Record Information |
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Version | 1.0 |
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Created at | 2022-09-07 05:38:50 UTC |
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Updated at | 2022-09-07 05:38:50 UTC |
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NP-MRD ID | NP0244774 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (2r,2as,7r,7as,7br)-2a,7-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 2-hydroxy-4-methoxy-6-methylbenzoate |
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Description | (2R,2aS,7R,7aS,7bR)-2a,7-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1H,2H,2aH,4aH,5H,6H,7H,7aH,7bH-cyclobuta[e]inden-2-yl 2-hydroxy-4-methoxy-6-methylbenzoate belongs to the class of organic compounds known as melleolides and analogues. Melleolides and analogues are compounds with a structure characterized by the presence of a 2-hydroxy-4-methoxy-6-methylbenzoic acid derivative linked to a 3,6,6,7b-tetramethyl-cyclobuta[e]indene moiety. (2r,2as,7r,7as,7br)-2a,7-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 2-hydroxy-4-methoxy-6-methylbenzoate is found in Armillaria. It was first documented in 2022 (PMID: 36088123). Based on a literature review a significant number of articles have been published on (2R,2aS,7R,7aS,7bR)-2a,7-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1H,2H,2aH,4aH,5H,6H,7H,7aH,7bH-cyclobuta[e]inden-2-yl 2-hydroxy-4-methoxy-6-methylbenzoate (PMID: 36088122) (PMID: 36088121) (PMID: 36088120) (PMID: 36088119) (PMID: 36088110) (PMID: 36088109). |
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Structure | COC1=CC(C)=C(C(=O)O[C@@H]2C[C@]3(C)[C@@H]4C(CC(C)(C)[C@@H]4O)C=C(CO)[C@]23O)C(O)=C1 InChI=1S/C24H32O7/c1-12-6-15(30-5)8-16(26)18(12)21(28)31-17-10-23(4)19-13(9-22(2,3)20(19)27)7-14(11-25)24(17,23)29/h6-8,13,17,19-20,25-27,29H,9-11H2,1-5H3/t13?,17-,19-,20-,23-,24+/m1/s1 |
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Synonyms | Value | Source |
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(2R,2AS,7R,7as,7BR)-2a,7-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1H,2H,2ah,4ah,5H,6H,7H,7ah,7BH-cyclobuta[e]inden-2-yl 2-hydroxy-4-methoxy-6-methylbenzoic acid | Generator |
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Chemical Formula | C24H32O7 |
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Average Mass | 432.5130 Da |
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Monoisotopic Mass | 432.21480 Da |
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IUPAC Name | Not Available |
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Traditional Name | Not Available |
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CAS Registry Number | Not Available |
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SMILES | COC1=CC(C)=C(C(=O)O[C@@H]2C[C@]3(C)[C@@H]4C(CC(C)(C)[C@@H]4O)C=C(CO)[C@]23O)C(O)=C1 |
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InChI Identifier | InChI=1S/C24H32O7/c1-12-6-15(30-5)8-16(26)18(12)21(28)31-17-10-23(4)19-13(9-22(2,3)20(19)27)7-14(11-25)24(17,23)29/h6-8,13,17,19-20,25-27,29H,9-11H2,1-5H3/t13?,17-,19-,20-,23-,24+/m1/s1 |
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InChI Key | NHDJKXOHRUHQHG-MFWOBCTISA-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 | Species Name | Source | Reference |
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Armillaria | LOTUS Database | |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as melleolides and analogues. Melleolides and analogues are compounds with a structure characterized by the presence of a 2-hydroxy-4-methoxy-6-methylbenzoic acid derivative linked to a 3,6,6,7b-tetramethyl-cyclobuta[e]indene moiety. |
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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 | Sesquiterpenoids |
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Direct Parent | Melleolides and analogues |
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Alternative Parents | |
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Substituents | - Melleolide-skeleton
- O-hydroxybenzoic acid ester
- P-methoxybenzoic acid or derivatives
- Salicylic acid or derivatives
- Methoxyphenol
- Benzoate ester
- Benzoic acid or derivatives
- Phenoxy compound
- Methoxybenzene
- Phenol ether
- M-cresol
- Benzoyl
- Anisole
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Toluene
- Phenol
- Alkyl aryl ether
- Benzenoid
- Monocyclic benzene moiety
- Vinylogous acid
- Tertiary alcohol
- Cyclic alcohol
- Secondary alcohol
- Cyclobutanol
- Carboxylic acid ester
- Monocarboxylic acid or derivatives
- Ether
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Primary alcohol
- Organooxygen compound
- Alcohol
- Aromatic homopolycyclic compound
