CHEBI:17780 - 5-hydroxy-L-tryptophan

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ChEBI Name 5-hydroxy-L-tryptophan
ChEBI ID CHEBI:17780
ChEBI ASCII Name 5-hydroxy-L-tryptophan
Definition The L-enantiomer of 5-hydroxytryptophan.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:12133, CHEBI:2064, CHEBI:20577
Supplier Information ChemicalBook:CB7853704, ChemicalBook:CB3777943, eMolecules:26405050, eMolecules:29534153, eMolecules:492402, Selleckchem:vitamin-c-ascorbic-acid, ZINC000100006770
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Vitamin C (also known as ascorbic acid and ascorbate) is a water-soluble vitamin found in citrus and other fruits, berries and vegetables. It is also a generic prescription medication and in some countries is sold as a non-prescription dietary supplement. As a therapy, it is used to prevent and treat scurvy, a disease caused by vitamin C deficiency. Vitamin C is an essential nutrient involved in the repair of tissue, the formation of collagen, and the enzymatic production of certain neurotransmitters. It is required for the functioning of several enzymes and is important for immune system function. It also functions as an antioxidant. Vitamin C may be taken by mouth or by intramuscular, subcutaneous or intravenous injection. Various health claims exist on the basis that moderate vitamin C deficiency increases disease risk, such as for the common cold, cancer or COVID-19. There are also claims of benefits from vitamin C supplementation in excess of the recommended dietary intake for people who are not considered vitamin C deficient. Vitamin C is generally well tolerated. Large doses may cause gastrointestinal discomfort, headache, trouble sleeping, and flushing of the skin. The United States Institute of Medicine recommends against consuming large amounts.: 155–165  Most animals are able to synthesize their own vitamin C. However, apes (including humans) and monkeys (but not all primates), most bats, most fish, some rodents, and certain other animals must acquire it from dietary sources because a gene for a synthesis enzyme has mutations that render it dysfunctional. Vitamin C was discovered in 1912, isolated in 1928, and in 1933, was the first vitamin to be chemically produced. Partly for its discovery, Albert Szent-Györgyi was awarded the 1937 Nobel Prize in Physiology or Medicine.
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Formula C11H12N2O3
Net Charge 0
Average Mass 220.228
Monoisotopic Mass 220.08479
InChI 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
InChIKey LDCYZAJDBXYCGN-VIFPVBQESA-N
SMILES N[C@H](C(=O)O)CC=1C2=C(NC1)C=CC(=C2)O
Metabolite of Species Details
Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Homo sapiens (NCBI:txid9606) See: DOI
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
(via 5-hydroxytryptophan )
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
neurotransmitter
An endogenous compound that is used to transmit information across the synapse between a neuron and another cell.
(via 5-hydroxytryptophan )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 5-hydroxy-L-tryptophan (CHEBI:17780) has role human metabolite (CHEBI:77746)
5-hydroxy-L-tryptophan (CHEBI:17780) has role mouse metabolite (CHEBI:75771)
5-hydroxy-L-tryptophan (CHEBI:17780) has role plant metabolite (CHEBI:76924)
5-hydroxy-L-tryptophan (CHEBI:17780) is a 5-hydroxytryptophan (CHEBI:28171)
5-hydroxy-L-tryptophan (CHEBI:17780) is a hydroxy-L-tryptophan (CHEBI:47995)
5-hydroxy-L-tryptophan (CHEBI:17780) is a non-proteinogenic L-α-amino acid (CHEBI:83822)
5-hydroxy-L-tryptophan (CHEBI:17780) is enantiomer of 5-hydroxy-D-tryptophan (CHEBI:43186)
5-hydroxy-L-tryptophan (CHEBI:17780) is tautomer of 5-hydroxy-L-tryptophan zwitterion (CHEBI:58266)
Incoming 5-hydroxy-D-tryptophan (CHEBI:43186) is enantiomer of 5-hydroxy-L-tryptophan (CHEBI:17780)
5-hydroxy-L-tryptophan zwitterion (CHEBI:58266) is tautomer of 5-hydroxy-L-tryptophan (CHEBI:17780)
IUPAC Names
(2S)-2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoic acid
5-hydroxy-L-tryptophan
Synonyms Sources
5-hydroxy-L-tryptophan ChEBI
5-Hydroxy-L-tryptophan KEGG COMPOUND
5-hydroxytryptophan L-form ChemIDplus
Cincofarm ChemIDplus
L-5-hydroxytryptophan ChemIDplus
Levothym ChemIDplus
oxitriptan ChemIDplus
Oxitriptan KEGG COMPOUND
Tript-OH ChemIDplus
Manual Xrefs Databases
4006 DrugCentral
4PQ PDBeChem
5-HYDROXY-TRYPTOPHAN MetaCyc
5-Hydroxytryptophan Wikipedia
C00001371 KNApSAcK
C00643 KEGG COMPOUND
D07339 KEGG DRUG
DB02959 DrugBank
HMDB0000472 HMDB
View more database links
Registry Numbers Types Sources
1862149 Gmelin Registry Number Gmelin
4350-09-8 CAS Registry Number ChemIDplus
88200 Reaxys Registry Number Reaxys
Citations Types Sources
22964922 PubMed citation Europe PMC
24321061 PubMed citation Europe PMC
24369991 PubMed citation Europe PMC
5297581 PubMed citation Europe PMC
9295177 PubMed citation Europe PMC
Last Modified
21 November 2019