Record Information |
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Version | 1.0 |
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Created at | 2022-09-03 22:58:55 UTC |
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Updated at | 2022-09-03 22:58:55 UTC |
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NP-MRD ID | NP0183970 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | 3-{[(2r)-2-[(1r,3ar,5ar,9as,11ar)-3a,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,3h,5h,5ah,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]-6-methylhept-5-en-1-yl]oxy}-3-oxopropanoic acid |
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Description | Fomitopsic acid B, also known as fomitopsate b, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. 3-{[(2r)-2-[(1r,3ar,5ar,9as,11ar)-3a,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,3h,5h,5ah,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]-6-methylhept-5-en-1-yl]oxy}-3-oxopropanoic acid is found in Fomitopsis pinicola. It was first documented in 2020 (PMID: 36046777). Based on a literature review a significant number of articles have been published on Fomitopsic acid B (PMID: 36057144) (PMID: 36031232) (PMID: 36029991) (PMID: 35991894) (PMID: 36016553) (PMID: 36015626). |
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Structure | CC(C)=CCC[C@@H](COC(=O)CC(O)=O)[C@H]1CC[C@@]2(C)C3=CC[C@H]4C(C)(C)C(=O)CC[C@]4(C)C3=CC[C@]12C InChI=1S/C33H48O5/c1-21(2)9-8-10-22(20-38-29(37)19-28(35)36)23-13-17-33(7)25-11-12-26-30(3,4)27(34)15-16-31(26,5)24(25)14-18-32(23,33)6/h9,11,14,22-23,26H,8,10,12-13,15-20H2,1-7H3,(H,35,36)/t22-,23+,26-,31+,32+,33-/m0/s1 |
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Synonyms | Value | Source |
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Fomitopsate b | Generator |
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Chemical Formula | C33H48O5 |
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Average Mass | 524.7420 Da |
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Monoisotopic Mass | 524.35017 Da |
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IUPAC Name | 3-{[(2R)-6-methyl-2-[(2S,7R,11R,14R,15R)-2,6,6,11,15-pentamethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(17),9-dien-14-yl]hept-5-en-1-yl]oxy}-3-oxopropanoic acid |
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Traditional Name | 3-{[(2R)-6-methyl-2-[(2S,7R,11R,14R,15R)-2,6,6,11,15-pentamethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(17),9-dien-14-yl]hept-5-en-1-yl]oxy}-3-oxopropanoic acid |
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CAS Registry Number | Not Available |
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SMILES | CC(C)=CCC[C@@H](COC(=O)CC(O)=O)[C@H]1CC[C@@]2(C)C3=CC[C@H]4C(C)(C)C(=O)CC[C@]4(C)C3=CC[C@]12C |
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InChI Identifier | InChI=1S/C33H48O5/c1-21(2)9-8-10-22(20-38-29(37)19-28(35)36)23-13-17-33(7)25-11-12-26-30(3,4)27(34)15-16-31(26,5)24(25)14-18-32(23,33)6/h9,11,14,22-23,26H,8,10,12-13,15-20H2,1-7H3,(H,35,36)/t22-,23+,26-,31+,32+,33-/m0/s1 |
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InChI Key | SXYOHWHWZQDZED-YAIYFESBSA-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 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
- Cholesterol-skeleton
- Cholestane-skeleton
- Bile acid, alcohol, or derivatives
