| Record Information |
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| Version | 4.0 |
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| Creation Date | 2006-05-22 14:17:42 UTC |
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| Update Date | 2017-09-27 08:24:14 UTC |
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| HMDB ID | HMDB0002215 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | 4a-Carbinolamine tetrahydrobiopterin |
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| Description | Carbinolamine 4a-hydroxytetrahydrobiopterin is formed as a consequence of the hydroxylation of phenylalanine to tyrosine. During the physiological reaction tetrahydrobiopterin (the naturally occurring cofactor for phenylalanine hydroxylase), and the two substrates phenylalanine and molecular oxygen combine with phenylalanine hydroxylase to form a quarternary complex. An enzyme, 4a-carbinolamine dehydratase, catalyzes the reaction. (PMID: 2722790 ). |
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| Structure | |
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| Synonyms | | Value | Source |
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| 6,7-Dihydrobiopterin | Kegg | | Quinoid-dihydrobiopterin | Kegg | | (6R)-6-(L-erythro-1,2-Dihydroxypropyl)-7,8-dihydro-6H-pterin | Kegg | | 1,3,5-Benzenetriol | HMDB | | 1,3,5-Trihydroxybenzene | HMDB | | 1,3,5-Trihydroxybenzene anhydrate | HMDB | | 1,3,5-Trihydroxybenzene anhydrous | HMDB | | 1,3,5-Trihydroxybenzene dihydrate | HMDB | | 1.3.5-Trihydroxybenzene | HMDB | | 4a-Hydroxy-BH4 | HMDB | | Phloroglucin | HMDB | | Phloroglucinol | HMDB | | Phloroglucinol 2-hydrate | HMDB | | Phloroglucinol anhydrous | HMDB | | Phloroglucinol dihydrate | HMDB |
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| Chemical Formula | C9H13N5O3 |
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| Average Molecular Weight | 239.2312 |
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| Monoisotopic Molecular Weight | 239.101839307 |
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| IUPAC Name | (6R)-2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-1,4,6,7-tetrahydropteridin-4-one |
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| Traditional Name | (6R)-2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-6,7-dihydro-1H-pteridin-4-one |
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| CAS Registry Number | 79647-29-3 |
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| SMILES | [H][C@@]1(CN=C2NC(N)=NC(=O)C2=N1)[C@@H](O)[C@H](C)O |
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| InChI Identifier | InChI=1S/C9H13N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h3-4,6,15-16H,2H2,1H3,(H3,10,11,13,14,17)/t3-,4+,6-/m0/s1 |
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| InChI Key | ZHQJVZLJDXWFFX-RPDRRWSUSA-N |
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| Chemical Taxonomy |
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| Description | This compound belongs to the class of chemical entities 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 | Chemical entities |
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| Super Class | Organic compounds |
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| Class | Organoheterocyclic compounds |
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| Sub Class | Pteridines and derivatives |
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| Direct Parent | Biopterins and derivatives |
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| Alternative Parents | |
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| Substituents | - Biopterin
- Aminopyrimidine
- Pyrimidone
- Primary aromatic amine
- Pyrimidine
- Imidolactam
- Vinylogous amide
- Heteroaromatic compound
- Secondary alcohol
- 1,2-diol
- Azacycle
- Amine
- Alcohol
- Organopnictogen compound
- Organic oxygen compound
- Primary amine
- Organooxygen compound
- Organonitrogen compound
- Organic nitrogen compound
- Hydrocarbon derivative
- Organic oxide
- Aromatic heteropolycyclic compound
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| Molecular Framework | Aromatic heteropolycyclic compounds |
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| External Descriptors | Not Available |
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| Ontology |
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| Disposition | Biological Location: Subcellular: Biofluid and excreta: Tissue and substructures: Source: |
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| Role | Industrial application: Pharmaceutical industry: |
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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 | 218 - 221 °C | 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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| General References | - Schallreuter KU, Wood JM, Pittelkow MR, Gutlich M, Lemke KR, Rodl W, Swanson NN, Hitzemann K, Ziegler I: Regulation of melanin biosynthesis in the human epidermis by tetrahydrobiopterin. Science. 1994 Mar 11;263(5152):1444-6. [PubMed:8128228 ]
- Kim H, Roh H, Lee HJ, Chung SY, Choi SO, Lee KR, Han SB: Determination of phloroglucinol in human plasma by high-performance liquid chromatography-mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 25;792(2):307-12. [PubMed:12860038 ]
- Ismaili L, Refouvelet B, Xicluna A, Robert JF, Guillaume YC: Phloroglucinol: novel synthesis and role of the magnesium cation on its binding with human serum albumin (HSA) using a biochromatographic approach based on Langmuir isotherms. J Pharm Biomed Anal. 2003 Jul 14;32(3):549-53. [PubMed:14565560 ]
- Jafri W, Yakoob J, Hussain S, Jafri N, Islam M: Phloroglucinol in irritable bowel syndrome. J Pak Med Assoc. 2006 Jan;56(1):5-8. [PubMed:16454126 ]
- Fiset C, LeBel M: Influence of the menstrual cycle on the absorption and elimination of D-xylose. Clin Pharmacol Ther. 1990 Nov;48(5):529-36. [PubMed:2225712 ]
- Armarego WL, Randles D, Taguchi H: Peroxidase catalysed aerobic degradation of 5,6,7,8-tetrahydrobiopterin at physiological pH. Eur J Biochem. 1983 Oct 3;135(3):393-403. [PubMed:6617639 ]
- Davis MD, Kaufman S: Evidence for the formation of the 4a-carbinolamine during the tyrosine-dependent oxidation of tetrahydrobiopterin by rat liver phenylalanine hydroxylase. J Biol Chem. 1989 May 25;264(15):8585-96. [PubMed:2722790 ]
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