Record Information |
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Version | 1.0 |
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Created at | 2022-09-10 02:50:35 UTC |
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Updated at | 2022-09-10 02:50:35 UTC |
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NP-MRD ID | NP0294345 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (1s,2r,4r,5r,6s,8r,10s,11s,12r,14r,15r,16r,19r,20r,21s)-4,20,21-tris(acetyloxy)-6-(furan-3-yl)-12,19-dihydroxy-5,11,15-trimethyl-3-oxo-9,17-dioxahexacyclo[13.3.3.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0⁸,¹⁰]henicosan-16-yl (2r)-2-methylbutanoate |
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Description | (1S,2R,4R,5R,6R,8R,10S,11S,12R,14R,15R,16R,19R,20R,21S)-4,20,21-tris(acetyloxy)-6-(furan-3-yl)-12,19-dihydroxy-5,11,15-trimethyl-3-oxo-9,17-dioxahexacyclo[13.3.3.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0⁸,¹⁰]Henicosan-16-yl (2R)-2-methylbutanoate belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17. (1s,2r,4r,5r,6s,8r,10s,11s,12r,14r,15r,16r,19r,20r,21s)-4,20,21-tris(acetyloxy)-6-(furan-3-yl)-12,19-dihydroxy-5,11,15-trimethyl-3-oxo-9,17-dioxahexacyclo[13.3.3.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0⁸,¹⁰]henicosan-16-yl (2r)-2-methylbutanoate is found in Melia azedarach. It was first documented in 2022 (PMID: 36115695). Based on a literature review a significant number of articles have been published on (1S,2R,4R,5R,6R,8R,10S,11S,12R,14R,15R,16R,19R,20R,21S)-4,20,21-tris(acetyloxy)-6-(furan-3-yl)-12,19-dihydroxy-5,11,15-trimethyl-3-oxo-9,17-dioxahexacyclo[13.3.3.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0⁸,¹⁰]Henicosan-16-yl (2R)-2-methylbutanoate (PMID: 36115679) (PMID: 36115691) (PMID: 36115690) (PMID: 36115694) (PMID: 36115693) (PMID: 36115692). |
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Structure | CC[C@@H](C)C(=O)O[C@H]1OC[C@]23[C@@H](O)[C@@H](OC(C)=O)[C@@H](OC(C)=O)[C@@]1(C)[C@@H]2C[C@@H](O)[C@]1(C)[C@@H]3C(=O)[C@H](OC(C)=O)[C@@]2(C)[C@@H](C[C@H]3O[C@@]123)C1=COC=C1 InChI=1S/C37H48O14/c1-9-16(2)31(44)50-32-33(6)22-13-23(41)35(8)27(36(22,15-46-32)28(43)26(47-17(3)38)30(33)49-19(5)40)25(42)29(48-18(4)39)34(7)21(20-10-11-45-14-20)12-24-37(34,35)51-24/h10-11,14,16,21-24,26-30,32,41,43H,9,12-13,15H2,1-8H3/t16-,21+,22+,23-,24-,26-,27+,28+,29+,30-,32-,33-,34-,35-,36+,37-/m1/s1 |
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Synonyms | Value | Source |
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(1S,2R,4R,5R,6R,8R,10S,11S,12R,14R,15R,16R,19R,20R,21S)-4,20,21-Tris(acetyloxy)-6-(furan-3-yl)-12,19-dihydroxy-5,11,15-trimethyl-3-oxo-9,17-dioxahexacyclo[13.3.3.0,.0,.0,.0,]henicosan-16-yl (2R)-2-methylbutanoic acid | Generator |
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Chemical Formula | C37H48O14 |
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Average Mass | 716.7770 Da |
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Monoisotopic Mass | 716.30441 Da |
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IUPAC Name | (1S,2R,4R,5R,6R,8R,10S,11S,12R,14R,15R,16R,19R,20R,21S)-4,20,21-tris(acetyloxy)-6-(furan-3-yl)-12,19-dihydroxy-5,11,15-trimethyl-3-oxo-9,17-dioxahexacyclo[13.3.3.0^{1,14}.0^{2,11}.0^{5,10}.0^{8,10}]henicosan-16-yl (2R)-2-methylbutanoate |
