| Record Information |
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| Version | 2.0 |
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| Created at | 2022-09-12 00:38:06 UTC |
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| Updated at | 2022-09-12 00:38:06 UTC |
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| NP-MRD ID | NP0322070 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | (3s)-12,14-dihydroxy-3-methyl-4,5,6,7,8,10-hexahydro-3h-2-benzoxacyclododecine-1,9-dione |
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| Description | Dihydroresorcylide belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members. (3s)-12,14-dihydroxy-3-methyl-4,5,6,7,8,10-hexahydro-3h-2-benzoxacyclododecine-1,9-dione is found in Sarocladium zeae. (3s)-12,14-dihydroxy-3-methyl-4,5,6,7,8,10-hexahydro-3h-2-benzoxacyclododecine-1,9-dione was first documented in 2008 (PMID: 18416554). Based on a literature review a small amount of articles have been published on Dihydroresorcylide (PMID: 27417331) (PMID: 28436691) (PMID: 21425679). |
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| Structure | C[C@H]1CCCCCC(=O)CC2=CC(O)=CC(O)=C2C(=O)O1 InChI=1S/C16H20O5/c1-10-5-3-2-4-6-12(17)7-11-8-13(18)9-14(19)15(11)16(20)21-10/h8-10,18-19H,2-7H2,1H3/t10-/m0/s1 |
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| Synonyms | Not Available |
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| Chemical Formula | C16H20O5 |
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| Average Mass | 292.3310 Da |
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| Monoisotopic Mass | 292.13107 Da |
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| IUPAC Name | (3S)-12,14-dihydroxy-3-methyl-3,4,5,6,7,8,9,10-octahydro-1H-2-benzoxacyclododecine-1,9-dione |
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| Traditional Name | (3S)-12,14-dihydroxy-3-methyl-4,5,6,7,8,10-hexahydro-3H-2-benzoxacyclododecine-1,9-dione |
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| CAS Registry Number | Not Available |
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| SMILES | C[C@H]1CCCCCC(=O)CC2=CC(O)=CC(O)=C2C(=O)O1 |
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| InChI Identifier | InChI=1S/C16H20O5/c1-10-5-3-2-4-6-12(17)7-11-8-13(18)9-14(19)15(11)16(20)21-10/h8-10,18-19H,2-7H2,1H3/t10-/m0/s1 |
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| InChI Key | ZUWLHVBAEWLIDQ-JTQLQIEISA-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 macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members. |
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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 | Not Available |
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| Direct Parent | Macrolides and analogues |
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| Alternative Parents | |
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| Substituents | - Macrolide
- Dihydroxybenzoic acid
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Benzenoid
- Vinylogous acid
- Carboxylic acid ester
- Ketone
- Lactone
- Cyclic ketone
- Carboxylic acid derivative
- Oxacycle
- Organoheterocyclic compound
- Organooxygen compound
- Organic oxide
- Carbonyl group
- Organic oxygen compound
- Hydrocarbon derivative
- 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 | - He WJ, Zhou XJ, Qin XC, Mai YX, Lin XP, Liao SR, Yang B, Zhang T, Tu ZC, Wang JF, Liu Y: Quinone/hydroquinone meroterpenoids with antitubercular and cytotoxic activities produced by the sponge-derived fungus Gliomastix sp. ZSDS1-F7. Nat Prod Res. 2017 Mar;31(5):604-609. doi: 10.1080/14786419.2016.1207076. Epub 2016 Jul 15. [PubMed:27417331 ]
- Poling SM, Wicklow DT, Rogers KD, Gloer JB: Acremonium zeae, a protective endophyte of maize, produces dihydroresorcylide and 7-hydroxydihydroresorcylides. J Agric Food Chem. 2008 May 14;56(9):3006-9. doi: 10.1021/jf073274f. Epub 2008 Apr 17. [PubMed:18416554 ]
- Jiang CS, Zhang L, Gong JX, Li JY, Yao LG, Li J, Guo YW: Concise synthesis and PTP1B inhibitory activity of (R)- and (S)-dihydroresorcylide. J Asian Nat Prod Res. 2017 Dec;19(12):1204-1213. doi: 10.1080/10286020.2017.1317752. Epub 2017 Apr 24. [PubMed:28436691 ]
- Zeng J, Valiente J, Zhan J: Generation of two new macrolactones through sequential biotransformation of dihydroresorcylide. Nat Prod Commun. 2011 Feb;6(2):223-6. [PubMed:21425679 ]
- LOTUS database [Link]
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