Record Information |
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Version | 1.0 |
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Created at | 2022-03-17 21:00:29 UTC |
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Updated at | 2022-03-17 21:00:29 UTC |
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NP-MRD ID | NP0048680 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Armillaric acid |
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Description | Armillaric acid, also known as armillarate, 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. Armillaric acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Armillaric acid has been detected, but not quantified in, mushrooms. Armillaric acid is found in Armillaria mellea . It was first documented in 2000 (PMID: 11413487). This could make armillaric acid a potential biomarker for the consumption of these foods (PMID: 16902246) (PMID: 17374880) (PMID: 20044567). |
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Structure | CC1=CC(O)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C(O)=O)C12O InChI=1S/C23H28O7/c1-11-5-13(24)7-16(25)18(11)20(28)30-17-10-22(4)15-9-21(2,3)8-12(15)6-14(19(26)27)23(17,22)29/h5-7,12,15,17,24-25,29H,8-10H2,1-4H3,(H,26,27) |
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Synonyms | Value | Source |
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Armillarate | Generator | 2-(2,4-Dihydroxy-6-methylbenzoyloxy)-2a-hydroxy-6,6,7b-trimethyl-1H,2H,2ah,4ah,5H,6H,7H,7ah,7BH-cyclobuta[e]indene-3-carboxylate | Generator |
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Chemical Formula | C23H28O7 |
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Average Mass | 416.4642 Da |
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Monoisotopic Mass | 416.18350 Da |
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IUPAC Name | 2-(2,4-dihydroxy-6-methylbenzoyloxy)-2a-hydroxy-6,6,7b-trimethyl-1H,2H,2aH,4aH,5H,6H,7H,7aH,7bH-cyclobuta[e]indene-3-carboxylic acid |
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Traditional Name | 2-(2,4-dihydroxy-6-methylbenzoyloxy)-2a-hydroxy-6,6,7b-trimethyl-1H,2H,4aH,5H,7H,7aH-cyclobuta[e]indene-3-carboxylic acid |
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CAS Registry Number | 129251-06-5 |
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SMILES | CC1=CC(O)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C(O)=O)C12O |
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InChI Identifier | InChI=1S/C23H28O7/c1-11-5-13(24)7-16(25)18(11)20(28)30-17-10-22(4)15-9-21(2,3)8-12(15)6-14(19(26)27)23(17,22)29/h5-7,12,15,17,24-25,29H,8-10H2,1-4H3,(H,26,27) |
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InChI Key | AOCKXACXCVTXBB-UHFFFAOYSA-N |
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Experimental Spectra |
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| Not Available | Predicted Spectra |
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| Not Available | 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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Agaricus bisporus | FooDB | - Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
| Armillaria mellea | Fungi | | Pleurotus ostreatus | FooDB | - Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
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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
- P-hydroxybenzoic acid alkyl ester
- P-hydroxybenzoic acid ester
- O-hydroxybenzoic acid ester
- Dihydroxybenzoic acid
- Benzoate ester
- Salicylic acid or derivatives
- Benzoic acid or derivatives
- M-cresol
- Benzoyl
- Resorcinol
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Toluene
- Monocyclic benzene moiety
- Dicarboxylic acid or derivatives
- Benzenoid
- Vinylogous acid
- Tertiary alcohol
- Cyclobutanol
- Carboxylic acid ester
- Carboxylic acid derivative
- Carboxylic acid
- Carbonyl group
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen 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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