Record Information |
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Version | 1.0 |
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Created at | 2022-09-03 17:03:21 UTC |
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Updated at | 2022-09-03 17:03:21 UTC |
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NP-MRD ID | NP0178951 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | [(3ar,5ar,6s,9s,10ar)-6,9-dihydroxy-1-[(2r)-1-hydroxypropan-2-yl]-3a,5a-dimethyl-2h,3h,4h,5h,6h,9h,10h,10ah-cyclohepta[e]inden-8-yl]methyl benzoate |
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Description | Scabronine H belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. [(3ar,5ar,6s,9s,10ar)-6,9-dihydroxy-1-[(2r)-1-hydroxypropan-2-yl]-3a,5a-dimethyl-2h,3h,4h,5h,6h,9h,10h,10ah-cyclohepta[e]inden-8-yl]methyl benzoate is found in Sarcodon scabrosus. It was first documented in 2011 (PMID: 21530015). Based on a literature review a significant number of articles have been published on Scabronine H (PMID: 36057450) (PMID: 36057449) (PMID: 36057448) (PMID: 33281604). |
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Structure | C[C@@H](CO)C1=C2[C@H]3C[C@H](O)C(COC(=O)C4=CC=CC=C4)=C[C@H](O)[C@]3(C)CC[C@@]2(C)CC1 InChI=1S/C27H36O5/c1-17(15-28)20-9-10-26(2)11-12-27(3)21(24(20)26)14-22(29)19(13-23(27)30)16-32-25(31)18-7-5-4-6-8-18/h4-8,13,17,21-23,28-30H,9-12,14-16H2,1-3H3/t17-,21+,22-,23-,26+,27+/m0/s1 |
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Synonyms | Not Available |
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Chemical Formula | C27H36O5 |
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Average Mass | 440.5800 Da |
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Monoisotopic Mass | 440.25627 Da |
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IUPAC Name | [(3aR,5aR,6S,9S,10aR)-6,9-dihydroxy-1-[(2R)-1-hydroxypropan-2-yl]-3a,5a-dimethyl-2H,3H,3aH,4H,5H,5aH,6H,9H,10H,10aH-cyclohepta[e]inden-8-yl]methyl benzoate |
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Traditional Name | [(3aR,5aR,6S,9S,10aR)-6,9-dihydroxy-1-[(2R)-1-hydroxypropan-2-yl]-3a,5a-dimethyl-2H,3H,4H,5H,6H,9H,10H,10aH-cyclohepta[e]inden-8-yl]methyl benzoate |
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CAS Registry Number | Not Available |
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SMILES | C[C@@H](CO)C1=C2[C@H]3C[C@H](O)C(COC(=O)C4=CC=CC=C4)=C[C@H](O)[C@]3(C)CC[C@@]2(C)CC1 |
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InChI Identifier | InChI=1S/C27H36O5/c1-17(15-28)20-9-10-26(2)11-12-27(3)21(24(20)26)14-22(29)19(13-23(27)30)16-32-25(31)18-7-5-4-6-8-18/h4-8,13,17,21-23,28-30H,9-12,14-16H2,1-3H3/t17-,21+,22-,23-,26+,27+/m0/s1 |
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InChI Key | QZEMMWXYJUKIBS-GIXUWZPISA-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 diterpenoids. These are terpene compounds formed by four isoprene units. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Prenol lipids |
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Sub Class | Diterpenoids |
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Direct Parent | Diterpenoids |
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Alternative Parents | |
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Substituents | - Diterpenoid
- Benzoate ester
- Benzoic acid or derivatives
- Benzoyl
- Benzenoid
- Monocyclic benzene moiety
- Secondary alcohol
- Carboxylic acid ester
- Carboxylic acid derivative
- Hydrocarbon derivative
- Primary alcohol
- Organooxygen compound
- Organic oxygen compound
- Alcohol
- Organic oxide
- Aromatic homopolycyclic compound
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Molecular Framework | Aromatic homopolycyclic 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 | - Shi XW, Liu L, Gao JM, Zhang AL: Cyathane diterpenes from Chinese mushroom Sarcodon scabrosus and their neurite outgrowth-promoting activity. Eur J Med Chem. 2011 Jul;46(7):3112-7. doi: 10.1016/j.ejmech.2011.04.006. Epub 2011 Apr 9. [PubMed:21530015 ]
- Micalizzi E, Vaudano AE, Ballerini A, Talami F, Giovannini G, Turchi G, Cioclu MC, Giunta L, Meletti S: Ictal Apnea: a prospective monocentric study in patients with epilepsy. Eur J Neurol. 2022 Sep 3. doi: 10.1111/ene.15547. [PubMed:36057450 ]
- Jiang S, Guo P, Heo HY, Zhang Y, Wu J, Jin Y, Laterra J, Eberhart CG, Lim M, Blakeley JO: Radiomics analysis of amide proton transfer-weighted and structural MR images for treatment response assessment in malignant gliomas. NMR Biomed. 2022 Sep 3:e4824. doi: 10.1002/nbm.4824. [PubMed:36057449 ]
- Agarwal K, Saikia P, Podder I: Metabolic syndrome and Dyslipidemia in xanthelasma palpebrarum and associated risk-factors- a case-control study. J Cosmet Dermatol. 2022 Sep 3. doi: 10.1111/jocd.15353. [PubMed:36057448 ]
- Nakagawasai O, Lin JR, Odaira T, Takahashi K, Nemoto W, Moriguchi S, Yabuki Y, Kobayakawa Y, Fukunaga K, Nakada M, Tan-No K: Scabronine G Methyl Ester Improves Memory-Related Behavior and Enhances Hippocampal Cell Proliferation and Long-Term Potentiation via the BDNF-CREB Pathway in Olfactory Bulbectomized Mice. Front Pharmacol. 2020 Nov 12;11:583291. doi: 10.3389/fphar.2020.583291. eCollection 2020. [PubMed:33281604 ]
- LOTUS database [Link]
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