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Molecular Framework | Aromatic homopolycyclic 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 | - Xu X, Rothrock MJ Jr, Reeves J, Kumar GD, Mishra A: Using E. coli population to predict foodborne pathogens in pastured poultry farms. Food Microbiol. 2022 Dec;108:104092. doi: 10.1016/j.fm.2022.104092. Epub 2022 Jul 14. [PubMed:36088123 ]
- Lanzl MI, Zwietering MH, Abee T, den Besten HMW: Combining enrichment with multiplex real-time PCR leads to faster detection and identification of Campylobacter spp. in food compared to ISO 10272-1:2017. Food Microbiol. 2022 Dec;108:104117. doi: 10.1016/j.fm.2022.104117. Epub 2022 Aug 19. [PubMed:36088122 ]
- Cacciatore FA, Maders C, Alexandre B, Barreto Pinilla CM, Brandelli A, da Silva Malheiros P: Carvacrol encapsulation into nanoparticles produced from chia and flaxseed mucilage: Characterization, stability and antimicrobial activity against Salmonella and Listeria monocytogenes. Food Microbiol. 2022 Dec;108:104116. doi: 10.1016/j.fm.2022.104116. Epub 2022 Aug 18. [PubMed:36088121 ]
- Liu X, Li Y, Micallef SA: Developmentally related and drought-induced shifts in the kale metabolome limited Salmonella enterica association, providing novel insights to enhance food safety. Food Microbiol. 2022 Dec;108:104113. doi: 10.1016/j.fm.2022.104113. Epub 2022 Aug 18. [PubMed:36088120 ]
- Dos Santos AMP, Panzenhagen P, Ferrari RG, Conte-Junior CA: Large-scale genomic analysis reveals the pESI-like megaplasmid presence in Salmonella Agona, Muenchen, Schwarzengrund, and Senftenberg. Food Microbiol. 2022 Dec;108:104112. doi: 10.1016/j.fm.2022.104112. Epub 2022 Aug 12. [PubMed:36088119 ]
- Soare C, Mazeri S, McAteer S, McNeilly TN, Seguino A, Chase-Topping M: The microbial condition of Scottish wild deer carcasses collected for human consumption and the hygiene risk factors associated with Escherichia coli and total coliforms contamination. Food Microbiol. 2022 Dec;108:104102. doi: 10.1016/j.fm.2022.104102. Epub 2022 Aug 7. [PubMed:36088110 ]
- Zhao Y, Liu S, Han X, Zhou Z, Mao J: Combined effects of fermentation temperature and Saccharomyces cerevisiae strains on free amino acids, flavor substances, and undesirable secondary metabolites in huangjiu fermentation. Food Microbiol. 2022 Dec;108:104091. doi: 10.1016/j.fm.2022.104091. Epub 2022 Jul 12. [PubMed:36088109 ]
- Centeno JA, Lorenzo JM, Carballo J: Effects of autochthonous Kluyveromyces lactis and commercial Enterococcus faecium adjunct cultures on the volatile profile and the sensory characteristics of short-ripened acid-curd Cebreiro cheese. Food Microbiol. 2022 Dec;108:104101. doi: 10.1016/j.fm.2022.104101. Epub 2022 Aug 1. [PubMed:36088116 ]
- Liu MK, Liu CY, Tian XH, Feng J, Guo XJ, Liu Y, Zhang XY, Tang YM: Bioremediation of degraded pit mud by indigenous microbes for Baijiu production. Food Microbiol. 2022 Dec;108:104096. doi: 10.1016/j.fm.2022.104096. Epub 2022 Aug 4. [PubMed:36088112 ]
- Chen J, Yang R, Wang Y, Koseki S, Fu L, Wang Y: Inhibitory effect of d-Tryptophan on the spoilage potential of Shewanella baltica and Pseudomonas fluorescens and its potential application in salmon fillet preservation. Food Microbiol. 2022 Dec;108:104104. doi: 10.1016/j.fm.2022.104104. Epub 2022 Aug 9. [PubMed:36088118 ]
- Wicaksono WA, Buko A, Kusstatscher P, Sinkkonen A, Laitinen OH, Virtanen SM, Hyoty H, Cernava T, Berg G: Modulation of the food microbiome by apple fruit processing. Food Microbiol. 2022 Dec;108:104103. doi: 10.1016/j.fm.2022.104103. Epub 2022 Aug 4. [PubMed:36088117 ]
- Jyung S, Kang JW, Kang DH: L. monocytogens exhibited less cell membrane damage, lipid peroxidation, and intracellular reactive oxygen species accumulation after plasma-activated water treatment compared to E. coli O157:H7 and S. Typhimurium. Food Microbiol. 2022 Dec;108:104098. doi: 10.1016/j.fm.2022.104098. Epub 2022 Jul 30. [PubMed:36088114 ]
- Parafati L, Restuccia C, Cirvilleri G: Efficacy and mechanism of action of food isolated yeasts in the control of Aspergillus flavus growth on pistachio nuts. Food Microbiol. 2022 Dec;108:104100. doi: 10.1016/j.fm.2022.104100. Epub 2022 Aug 6. [PubMed:36088115 ]
- Tofalo R, Perpetuini G, Rossetti AP, Gaggiotti S, Piva A, Olivastri L, Cichelli A, Compagnone D, Arfelli G: Impact of Saccharomyces cerevisiae and non-Saccharomyces yeasts to improve traditional sparkling wines production. Food Microbiol. 2022 Dec;108:104097. doi: 10.1016/j.fm.2022.104097. Epub 2022 Jul 20. [PubMed:36088113 ]
- Taibi A, Diop A, Leneveu-Jenvrin C, Broussolle V, Lortal S, Meot JM, Soria C, Chillet M, Lechaudel M, Minier J, Constancias F, Remize F, Meile JC: Dynamics of bacterial and fungal communities of mango: From the tree to ready-to-Eat products. Food Microbiol. 2022 Dec;108:104095. doi: 10.1016/j.fm.2022.104095. Epub 2022 Jul 18. [PubMed:36088111 ]
- LOTUS database [Link]
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