Record Information |
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Version | 1.0 |
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Created at | 2022-09-04 23:33:10 UTC |
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Updated at | 2022-09-04 23:33:10 UTC |
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NP-MRD ID | NP0203965 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (3s,8s,9r,11e)-8,9,16-trihydroxy-13,14-dimethoxy-3-methyl-4,5,6,8,9,10-hexahydro-3h-2-benzoxacyclotetradecine-1,7-dione |
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Description | Hamigeromycin C belongs to the class of organic compounds known as zearalenones. These are macrolides which contains a fourteen-member lactone fused to 1,3-dihydroxybenzene. (3s,8s,9r,11e)-8,9,16-trihydroxy-13,14-dimethoxy-3-methyl-4,5,6,8,9,10-hexahydro-3h-2-benzoxacyclotetradecine-1,7-dione is found in Hamigera avellanea. It was first documented in 2022 (PMID: 36070879). Based on a literature review a significant number of articles have been published on Hamigeromycin C (PMID: 36070862) (PMID: 36070861) (PMID: 36070818) (PMID: 36070817) (PMID: 36070688) (PMID: 36070805). |
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Structure | COC1=CC(O)=C2C(\C=C\C[C@@H](O)[C@H](O)C(=O)CCC[C@H](C)OC2=O)=C1OC InChI=1S/C20H26O8/c1-11-6-4-8-13(21)18(24)14(22)9-5-7-12-17(20(25)28-11)15(23)10-16(26-2)19(12)27-3/h5,7,10-11,14,18,22-24H,4,6,8-9H2,1-3H3/b7-5+/t11-,14+,18+/m0/s1 |
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Synonyms | Not Available |
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Chemical Formula | C20H26O8 |
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Average Mass | 394.4200 Da |
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Monoisotopic Mass | 394.16277 Da |
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IUPAC Name | (3S,8S,9R)-8,9,16-trihydroxy-13,14-dimethoxy-3-methyl-3,4,5,6,7,8,9,10-octahydro-1H-2-benzoxacyclotetradecine-1,7-dione |
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Traditional Name | (3S,8S,9R)-8,9,16-trihydroxy-13,14-dimethoxy-3-methyl-4,5,6,8,9,10-hexahydro-3H-2-benzoxacyclotetradecine-1,7-dione |
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CAS Registry Number | Not Available |
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SMILES | COC1=CC(O)=C2C(\C=C\C[C@@H](O)[C@H](O)C(=O)CCC[C@H](C)OC2=O)=C1OC |
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InChI Identifier | InChI=1S/C20H26O8/c1-11-6-4-8-13(21)18(24)14(22)9-5-7-12-17(20(25)28-11)15(23)10-16(26-2)19(12)27-3/h5,7,10-11,14,18,22-24H,4,6,8-9H2,1-3H3/b7-5+/t11-,14+,18+/m0/s1 |
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InChI Key | INOAIAVUQLBIID-YARXNDSESA-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 zearalenones. These are macrolides which contains a fourteen-member lactone fused to 1,3-dihydroxybenzene. |
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Kingdom | Organic compounds |
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Super Class | Phenylpropanoids and polyketides |
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Class | Macrolides and analogues |
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Sub Class | Zearalenones |
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Direct Parent | Zearalenones |
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Alternative Parents | |
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Substituents | - Zearalenone-skeleton
- Anisole
- Phenol ether
- 1-hydroxy-2-unsubstituted benzenoid
- Alkyl aryl ether
- Phenol
- Benzenoid
- Vinylogous acid
- Cyclic ketone
- 1,2-diol
- Secondary alcohol
- Carboxylic acid ester
- Ketone
- Lactone
- Organoheterocyclic compound
- Carboxylic acid derivative
- Polyol
- Ether
- Oxacycle
- Alcohol
- Carbonyl group
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic 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 | - Premalatha A, Vijayalakshmi K, Shanmugavel M, Rajakumar GS: Optimization of culture conditions for enhanced production of extracellular alpha-amylase using solid-state and submerged fermentation from Aspergillus tamarii MTCC5152. Biotechnol Appl Biochem. 2022 Sep 7. doi: 10.1002/bab.2403. [PubMed:36070879 ]
- Huang W, Le S, Sun Y, Lin DJ, Yao M, Shi Y, Yan J: Mechanical Stabilization of a Bacterial Adhesion Complex. J Am Chem Soc. 2022 Sep 21;144(37):16808-16818. doi: 10.1021/jacs.2c03961. Epub 2022 Sep 7. [PubMed:36070862 ]
- Byrne C, Cosnefroy A, Eston R, Lee JKW, Noakes T: Continuous Thermoregulatory Responses to a Mass-Participation 89-km Ultramarathon Road Race. Int J Sports Physiol Perform. 2022 Sep 6:1-9. doi: 10.1123/ijspp.2022-0043. [PubMed:36070861 ]
- Wang B, Qi J, Xie M, Wang X, Xu J, Yu Z, Zhao W, Xiao Y, Wei W: Enhancement of sugar release from sugarcane bagasse through NaOH-catalyzed ethylene glycol pretreatment and water-soluble sulfonated lignin. Int J Biol Macromol. 2022 Sep 5;221:38-47. doi: 10.1016/j.ijbiomac.2022.08.193. [PubMed:36070818 ]
- Balog M, Anderson A, Gurumurthy CB, Quadros RM, Korade Z, Mirnics K: Knock-in mouse models for studying somatostatin and cholecystokinin expressing cells. J Neurosci Methods. 2022 Nov 1;381:109704. doi: 10.1016/j.jneumeth.2022.109704. Epub 2022 Sep 5. [PubMed:36070817 ]
- Caires R, Garrud TAC, Romero LO, Fernandez-Pena C, Vasquez V, Jaggar JH, Cordero-Morales JF: Genetic- and diet-induced omega-3 fatty acid enrichment enhances TRPV4-mediated vasodilation in mice. Cell Rep. 2022 Sep 6;40(10):111306. doi: 10.1016/j.celrep.2022.111306. [PubMed:36070688 ]
- Vudriko P, Echodu R, Tashiro M, Oka N, Hayashi K, Ichikawa-Seki M: Population structure, molecular characterization, and phylogenetic analysis of Fasciola gigantica from two locations in Uganda. Infect Genet Evol. 2022 Oct;104:105359. doi: 10.1016/j.meegid.2022.105359. Epub 2022 Sep 5. [PubMed:36070805 ]
- Pergialiotis V, Psarris A, Antsaklis P, Theodora M, Papapanagiotou A, Rodolakis A, Daskalakis G: Cervical Cerclage vs. Pessary in Women with a Short Cervix on Ultrasound. Ultraschall Med. 2023 Mar 7. doi: 10.1055/a-1938-6042. [PubMed:36070802 ]
- Halder S, Sanchez A, Ranjha L, Reginato G, Ceppi I, Acharya A, Anand R, Cejka P: Double-stranded DNA binding function of RAD51 in DNA protection and its regulation by BRCA2. Mol Cell. 2022 Oct 6;82(19):3553-3565.e5. doi: 10.1016/j.molcel.2022.08.014. Epub 2022 Sep 6. [PubMed:36070766 ]
- Dai S, Tang X, Li L, Ishidate T, Ozturk AR, Chen H, Dude AL, Yan YH, Dong MQ, Shen EZ, Mello CC: A family of C. elegans VASA homologs control Argonaute pathway specificity and promote transgenerational silencing. Cell Rep. 2022 Sep 6;40(10):111265. doi: 10.1016/j.celrep.2022.111265. [PubMed:36070689 ]
- LOTUS database [Link]
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