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Traditional Name | (1S,2R,4R,5R,6R,8R,10S,11S,12R,14R,15R,16R,19R,20R,21S)-4,20,21-tris(acetyloxy)-6-(furan-3-yl)-12,19-dihydroxy-5,11,15-trimethyl-3-oxo-9,17-dioxahexacyclo[13.3.3.0^{1,14}.0^{2,11}.0^{5,10}.0^{8,10}]henicosan-16-yl (2R)-2-methylbutanoate |
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CAS Registry Number | Not Available |
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SMILES | CC[C@@H](C)C(=O)O[C@H]1OC[C@]23[C@@H](O)[C@@H](OC(C)=O)[C@@H](OC(C)=O)[C@@]1(C)[C@@H]2C[C@@H](O)[C@]1(C)[C@@H]3C(=O)[C@H](OC(C)=O)[C@@]2(C)[C@@H](C[C@H]3O[C@@]123)C1=COC=C1 |
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InChI Identifier | InChI=1S/C37H48O14/c1-9-16(2)31(44)50-32-33(6)22-13-23(41)35(8)27(36(22,15-46-32)28(43)26(47-17(3)38)30(33)49-19(5)40)25(42)29(48-18(4)39)34(7)21(20-10-11-45-14-20)12-24-37(34,35)51-24/h10-11,14,16,21-24,26-30,32,41,43H,9,12-13,15H2,1-8H3/t16-,21+,22+,23-,24-,26-,27+,28+,29+,30-,32-,33-,34-,35-,36+,37-/m1/s1 |
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InChI Key | AVSOCPWJWLVCAL-OZMWLVAWSA-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 limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17. |
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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 | Triterpenoids |
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Direct Parent | Limonoids |
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Alternative Parents | |
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Substituents | - Limonoid skeleton
- 17-furanylsteroid skeleton
- Steroid ester
- Naphthopyran
- Tetracarboxylic acid or derivatives
- Naphthalene
- Alpha-acyloxy ketone
- Fatty acid ester
- Fatty acyl
- Oxane
- Pyran
- Cyclic alcohol
- Furan
- Heteroaromatic compound
- Secondary alcohol
- Carboxylic acid ester
- Ketone
- Carboxylic acid derivative
- Organoheterocyclic compound
- Dialkyl ether
- Oxirane
- Ether
- Oxacycle
- Acetal
- Alcohol
- Organooxygen compound
- Carbonyl group
- Hydrocarbon derivative
- Organic oxygen compound
- Organic oxide
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic 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 | - Sharma S, Zaher S, Rodrigues PRS, Davies LC, Edkins S, Strang A, Chakraborty M, Watkins WJ, Andrews R, Parkinson E, Angelopoulos N, Moet L, Shepherd F, Davies KMM, White D, Oram S, Siddall K, Keeping V, Simpson K, Faggian F, Bray M, Bertorelli C, Bell S, Collis RE, McLaren JE, Labeta M, O'Donnell VB, Ghazal P: mSep: investigating physiological and immune-metabolic biomarkers in septic and healthy pregnant women to predict feto-maternal immune health - a prospective observational cohort study protocol. BMJ Open. 2022 Sep 17;12(9):e066382. doi: 10.1136/bmjopen-2022-066382. [PubMed:36115679 ]
- Hosokawa K, Nakao S: Somatic mutations and clonal expansions in paroxysmal nocturnal hemoglobinuria. Semin Hematol. 2022 Jul;59(3):143-149. doi: 10.1053/j.seminhematol.2022.08.004. Epub 2022 Aug 22. [PubMed:36115691 ]
- Durrani J, Groarke EM: Clonality in immune aplastic anemia: Mechanisms of immune escape or malignant transformation. Semin Hematol. 2022 Jul;59(3):137-142. doi: 10.1053/j.seminhematol.2022.08.001. Epub 2022 Aug 12. [PubMed:36115690 ]
