities focused on 'small' chemical compounds, that is part of the Open Biomedical Ontologies effort. The term "molecular entity" refers to any constitutionally or isotopically distinct atom, molecule, ion, ion pair, radical, radical ion, complex, conformer, etc., identifiable as a separately distinguishable entity. L-tryptophan is a white powder with a flat taste. An essential amino acid; occurs in isomeric forms. (NTP, 1992) CAMEO Chemicals Source: CAMEO Chemicals Record Name: L-TRYPTOPHAN URL: https://cameochemicals.noaa.gov/chemical/21204 Description: CAMEO Chemicals is a chemical database designed for people who are involved in hazardous material incident response and planning. CAMEO Chemicals contains a library with thousands of datasheets containing response-related information and recommendations for hazardous materials that are commonly transported, used, or stored in the United States. CAMEO Chemicals was developed by the National Oceanic and Atmospheric Administration's Office of Response and Restoration in partnership with the Environmental Protection Agency's Office of Emergency Management. License Note: CAMEO Chemicals and all other CAMEO products are available at no charge to those organizations and individuals (recipients) responsible for the safe handling of chemicals. However, some of the chemical data itself is subject to the copyright restrictions of the companies or organizations that provided the data. License URL: https://cameochemicals.noaa.gov/help/reference/terms_and_conditions.htm?d_f=false https://pubchem.ncb.nlm.nh.gov/compound/Tryptophan#secton=Pathways 1/68 07.01.2021 Tryptophan | C11H12N2O2 - PubChem 1 Structures 1.1 2D Structure Chemical Structure Depiction PubChem 1.2 3D Conformer Interactive Chemical Structure Model Ball and Stick Sticks Wire-Frame Space-Filling Show Hydrogens Animate PubChem 1.3 Crystal Structures Showing 1 of 3 View More CCDC Number 986568 Crystal Structure Data DOI:10.5517/cc123lsk Crystal Structure Depiction Associated Article DOI:10.1107/S0108768112033484 The Cambridge Structural Database https://pubchem.ncb.nlm.nh.gov/compound/Tryptophan#secton=Pathways 2/68 07.01.2021 Tryptophan | C11H12N2O2 - PubChem 2 Biologic Description SVG Image IUPAC Condensed H-Trp-OH Sequence W PLN H-W-OH HELM PEPTIDE1{W}$$$$ IUPAC L-tryptophan PubChem https://pubchem.ncb.nlm.nh.gov/compound/Tryptophan#secton=Pathways 3/68 07.01.2021 Tryptophan | C11H12N2O2 - PubChem 3 Names and Identifiers 3.1 Computed Descriptors 3.1.1 IUPAC Name (2S)-2-amino-3-(1H-indol-3-yl)propanoic acid Computed by LexiChem 2.6.6 (PubChem release 2019.06.18) PubChem 3.1.2 InChI InChI=1S/C11H12N2O2/c12-9(11(14)15)5-7-6-13-10-4-2-1-3-8(7)10/h1-4,6,9,13H,5,12H2,(H,14,15)/t9-/m0/s1 Computed by InChI 1.0.5 (PubChem release 2019.06.18) PubChem 3.1.3 InChI Key QIVBCDIJIAJPQS-VIFPVBQESA-N Computed by InChI 1.0.5 (PubChem release 2019.06.18) PubChem 3.1.4 Canonical SMILES C1=CC=C2C(=C1)C(=CN2)CC(C(=O)O)N Computed by OEChem 2.1.5 (PubChem release 2019.06.18) PubChem 3.1.5 Isomeric SMILES C1=CC=C2C(=C1)C(=CN2)C[C@@H](C(=O)O)N Computed by OEChem 2.1.5 (PubChem release 2019.06.18) PubChem 3.2 Molecular Formula C11H12N2O2 CAMEO Chemicals; Wikipedia; PubChem 3.3 Other Identifiers 3.3.1 CAS 73-22-3 ChemIDplus; DrugBank; DTP/NCI; EPA Chemicals under the TSCA; EPA DSSTox; European Chemicals Agency (ECHA); Hazardous Substances Data Bank (HSDB); Human Metabolome Database (HMDB) 3.3.2 Deprecated CAS 6912-86-3, 80206-30-0, 154635-35-5 ChemIDplus 3.3.3 European Community (EC) Number 200-795-6 European Chemicals Agency (ECHA) 3.3.4 NSC Number 757373 DTP/NCI 3.3.5 UNII