| Record Information |
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| Version | 2.0 |
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| Created at | 2020-12-09 00:57:09 UTC |
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| Updated at | 2021-07-15 16:47:25 UTC |
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| NP-MRD ID | NP0003804 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | Terphenyllin |
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| Provided By | NPAtlas |
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| Description | Terphenyllin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Terphenyllin is found in Aspergillus, Aspergillus campestris and Aspergillus candidus. Terphenyllin was first documented in 1975 (PMID: 1150533). Based on a literature review a small amount of articles have been published on terphenyllin (PMID: 21486068) (PMID: 22196792) (PMID: 1011375) (PMID: 613931). |
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| Structure | [H]OC1=C([H])C([H])=C(C([H])=C1[H])C1=C(OC([H])([H])[H])C(O[H])=C(C(OC([H])([H])[H])=C1[H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] InChI=1S/C20H18O5/c1-24-17-11-16(12-3-7-14(21)8-4-12)20(25-2)19(23)18(17)13-5-9-15(22)10-6-13/h3-11,21-23H,1-2H3 |
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| Synonyms | Not Available |
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| Chemical Formula | C20H18O5 |
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| Average Mass | 338.3590 Da |
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| Monoisotopic Mass | 338.11542 Da |
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| IUPAC Name | 4-(4-hydroxyphenyl)-3,6-dimethoxy-[1,1'-biphenyl]-2,4'-diol |
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| Traditional Name | 4-(4-hydroxyphenyl)-3,6-dimethoxy-[1,1'-biphenyl]-2,4'-diol |
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| CAS Registry Number | Not Available |
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| SMILES | COC1=C(C(O)=C(OC)C(=C1)C1=CC=C(O)C=C1)C1=CC=C(O)C=C1 |
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| InChI Identifier | InChI=1S/C20H18O5/c1-24-17-11-16(12-3-7-14(21)8-4-12)20(25-2)19(23)18(17)13-5-9-15(22)10-6-13/h3-11,21-23H,1-2H3 |
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| InChI Key | YNEMPXKRLPZFAX-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, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, 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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| Species Where Detected | |
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| Chemical Taxonomy |
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| Description | This compound belongs to the class of organic compounds known as p-terphenyls. These are terphenyls with a structure containing the 1,4-diphenylbenzene skeleton. |
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| Kingdom | Organic compounds |
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| Super Class | Benzenoids |
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| Class | Benzene and substituted derivatives |
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| Sub Class | Terphenyls |
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| Direct Parent | P-terphenyls |
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| Alternative Parents | |
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| Substituents | - Para-terphenyl
- Biphenyl
- P-dimethoxybenzene
- Dimethoxybenzene
- Methoxyphenol
- Phenoxy compound
- Anisole
- Methoxybenzene
- Phenol ether
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Alkyl aryl ether
- Phenol
- Ether
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxygen compound
- Aromatic homomonocyclic compound
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| Molecular Framework | Aromatic homomonocyclic compounds |
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| External Descriptors | |
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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 | - Marchelli R, Vining LC: Terphenyllin, a novel p-terphenyl metabolite from aspergillus candidus. J Antibiot (Tokyo). 1975 Apr;28(4):328-31. doi: 10.7164/antibiotics.28.328. [PubMed:1150533 ]
- Cai S, Sun S, Zhou H, Kong X, Zhu T, Li D, Gu Q: Prenylated Polyhydroxy-p-terphenyls from Aspergillus taichungensis ZHN-7-07. J Nat Prod. 2011 May 27;74(5):1106-10. doi: 10.1021/np2000478. Epub 2011 Apr 12. [PubMed:21486068 ]
- Guo ZK, Yan T, Guo Y, Song YC, Jiao RH, Tan RX, Ge HM: p-Terphenyl and diterpenoid metabolites from endophytic Aspergillus sp. YXf3. J Nat Prod. 2012 Jan 27;75(1):15-21. doi: 10.1021/np200321s. Epub 2011 Dec 23. [PubMed:22196792 ]
- Ohtsubo K, Horiuchi T, Hatanaka Y, Saito M: Hepato- and cardiotoxicity of xanthoascin, a new metabolite of A. candidus Link, to mice. I. Blood chemistry and histological changes in mice. Jpn J Exp Med. 1976 Oct;46(5):277-87. [PubMed:1011375 ]
- Ohtsubo K, Saito M: Hepato-and cardiotoxicity of xanthoascin, a new xanthocillin analogue produced by Aspergillus candidus. II. A preliminary electron microscopic observation of the heart and lung with intranuclear myelin-like figures. Ann Nutr Aliment. 1977;31(4-6):771-80. [PubMed:613931 ]
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