Showing metabocard for 4a-Hydroxytetrahydrobiopterin (BMDB0002281)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:53:33 UTC
Update Date2020-04-22 15:10:29 UTC
BMDB IDBMDB0002281
Secondary Accession Numbers
  • BMDB02281
Metabolite Identification
Common Name4a-Hydroxytetrahydrobiopterin
Description4a-Hydroxytetrahydrobiopterin, also known as 4a-hydroxytetrahydrobiopterin, 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. 4a-Hydroxytetrahydrobiopterin is possibly soluble (in water) and a strong basic compound (based on its pKa). Dopamine and 4a-hydroxytetrahydrobiopterin can be biosynthesized from L-dopa and tetrahydrobiopterin; which is catalyzed by the enzyme aromatic-L-amino-acid decarboxylase. In cattle, 4a-hydroxytetrahydrobiopterin is involved in the metabolic pathway called the tyrosine metabolism pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
4a-Hydroxy-5,6,4,8-tetrahydrobiopterinChEBI
(6R)-6-(L-erythro-1,2-Dihydroxypropyl)-5,6,7,8-tetrahydro-4a-hydroxypterinChEBI, HMDB
2-amino-6-(1,2-Dihydroxypropyl)-4a-hydroxy-5,6,7,8-tetrahydropteridin-4(4ah)-oneHMDB
2-amino-6-(1,2-Dihydroxypropyl)-5,6,7,8-tetrahydro-4a-hydroxy-4(4ah)-pteridinoneHMDB
2-amino-6-[(1R,2S)-1,2-Dihydroxypropyl]-4a-hydroxy-1,5,6,7-tetrahydropteridin-4-oneHMDB
4a-Hydroxy-5,6,7,8-tetrahydrobiopterinHMDB
4alpha-HydroxytetrahydrobiopterinHMDB
4a-HTHBMeSH, HMDB
Chemical FormulaC9H15N5O4
Average Molecular Weight257.2465
Monoisotopic Molecular Weight257.112403993
IUPAC Name2-amino-6-(1,2-dihydroxypropyl)-4a-hydroxy-4,4a,5,6,7,8-hexahydropteridin-4-one
Traditional Name4a-hydroxytetrahydrobiopterin
CAS Registry Number70110-58-6
SMILES
CC(O)C(O)C1CNC2=NC(N)=NC(=O)C2(O)N1
InChI Identifier
InChI=1S/C9H15N5O4/c1-3(15)5(16)4-2-11-6-9(18,14-4)7(17)13-8(10)12-6/h3-5,14-16,18H,2H2,1H3,(H3,10,11,12,13,17)
InChI KeyKJKIEFUPAPPGBC-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
  • Hydropyrimidine
  • 1,2,5,6-tetrahydropyrimidine
  • Imidolactam
  • 1,2-diol
  • Secondary alcohol
  • Alkanolamine
  • Amidine
  • Carboxylic acid amidine
  • Secondary aliphatic amine
  • Azacycle
  • Secondary amine
  • Carboximidamide
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Imine
  • Organonitrogen compound
  • Organooxygen compound
  • Alcohol
  • Amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Mitochondria
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-2.3ALOGPS
logP-3.1ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)9.81ChemAxon
pKa (Strongest Basic)3.85ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area152.56 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity58.6 m³·mol⁻¹ChemAxon
Polarizability24.2 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-4930000000-89d1b72adfc56cf4e3fdView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0zfr-5293600000-e1bc928bae70ea520f93View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4l-0090000000-364ec2c50acd77d83ef0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00gl-0690000000-f15f00b5ba6b8f2959b9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0005-9720000000-7a2198134bfe87159831View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0bt9-2290000000-43723819afb4c98b5cebView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9210000000-fa8eb33fdfed731f1c82View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-c550affb7745a16d59b4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0090000000-2e38d752208e421512bfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4l-0390000000-8910ee8de849000f68e5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-5900000000-b0f630ab5b90aa052132View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0090000000-195221ba76407cd71968View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ox-1690000000-492a38357ab54f3370a4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0296-9820000000-44ae87e7d45d04a8c51aView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0304198
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB030533
KNApSAcK IDNot Available
Chemspider ID114908
KEGG Compound IDNot Available
BioCyc IDCPD-5881
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound129803
PDB IDNot Available
ChEBI ID15374
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Tyrosine 3-monooxygenase
General function:
Amino acid transport and metabolism
Specific function:
Plays an important role in the physiology of adrenergic neurons.
Gene Name:
TH
Uniprot ID:
P17289
Molecular weight:
55123.0
Enzyme Details
2. Phenylalanine-4-hydroxylase
General function:
Amino acid transport and metabolism
Specific function:
Catalyzes the hydroxylation of L-phenylalanine to L-tyrosine.
Gene Name:
PAH
Uniprot ID:
Q2KIH7
Molecular weight:
51727.0