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Record Information
Version1.0
Creation Date2016-09-30 22:18:39 UTC
Update Date2020-05-21 16:29:04 UTC
BMDB IDBMDB0000027
Secondary Accession Numbers
  • BMDB0000787
  • BMDB00027
  • BMDB00787
Metabolite Identification
Common NameTetrahydrobiopterin
DescriptionL-erythro-tetrahydrobiopterin, also known as 5,6,7,8-tetrahydrobiopterin or 6R-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. L-erythro-tetrahydrobiopterin is a drug which is used for the treatment of tetrahydrobiopterin (bh4) deficiency. L-erythro-tetrahydrobiopterin is a moderately basic compound (based on its pKa). L-erythro-tetrahydrobiopterin exists in all living organisms, ranging from bacteria to humans. L-phenylalanine and L-erythro-tetrahydrobiopterin can be converted into L-tyrosine and 4a-hydroxytetrahydrobiopterin through its interaction with the enzyme phenylalanine-4-hydroxylase. In cattle, L-erythro-tetrahydrobiopterin is involved in the metabolic pathway called the phenylalanine and tyrosine metabolism pathway.
Structure
Thumb
Synonyms
ValueSource
(-)-(6R)-2-Amino-6-((1R,2S)-1,2-dihydroxypropyl)-5,6,7,8-tetrahydro-4(3H)-pteridinoneChEBI
(6R)-L-Erythro-5,6,7,8-tetrahydrobiopterinChEBI
(6R)-L-Erythro-tetrahydrobiopterinChEBI
2-Amino-6-(1,2-dihydroxypropyl)-5,6,7,8-tetrahydoro-4(1H)-pteridinoneChEBI
5,6,7,8-TetrahydrobiopterinChEBI
6R-5,6,7,8-TetrahydrobiopterinChEBI
6R-BH4ChEBI
6R-L-5,6,7,8-TetrahydrobiopterinChEBI
R-THBPChEBI
SapropterinaChEBI
SapropterinumChEBI
TetrahydrobiopterinChEBI
5,6,7,8-erythro-TetrahydrobiopterinMeSH, HMDB
5,6,7,8-tetrahydro-L-ErythrobiopterinMeSH, HMDB
5,6,7,8-Tetrahydrobiopterin, (S-(r*,s*))-isomerMeSH, HMDB
5,6,7,8-TetrahydrodictyopterinMeSH, HMDB
6R-L-erythro-5,6,7,8-TetrahydrobiopterinMeSH, HMDB
BPH4MeSH, HMDB
D-threo-TetrahydrobiopterinMeSH, HMDB
THBPMeSH, HMDB
KuvanMeSH, HMDB
Phenylalanine hydroxylase cofactorMeSH, HMDB
Sapropterin dihydrochlorideMeSH, HMDB
tetrahydro-6-BiopterinMeSH, HMDB
2',4',5'-TrihydroxybutyrophenoneMeSH
SapropterinMeSH
TrihydroxybutyrophenoneMeSH
1-Butanone, 1-(2,4,5-trihydroxyphenyl)MeSH
2,4,5-TrihydroxybutyrophenoneMeSH
(6R)-5,6,7,8-Tetrahydro-L-biopterinHMDB
(6R)-5,6,7,8-TetrahydrobiopterinHMDB
(6R)-TetrahydrobiopterinHMDB
2-Amino-6-(1,2-dihydroxypropyl)-5,6,7,8-tetrahydro-4(3H)-pteridinoneHMDB
6R-Tetrahydro-L-biopterinHMDB
6beta-5,6,7,8-Tetrahydro-L-biopterinHMDB
6β-5,6,7,8-Tetrahydro-L-biopterinHMDB
L-erythro-TetrahydrobiopterinHMDB
(6R)-2-Amino-6-[(1R,2S)-1,2-dihydroxypropyl]-5,6,7,8-tetrahydro-4(1H)-pteridinoneHMDB
Chemical FormulaC9H15N5O3
Average Molecular Weight241.2471
Monoisotopic Molecular Weight241.117489371
IUPAC Name(6R)-2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-1,4,5,6,7,8-hexahydropteridin-4-one
Traditional Nametetrahydrobiopterin
CAS Registry Number17528-72-2
SMILES
[H][C@@]1(CNC2=C(N1)C(=O)N=C(N)N2)[C@@H](O)[C@H](C)O
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)/t3-,4+,6-/m0/s1
InChI KeyFNKQXYHWGSIFBK-RPDRRWSUSA-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
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Mitochondria
  • Nucleus
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point250 - 255 °C (hydrochloride salt)Not Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1.7ALOGPS
logP-2.7ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)13.52ChemAxon
pKa (Strongest Basic)1.58ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area132 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity68.43 m³·mol⁻¹ChemAxon
