Record Information
Version1.0
Created at2020-04-17 18:36:31 UTC
Updated at2020-12-07 19:10:55 UTC
CannabisDB IDCDB004785
Secondary Accession NumbersNot Available
Cannabis Compound 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. It is also essential in the conversion of phenylalanine to tyrosine by the enzyme phenylalanine-4-hydroxylase; the conversion of tyrosine to L-dopa by the enzyme tyrosine hydroxylase; and conversion of tryptophan to 5-hydroxytryptophan via tryptophan hydroxylase. In the hydroxylation process, the co-enzyme loses two electrons and is regenerated in vivo in an NADH-dependent reaction. L-erythro-tetrahydrobiopterin is a drug which is used for the treatment of tetrahydrobiopterin (bh4) deficiency. Tetrahydrobiopterin is also a natural co-factor for nitrate oxide synthase. 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; which is mediated by the enzyme phenylalanine-4-hydroxylase. Individuals with a deficiency in tetrahydrobiopterin are not able to efficiently convert phenylalanine to tyrosine. These genes make the enzymes that are critical for producing and recycling tetrahydrobiopterin. In humans, L-erythro-tetrahydrobiopterin is involved in the metabolic disorder called tyrosinemia type 3 (tyro3). As a co-factor for tyrosine hydroxylase, BH4 facilitates the conversion of tyrosine to L-dopa while as a co-factor for tryptophan hydroxylase, BH4 allows the conversion of tryptophan to 5-hydroxytryptophan, which is then converted to serotonin. Tetrahydrobiopterin (BH4) is used to convert several amino acids, including phenylalanine, to other essential molecules in the body including neurotransmitters. As a result, phenylalanine from the diet builds up in the bloodstream and other tissues and can damage nerve cells in the brain. Tetrahydrobiopterin is expected to be in Cannabis as all living plants are known to produce and metabolize it.
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 Weight241.25
Monoisotopic Molecular Weight241.1175
IUPAC Name(6R)-2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-1,4,5,6,7,8-hexahydropteridin-4-one
Traditional Nametetrahydrobiopterin
CAS Registry Number62989-33-7
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
Physiological effect

Health effect:

Disposition

Source:

Biological location:

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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSTetrahydrobiopterin, 6 TMS, GC-MS Spectrumsplash10-0zfr-2921300000-63bf6ee58b9df85919f6Spectrum
GC-MSTetrahydrobiopterin, non-derivatized, GC-MS Spectrumsplash10-0zfr-2921300000-63bf6ee58b9df85919f6Spectrum
Predicted GC-MSTetrahydrobiopterin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0005-9810000000-1bfd11724596b460cae9Spectrum
Predicted GC-MSTetrahydrobiopterin, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-014i-6945000000-07faa91218e86d3bfe0dSpectrum
Predicted GC-MSTetrahydrobiopterin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSTetrahydrobiopterin, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSTetrahydrobiopterin, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSTetrahydrobiopterin, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSTetrahydrobiopterin, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSTetrahydrobiopterin, TMS_1_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSTetrahydrobiopterin, TMS_1_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSTetrahydrobiopterin, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSTetrahydrobiopterin, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSTetrahydrobiopterin, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSTetrahydrobiopterin, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSTetrahydrobiopterin, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSTetrahydrobiopterin, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSTetrahydrobiopterin, TMS_2_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSTetrahydrobiopterin, TMS_2_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSTetrahydrobiopterin, TMS_2_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSTetrahydrobiopterin, TMS_2_10, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSTetrahydrobiopterin, TMS_2_11, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSTetrahydrobiopterin, TMS_2_12, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSTetrahydrobiopterin, TMS_2_13, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSTetrahydrobiopterin, TMS_2_14, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - QTOF 4V, positivesplash10-0006-0290000000-cd4c8c11b8279075b00a2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 5V, positivesplash10-0006-0390000000-35dddce9e2df2a9ac1982020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 7V, positivesplash10-0006-0590000000-cda875209a034e44cbe12020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 10V, positivesplash10-00kf-0980000000-53721c484501c528e7a82020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 15V, positivesplash10-014l-0930000000-533fabd35a8c5ca7830e2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 17V, positivesplash10-014i-0910000000-580c038db540047891c82020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 20V, positivesplash10-014i-0910000000-8d6b754dadadb63309062020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 3V, positivesplash10-0006-0090000000-f21b677255493f1f2d1f2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 23V, positivesplash10-014i-0900000000-5c1b60d0d7ea4dd4dbff2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 25V, positivesplash10-014i-1900000000-6f22457ab99b14bb653e2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 27V, positivesplash10-014i-1900000000-cd0410f4da61716c7f9e2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 30V, positivesplash10-014i-2900000000-d4f18a979b6d07e83a632020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 16V, positivesplash10-0002-0900000000-87174b78444828c3b52d2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 16V, positivesplash10-0a4i-0900000000-dc272a476d306f26c7222020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 16V, positivesplash10-014i-0900000000-ae19513d01a0046ed2e82020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 16V, positivesplash10-004i-0900000000-d4a52489d35bde573bd02020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 16V, positivesplash10-0f79-0900000000-af02b0d9eb8f6577afb82020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 16V, positivesplash10-014i-0900000000-c2259602e8f1fd522fd02020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-0006-0090000000-c88ed5ea9e11715bc2752020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006x-0090000000-e6b01d1139ccb3c6338d2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gi3-0980000000-8963ef41f1138b05a8132015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00xr-1900000000-bcfa359703563c696c0f2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0390000000-4810efa20f31adea38242015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006y-1930000000-5b32feeb643e238bb1592015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9400000000-a7dbebeb1df4ea1109482015-09-15View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
TyrosinaseTYR11q14-q21P14679 details
Tyrosine 3-monooxygenaseTH11p15.5P07101 details
Phenylalanine-4-hydroxylasePAH12q22-q24.2P00439 details
6-pyruvoyl tetrahydrobiopterin synthasePTS11q22.3Q03393 details
Sepiapterin reductaseSPR2p14-p12P35270 details
Tryptophan 5-hydroxylase 1TPH111p15.3-p14P17752 details
Tryptophan 5-hydroxylase 2TPH212q21.1Q8IWU9 details
Dihydropteridine reductaseQDPR4p15.31P09417 details
Nitric oxide synthase, inducibleNOS217q11.2-q12P35228 details
Nitric oxide synthase, brainNOS112q24.2-q24.31P29475 details
Nitric oxide synthase, endothelialNOS37q36P29474 details
GTP cyclohydrolase 1GCH114q22.1-q22.2P30793 details
GTP cyclohydrolase 1 feedback regulatory proteinGCHFR15q15P30047 details
Pterin-4-alpha-carbinolamine dehydratasePCBD110q22P61457 details
Calcium-calmodulin independent nitric oxide synthase iNOS proteinQ9UM94 details
Transporters
Protein NameGene NameLocusUniprot IDDetails
Nitric oxide synthase, inducibleNOS217q11.2-q12P35228 details
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Tyrosine 3-monooxygenaseTH11p15.5P07101 details
Phenylalanine-4-hydroxylasePAH12q22-q24.2P00439 details
6-pyruvoyl tetrahydrobiopterin synthasePTS11q22.3Q03393 details
Tryptophan 5-hydroxylase 1TPH111p15.3-p14P17752 details
Tryptophan 5-hydroxylase 2TPH212q21.1Q8IWU9 details
Nitric oxide synthase, inducibleNOS217q11.2-q12P35228 details
Nitric oxide synthase, brainNOS112q24.2-q24.31P29475 details
Nitric oxide synthase, endothelialNOS37q36P29474 details
Receptors
Protein NameGene NameLocusUniprot IDDetails
Tyrosine 3-monooxygenaseTH11p15.5P07101 details
Nitric oxide synthase, brainNOS112q24.2-q24.31P29475 details
Transcriptional Factors
Protein NameGene NameLocusUniprot IDDetails
Nitric oxide synthase, brainNOS112q24.2-q24.31P29475 details
Pterin-4-alpha-carbinolamine dehydratasePCBD110q22P61457 details
Concentrations Data
Not Available
HMDB IDHMDB0059658
DrugBank IDDB00360
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID40270
KEGG Compound IDC00272
BioCyc IDCPD-14053
BiGG IDNot Available
Wikipedia LinkSapropterin
METLIN IDNot Available
PubChem Compound44257
PDB IDNot Available
ChEBI ID59560
References
General ReferencesNot Available

