Record Information |
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Version | 1.0 |
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Created at | 2023-06-09 20:02:21 UTC |
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Updated at | 2024-05-13 01:10:25 UTC |
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NP-MRD ID | NP0331682 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | 2-Methyl-1,4-Naphthoquinone |
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Description | Menadione, also known as vitamin K3 or aquinone, belongs to the class of organic compounds known as naphthoquinones. Naphthoquinones are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone). Large doses of menadione have been reported to cause adverse outcomes including hemolytic anemia due to G6PD deficiency, neonatal brain or liver damage, or neonatal death in some cases. Menadione is an extremely weak basic (essentially neutral) compound (based on its pKa). Menadione exists in all living organisms, ranging from bacteria to humans. In humans, menadione is involved in doxorubicin metabolism pathway. Outside of the human body, Menadione has been detected, but not quantified in, several different foods, such as wax gourds, garden rhubarbs, common buckwheats, chinese chives, and figs. This could make menadione a potential biomarker for the consumption of these foods. Menadione is a vitamin precursor of K2 which utilizes alkylation in the liver to yield menaquinones (MK-n, n=1-13; K2 vitamers), and hence, is better classified as a provitamin. Menadione is a potentially toxic compound. Moreover, menadione supplements have been banned by the FDA because of their high toxicity. Large doses have also been reported to cause brain damage. Menadione is a synthetic naphthoquinone without the isoprenoid side chain and biological activity, but can be converted to active vitamin K2, menaquinone, after alkylation in vivo. It was first documented in 1961 (PMID: 13779073). Despite the fact that it can serve as a precursor to various types of vitamin K, menadione is generally not used as a nutritional supplement (PMID: 28166217) (PMID: 1650428) (PMID: 15052609) (PMID: 16469140). |
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Structure | CC1=CC(=O)C2=CC=CC=C2C1=O InChI=1S/C11H8O2/c1-7-6-10(12)8-4-2-3-5-9(8)11(7)13/h2-6H,1H3 |
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Synonyms | Value | Source |
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2-Methyl-1,4-naphthalenedione | ChEBI | 2-Methyl-1,4-naphthochinon | ChEBI | 2-Methyl-1,4-naphthoquinone | ChEBI | Vitamin K3 | ChEBI | Kappaxin | Kegg | 2-Methyl-1,4-naftochinon | HMDB | 2-Methyl-1,4-naphthalendione | HMDB | 2-Methyl-1,4-naphthodione | HMDB | 2-Methylnaphthoquinone | HMDB | 3-Methyl-1,4-naphthoquinone | HMDB | Aquakay | HMDB | Aquinone | HMDB | Hemodal | HMDB | Juva-K | HMDB | K-Thrombyl | HMDB | K-Vitan | HMDB | Kaergona | HMDB | Kanone | HMDB | Kappaxan | HMDB | Karcon | HMDB | Kareon | HMDB | Kativ-g | HMDB | Kayklot | HMDB | Kaykot | HMDB | Kaynone | HMDB | Kayquinone | HMDB | Kipca | HMDB | Kipca-oil soluble | HMDB | Klottone | HMDB | Koaxin | HMDB | Kolklot | HMDB | Menadion | HMDB | Menaphthene | HMDB | Menaphthon | HMDB | Menaphthone | HMDB | Menaphtone | HMDB | Menaquinone | HMDB | Menaquinone O | HMDB | Mitenon | HMDB | Mitenone | HMDB | MNQ | HMDB | Panosine | HMDB | Prokayvit | HMDB | Synkay | HMDB | Thyloquinone | HMDB | Vitamin K0 | HMDB | Vitamin K2 | HMDB | Vitamin K3: 1,4-dihydro-1,4-dioxo-2-methylnaphthalene | HMDB | Bisulfite, menadione | HMDB | Vicasol | HMDB | Bisulfite, menadione sodium | HMDB | Menadione sodium bisulfite | HMDB | Vikasol | HMDB | Vitamin K 3 | HMDB | Menadione sodium bisulfite, trihydrate | HMDB | Vitamin K3 sodium bisulfite | HMDB | Menadione bisulfite | HMDB | Sodium bisulfite, menadione | HMDB |
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Chemical Formula | C11H8O2 |
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Average Mass | 172.1800 Da |
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Monoisotopic Mass | 172.05243 Da |
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IUPAC Name | 2-methyl-1,4-dihydronaphthalene-1,4-dione |
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Traditional Name | menadione |
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CAS Registry Number | Not Available |
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SMILES | CC1=CC(=O)C2=CC=CC=C2C1=O |
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InChI Identifier | InChI=1S/C11H8O2/c1-7-6-10(12)8-4-2-3-5-9(8)11(7)13/h2-6H,1H3 |
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InChI Key | MJVAVZPDRWSRRC-UHFFFAOYSA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental) | ztmnb@umsystem.edu | Not Available | Not Available | 2024-05-11 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental) | ztmnb@umsystem.edu | Not Available | Not Available | 2024-05-11 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental) | ztmnb@umsystem.edu | Not Available | Not Available | 2024-05-11 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Not Available | Chemical Shift Submissions |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 1H NMR Spectrum (1D, 600.133705802, CD3OD, simulated) | ztmnb@umsystem.edu | Sumner lab, University of Missouri | Zach Tretter | 2024-05-11 | View Spectrum |
| Species |
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Species of Origin | Not Available |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as naphthoquinones. Naphthoquinones are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone). |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Naphthalenes |
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Sub Class | Naphthoquinones |
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Direct Parent | Naphthoquinones |
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Alternative Parents | |
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Substituents | - Naphthoquinone
- Aryl ketone
- Quinone
- Ketone
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Aromatic homopolycyclic compound
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Molecular Framework | Aromatic homopolycyclic 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 | - Keller AN, Eckle SB, Xu W, Liu L, Hughes VA, Mak JY, Meehan BS, Pediongco T, Birkinshaw RW, Chen Z, Wang H, D'Souza C, Kjer-Nielsen L, Gherardin NA, Godfrey DI, Kostenko L, Corbett AJ, Purcell AW, Fairlie DP, McCluskey J, Rossjohn J: Drugs and drug-like molecules can modulate the function of mucosal-associated invariant T cells. Nat Immunol. 2017 Apr;18(4):402-411. doi: 10.1038/ni.3679. Epub 2017 Feb 6. [PubMed:28166217 ]
- Varga JM, Kalchschmid G, Klein GF, Fritsch P: Mechanism of allergic cross-reactions--I. Multispecific binding of ligands to a mouse monoclonal anti-DNP IgE antibody. Mol Immunol. 1991 Jun;28(6):641-54. doi: 10.1016/0161-5890(91)90133-5. [PubMed:1650428 ]
- ULBRICH AP: Topical application of menadione, a synthetic vitamin K: preliminary report. J Am Osteopath Assoc. 1961 Jan;60:370-4. [PubMed:13779073 ]
- Osman AM, Rotteveel S, den Besten PJ, van Noort PC: In vivo exposure of Dreissena polymorpha mussels to the quinones menadione and lawsone: menadione is more toxic to mussels than lawsone. J Appl Toxicol. 2004 Mar-Apr;24(2):135-41. doi: 10.1002/jat.963. [PubMed:15052609 ]
- Thijssen HH, Vervoort LM, Schurgers LJ, Shearer MJ: Menadione is a metabolite of oral vitamin K. Br J Nutr. 2006 Feb;95(2):260-6. doi: 10.1079/bjn20051630. [PubMed:16469140 ]
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