Record Information |
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Version | 1.0 |
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Created at | 2022-09-08 21:28:46 UTC |
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Updated at | 2022-09-08 21:28:47 UTC |
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NP-MRD ID | NP0274185 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (2s,4ar,6s,7as,7br)-2-hydroxy-6-(hydroxymethyl)-3,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-4-one |
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Description | Plorantinone D belongs to the class of organic compounds known as illudanes and illudins. These are sesquiterpenoids containing either the illudane moiety (based on a 3,6,6,7b-tetramethyl-decahydro-1H-cyclobuta[e]indene ring system), the illudin moiety (2',2',4',6'-tetramethyl-octahydrospiro[cyclopropane-1,5'-indene]), or a derivative thereof. (2s,4ar,6s,7as,7br)-2-hydroxy-6-(hydroxymethyl)-3,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-4-one is found in Russula delica. It was first documented in 1993 (PMID: 36108117). Based on a literature review a significant number of articles have been published on Plorantinone D (PMID: 36108986) (PMID: 36108951) (PMID: 36108928) (PMID: 36108927). |
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Structure | CC1=C2[C@@H](O)C[C@]2(C)[C@H]2C[C@](C)(CO)C[C@H]2C1=O InChI=1S/C15H22O3/c1-8-12-11(17)6-15(12,3)10-5-14(2,7-16)4-9(10)13(8)18/h9-11,16-17H,4-7H2,1-3H3/t9-,10+,11+,14-,15-/m1/s1 |
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Synonyms | Not Available |
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Chemical Formula | C15H22O3 |
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Average Mass | 250.3380 Da |
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Monoisotopic Mass | 250.15689 Da |
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IUPAC Name | (2S,4aR,6S,7aS,7bR)-2-hydroxy-6-(hydroxymethyl)-3,6,7b-trimethyl-1H,2H,4H,4aH,5H,6H,7H,7aH,7bH-cyclobuta[e]inden-4-one |
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Traditional Name | (2S,4aR,6S,7aS,7bR)-2-hydroxy-6-(hydroxymethyl)-3,6,7b-trimethyl-1H,2H,4aH,5H,7H,7aH-cyclobuta[e]inden-4-one |
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CAS Registry Number | Not Available |
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SMILES | CC1=C2[C@@H](O)C[C@]2(C)[C@H]2C[C@](C)(CO)C[C@H]2C1=O |
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InChI Identifier | InChI=1S/C15H22O3/c1-8-12-11(17)6-15(12,3)10-5-14(2,7-16)4-9(10)13(8)18/h9-11,16-17H,4-7H2,1-3H3/t9-,10+,11+,14-,15-/m1/s1 |
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InChI Key | JMCRLYORYXAMMG-CDYMVBJSSA-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 illudanes and illudins. These are sesquiterpenoids containing either the illudane moiety (based on a 3,6,6,7b-tetramethyl-decahydro-1H-cyclobuta[e]indene ring system), the illudin moiety (2',2',4',6'-tetramethyl-octahydrospiro[cyclopropane-1,5'-indene]), or a derivative thereof. |
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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 | Illudanes and illudins |
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Alternative Parents | |
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Substituents | - Illudane sesquiterpenoid
- Cyclohexenone
- Secondary alcohol
- Ketone
- Cyclobutanol
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Primary alcohol
- Organooxygen compound
- Carbonyl group
- Alcohol
- Aliphatic homopolycyclic compound
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Molecular Framework | Aliphatic 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 | - van Dijk FS, Ghali N, Demirdas S, Baker D: TNXB-Related Classical-Like Ehlers-Danlos Syndrome. 1993. [PubMed:36108117 ]
- Liu T, Chen X, Hu Y, Li M, Wu Y, Dai M, Huang Z, Sun P, Zheng J, Ren Z, Wang Y: Sesquiterpenoids and triterpenoids with anti-inflammatory effects from Artemisia vulgaris L. Phytochemistry. 2022 Sep 13;204:113428. doi: 10.1016/j.phytochem.2022.113428. [PubMed:36108986 ]
- Ohara R, Sugahara T, Sugie Y, Onda H, Yoshino N, Nishi K, Ishida M, Kikuzaki H: Identification of components in coriander (Coriandrum sativum L.) inhibiting degranulation of RBL-2H3 cells. Fitoterapia. 2022 Sep 13;163:105298. doi: 10.1016/j.fitote.2022.105298. [PubMed:36108951 ]
- Chen YS, Lee-Sarwar KA, Mirzakhani H, O'Connor GT, Bacharier LB, Zeiger RS, Knihtila HM, Jha A, Kelly RS, Laranjo N, Fichorova RN, Luu N, Weiss ST, Litonjua AA: The Association of Prenatal C-Reactive Protein Levels With Childhood Asthma and Atopy. J Allergy Clin Immunol Pract. 2022 Sep 13. pii: S2213-2198(22)00928-X. doi: 10.1016/j.jaip.2022.08.044. [PubMed:36108928 ]
- Romano A, Valluzzi RL, Gaeta F, Caruso C, Zaffiro A, Quaratino D, Ebo D, Sabato V: The Combined Use of Chronological and Morphological Criteria in the Evaluation of Immediate Penicillin Reactions: Evidence From a Large Study. J Allergy Clin Immunol Pract. 2022 Sep 13. pii: S2213-2198(22)00929-1. doi: 10.1016/j.jaip.2022.08.045. [PubMed:36108927 ]
- LOTUS database [Link]
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