Record Information |
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Version | 1.0 |
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Created at | 2022-09-11 21:35:19 UTC |
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Updated at | 2022-09-11 21:35:20 UTC |
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NP-MRD ID | NP0320130 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (2e,5s,6s)-6-[(1r,3s,3ar,5ar,7r,9as,11ar)-3,7-bis(acetyloxy)-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]-5-(acetyloxy)-2-methylhept-2-enoic acid |
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Description | Ganoderic Acid T, also known as ganoderate T or ga-T acid CPD, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. It was first documented in 2011 (PMID: 21353507). Based on a literature review a significant number of articles have been published on Ganoderic Acid T (PMID: 23280041) (PMID: 22366428) (PMID: 34141167) (PMID: 30317980) (PMID: 29748985) (PMID: 28078535). |
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Structure | C[C@H]([C@H](C\C=C(/C)C(O)=O)OC(C)=O)[C@H]1C[C@H](OC(C)=O)[C@@]2(C)C3=CC[C@H]4C(C)(C)[C@@H](CC[C@]4(C)C3=CC[C@]12C)OC(C)=O InChI=1S/C36H52O8/c1-20(32(40)41)11-13-28(42-22(3)37)21(2)27-19-31(44-24(5)39)36(10)26-12-14-29-33(6,7)30(43-23(4)38)16-17-34(29,8)25(26)15-18-35(27,36)9/h11-12,15,21,27-31H,13-14,16-19H2,1-10H3,(H,40,41)/b20-11+/t21-,27+,28-,29-,30+,31-,34+,35+,36+/m0/s1 |
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Synonyms | Value | Source |
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Ganoderate T | Generator | GA-T acid CPD | MeSH |
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Chemical Formula | C36H52O8 |
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Average Mass | 612.8040 Da |
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Monoisotopic Mass | 612.36622 Da |
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IUPAC Name | (2E,5S,6S)-5-(acetyloxy)-6-[(2S,5R,7R,11R,12S,14R,15R)-5,12-bis(acetyloxy)-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(17),9-dien-14-yl]-2-methylhept-2-enoic acid |
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Traditional Name | (2E,5S,6S)-5-(acetyloxy)-6-[(2S,5R,7R,11R,12S,14R,15R)-5,12-bis(acetyloxy)-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(17),9-dien-14-yl]-2-methylhept-2-enoic acid |
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CAS Registry Number | Not Available |
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SMILES | C[C@H]([C@H](C\C=C(/C)C(O)=O)OC(C)=O)[C@H]1C[C@H](OC(C)=O)[C@@]2(C)C3=CC[C@H]4C(C)(C)[C@@H](CC[C@]4(C)C3=CC[C@]12C)OC(C)=O |
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InChI Identifier | InChI=1S/C36H52O8/c1-20(32(40)41)11-13-28(42-22(3)37)21(2)27-19-31(44-24(5)39)36(10)26-12-14-29-33(6,7)30(43-23(4)38)16-17-34(29,8)25(26)15-18-35(27,36)9/h11-12,15,21,27-31H,13-14,16-19H2,1-10H3,(H,40,41)/b20-11+/t21-,27+,28-,29-,30+,31-,34+,35+,36+/m0/s1 |
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InChI Key | OCLVBEOPEKEKNM-CAXIOAJTSA-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 | Not Available |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six 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 | Triterpenoids |
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Direct Parent | Triterpenoids |
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Alternative Parents | |
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Substituents | - Triterpenoid
- Cholane-skeleton
- Bile acid, alcohol, or derivatives
- Steroid ester
- Steroid acid
- 14-alpha-methylsteroid
- Delta-7-steroid
- Steroid
- Tetracarboxylic acid or derivatives
- Carboxylic acid ester
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Organooxygen compound
- Carbonyl group
- Hydrocarbon derivative
- 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 | - Isaka M, Chinthanom P, Kongthong S, Srichomthong K, Choeyklin R: Lanostane triterpenes from cultures of the Basidiomycete Ganoderma orbiforme BCC 22324. Phytochemistry. 2013 Mar;87:133-9. doi: 10.1016/j.phytochem.2012.11.022. Epub 2012 Dec 29. [PubMed:23280041 ]
- Liu RM, Li YB, Zhong JJ: Cytotoxic and pro-apoptotic effects of novel ganoderic acid derivatives on human cervical cancer cells in vitro. Eur J Pharmacol. 2012 Apr 15;681(1-3):23-33. doi: 10.1016/j.ejphar.2012.02.007. Epub 2012 Feb 17. [PubMed:22366428 ]
- Shao CS, Feng N, Zhou S, Zheng XX, Wang P, Zhang JS, Huang Q: Ganoderic acid T improves the radiosensitivity of HeLa cells via converting apoptosis to necroptosis. Toxicol Res (Camb). 2021 May 13;10(3):531-541. doi: 10.1093/toxres/tfab030. eCollection 2021 May. [PubMed:34141167 ]
- Zhou S, Tang Q, Tang C, Liu Y, Ma F, Zhang X, Zhang JS: Triterpenes and Soluble Polysaccharide Changes in Lingzhi or Reishi Medicinal Mushroom, Ganoderma lucidum (Agaricomycetes), During Fruiting Growth. Int J Med Mushrooms. 2018;20(9):859-871. doi: 10.1615/IntJMedMushrooms.2018027357. [PubMed:30317980 ]
- Feng N, Wei Y, Feng J, Tang Q, Zhang Z, Zhang J, Han W: Preparative isolation of ganoderic acid S, ganoderic acid T and ganoderol B from Ganoderma lucidum mycelia by high-speed counter-current chromatography. Biomed Chromatogr. 2018 Oct;32(10):e4283. doi: 10.1002/bmc.4283. Epub 2018 May 31. [PubMed:29748985 ]
- Kohno T, Hai-Bang T, Zhu Q, Amen Y, Sakamoto S, Tanaka H, Morimoto S, Shimizu K: Tubulin polymerization-stimulating activity of Ganoderma triterpenoids. J Nat Med. 2017 Apr;71(2):457-462. doi: 10.1007/s11418-017-1072-y. Epub 2017 Jan 11. [PubMed:28078535 ]
- Wang XL, Ding ZY, Liu GQ, Yang H, Zhou GY: Improved Production and Antitumor Properties of Triterpene Acids from Submerged Culture of Ganoderma lingzhi. Molecules. 2016 Oct 20;21(10):1395. doi: 10.3390/molecules21101395. [PubMed:27775633 ]
- Zhu Q, Bang TH, Ohnuki K, Sawai T, Sawai K, Shimizu K: Inhibition of neuraminidase by Ganoderma triterpenoids and implications for neuraminidase inhibitor design. Sci Rep. 2015 Aug 26;5:13194. doi: 10.1038/srep13194. [PubMed:26307417 ]
- Wang JL, Gu T, Zhong JJ: Enhanced recovery of antitumor ganoderic acid T from Ganoderma lucidum mycelia by novel chemical conversion strategy. Biotechnol Bioeng. 2012 Mar;109(3):754-62. doi: 10.1002/bit.24358. Epub 2011 Nov 9. [PubMed:22038732 ]
- Chen NH, Zhong JJ: p53 is important for the anti-invasion of ganoderic acid T in human carcinoma cells. Phytomedicine. 2011 Jun 15;18(8-9):719-25. doi: 10.1016/j.phymed.2011.01.011. Epub 2011 Feb 25. [PubMed:21353507 ]
- LOTUS database [Link]
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