Record Information |
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Version | 1.0 |
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Created at | 2022-09-05 02:28:57 UTC |
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Updated at | 2022-09-05 02:28:58 UTC |
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NP-MRD ID | NP0206288 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | [8-formyl-5-methoxy-2-methyl-2-(4-methyl-2-oxopent-3-en-1-yl)-3,4-dihydro-1-benzopyran-7-yl]methyl (9z,12z)-octadeca-9,12-dienoate |
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Description | Hericenone H belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. [8-formyl-5-methoxy-2-methyl-2-(4-methyl-2-oxopent-3-en-1-yl)-3,4-dihydro-1-benzopyran-7-yl]methyl (9z,12z)-octadeca-9,12-dienoate is found in Hericium erinaceus. It was first documented in 2015 (PMID: 26481911). Based on a literature review a significant number of articles have been published on Hericenone H (PMID: 31555775) (PMID: 34203691) (PMID: 33492133) (PMID: 32738392) (PMID: 28181079) (PMID: 27094113). |
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Structure | CCCCC\C=C/C\C=C/CCCCCCCC(=O)OCC1=CC(OC)=C2CCC(C)(CC(=O)C=C(C)C)OC2=C1C=O InChI=1S/C37H54O6/c1-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-35(40)42-28-30-25-34(41-5)32-22-23-37(4,26-31(39)24-29(2)3)43-36(32)33(30)27-38/h10-11,13-14,24-25,27H,6-9,12,15-23,26,28H2,1-5H3/b11-10-,14-13- |
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Synonyms | Not Available |
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Chemical Formula | C37H54O6 |
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Average Mass | 594.8330 Da |
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Monoisotopic Mass | 594.39204 Da |
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IUPAC Name | [8-formyl-5-methoxy-2-methyl-2-(4-methyl-2-oxopent-3-en-1-yl)-3,4-dihydro-2H-1-benzopyran-7-yl]methyl (9Z,12Z)-octadeca-9,12-dienoate |
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Traditional Name | [8-formyl-5-methoxy-2-methyl-2-(4-methyl-2-oxopent-3-en-1-yl)-3,4-dihydro-1-benzopyran-7-yl]methyl (9Z,12Z)-octadeca-9,12-dienoate |
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CAS Registry Number | Not Available |
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SMILES | CCCCC\C=C/C\C=C/CCCCCCCC(=O)OCC1=CC(OC)=C2CCC(C)(CC(=O)C=C(C)C)OC2=C1C=O |
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InChI Identifier | InChI=1S/C37H54O6/c1-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-35(40)42-28-30-25-34(41-5)32-22-23-37(4,26-31(39)24-29(2)3)43-36(32)33(30)27-38/h10-11,13-14,24-25,27H,6-9,12,15-23,26,28H2,1-5H3/b11-10-,14-13- |
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InChI Key | WQODVCURNLADTH-XVTLYKPTSA-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 lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Fatty Acyls |
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Sub Class | Lineolic acids and derivatives |
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Direct Parent | Lineolic acids and derivatives |
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Alternative Parents | |
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Substituents | - Octadecanoid
- Chromane
- Benzopyran
- 1-benzopyran
- Anisole
- Phenol ether
- Alkyl aryl ether
- Aryl-aldehyde
- Fatty acid ester
- Benzenoid
- Alpha,beta-unsaturated ketone
- Acryloyl-group
- Enone