Polarizability23.67 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (6 TMS)splash10-0zfr-2921300000-63bf6ee58b9df85919f6View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0zfr-2921300000-63bf6ee58b9df85919f6View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0005-9810000000-1bfd11724596b460cae9View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-014i-6945000000-07faa91218e86d3bfe0dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006x-0090000000-e6b01d1139ccb3c6338dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gi3-0980000000-8963ef41f1138b05a813View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00xr-1900000000-bcfa359703563c696c0fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0390000000-4810efa20f31adea3824View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006y-1930000000-5b32feeb643e238bb159View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9400000000-a7dbebeb1df4ea110948View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
  • Nucleus
Biospecimen Locations
  • All Tissues
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000027
DrugBank IDDB00360
Phenol Explorer Compound IDNot Available
FooDB IDFDB021880
KNApSAcK IDC00018229
Chemspider ID40270
KEGG Compound IDC00272
BioCyc IDCPD-14053
BiGG IDNot Available
Wikipedia LinkTetrahydrobiopterin
METLIN IDNot Available
PubChem Compound44257
PDB IDNot Available
ChEBI ID59560
References
Synthesis ReferenceSteven S. Gross, "Blocking utilization of tetrahydrobiopterin to block induction of nitric oxide synthesis." U.S. Patent US5502050, issued October, 1984.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Inorganic ion transport and metabolism
Specific function:
Produces nitric oxide (NO) which is implicated in vascular smooth muscle relaxation through a cGMP-mediated signal transduction pathway. NO mediates vascular endothelial growth factor (VEGF)-induced angiogenesis in coronary vessels and promotes blood clotting through the activation of platelets.
Gene Name:
NOS3
Uniprot ID:
P29473
Molecular weight:
133287.0
General function:
Inorganic ion transport and metabolism
Specific function:
Produces nitric oxide (NO) which is a messenger molecule with diverse functions throughout the body. In macrophages, NO mediates tumoricidal and bactericidal actions. Also has nitrosylase activity and mediates cysteine S-nitrosylation of cytoplasmic target proteins such PTGS2/COX2. As component of the iNOS-S100A8/9 transnitrosylase complex involved in the selective inflammatory stimulus-dependent S-nitrosylation of GAPDH implicated in regulation of the GAIT complex activity and probably multiple targets including ANXA5, EZR, MSN and VIM. Involved in inflammation, enhances the synthesis of proinflammatory mediators such as IL6 and IL8.
Gene Name:
NOS2
Uniprot ID:
Q27995
Molecular weight:
131208.0
General function:
Lipid transport and metabolism
Specific function:
Catalyzes the final one or two reductions in tetra-hydrobiopterin biosynthesis to form 5,6,7,8-tetrahydrobiopterin.
Gene Name:
SPR
Uniprot ID:
Q17QK8
Molecular weight:
28939.0
Reactions
6-Lactoyltetrahydropterin + NADP → Tetrahydrobiopterin + NADPHdetails
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
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
General function:
Involved in arginine binding
Specific function:
Not Available
Gene Name:
iNOS
Uniprot ID:
Q6ZXD5
Molecular weight:
12093.0
General function:
Lipid transport and metabolism
Specific function:
The product of this enzyme, tetrahydrobiopterin (BH-4), is an essential cofactor for phenylalanine, tyrosine, and tryptophan hydroxylases.
Gene Name:
QDPR
Uniprot ID:
Q3T0Z7
Molecular weight:
25504.0
Reactions
Tetrahydrobiopterin + NADP → Dihydrobiopterin + NADPHdetails
General function:
Coenzyme transport and metabolism
Specific function:
Key enzyme in folate metabolism. Contributes to the de novo mitochondrial thymidylate biosynthesis pathway. Catalyzes an essential reaction for de novo glycine and purine synthesis, and for DNA precursor synthesis. Binds its own mRNA and that of DHFR2 (By similarity).
Gene Name:
DHFR
Uniprot ID:
P00376
Molecular weight:
21604.0
Reactions
7,8-Dihydroneopterin + NADPH → NADP + Tetrahydrobiopterin + Waterdetails