Record Information |
---|
Version | 1.0 |
---|
Created at | 2022-02-14 20:36:53 UTC |
---|
Updated at | 2022-03-10 22:22:35 UTC |
---|
NP-MRD ID | NP0044243 |
---|
Secondary Accession Numbers | None |
---|
Natural Product Identification |
---|
Common Name | Tetrahydrobiopterin |
---|
Description | L-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 | [H][C@@]1(CNC2=C(N1)C(=O)N=C(N)N2)[C@@H](O)[C@H](C)O 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 |
---|
Synonyms | Value | Source |
---|
(-)-(6R)-2-Amino-6-((1R,2S)-1,2-dihydroxypropyl)-5,6,7,8-tetrahydro-4(3H)-pteridinone | ChEBI | (6R)-L-Erythro-5,6,7,8-tetrahydrobiopterin | ChEBI | (6R)-L-Erythro-tetrahydrobiopterin | ChEBI | 2-Amino-6-(1,2-dihydroxypropyl)-5,6,7,8-tetrahydoro-4(1H)-pteridinone | ChEBI | 5,6,7,8-Tetrahydrobiopterin | ChEBI | 6R-5,6,7,8-Tetrahydrobiopterin | ChEBI | 6R-BH4 | ChEBI | 6R-L-5,6,7,8-Tetrahydrobiopterin | ChEBI | R-THBP | ChEBI | Sapropterina | ChEBI | Sapropterinum | ChEBI | Tetrahydrobiopterin | ChEBI | 5,6,7,8-erythro-Tetrahydrobiopterin | MeSH, HMDB | 5,6,7,8-tetrahydro-L-Erythrobiopterin | MeSH, HMDB | 5,6,7,8-Tetrahydrobiopterin, (S-(r*,s*))-isomer | MeSH, HMDB | 5,6,7,8-Tetrahydrodictyopterin | MeSH, HMDB | 6R-L-erythro-5,6,7,8-Tetrahydrobiopterin | MeSH, HMDB | BPH4 | MeSH, HMDB | D-threo-Tetrahydrobiopterin | MeSH, HMDB | THBP | MeSH, HMDB | Kuvan | MeSH, HMDB | Phenylalanine hydroxylase cofactor | MeSH, HMDB | Sapropterin dihydrochloride | MeSH, HMDB | tetrahydro-6-Biopterin | MeSH, HMDB | 2',4',5'-Trihydroxybutyrophenone | MeSH | Sapropterin | MeSH | Trihydroxybutyrophenone | MeSH | 1-Butanone, 1-(2,4,5-trihydroxyphenyl) | MeSH | 2,4,5-Trihydroxybutyrophenone | MeSH | (6R)-5,6,7,8-Tetrahydro-L-biopterin | HMDB | (6R)-5,6,7,8-Tetrahydrobiopterin | HMDB | (6R)-Tetrahydrobiopterin | HMDB | 2-Amino-6-(1,2-dihydroxypropyl)-5,6,7,8-tetrahydro-4(3H)-pteridinone | HMDB | 6R-Tetrahydro-L-biopterin | HMDB | 6beta-5,6,7,8-Tetrahydro-L-biopterin | HMDB | 6β-5,6,7,8-Tetrahydro-L-biopterin | HMDB | L-erythro-Tetrahydrobiopterin | HMDB | (6R)-2-Amino-6-[(1R,2S)-1,2-dihydroxypropyl]-5,6,7,8-tetrahydro-4(1H)-pteridinone | HMDB |
|
---|
Chemical Formula | C9H15N5O3 |
---|
Average Mass | 241.2471 Da |
---|
Monoisotopic Mass | 241.11749 Da |
---|
IUPAC Name | (6R)-2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-1,4,5,6,7,8-hexahydropteridin-4-one |
---|
Traditional Name | tetrahydrobiopterin |
---|
CAS Registry Number | 62989-33-7 |
---|
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 Key | FNKQXYHWGSIFBK-RPDRRWSUSA-N |
---|
Experimental Spectra |
---|
|
| Not Available | Predicted Spectra |
---|
|
| Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
---|
1D NMR | 13C NMR Spectrum (1D, 25 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Chemical Shift Submissions |
---|
|
| Not Available | Species |
---|
Species of Origin | |
---|
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. |
---|
Kingdom | Organic compounds |
---|
Super Class | Organoheterocyclic compounds |
---|
Class | Pteridines and derivatives |
---|
Sub Class | Pterins and derivatives |
---|
Direct Parent | Biopterins 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 Framework | Aromatic heteropolycyclic compounds |
---|
External Descriptors | |
---|
Physical Properties |
---|
State | Not Available |
---|
Experimental Properties | Property | Value | Reference |
---|
Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
|
---|
Predicted Properties | |
---|
General References | - Cho SH, Na JU, Youn H, Hwang CS, Lee CH, Kang SO: Sepiapterin reductase producing L-threo-dihydrobiopterin from Chlorobium tepidum. Biochem J. 1999 Jun 1;340 ( Pt 2):497-503. [PubMed:10333495 ]
- Kaufman S: Biopterin-responsive hyperphenylalaninemia. J Nutr Sci Vitaminol (Tokyo). 1992;Spec No:601-6. doi: 10.3177/jnsv.38.special_601. [PubMed:1297822 ]
- Supangat S, Choi YK, Park YS, Son D, Han CD, Lee KH: Expression, purification, crystallization and preliminary X-ray analysis of sepiapterin reductase from Chlorobium tepidum. Acta Crystallogr Sect F Struct Biol Cryst Commun. 2005 Feb 1;61(Pt 2):202-4. doi: 10.1107/S174430910403444X. Epub 2005 Jan 20. [PubMed:16510994 ]
- Sanford M, Keating GM: Spotlight on sapropterin in primary hyperphenylalaninemia. BioDrugs. 2009;23(3):201-2. doi: 10.2165/00063030-200923030-00007. [PubMed:19627172 ]
- MacDonald A, Ahring K, Dokoupil K, Gokmen-Ozel H, Lammardo AM, Motzfeldt K, Robert M, Rocha JC, van Rijn M, Belanger-Quintana A: Adjusting diet with sapropterin in phenylketonuria: what factors should be considered? Br J Nutr. 2011 Jul;106(2):175-82. doi: 10.1017/S0007114511000298. [PubMed:21466737 ]
|
---|