| Record Information |
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| Version | 2.0 |
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| Created at | 2022-09-12 14:28:43 UTC |
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| Updated at | 2022-09-12 14:28:43 UTC |
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| NP-MRD ID | NP0329770 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | 6-methyl-5-(3-oxobutyl)-2-(propan-2-ylidene)cyclohept-4-en-1-one |
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| Description | Curcumadione belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. 6-methyl-5-(3-oxobutyl)-2-(propan-2-ylidene)cyclohept-4-en-1-one is found in Curcuma aromatica and Curcuma zedoaria. 6-methyl-5-(3-oxobutyl)-2-(propan-2-ylidene)cyclohept-4-en-1-one was first documented in 2008 (PMID: 18589781). Based on a literature review a small amount of articles have been published on Curcumadione (PMID: 18663560) (PMID: 35851121) (PMID: 33866197). |
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| Structure | CC1CC(=O)C(CC=C1CCC(C)=O)=C(C)C InChI=1S/C15H22O2/c1-10(2)14-8-7-13(6-5-12(4)16)11(3)9-15(14)17/h7,11H,5-6,8-9H2,1-4H3 |
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| Synonyms | Not Available |
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| Chemical Formula | C15H22O2 |
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| Average Mass | 234.3390 Da |
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| Monoisotopic Mass | 234.16198 Da |
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| IUPAC Name | 6-methyl-5-(3-oxobutyl)-2-(propan-2-ylidene)cyclohept-4-en-1-one |
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| Traditional Name | 6-methyl-5-(3-oxobutyl)-2-(propan-2-ylidene)cyclohept-4-en-1-one |
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| CAS Registry Number | Not Available |
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| SMILES | CC1CC(=O)C(CC=C1CCC(C)=O)=C(C)C |
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| InChI Identifier | InChI=1S/C15H22O2/c1-10(2)14-8-7-13(6-5-12(4)16)11(3)9-15(14)17/h7,11H,5-6,8-9H2,1-4H3 |
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| InChI Key | JWUVBGKPYDWLJC-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 sesquiterpenoids. These are terpenes with three consecutive isoprene units. |
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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 | Sesquiterpenoids |
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| Alternative Parents | |
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| Substituents | - Xanthane sesquiterpenoid
- Sesquiterpenoid
- Cyclic ketone
- Ketone
- 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 | - Qu Y, Xu F, Nakamura S, Matsuda H, Pongpiriyadacha Y, Wu L, Yoshikawa M: Sesquiterpenes from Curcuma comosa. J Nat Med. 2009 Jan;63(1):102-4. doi: 10.1007/s11418-008-0282-8. Epub 2008 Jul 29. [PubMed:18663560 ]
- Fei CH, Tong HJ, Li Y, Xu Z, Qin YW, Bian ZH, Su LL, Ji, Lu TL, Mao CQ: [Prediction of material basis and mechanism of Curcumae Rhizoma in treatment of coronary heart disease]. Zhongguo Zhong Yao Za Zhi. 2022 Jun;47(12):3270-3284. doi: 10.19540/j.cnki.cjcmm.20220118.201. [PubMed:35851121 ]
- Tong H, Yu M, Fei C, Ji, Dong J, Su L, Gu W, Mao C, Li L, Bian Z, Lu T, Hao M, Zeng B: Bioactive constituents and the molecular mechanism of Curcumae Rhizoma in the treatment of primary dysmenorrhea based on network pharmacology and molecular docking. Phytomedicine. 2021 Jun;86:153558. doi: 10.1016/j.phymed.2021.153558. Epub 2021 Mar 27. [PubMed:33866197 ]
- Wang LX, Deng ZW, Huang KX, Lin WH: [Sesquiterpenes from stems and leaves of Curcuma wenyujin]. Zhongguo Zhong Yao Za Zhi. 2008 Apr;33(7):785-8. [PubMed:18589781 ]
- LOTUS database [Link]
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