| Record Information |
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| Version | 2.0 |
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| Created at | 2022-09-12 01:36:03 UTC |
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| Updated at | 2022-09-12 01:36:03 UTC |
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| NP-MRD ID | NP0322683 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | calaxin |
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| Description | Calaxin belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. calaxin is found in Heliomeris obscura, Sclerocarpus sessilifolius and Dendroviguiera eriophora. calaxin was first documented in 2017 (PMID: 28883641). Based on a literature review a small amount of articles have been published on Calaxin (PMID: 33845135) (PMID: 31286071) (PMID: 31240264) (PMID: 29386625). |
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| Structure | CC(=C)C(=O)O[C@@H]1C[C@@]2(C)OC(=CC2=O)\C(C)=C/[C@H]2OC(=O)C(=C)[C@H]12 InChI=1S/C19H20O6/c1-9(2)17(21)24-14-8-19(5)15(20)7-12(25-19)10(3)6-13-16(14)11(4)18(22)23-13/h6-7,13-14,16H,1,4,8H2,2-3,5H3/b10-6-/t13-,14-,16+,19-/m1/s1 |
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| Synonyms | Not Available |
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| Chemical Formula | C19H20O6 |
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| Average Mass | 344.3630 Da |
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| Monoisotopic Mass | 344.12599 Da |
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| IUPAC Name | (2Z,4R,8R,9R,11R)-2,11-dimethyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0^{4,8}]tetradeca-1(13),2-dien-9-yl 2-methylprop-2-enoate |
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| Traditional Name | (2Z,4R,8R,9R,11R)-2,11-dimethyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0^{4,8}]tetradeca-1(13),2-dien-9-yl 2-methylprop-2-enoate |
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| CAS Registry Number | Not Available |
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| SMILES | CC(=C)C(=O)O[C@@H]1C[C@@]2(C)OC(=CC2=O)\C(C)=C/[C@H]2OC(=O)C(=C)[C@H]12 |
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| InChI Identifier | InChI=1S/C19H20O6/c1-9(2)17(21)24-14-8-19(5)15(20)7-12(25-19)10(3)6-13-16(14)11(4)18(22)23-13/h6-7,13-14,16H,1,4,8H2,2-3,5H3/b10-6-/t13-,14-,16+,19-/m1/s1 |
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| InChI Key | RYBHZNMPMHOBAR-IRNKKCRZSA-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 terpene lactones. These are prenol lipids containing a lactone ring. |
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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 | Terpene lactones |
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| Direct Parent | Terpene lactones |
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| Alternative Parents | |
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| Substituents | - Terpene lactone
- Sesquiterpenoid
- Dicarboxylic acid or derivatives
- 3-furanone
- Gamma butyrolactone
- Dihydrofuran
- Tetrahydrofuran
- Enoate ester
- Alpha,beta-unsaturated carboxylic ester
- Vinylogous ester
- Lactone
- Ketone
- Carboxylic acid ester
- Oxacycle
- Organoheterocyclic compound
- Carboxylic acid derivative
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxide
- Carbonyl group
- Organic oxygen compound
- Aliphatic heteropolycyclic compound
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| Molecular Framework | Aliphatic heteropolycyclic compounds |
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| External Descriptors | |
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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 | - Huan P, Cui M, Wang Q, Liu B: CRISPR/Cas9-mediated mutagenesis reveals the roles of calaxin in gastropod larval cilia. Gene. 2021 Jun 30;787:145640. doi: 10.1016/j.gene.2021.145640. Epub 2021 Apr 21. [PubMed:33845135 ]
- Sasaki K, Shiba K, Nakamura A, Kawano N, Satouh Y, Yamaguchi H, Morikawa M, Shibata D, Yanase R, Jokura K, Nomura M, Miyado M, Takada S, Ueno H, Nonaka S, Baba T, Ikawa M, Kikkawa M, Miyado K, Inaba K: Erratum: Publisher Correction: Calaxin is required for cilia-driven determination of vertebrate laterality. Commun Biol. 2019 Jul 4;2:254. doi: 10.1038/s42003-019-0512-5. eCollection 2019. [PubMed:31286071 ]
- Sasaki K, Shiba K, Nakamura A, Kawano N, Satouh Y, Yamaguchi H, Morikawa M, Shibata D, Yanase R, Jokura K, Nomura M, Miyado M, Takada S, Ueno H, Nonaka S, Baba T, Ikawa M, Kikkawa M, Miyado K, Inaba K: Calaxin is required for cilia-driven determination of vertebrate laterality. Commun Biol. 2019 Jun 20;2:226. doi: 10.1038/s42003-019-0462-y. eCollection 2019. [PubMed:31240264 ]
- Shojima T, Hou F, Takahashi Y, Matsumura Y, Okai M, Nakamura A, Mizuno K, Inaba K, Kojima M, Miyakawa T, Tanokura M: Crystal structure of a Ca(2+)-dependent regulator of flagellar motility reveals the open-closed structural transition. Sci Rep. 2018 Jan 31;8(1):2014. doi: 10.1038/s41598-018-19898-7. [PubMed:29386625 ]
- Mizuno K, Shiba K, Yaguchi J, Shibata D, Yaguchi S, Pruliere G, Chenevert J, Inaba K: Calaxin establishes basal body orientation and coordinates movement of monocilia in sea urchin embryos. Sci Rep. 2017 Sep 7;7(1):10751. doi: 10.1038/s41598-017-10822-z. [PubMed:28883641 ]
- LOTUS database [Link]
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