Only showing the first 10 proteins. There are 28 proteins in total.

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
This is a copper-containing oxidase that functions in the formation of pigments such as melanins and other polyphenolic compounds. Catalyzes the rate-limiting conversions of tyrosine to DOPA, DOPA to DOPA-quinone and possibly 5,6-dihydroxyindole to indole-5,6 quinone.
Gene Name:
TYR
Uniprot ID:
P14679
Molecular weight:
60392.69
General function:
Involved in monooxygenase activity
Specific function:
Plays an important role in the physiology of adrenergic neurons.
Gene Name:
TH
Uniprot ID:
P07101
Molecular weight:
55611.26
General function:
Involved in amino acid binding
Specific function:
Not Available
Gene Name:
PAH
Uniprot ID:
P00439
Molecular weight:
51861.565
General function:
Involved in 6-pyruvoyltetrahydropterin synthase activity
Specific function:
Involved in the biosynthesis of tetrahydrobiopterin, an essential cofactor of aromatic amino acid hydroxylases. Catalyzes the transformation of 7,8-dihydroneopterin triphosphate into 6-pyruvoyl tetrahydropterin.
Gene Name:
PTS
Uniprot ID:
Q03393
Molecular weight:
16385.63
General function:
Involved in oxidoreductase activity
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:
P35270
Molecular weight:
28048.13
General function:
Involved in amino acid binding
Specific function:
Not Available
Gene Name:
TPH1
Uniprot ID:
P17752
Molecular weight:
50984.725
General function:
Involved in amino acid binding
Specific function:
Not Available
Gene Name:
TPH2
Uniprot ID:
Q8IWU9
Molecular weight:
56056.295
General function:
Involved in oxidoreductase activity
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:
P09417
Molecular weight:
25789.295
General function:
Involved in oxidoreductase activity
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 COX2.
Gene Name:
NOS2
Uniprot ID:
P35228
Molecular weight:
131116.3
General function:
Involved in oxidoreductase activity
Specific function:
Produces nitric oxide (NO) which is a messenger molecule with diverse functions throughout the body. In the brain and peripheral nervous system, NO displays many properties of a neurotransmitter. Probably has nitrosylase activity and mediates cysteine S-nitrosylation of cytoplasmic target proteins such SRR.
Gene Name:
NOS1
Uniprot ID:
P29475
Molecular weight:
160969.095

Transporters

General function:
Involved in oxidoreductase activity
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 COX2.
Gene Name:
NOS2
Uniprot ID:
P35228
Molecular weight:
131116.3

Only showing the first 10 proteins. There are 28 proteins in total.