Record Information |
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Version | 1.0 |
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Created at | 2022-09-05 10:32:20 UTC |
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Updated at | 2022-09-05 10:32:20 UTC |
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NP-MRD ID | NP0212013 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (1r,4r,5r,7s,9r,10e,12s,13s,14r)-1-(acetyloxy)-4,13-dihydroxy-6,6,10,14-tetramethyl-3-methylidene-2-oxotricyclo[10.3.0.0⁵,⁷]pentadec-10-en-9-yl (2e,4z)-octa-2,4-dienoate |
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Description | Euphohelioscopin C belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. (1r,4r,5r,7s,9r,10e,12s,13s,14r)-1-(acetyloxy)-4,13-dihydroxy-6,6,10,14-tetramethyl-3-methylidene-2-oxotricyclo[10.3.0.0⁵,⁷]pentadec-10-en-9-yl (2e,4z)-octa-2,4-dienoate is found in Euphorbia helioscopia. It was first documented in 2008 (PMID: 18452010). Based on a literature review a significant number of articles have been published on Euphohelioscopin C (PMID: 24417144) (PMID: 26882659) (PMID: 22921066) (PMID: 36075691) (PMID: 36075690) (PMID: 36075689). |
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Structure | CCC\C=C/C=C/C(=O)O[C@@H]1C[C@H]2[C@@H]([C@@H](O)C(=C)C(=O)[C@]3(C[C@@H](C)[C@H](O)[C@@H]3\C=C1/C)OC(C)=O)C2(C)C InChI=1S/C30H42O7/c1-8-9-10-11-12-13-24(32)36-23-15-21-25(29(21,6)7)27(34)19(4)28(35)30(37-20(5)31)16-18(3)26(33)22(30)14-17(23)2/h10-14,18,21-23,25-27,33-34H,4,8-9,15-16H2,1-3,5-7H3/b11-10-,13-12+,17-14+/t18-,21+,22+,23-,25+,26+,27+,30-/m1/s1 |
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Synonyms | Not Available |
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Chemical Formula | C30H42O7 |
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Average Mass | 514.6590 Da |
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Monoisotopic Mass | 514.29305 Da |
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IUPAC Name | Not Available |
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Traditional Name | Not Available |
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CAS Registry Number | Not Available |
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SMILES | CCC\C=C/C=C/C(=O)O[C@@H]1C[C@H]2[C@@H]([C@@H](O)C(=C)C(=O)[C@]3(C[C@@H](C)[C@H](O)[C@@H]3\C=C1/C)OC(C)=O)C2(C)C |
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InChI Identifier | InChI=1S/C30H42O7/c1-8-9-10-11-12-13-24(32)36-23-15-21-25(29(21,6)7)27(34)19(4)28(35)30(37-20(5)31)16-18(3)26(33)22(30)14-17(23)2/h10-14,18,21-23,25-27,33-34H,4,8-9,15-16H2,1-3,5-7H3/b11-10-,13-12+,17-14+/t18-,21+,22+,23-,25+,26+,27+,30-/m1/s1 |
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InChI Key | YFOHYGYAAZXXFL-YARMFWEBSA-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 diterpenoids. These are terpene compounds formed by four 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 | Diterpenoids |
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Direct Parent | Diterpenoids |
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Alternative Parents | |
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Substituents | - Diterpenoid
- Lathyrane diterpenoid
- Alpha-acyloxy ketone
- Fatty acid ester
- Dicarboxylic acid or derivatives
- Fatty acyl
- Cyclic alcohol
- Alpha,beta-unsaturated carboxylic ester
- Enoate ester
- Ketone
- Carboxylic acid ester
- Secondary alcohol
- Carboxylic acid derivative
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen compound
- Alcohol
- Organooxygen compound
- Carbonyl group
- 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 | - Mu SZ, Shang S, Yan C, Yang FM, Hao XJ: [Study on chemical constituents of Euphorbia helioscopia and their antitumor activities]. Zhong Yao Cai. 2013 Jul;36(7):1092-6. [PubMed:24417144 ]
- Hua J, Liu YC, Jing SX, Luo SH, Li SH: Macrocyclic Diterpenoids from the Latex of Euphorbia helioscopia. Nat Prod Commun. 2015 Dec;10(12):2037-9. [PubMed:26882659 ]
- de Lichtervelde L, Antal CE, Boitano AE, Wang Y, Krastel P, Petersen F, Newton AC, Cooke MP, Schultz PG: Euphohelioscopin A is a PKC activator capable of inducing macrophage differentiation. Chem Biol. 2012 Aug 24;19(8):994-1000. doi: 10.1016/j.chembiol.2012.06.010. [PubMed:22921066 ]
- Barile E, Borriello M, Di Pietro A, Doreau A, Fattorusso C, Fattorusso E, Lanzotti V: Discovery of a new series of jatrophane and lathyrane diterpenes as potent and specific P-glycoprotein modulators. Org Biomol Chem. 2008 May 21;6(10):1756-62. doi: 10.1039/b800485d. Epub 2008 Mar 28. [PubMed:18452010 ]
- Abioye AI, Sudfeld CR, Hughes MD, Aboud S, Muhihi A, Ulenga N, Nagu TJ, Wang M, Mugusi F, Fawzi WW: Iron status among HIV-infected adults during the first year of antiretroviral therapy in Tanzania. HIV Med. 2022 Sep 8. doi: 10.1111/hiv.13396. [PubMed:36075691 ]
- Authors unspecified: Resources Round-up. Altern Lab Anim. 2022 Sep 8:2611929221121256. doi: 10.1177/02611929221121256. [PubMed:36075690 ]
- Kim JU, Khan W, Arowoshola L, Ahmad M: Correspondence. Eur Heart J Qual Care Clin Outcomes. 2022 Aug 26. pii: 6677390. doi: 10.1093/ehjqcco/qcac051. [PubMed:36075689 ]
- DaVault L: Field Amputations Facilitated by a Surgical Extraction Team. Am Surg. 2022 Sep 8:31348221114521. doi: 10.1177/00031348221114521. [PubMed:36075688 ]
- Szanyi J, Walles JK, Tesfaye F, Gudeta AN, Bjorkman P: Intrauterine HIV exposure is associated with linear growth restriction among Ethiopian children in the first 18 months of life. Trop Med Int Health. 2022 Sep;27(9):823-830. doi: 10.1111/tmi.13805. Epub 2022 Aug 17. [PubMed:36075687 ]
- LOTUS database [Link]
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