| Record Information |
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| Version | 2.0 |
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| Created at | 2022-05-11 16:41:59 UTC |
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| Updated at | 2022-05-11 16:41:59 UTC |
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| NP-MRD ID | NP0087166 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | 7-Hydroxy-6-methyl-8-ribityl lumazine |
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| Description | 7-Hydroxy-6-methyl-8-ribityl lumazine, also known as masuda's compound V or RL-6-me-7-OH, belongs to the class of organic compounds known as pteridines and derivatives. These are polycyclic aromatic compounds containing a pteridine moiety, which consists of a pyrimidine fused to a pyrazine ring to form pyrimido(4,5-b)pyrazine. The pteridine that is lumazine substituted with a methyl group at C-6, a hydroxy group at C-7 and a 1-D-ribityl group at N-8. 7-Hydroxy-6-methyl-8-ribityl lumazine is an extremely weak basic (essentially neutral) compound (based on its pKa). In humans, 7-hydroxy-6-methyl-8-ribityl lumazine is involved in riboflavin metabolism. |
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| Structure | CC1=C(O)N(C[C@H](O)[C@H](O)[C@H](O)CO)C2=NC(=O)NC(=O)C2=N1 InChI=1S/C12H16N4O7/c1-4-11(22)16(2-5(18)8(20)6(19)3-17)9-7(13-4)10(21)15-12(23)14-9/h5-6,8,17-20,22H,2-3H2,1H3,(H,15,21,23)/t5-,6+,8-/m0/s1 |
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| Synonyms | | Value | Source |
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| 1-Deoxy-1-(3,4-dihydro-7-hydroxy-6-methyl-2,4-dioxo-8(2H)-pteridinyl)-D-ribitol | ChEBI | | 7-Hydroxy-6-methyl-8-D-ribityllumazine | ChEBI | | Masuda's compound V | ChEBI | | RL-6-Me-7-OH | ChEBI | | 7-Oxolumazine | Kegg | | 6-Methyl-7-oxo-8-ribityllumazine | Kegg | | CRM | HMDB |
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| Chemical Formula | C12H16N4O7 |
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| Average Mass | 328.2780 Da |
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| Monoisotopic Mass | 328.10190 Da |
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| IUPAC Name | 7-hydroxy-6-methyl-8-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-2,3,4,8-tetrahydropteridine-2,4-dione |
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| Traditional Name | 7-hydroxy-6-methyl-8-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-3H-pteridine-2,4-dione |
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| CAS Registry Number | Not Available |
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| SMILES | CC1=C(O)N(C[C@H](O)[C@H](O)[C@H](O)CO)C2=NC(=O)NC(=O)C2=N1 |
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| InChI Identifier | InChI=1S/C12H16N4O7/c1-4-11(22)16(2-5(18)8(20)6(19)3-17)9-7(13-4)10(21)15-12(23)14-9/h5-6,8,17-20,22H,2-3H2,1H3,(H,15,21,23)/t5-,6+,8-/m0/s1 |
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| InChI Key | COXMGTTXHPRZBO-BBVRLYRLSA-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 pteridines and derivatives. These are polycyclic aromatic compounds containing a pteridine moiety, which consists of a pyrimidine fused to a pyrazine ring to form pyrimido(4,5-b)pyrazine. |
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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 | Not Available |
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| Direct Parent | Pteridines and derivatives |
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| Alternative Parents | |
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| Substituents | - Pteridine
- Pyrimidone
- Pyrazine
- Pyrimidine
- Heteroaromatic compound
- Vinylogous amide
- Lactam
- Secondary alcohol
- Polyol
- Azacycle
- Organic oxide
- Organopnictogen compound
- Organic oxygen compound
- Primary alcohol
- Alcohol
- Organooxygen compound
- Organonitrogen compound
- Organic nitrogen compound
- Hydrocarbon derivative
- Aromatic heteropolycyclic compound
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| Molecular Framework | Aromatic heteropolycyclic compounds |
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| External Descriptors | |
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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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