Record Information |
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Version | 1.0 |
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Created at | 2021-06-21 00:15:42 UTC |
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Updated at | 2021-06-30 00:17:51 UTC |
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NP-MRD ID | NP0042649 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (4R,5S,10S)-5-hydroxy-11,12,13-trinoreudesm-6-en-8-one |
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Provided By | JEOL Database |
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Description | (4AS)-4aalpha-Hydroxy-5alpha,8aalpha-dimethyl-4a,5,6,7,8,8a-hexahydronaphthalene-2(1H)-one belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond. (4R,5S,10S)-5-hydroxy-11,12,13-trinoreudesm-6-en-8-one is found in Inula racemosa. It was first documented in 2006 (PMID: 29999960). Based on a literature review a small amount of articles have been published on (4aS)-4aalpha-Hydroxy-5alpha,8aalpha-dimethyl-4a,5,6,7,8,8a-hexahydronaphthalene-2(1H)-one (PMID: 30468024) (PMID: 29999636) (PMID: 29504554) (PMID: 21589050). |
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Structure | [H]O[C@@]12C([H])=C([H])C(=O)C([H])([H])[C@]1(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])[C@@]2([H])C([H])([H])[H] InChI=1S/C12H18O2/c1-9-4-3-6-11(2)8-10(13)5-7-12(9,11)14/h5,7,9,14H,3-4,6,8H2,1-2H3/t9-,11+,12-/m1/s1 |
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Synonyms | Value | Source |
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(4AS)-4aalpha-hydroxy-5a,8aalpha-dimethyl-4a,5,6,7,8,8a-hexahydronaphthalene-2(1H)-one | Generator | (4AS)-4aalpha-hydroxy-5α,8aalpha-dimethyl-4a,5,6,7,8,8a-hexahydronaphthalene-2(1H)-one | Generator |
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Chemical Formula | C12H18O2 |
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Average Mass | 194.2740 Da |
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Monoisotopic Mass | 194.13068 Da |
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IUPAC Name | (4aS,5R,8aS)-4a-hydroxy-5,8a-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-2-one |
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Traditional Name | (4aS,5R,8aS)-4a-hydroxy-5,8a-dimethyl-5,6,7,8-tetrahydro-1H-naphthalen-2-one |
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CAS Registry Number | Not Available |
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SMILES | [H]O[C@@]12C([H])=C([H])C(=O)C([H])([H])[C@]1(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])[C@@]2([H])C([H])([H])[H] |
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InChI Identifier | InChI=1S/C12H18O2/c1-9-4-3-6-11(2)8-10(13)5-7-12(9,11)14/h5,7,9,14H,3-4,6,8H2,1-2H3/t9-,11+,12-/m1/s1 |
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InChI Key | RTYOTMKUFIVWRN-ADEWGFFLSA-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 | 13C NMR Spectrum (1D, 400 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, CDCl3, simulated) | 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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| Not Available | Species |
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Species of Origin | Species Name | Source | Reference |
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Inula racemosa | JEOL database | - Ma, Y.-Y., et al, Phytochem. Lett. 6, 645 (2013)
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond. |
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Kingdom | Organic compounds |
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Super Class | Organic oxygen compounds |
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Class | Organooxygen compounds |
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Sub Class | Carbonyl compounds |
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Direct Parent | Cyclohexenones |
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Alternative Parents | |
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Substituents | - Cyclohexenone
- Tertiary alcohol
- Cyclic alcohol
- Organic oxide
- Hydrocarbon derivative
- 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 | - Liu LF, Yao MJ, Li MY, Wu XZ, Yuan CS: Iridoid Derivatives with Cytotoxic Activity from Pedicularis uliginosa Bunge. Chem Biodivers. 2019 Feb;16(2):e1800524. doi: 10.1002/cbdv.201800524. Epub 2019 Jan 23. [PubMed:30468024 ]
- Authors unspecified: Docetaxel. 2006. [PubMed:29999960 ]
- Authors unspecified: Paclitaxel. 2006. [PubMed:29999636 ]
- Goncalves KO, Ribeiro L, Oliveira CMA, Carvalho JF, Martins FT: New solvates of the drug naltrexone: protonation, conformation and interplay of synthons. Acta Crystallogr C Struct Chem. 2018 Mar 1;74(Pt 3):274-282. doi: 10.1107/S2053229618001791. Epub 2018 Feb 6. [PubMed:29504554 ]
- Cai X, Zhou X, Zheng Z, Zhong W, Li S: (3S,4R,4aS,7aR,12bS)-3-Cyclo-propyl-meth-yl-4a,9-dihy-droxy-3-methyl-7-oxo-2,3,4, 4a,5,6,7,7a-octa-hydro-1H-4,12-methano-1-benzofuro[3,2-e]isoquinolin-3-ium 2,2,2-trifluoro-acetate methanol solvate. Acta Crystallogr Sect E Struct Rep Online. 2010 Oct 20;66(Pt 11):o2868. doi: 10.1107/S1600536810041164. [PubMed:21589050 ]
- Ma, Y.-Y., et al. (2013). Ma, Y.-Y., et al, Phytochem. Lett. 6, 645 (2013). Phytochem..
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