https://pubchem.ncb.nlm.nh.gov/compound/Tryptophan#secton=Pathways 4/68 07.01.2021 Tryptophan | C11H12N2O2 - PubChem 8DUH1N11BX FDA/SPL Indexing Data 3.3.6 DSSTox Substance ID DTXSID5021419 EPA DSSTox 3.3.7 Wikipedia Tryptophan Wikipedia 3.4 Synonyms 3.4.1 MeSH Entry Terms Ardeydorm ratio-Tryptophan Ardeytropin Trofan L Tryptophan Tryptacin L Tryptophan ratiopharm Tryptan L-Tryptophan Tryptophan L-Tryptophan-ratiopharm Tryptophan Metabolism Alterations Levotryptophan Lyphan Naturruhe Optimax PMS Tryptophan PMS-Tryptophan ratio Tryptophan MeSH 3.4.2 Depositor-Supplied Synonyms L-tryptophan (2S)-2-amino-3-(1H-indol-3-yl)propanoic acid Tryptophan (VAN) Tryptophan, L- trp 73-22-3 Pacitron 1-beta-3-Indolylalanine Alanine, 3-indol-3-yl- (L)-TRYPTOPHAN tryptophan Indole-3-alanine Tryptophan (H-3) (S)-2-Amino-3-(3-indolyl)propionic acid (-)-Tryptophan L-Tryptophane Kalma Triptofano [Spanish] alpha'-Amino-3-indolepropionic acid CCRIS 617 (S)-Tryptophan L-beta-3-Indolylalanine Tryptophanum [Latin] Tryptophan [USAN:INN] L-Alanine, 3-(1H-indol-3-yl)- Tryptophane L-Tryptofan 1H-Indole-3-alanine L-alpha-amino-3-indolepropionic acid 1H-Indole-3-alanine, (S)- h-Trp-oh L-Trp 1beta-3-Indolylalanine L-alpha-Aminoindole-3-propionic acid alpha-Amino-3-indolepropionic acid, L- Optimax L-(-)-Tryptophan 2-Amino-3-indolylpropanoic acid Sedanoct HSDB 4142 trofan 3-Indol-3-ylalanine triptofano (S)-alpha-Aminoindole-3-propionic acid (S)-alpha-amino-beta-(3-indolyl)-propionic acid Tryptan Tryptophanum tryptacin 1H-Indole-3-alanine (VAN) NCI-C01729 Lyphan (S)-alpha-Amino-1H-indole-3-propanoic acid Ardeytropin EH 121 AI3-18478 Tryptophane [French] PubChem https://pubchem.ncb.nlm.nh.gov/compound/Tryptophan#secton=Pathways 5/68 07.01.2021 Tryptophan | C11H12N2O2 - PubChem 4 Chemical and Physical Properties 4.1 Computed Properties Property Name Property Value Reference Molecular Weight 204.22 g/mol Computed by PubChem 2.1 (PubChem release 2019.06.18) XLogP3 -1.1 Computed by XLogP3 3.0 (PubChem release 2019.06.18) Hydrogen Bond Donor Count 3 Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18) Hydrogen Bond Acceptor Count 3 Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18) Rotatable Bond Count 3 Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18) Exact Mass 204.089878 g/mol Computed by PubChem 2.1 (PubChem release 2019.06.18) Monoisotopic Mass 204.089878 g/mol Computed by PubChem 2.1 (PubChem release 2019.06.18) Topological Polar Surface Area 79.1 Ų Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18) Heavy Atom Count 15 Computed by PubChem Formal Charge 0 Computed by PubChem Complexity 245 Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18) Isotope Atom Count 0 Computed by PubChem Defined Atom Stereocenter Count 1 Computed by PubChem Undefined Atom Stereocenter Count 0 Computed by PubChem Defined Bond Stereocenter Count 0 Computed by PubChem Undefined Bond Stereocenter Count 0 Computed by PubChem Covalently-Bonded Unit Count 1 Computed by PubChem Compound Is Canonicalized Yes Computed by PubChem (release 2019.01.04) PubChem 4.2 Experimental Properties 4.2.1 Physical Description L-tryptophan is a white powder with a flat taste. An essential amino acid; occurs in isomeric forms. (NTP, 1992) National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina. CAMEO Chemicals Solid Human Metabolome Database (HMDB) 4.2.2 Color/Form Leaflets or plates from dilute alcohol O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 1682 Hazardous Substances Data Bank (HSDB) White to slightly yellowish-white ... crystals or crystalline powder Reynolds, J.E.F., Prasad, A.B.
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