Record Information |
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Version | 1.0 |
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Created at | 2022-09-07 21:41:30 UTC |
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Updated at | 2022-09-07 21:41:30 UTC |
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NP-MRD ID | NP0256760 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | 5-heptadecyl-2,3-dihydroxycyclohexa-2,5-diene-1,4-dione |
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Description | 5-Heptadecyl-2,3-dihydroxycyclohexa-2,5-diene-1,4-dione belongs to the class of organic compounds known as ubiquinones. These are coenzyme Q derivatives containing a 5, 6-dimethoxy-3-methyl(1,4-benzoquinone) moiety to which an isoprenyl group is attached at ring position 2(or 6). 5-heptadecyl-2,3-dihydroxycyclohexa-2,5-diene-1,4-dione is found in Myrsine africana. It was first documented in 2021 (PMID: 34975464). Based on a literature review a significant number of articles have been published on 5-heptadecyl-2,3-dihydroxycyclohexa-2,5-diene-1,4-dione (PMID: 35837172) (PMID: 35788500) (PMID: 35245619) (PMID: 35052956). |
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Structure | CCCCCCCCCCCCCCCCCC1=CC(=O)C(O)=C(O)C1=O InChI=1S/C23H38O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-19-18-20(24)22(26)23(27)21(19)25/h18,26-27H,2-17H2,1H3 |
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Synonyms | Not Available |
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Chemical Formula | C23H38O4 |
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Average Mass | 378.5530 Da |
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Monoisotopic Mass | 378.27701 Da |
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IUPAC Name | 5-heptadecyl-2,3-dihydroxycyclohexa-2,5-diene-1,4-dione |
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Traditional Name | 5-heptadecyl-2,3-dihydroxycyclohexa-2,5-diene-1,4-dione |
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CAS Registry Number | Not Available |
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SMILES | CCCCCCCCCCCCCCCCCC1=CC(=O)C(O)=C(O)C1=O |
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InChI Identifier | InChI=1S/C23H38O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-19-18-20(24)22(26)23(27)21(19)25/h18,26-27H,2-17H2,1H3 |
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InChI Key | OQACHSQOSJXQFV-UHFFFAOYSA-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, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, H2O, 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 ubiquinones. These are coenzyme Q derivatives containing a 5, 6-dimethoxy-3-methyl(1,4-benzoquinone) moiety to which an isoprenyl group is attached at ring position 2(or 6). |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Prenol lipids |
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Sub Class | Quinone and hydroquinone lipids |
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Direct Parent | Ubiquinones |
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Alternative Parents | |
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Substituents | - Ubiquinone skeleton
- Quinone
- P-benzoquinone
- Vinylogous acid
- Cyclic ketone
- Ketone
- Enediol
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aliphatic homomonocyclic compound
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Molecular Framework | Aliphatic homomonocyclic 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 | - He Y, Li Y, Liang T, Mo S, Liao Y, Chen Z, Zhao S, Ran Q, Han C, Hoa PTT: Effects of 2-dodecyl-6-methoxycyclohexa-2,5-diene-1,4-dione on autophagy and the PI3K/AKT/mTOR signaling pathway in human cholangiocarcinoma QBC939 cells. J Gastrointest Oncol. 2022 Jun;13(3):1423-1432. doi: 10.21037/jgo-22-298. [PubMed:35837172 ]
- Kachi-Terajima C, Inaba Y, Tsuruga K: Synthesis, crystal structure and determination of the pK(a) value of 2,6-dimethoxycyclohexa-2,5-diene-1,4-dione 1-[2-(quinolin-8-yl)hydrazone]. Acta Crystallogr C Struct Chem. 2022 Jul 1;78(Pt 7):371-375. doi: 10.1107/S2053229622005368. Epub 2022 Jun 7. [PubMed:35788500 ]
- Hiki K, Yamamoto H: Concentration and leachability of N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylenediamine (6PPD) and its quinone transformation product (6PPD-Q) in road dust collected in Tokyo, Japan. Environ Pollut. 2022 Jun 1;302:119082. doi: 10.1016/j.envpol.2022.119082. Epub 2022 Mar 1. [PubMed:35245619 ]
- Qureshi KA, Imtiaz M, Parvez A, Rai PK, Jaremko M, Emwas AH, Bholay AD, Fatmi MQ: In Vitro and In Silico Approaches for the Evaluation of Antimicrobial Activity, Time-Kill Kinetics, and Anti-Biofilm Potential of Thymoquinone (2-Methyl-5-propan-2-ylcyclohexa-2,5-diene-1,4-dione) against Selected Human Pathogens. Antibiotics (Basel). 2022 Jan 10;11(1):79. doi: 10.3390/antibiotics11010079. [PubMed:35052956 ]
- Wang L, Cao J, Xu Q, Lu X, Yang X, Song Q, Chen S, Du K, Huang R, Zou C: 2-Dodecyl-6-Methoxycyclohexa-2,5-Diene-1,4-Dione Ameliorates Diabetic Cognitive Impairment Through Inhibiting Hif3alpha and Apoptosis. Front Pharmacol. 2021 Dec 16;12:708141. doi: 10.3389/fphar.2021.708141. eCollection 2021. [PubMed:34975464 ]
- LOTUS database [Link]
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