- Steroid ester
- 3-oxo-delta-7-steroid
- 3-oxosteroid
- 14-alpha-methylsteroid
- 3-oxo-5-alpha-steroid
- Oxosteroid
- Steroid
- Delta-7-steroid
- 1,3-dicarbonyl compound
- Dicarboxylic acid or derivatives
- Carboxylic acid ester
- Cyclic ketone
- Ketone
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Carbonyl group
- Hydrocarbon derivative
- Organic oxide
- Organooxygen compound
- 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 | - Yao L, Zhao R, He S, Feng Q, Qiao Y, Wang P, Li J: Effects of salvianolic acid A and salvianolic acid B in renal interstitial fibrosis via PDGF-C/PDGFR-alpha signaling pathway. Phytomedicine. 2022 Aug 27;106:154414. doi: 10.1016/j.phymed.2022.154414. [PubMed:36057144 ]
- Kong XL, Lyu Q, Zhang YQ, Kang DF, Li C, Zhang L, Gao ZC, Liu XX, Wu JB, Li YL: Effect of astragaloside IV and salvianolic acid B on antioxidant stress and vascular endothelial protection in the treatment of atherosclerosis based on metabonomics. Chin J Nat Med. 2022 Aug;20(8):601-613. doi: 10.1016/S1875-5364(22)60186-9. [PubMed:36031232 ]
- Yang L, Gu T, Xu Y, Liu Y, Zhang Y, Jiang Z, Peng L: Plant polysaccharides as novel biomaterials for microcapsule construction and therapeutics delivery. Int J Pharm. 2022 Sep 25;625:122137. doi: 10.1016/j.ijpharm.2022.122137. Epub 2022 Aug 24. [PubMed:36029991 ]
- Jiang N, Zhang J, Ping J, Xu L: Salvianolic acid B inhibits autophagy and activation of hepatic stellate cells induced by TGF-beta1 by downregulating the MAPK pathway. Front Pharmacol. 2022 Aug 4;13:938856. doi: 10.3389/fphar.2022.938856. eCollection 2022. [PubMed:35991894 ]
- Fu L, Mou J, Deng Y, Ren X: Structural modifications of berberine and their binding effects towards polymorphic deoxyribonucleic acid structures: A review. Front Pharmacol. 2022 Aug 9;13:940282. doi: 10.3389/fphar.2022.940282. eCollection 2022. [PubMed:36016553 ]
- Gu W, Fan R, Quan J, Cheng Y, Wang S, Zhang H, Zheng A, Song S: Intracranial In Situ Thermosensitive Hydrogel Delivery of Temozolomide Accomplished by PLGA-PEG-PLGA Triblock Copolymer Blending for GBM Treatment. Polymers (Basel). 2022 Aug 18;14(16):3368. doi: 10.3390/polym14163368. [PubMed:36015626 ]
- Zhang X, Lv W, Fu Y, Li Y, Wang J, Chen D, Han X, Li Z: Hepatoprotective Activity of Ethanol Extract of Rice Solid-State Fermentation of Ganoderma tsugae against CCl(4)-Induced Acute Liver Injury in Mice. Molecules. 2022 Aug 22;27(16):5347. doi: 10.3390/molecules27165347. [PubMed:36014587 ]
- Kolniak-Ostek J, Oszmianski J, Szyjka A, Moreira H, Barg E: Anticancer and Antioxidant Activities in Ganoderma lucidum Wild Mushrooms in Poland, as Well as Their Phenolic and Triterpenoid Compounds. Int J Mol Sci. 2022 Aug 19;23(16):9359. doi: 10.3390/ijms23169359. [PubMed:36012645 ]
- Wang P, Nan S, Zhang Y, Fan J: Effects of GABA(B) receptor positive allosteric modulator BHF177 and IRS-1 on apoptosis of hippocampal neurons in rats with refractory epilepsy via the PI3K/Akt pathway. Cell Biol Int. 2022 Nov;46(11):1775-1786. doi: 10.1002/cbin.11839. Epub 2022 Aug 21. [PubMed:35989486 ]
- Shahzadi I, Ali Z, Bukhari S, Narula AS, Mirza B, Mohammadinejad R: Possible applications of salvianolic acid B against different cancers. Explor Target Antitumor Ther. 2020;1(4):218-238. doi: 10.37349/etat.2020.00014. Epub 2020 Aug 31. [PubMed:36046777 ]
- LOTUS database [Link]
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