Record Information |
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Version | 1.0 |
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Created at | 2022-02-14 20:48:05 UTC |
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Updated at | 2022-03-10 22:17:46 UTC |
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NP-MRD ID | NP0044291 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | 6,7-Dimethyl-8-(1-D-ribityl)lumazine |
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Description | 6,7-Dimethyl-8-(1-D-ribityl)lumazine, also known as DMDRL or RL-6,7-dime, 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 methyl groups at C-6 and -7 and with a 1-D-ribityl group on N-8. 6,7-Dimethyl-8-(1-D-ribityl)lumazine is an extremely weak basic (essentially neutral) compound (based on its pKa). In humans, 6,7-dimethyl-8-(1-D-ribityl)lumazine is involved in riboflavin metabolism. 6,7-Dimethyl-8-(1-D-ribityl)lumazine is expected to be in Cannabis as all living plants are known to produce and metabolize it. |
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Structure | CC1=C(C)N(C[C@H](O)[C@H](O)[C@H](O)CO)C2=NC(=O)NC(=O)C2=N1 InChI=1S/C13H18N4O6/c1-5-6(2)17(3-7(19)10(21)8(20)4-18)11-9(14-5)12(22)16-13(23)15-11/h7-8,10,18-21H,3-4H2,1-2H3,(H,16,22,23)/t7-,8+,10-/m0/s1 |
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Synonyms | Value | Source |
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6,7-Dimethyl-8-(1'-D-ribityl)lumazine | ChEBI | 6,7-Dimethyl-8-(D-ribityl)lumazine | ChEBI | 6,7-Dimethyl-8-D-ribityllumazine | ChEBI | 6,7-Dimethyl-8-ribityllumazine | ChEBI | DMDRL | ChEBI | RL-6,7-DiMe | ChEBI | 6,7-Dimethyl-8-ribityllumazine, 14C-labeled | HMDB | 6,7-Dimethyl-8-ribityllumazine, (D)-isomer | HMDB | 1-Deoxy-1-(3,4-dihydro-6,7-dimethyl-2,4-dioxo-8(2H)-pteridinyl)-D-ribitol | HMDB | 6,7-Dimethyl-8-(1’-D-ribityl)lumazine | HMDB | 6,7-Dimethylribityllumazine | HMDB | 6,7-Dimethylribolumazine | HMDB | 2,4(1H,3H)-Pteridinedione, 6,7-dimethyl-8-(2,3,4,5-tetrahydroxypentyl)-, [2S-(2R*,3R*,4S*)]- | HMDB |
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Chemical Formula | C13H18N4O6 |
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Average Mass | 326.3052 Da |
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Monoisotopic Mass | 326.12263 Da |
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IUPAC Name | 6,7-dimethyl-8-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-2,3,4,8-tetrahydropteridine-2,4-dione |
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Traditional Name | 6,7-dimethyl-8-ribityllumazine |
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CAS Registry Number | 2535-20-8 |
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SMILES | CC1=C(C)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/C13H18N4O6/c1-5-6(2)17(3-7(19)10(21)8(20)4-18)11-9(14-5)12(22)16-13(23)15-11/h7-8,10,18-21H,3-4H2,1-2H3,(H,16,22,23)/t7-,8+,10-/m0/s1 |
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InChI Key | SXDXRJZUAJBNFL-XKSSXDPKSA-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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General References | - Kjer-Nielsen L, Patel O, Corbett AJ, Le Nours J, Meehan B, Liu L, Bhati M, Chen Z, Kostenko L, Reantragoon R, Williamson NA, Purcell AW, Dudek NL, McConville MJ, O'Hair RA, Khairallah GN, Godfrey DI, Fairlie DP, Rossjohn J, McCluskey J: MR1 presents microbial vitamin B metabolites to MAIT cells. Nature. 2012 Nov 29;491(7426):717-23. doi: 10.1038/nature11605. Epub 2012 Oct 10. [PubMed:23051753 ]
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