- eBioMedicine: The dynamics of the immune system and gut in the pathophysiology of multiple sclerosis. EBioMedicine. 2022 Sep;83:104273. doi: 10.1016/j.ebiom.2022.104273. [PubMed:36115695 ]
- Lundgren S, Keranen M, Wartiovaara-Kautto U, Myllymaki M: Somatic compensation of inherited bone marrow failure. Semin Hematol. 2022 Jul;59(3):167-173. doi: 10.1053/j.seminhematol.2022.07.002. Epub 2022 Aug 3. [PubMed:36115694 ]
- Alcedo PE, Gutierrez-Rodrigues F, Patel BA: Somatic mutations in VEXAS Syndrome and Erdheim-Chester disease: Inflammatory myeloid diseases. Semin Hematol. 2022 Jul;59(3):156-166. doi: 10.1053/j.seminhematol.2022.07.003. Epub 2022 Aug 3. [PubMed:36115693 ]
- Todisco G, Moura PL, Hellstrom-Lindberg E: Clinical manifestations of clonal hematopoiesis: What has SF3B1-mutant MDS taught us? Semin Hematol. 2022 Jul;59(3):150-155. doi: 10.1053/j.seminhematol.2022.08.002. Epub 2022 Aug 11. [PubMed:36115692 ]
- Mangat C, Rich J, Sanghavi D, Schmidt R, Milosavljevic N, Linh T, Bansal P: Parents' perspective on COVID-19 vaccine in children 6 months through 4 years: a cross-sectional study from Northwest Wisconsin. BMJ Open. 2022 Sep 17;12(9):e065453. doi: 10.1136/bmjopen-2022-065453. [PubMed:36115680 ]
- Bedford LE, Tang EHM, Dong W, Wong CKH, Tse ETY, Ng APP, Cheung BMY, Wu T, Yu EYT, Lam CLK: Who reports insufficient and disturbed sleep? Results from a representative population-based health survey in Hong Kong. BMJ Open. 2022 Sep 17;12(9):e058169. doi: 10.1136/bmjopen-2021-058169. [PubMed:36115682 ]
- Shiota S, Kitagawa T, Goto N, Fujisita H, Tamekuni Y, Nakayama S, Mio N, Kanai K, Naka M, Yamaguchi M, Mochizuki M, Ochikubo H, Hidaka T, Yasunobu Y, Nakano Y, Kihara Y, Kimura H: Development and appropriateness of a scoring method for International Classification of Functioning, Disabilities, and Health assessment in older patients with heart failure: a Delphi survey of expert panel in Japan. BMJ Open. 2022 Sep 17;12(9):e060609. doi: 10.1136/bmjopen-2021-060609. [PubMed:36115681 ]
- Kawakami T, Nakazawa H, Ishida F: Somatic mutations in acquired pure red cell aplasia. Semin Hematol. 2022 Jul;59(3):131-136. doi: 10.1053/j.seminhematol.2022.07.001. Epub 2022 Jul 16. [PubMed:36115689 ]
- Savola P, Bhattacharya D, Huuhtanen J: The spectrum of somatic mutations in large granular lymphocyte leukemia, rheumatoid arthritis, and Felty's syndrome. Semin Hematol. 2022 Jul;59(3):123-130. doi: 10.1053/j.seminhematol.2022.07.004. Epub 2022 Aug 3. [PubMed:36115688 ]
- Mustjoki S: Somatic mutations in "benign" blood diseases. Semin Hematol. 2022 Jul;59(3):121-122. doi: 10.1053/j.seminhematol.2022.08.003. [PubMed:36115687 ]
- Campbell JW: Dysplasias in the Child's Spine. Neurosurg Clin N Am. 2022 Jan;33(1S):e1-e10. doi: 10.1016/j.nec.2022.02.001. Epub 2022 Aug 6. [PubMed:36115686 ]
- Yamazaki M, Yagi T, Tominaga M, Minato K, Ishikawa H: Role of intratumoral and peritumoral CT radiomics for the prediction of EGFR gene mutation in primary lung cancer. Br J Radiol. 2022 Dec 1;95(1140):20220374. doi: 10.1259/bjr.20220374. Epub 2022 Sep 26. [PubMed:36115683 ]
- LOTUS database [Link]
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