| Record Information |
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| Version | 2.0 |
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| Created at | 2022-05-11 16:34:29 UTC |
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| Updated at | 2022-05-11 16:34:29 UTC |
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| NP-MRD ID | NP0086912 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | 4a-Carbinolamine tetrahydrobiopterin |
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| Description | 4A-Carbinolamine tetrahydrobiopterin, also known as 6,7-dihydrobiopterin or 1,3,5-trihydroxybenzene, 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-Carbinolamine tetrahydrobiopterin is a moderately basic compound (based on its pKa). 4A-Carbinolamine tetrahydrobiopterin exists in all living organisms, ranging from bacteria to humans. 4a-Carbinolamine tetrahydrobiopterin was first documented in 1990 (PMID: 2225712). A 4a-Carbinolamine tetrahydrobiopterin that has R configuration at position 6 and in which the 1,2-dihydroxypropyl substituent has 1R,2S configuration (PMID: 12860038) (PMID: 14565560) (PMID: 8128228) (PMID: 16454126). |
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| Structure | [H][C@@]1(CN=C2NC(N)=NC(=O)C2=N1)[C@@H](O)[C@H](C)O 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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| Synonyms | | Value | Source |
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| (6R)-2-Amino-6-[(1R,2S)-1,2-dihydroxypropyl]-7,8-dihydro-6H-pteridin-4-one | ChEBI | | (6R)-6-[(1R,2S)-1,2-Dihydroxypropyl]-7,8-dihydro-6H-pterin | ChEBI | | 6,7-Dihydrobiopterin | ChEBI | | Q-H2BPT | ChEBI | | Quinoid-dihydrobiopterin | ChEBI | | Quinonoid 6,7-dihydrobiopterin | ChEBI | | (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 | | 4a-Carbinolamine tetrahydrobiopterin | ChEBI |
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| Chemical Formula | C9H13N5O3 |
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| Average Mass | 239.2312 Da |
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| Monoisotopic Mass | 239.10184 Da |
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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 | Not Available |
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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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| Experimental Spectra |
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| Not Available | | Predicted Spectra |
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| | Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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| 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 |
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| Not Available | | Species |
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| Species of Origin | |
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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
- Aminopyrimidine
- Pyrimidone
- Pyrimidine
- Imidolactam
- Vinylogous amide
- Heteroaromatic compound
- Secondary alcohol
- 1,2-diol
- Azacycle
- Organic oxygen compound
- Hydrocarbon derivative
- Alcohol
- Organic oxide
- Primary amine
- Organooxygen compound
- Organonitrogen compound
- Organic nitrogen compound
- Amine
- Organopnictogen compound
- Aromatic heteropolycyclic compound
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| Molecular Framework | Aromatic heteropolycyclic compounds |
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| External Descriptors | Not Available |
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| Physical Properties |
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| State | Not Available |
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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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| General References | - 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. doi: 10.1016/s1570-0232(03)00316-7. [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. doi: 10.1016/s0731-7085(03)00220-6. [PubMed:14565560 ]
- 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. doi: 10.1126/science.8128228. [PubMed:8128228 ]
- 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. doi: 10.1038/clpt.1990.189. [PubMed:2225712 ]
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