Record Information |
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Version | 2.0 |
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Created at | 2022-09-04 22:29:53 UTC |
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Updated at | 2022-09-04 22:29:53 UTC |
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NP-MRD ID | NP0203114 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | 4-[(3-butanoyl-2,6-dihydroxy-4-methoxy-5-methylphenyl)methyl]-3,5-dihydroxy-6,6-dimethyl-2-propanoylcyclohexa-2,4-dien-1-one |
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Description | Aspidin PB belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. 4-[(3-butanoyl-2,6-dihydroxy-4-methoxy-5-methylphenyl)methyl]-3,5-dihydroxy-6,6-dimethyl-2-propanoylcyclohexa-2,4-dien-1-one is found in Dryopteris fragrans. 4-[(3-butanoyl-2,6-dihydroxy-4-methoxy-5-methylphenyl)methyl]-3,5-dihydroxy-6,6-dimethyl-2-propanoylcyclohexa-2,4-dien-1-one was first documented in 2006 (PMID: 17039877). Based on a literature review a significant number of articles have been published on Aspidin PB (PMID: 30450082) (PMID: 26596576) (PMID: 26181229) (PMID: 26054450) (PMID: 24530873) (PMID: 23178381). |
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Structure | CCCC(=O)C1=C(O)C(CC2=C(O)C(C)(C)C(=O)C(C(=O)CC)=C2O)=C(O)C(C)=C1OC InChI=1S/C24H30O8/c1-7-9-15(26)16-19(28)12(18(27)11(3)21(16)32-6)10-13-20(29)17(14(25)8-2)23(31)24(4,5)22(13)30/h27-30H,7-10H2,1-6H3 |
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Synonyms | Not Available |
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Chemical Formula | C24H30O8 |
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Average Mass | 446.4960 Da |
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Monoisotopic Mass | 446.19407 Da |
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IUPAC Name | 4-[(3-butanoyl-2,6-dihydroxy-4-methoxy-5-methylphenyl)methyl]-3,5-dihydroxy-6,6-dimethyl-2-propanoylcyclohexa-2,4-dien-1-one |
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Traditional Name | 4-[(3-butanoyl-2,6-dihydroxy-4-methoxy-5-methylphenyl)methyl]-3,5-dihydroxy-6,6-dimethyl-2-propanoylcyclohexa-2,4-dien-1-one |
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CAS Registry Number | Not Available |
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SMILES | CCCC(=O)C1=C(O)C(CC2=C(O)C(C)(C)C(=O)C(C(=O)CC)=C2O)=C(O)C(C)=C1OC |
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InChI Identifier | InChI=1S/C24H30O8/c1-7-9-15(26)16-19(28)12(18(27)11(3)21(16)32-6)10-13-20(29)17(14(25)8-2)23(31)24(4,5)22(13)30/h27-30H,7-10H2,1-6H3 |
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InChI Key | VVTPVUMYNQURDS-UHFFFAOYSA-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 alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. |
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Kingdom | Organic compounds |
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Super Class | Organic oxygen compounds |
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Class | Organooxygen compounds |
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Sub Class | Carbonyl compounds |
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Direct Parent | Alkyl-phenylketones |
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Alternative Parents | |
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Substituents | - Alkyl-phenylketone
- Butyrophenone
- Methoxyphenol
- Phenoxy compound
- O-cresol
- P-cresol
- Phenol ether
- Resorcinol
- Anisole
- Methoxybenzene
- Aryl alkyl ketone
- Benzoyl
- Alkyl aryl ether
- Toluene
- Phenol
- Benzenoid
- Monocyclic benzene moiety
- Vinylogous acid
- Cyclic ketone
- Ether
- Enol
- Organic oxide
- Hydrocarbon derivative
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic 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 | - Ye L, Lin P, Du W, Wang Y, Tang C, Shen Z: Preparation, Antidermatophyte Activity, and Mechanism of Methylphloroglucinol Derivatives. Front Microbiol. 2018 Nov 2;9:2262. doi: 10.3389/fmicb.2018.02262. eCollection 2018. [PubMed:30450082 ]
- Gao C, Guo N, Li N, Peng X, Wang P, Wang W, Luo M, Fu YJ: Investigation of antibacterial activity of aspidin BB against Propionibacterium acnes. Arch Dermatol Res. 2016 Mar;308(2):79-86. doi: 10.1007/s00403-015-1603-x. Epub 2015 Nov 23. [PubMed:26596576 ]
- Wan D, Jiang C, Hua X, Wang T, Chai Y: Cell cycle arrest and apoptosis induced by aspidin PB through the p53/p21 and mitochondria-dependent pathways in human osteosarcoma cells. Anticancer Drugs. 2015 Oct;26(9):931-41. doi: 10.1097/CAD.0000000000000269. [PubMed:26181229 ]
- Song R, Li G, Li S: Aspidin PB, a novel natural anti-fibrotic compound, inhibited fibrogenesis in TGF-beta1-stimulated keloid fibroblasts via PI-3K/Akt and Smad signaling pathways. Chem Biol Interact. 2015 Aug 5;238:66-73. doi: 10.1016/j.cbi.2015.06.005. Epub 2015 Jun 6. [PubMed:26054450 ]
- Yang MH, Kim J, Khan IA, Walker LA, Khan SI: Nonsteroidal anti-inflammatory drug activated gene-1 (NAG-1) modulators from natural products as anti-cancer agents. Life Sci. 2014 Apr 1;100(2):75-84. doi: 10.1016/j.lfs.2014.01.075. Epub 2014 Feb 12. [PubMed:24530873 ]
- Sun Y, Gao C, Luo M, Wang W, Gu C, Zu Y, Li J, Efferth T, Fu Y: Aspidin PB, a phloroglucinol derivative, induces apoptosis in human hepatocarcinoma HepG2 cells by modulating PI3K/Akt/GSK3beta pathway. Chem Biol Interact. 2013 Jan 25;201(1-3):1-8. doi: 10.1016/j.cbi.2012.11.005. Epub 2012 Nov 21. [PubMed:23178381 ]
- Shen ZB, Luo WY, Yan YS, Zhu JF: [Studies on phloroglucinol derivatives of Dryopteris fragrans L]. Zhong Yao Cai. 2006 Jun;29(6):560-1. [PubMed:17039877 ]
- LOTUS database [Link]
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