| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-09-30 22:53:33 UTC |
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| Update Date | 2020-04-22 15:10:29 UTC |
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| BMDB ID | BMDB0002281 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | 4a-Hydroxytetrahydrobiopterin |
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| Description | 4a-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. |
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| Structure | |
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| Synonyms | | Value | Source |
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| 4a-Hydroxy-5,6,4,8-tetrahydrobiopterin | ChEBI | | (6R)-6-(L-erythro-1,2-Dihydroxypropyl)-5,6,7,8-tetrahydro-4a-hydroxypterin | ChEBI, HMDB | | 2-amino-6-(1,2-Dihydroxypropyl)-4a-hydroxy-5,6,7,8-tetrahydropteridin-4(4ah)-one | HMDB | | 2-amino-6-(1,2-Dihydroxypropyl)-5,6,7,8-tetrahydro-4a-hydroxy-4(4ah)-pteridinone | HMDB | | 2-amino-6-[(1R,2S)-1,2-Dihydroxypropyl]-4a-hydroxy-1,5,6,7-tetrahydropteridin-4-one | HMDB | | 4a-Hydroxy-5,6,7,8-tetrahydrobiopterin | HMDB | | 4alpha-Hydroxytetrahydrobiopterin | HMDB | | 4a-HTHB | MeSH, HMDB |
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| Chemical Formula | C9H15N5O4 |
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| Average Molecular Weight | 257.2465 |
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| Monoisotopic Molecular Weight | 257.112403993 |
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| IUPAC Name | 2-amino-6-(1,2-dihydroxypropyl)-4a-hydroxy-4,4a,5,6,7,8-hexahydropteridin-4-one |
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| Traditional Name | 4a-hydroxytetrahydrobiopterin |
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| CAS Registry Number | 70110-58-6 |
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| SMILES | CC(O)C(O)C1CNC2=NC(N)=NC(=O)C2(O)N1 |
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| 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) |
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| InChI Key | KJKIEFUPAPPGBC-UHFFFAOYSA-N |
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| Chemical Taxonomy |
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| 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. |
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| Kingdom | Organic compounds |
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| Super Class | Organoheterocyclic compounds |
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| Class | Pteridines and derivatives |
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| Sub Class | Pterins and derivatives |
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| Direct Parent | Biopterins and derivatives |
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| Alternative Parents | |
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| 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
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| Molecular Framework | Aliphatic heteropolycyclic compounds |
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| External Descriptors | |
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| Ontology |
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| Status | Expected but not Quantified |
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| Origin | |
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| Biofunction | Not Available |
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| Application | Not Available |
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| Cellular locations | |
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| Physical Properties |
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| State | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties | |
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| Spectra |
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| Spectra | |
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