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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 19:04:49 UTC
Update Date2021-09-26 23:14:33 UTC
HMDB IDHMDB0257929
Secondary Accession NumbersNone
Metabolite Identification
Common Name(6S)-2-Amino-6-[(1S,2S)-1,2-dihydroxypropyl]-5,6,7,8-tetrahydro-3H-pteridin-4-one
DescriptionTetrahydrobiopterin, also known as BH4, belongs to the class of organic compounds known as biopterins and derivatives. These are coenzymes containing a 2-amino-pteridine-4-one derivative. They are mainly synthesized in several parts of the body, including the pineal gland. Tetrahydrobiopterin exists in all living organisms, ranging from bacteria to humans. Tetrahydrobiopterin has been detected, but not quantified in, several different foods, such as mugworts (Artemisia vulgaris), agaves (Agave), salmonberries (Rubus spectabilis), watermelons (Citrullus lanatus), and green onion. This could make tetrahydrobiopterin a potential biomarker for the consumption of these foods. Tetrahydrobiopterin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review very few articles have been published on Tetrahydrobiopterin. This compound has been identified in human blood as reported by (PMID: 31557052 ). (6s)-2-amino-6-[(1s,2s)-1,2-dihydroxypropyl]-5,6,7,8-tetrahydro-3h-pteridin-4-one is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically (6S)-2-Amino-6-[(1S,2S)-1,2-dihydroxypropyl]-5,6,7,8-tetrahydro-3H-pteridin-4-one is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
Thumb
Synonyms
Chemical FormulaC9H15N5O3
Average Molecular Weight241.2471
Monoisotopic Molecular Weight241.117489371
IUPAC Name2-amino-6-(1,2-dihydroxypropyl)-1,4,5,6,7,8-hexahydropteridin-4-one
Traditional Nametetrahydrobiopterin
CAS Registry NumberNot Available
SMILES
CC(O)C(O)C1CNC2=C(N1)C(=O)N=C(N)N2
InChI Identifier
InChI=1S/C9H15N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h3-4,6,12,15-16H,2H2,1H3,(H4,10,11,13,14,17)
InChI KeyFNKQXYHWGSIFBK-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as biopterins and derivatives. These are coenzymes containing a 2-amino-pteridine-4-one derivative. They are mainly synthesized in several parts of the body, including the pineal gland.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPteridines and derivatives
Sub ClassPterins and derivatives
Direct ParentBiopterins and derivatives
Alternative Parents
Substituents
  • Biopterin
  • Aminopyrimidine
  • Pyrimidone
  • Secondary aliphatic/aromatic amine
  • Pyrimidine
  • 1,3-aminoalcohol
  • Vinylogous amide
  • Heteroaromatic compound
  • Secondary alcohol
  • 1,2-diol
  • 1,2-aminoalcohol
  • Secondary amine
  • Azacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB021880
KNApSAcK IDC00018229
Chemspider ID1093
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTetrahydrobiopterin
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID15372
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]