- Carboxylic acid ester
- Ketone
- Oxacycle
- Organoheterocyclic compound
- Carboxylic acid derivative
- Monocarboxylic acid or derivatives
- Ether
- Aldehyde
- Organooxygen compound
- Carbonyl group
- Organic oxide
- Hydrocarbon derivative
- Organic oxygen 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 | - Zhang CC, Yin X, Cao CY, Wei J, Zhang Q, Gao JM: Chemical constituents from Hericium erinaceus and their ability to stimulate NGF-mediated neurite outgrowth on PC12 cells. Bioorg Med Chem Lett. 2015 Nov 15;25(22):5078-82. doi: 10.1016/j.bmcl.2015.10.016. Epub 2015 Oct 16. [PubMed:26481911 ]
- Chen ZG, Bishop KS, Tanambell H, Buchanan P, Smith C, Quek SY: Characterization of the bioactivities of an ethanol extract and some of its constituents from the New Zealand native mushroom Hericium novae-zealandiae. Food Funct. 2019 Oct 16;10(10):6633-6643. doi: 10.1039/c9fo01672d. [PubMed:31555775 ]
- Roda E, Priori EC, Ratto D, De Luca F, Di Iorio C, Angelone P, Locatelli CA, Desiderio A, Goppa L, Savino E, Bottone MG, Rossi P: Neuroprotective Metabolites of Hericium erinaceus Promote Neuro-Healthy Aging. Int J Mol Sci. 2021 Jun 15;22(12):6379. doi: 10.3390/ijms22126379. [PubMed:34203691 ]
- Kobayashi S, Tamura T, Koshishiba M, Yasumoto T, Shimizu S, Kintaka T, Nagai K: Total Synthesis, Structure Revision, and Neuroprotective Effect of Hericenones C-H and Their Derivatives. J Org Chem. 2021 Feb 5;86(3):2602-2620. doi: 10.1021/acs.joc.0c02681. Epub 2021 Jan 25. [PubMed:33492133 ]
- Lee SK, Ryu SH, Turk A, Yeon SW, Jo YH, Han YK, Hwang BY, Lee KY, Lee MK: Characterization of alpha-glucosidase inhibitory constituents of the fruiting body of lion's mane mushroom (Hericium erinaceus). J Ethnopharmacol. 2020 Nov 15;262:113197. doi: 10.1016/j.jep.2020.113197. Epub 2020 Jul 29. [PubMed:32738392 ]
- Hiraki E, Furuta S, Kuwahara R, Takemoto N, Nagata T, Akasaka T, Shirouchi B, Sato M, Ohnuki K, Shimizu K: Anti-obesity activity of Yamabushitake (Hericium erinaceus) powder in ovariectomized mice, and its potentially active compounds. J Nat Med. 2017 Jul;71(3):482-491. doi: 10.1007/s11418-017-1075-8. Epub 2017 Feb 8. [PubMed:28181079 ]
- Wang XL, Xu KP, Long HP, Zou H, Cao XZ, Zhang K, Hu JZ, He SJ, Zhu GZ, He XA, Xu PS, Tan GS: New isoindolinones from the fruiting bodies of Hericium erinaceum. Fitoterapia. 2016 Jun;111:58-65. doi: 10.1016/j.fitote.2016.04.010. Epub 2016 Apr 16. [PubMed:27094113 ]
- Lee DG, Kang HW, Park CG, Ahn YS, Shin Y: Isolation and identification of phytochemicals and biological activities of Hericium ernaceus and their contents in Hericium strains using HPLC/UV analysis. J Ethnopharmacol. 2016 May 26;184:219-25. doi: 10.1016/j.jep.2016.02.038. Epub 2016 Feb 26. [PubMed:26924563 ]
- Noh HJ, Yang HH, Kim GS, Lee SE, Lee DY, Choi JH, Kim SY, Lee ES, Ji SH, Kang KS, Park HJ, Kim JR, Kim KH: Chemical constituents of Hericium erinaceum associated with the inhibitory activity against cellular senescence in human umbilical vascular endothelial cells. J Enzyme Inhib Med Chem. 2015 Dec;30(6):934-40. doi: 10.3109/14756366.2014.995181. Epub 2015 Feb 13. [PubMed:25676326 ]
- Li W, Zhou W, Kim EJ, Shim SH, Kang HK, Kim YH: Isolation and identification of aromatic compounds in Lion's Mane Mushroom and their anticancer activities. Food Chem. 2015 Mar 1;170:336-42. doi: 10.1016/j.foodchem.2014.08.078. Epub 2014 Aug 23. [PubMed:25306354 ]
- LOTUS database [Link]
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