Showing metabocard for 5-Hydroxy-L-tryptophan (BMDB0000472)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 22:31:12 UTC
Update Date2020-05-11 20:47:24 UTC
BMDB IDBMDB0000472
Secondary Accession Numbers
  • BMDB00472
Metabolite Identification
Common Name5-Hydroxy-L-tryptophan
Description5-Hydroxy-L-tryptophan, also known as 5-HTP or oxitriptan, 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 as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. 5-Hydroxy-L-tryptophan participates in a number of enzymatic reactions, within cattle. In particular, 5-Hydroxy-L-tryptophan and 4a-hydroxytetrahydrobiopterin can be biosynthesized from L-tryptophan and tetrahydrobiopterin through its interaction with the enzyme tryptophan 5-hydroxylase 1. In addition, 5-Hydroxy-L-tryptophan can be converted into serotonin through its interaction with the enzyme aromatic-L-amino-acid decarboxylase. In cattle, 5-hydroxy-L-tryptophan is involved in the metabolic pathway called the tryptophan metabolism pathway. 5-Hydroxy-L-tryptophan is a potentially toxic compound.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(+-)-5-HydroxytryptophanChEBI
5-HTPChEBI
5-Hydroxy-DL-tryptophanChEBI
5-Hydroxytryptophan DL-formChEBI
DL-5-HTPChEBI
DL-5-HydroxytryptophanChEBI
(S)-5-HydroxytryptophanHMDB
5-Hydroxy-tryptophanHMDB
5-Hydroxyl-L-tryptophanHMDB
5-HydroxytryptophanHMDB, MeSH
5-Hydroxytryptophan L formHMDB
5-Hydroxytryptophan L-formHMDB
CincofarmHMDB
HydroxytryptophanHMDB, MeSH
L-5-HydroxytryptophanHMDB
LevothymHMDB
LevotinineHMDB
OxitriptanHMDB, MeSH
OxyfanHMDB
OxytryptophanHMDB, MeSH
PretonineHMDB
QuietimHMDB
SerotonylHMDB
TelesolHMDB
TripteneHMDB
5 HydroxytryptophanMeSH
5-Hydroxy- tryptophanMeSH
Tryptophan, 5 hydroxyMeSH
Chemical FormulaC11H12N2O3
Average Molecular Weight220.2246
Monoisotopic Molecular Weight220.08479226
IUPAC Name2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoic acid
Traditional NameDL-5-hydroxytryptophan
CAS Registry Number56-69-9
SMILES
NC(CC1=CNC2=C1C=C(O)C=C2)C(O)=O
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)
InChI KeyLDCYZAJDBXYCGN-UHFFFAOYSA-N
Chemical Taxonomy
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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassTryptamines and derivatives
Direct ParentSerotonins
Alternative Parents
Substituents
  • Serotonin
  • Indolyl carboxylic acid derivative
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • Hydroxyindole
  • 3-alkylindole
  • Indole
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Substituted pyrrole
  • Benzenoid
  • Pyrrole
  • Heteroaromatic compound
  • Amino acid
  • Amino acid or derivatives
  • Azacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Primary amine
  • Carbonyl group
  • Organic nitrogen compound
  • Amine
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1.6ALOGPS
logP-1.4ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)2.15ChemAxon
pKa (Strongest Basic)9.18ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area99.34 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity58.18 m³·mol⁻¹ChemAxon
Polarizability22.03 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Milk
  • Prostate Tissue
  • Urine
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Prostate TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
Not Available
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDC00001371
Chemspider IDNot Available
KEGG Compound IDC01017
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link5-Hydroxytryptophan
METLIN IDNot Available
PubChem Compound144
PDB IDNot Available
ChEBI ID28171
References
Synthesis ReferenceBoroda, E.; Rakowska, S.; Kanski, R.; Kanska, M. Enzymatic synthesis of L-tryptophan and 5'-hydroxy-L-tryptophan labeled with deuterium and tritium at the a-carbon position. Journal of Labelled Compounds & Radiopharmaceuticals (2003), 46(8), 691-698.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Xi X, Kwok LY, Wang Y, Ma C, Mi Z, Zhang H: Ultra-performance liquid chromatography-quadrupole-time of flight mass spectrometry MS(E)-based untargeted milk metabolomics in dairy cows with subclinical or clinical mastitis. J Dairy Sci. 2017 Jun;100(6):4884-4896. doi: 10.3168/jds.2016-11939. Epub 2017 Mar 23. [PubMed:28342601 ]

Enzymes

Enzyme Details
1. Aromatic-L-amino-acid decarboxylase
General function:
Amino acid transport and metabolism
Specific function:
Catalyzes the decarboxylation of L-3,4-dihydroxyphenylalanine (DOPA) to dopamine, L-5-hydroxytryptophan to serotonin and L-tryptophan to tryptamine.
Gene Name:
DDC
Uniprot ID:
P27718
Molecular weight:
54294.0