Record Information |
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Version | 1.0 |
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Created at | 2022-09-08 18:59:38 UTC |
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Updated at | 2022-09-08 18:59:38 UTC |
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NP-MRD ID | NP0272390 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (5z)-6-[(3ar,4s,7s,9as,11ar)-4,7-dihydroxy-3a,6,6,9a,11a-pentamethyl-3,10-dioxo-1h,2h,4h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]-2-methyl-4-oxohept-5-enoic acid |
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Description | Ganoderenic Acid B, also known as ganoderenate b, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. It was first documented in 2015 (PMID: 25779097). Based on a literature review a significant number of articles have been published on Ganoderenic Acid B (PMID: 35331732) (PMID: 28875673) (PMID: 30317980) (PMID: 31681225). |
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Structure | CC(CC(=O)\C=C(\C)C1CC(=O)[C@@]2(C)C3=C(C(=O)C[C@]12C)[C@@]1(C)CC[C@H](O)C(C)(C)C1C[C@@H]3O)C(O)=O InChI=1S/C30H42O7/c1-15(10-17(31)11-16(2)26(36)37)18-12-23(35)30(7)25-19(32)13-21-27(3,4)22(34)8-9-28(21,5)24(25)20(33)14-29(18,30)6/h10,16,18-19,21-22,32,34H,8-9,11-14H2,1-7H3,(H,36,37)/b15-10-/t16?,18?,19-,21?,22-,28-,29+,30-/m0/s1 |
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Synonyms | Value | Source |
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Ganoderenate b | Generator |
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Chemical Formula | C30H42O7 |
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Average Mass | 514.6590 Da |
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Monoisotopic Mass | 514.29305 Da |
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IUPAC Name | (5Z)-6-[(2S,5S,9S,11R,15R)-5,9-dihydroxy-2,6,6,11,15-pentamethyl-12,17-dioxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-14-yl]-2-methyl-4-oxohept-5-enoic acid |
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Traditional Name | (5Z)-6-[(2S,5S,9S,11R,15R)-5,9-dihydroxy-2,6,6,11,15-pentamethyl-12,17-dioxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-14-yl]-2-methyl-4-oxohept-5-enoic acid |
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CAS Registry Number | Not Available |
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SMILES | CC(CC(=O)\C=C(\C)C1CC(=O)[C@@]2(C)C3=C(C(=O)C[C@]12C)[C@@]1(C)CC[C@H](O)C(C)(C)C1C[C@@H]3O)C(O)=O |
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InChI Identifier | InChI=1S/C30H42O7/c1-15(10-17(31)11-16(2)26(36)37)18-12-23(35)30(7)25-19(32)13-21-27(3,4)22(34)8-9-28(21,5)24(25)20(33)14-29(18,30)6/h10,16,18-19,21-22,32,34H,8-9,11-14H2,1-7H3,(H,36,37)/b15-10-/t16?,18?,19-,21?,22-,28-,29+,30-/m0/s1 |
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InChI Key | QECQJYAIIIIKJB-XYJGWYKWSA-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 | Not Available |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six 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 | Triterpenoids |
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Direct Parent | Triterpenoids |
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Alternative Parents | |
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Substituents | - Triterpenoid
- 23-oxosteroid
- Steroid acid
- 3-hydroxysteroid
- Hydroxysteroid
- 11-oxosteroid
- 15-oxosteroid
- Oxosteroid
- 3-beta-hydroxysteroid
- 7-alpha-hydroxysteroid
- 7-hydroxysteroid
- 14-alpha-methylsteroid
- Steroid
- Medium-chain keto acid
- Gamma-keto acid
- Branched fatty acid
- Methyl-branched fatty acid
- Cyclohexenone
- Hydroxy fatty acid
- Unsaturated fatty acid
- Fatty acyl
- Keto acid
- Cyclic alcohol
- Alpha,beta-unsaturated ketone
- Enone
- Acryloyl-group
- Secondary alcohol
- Ketone
- Carboxylic acid
- Carboxylic acid derivative
- Monocarboxylic acid or derivatives
- Organic oxide
- Organooxygen compound
- Alcohol
- Organic oxygen compound
- Hydrocarbon derivative
- Carbonyl group
- Aliphatic homopolycyclic compound
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Molecular Framework | Aliphatic 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 | - Biswal RP, Dandamudi RB, Patnana DP, Pandey M, Vutukuri VNRK: Metabolic fingerprinting of Ganoderma spp. using UHPLC-ESI-QTOF-MS and its chemometric analysis. Phytochemistry. 2022 Jul;199:113169. doi: 10.1016/j.phytochem.2022.113169. Epub 2022 Mar 22. [PubMed:35331732 ]
- Liu LY, Kang J, Wu CH, Li Y, Chen RY: [Triterpenoids from Ganoderma theaecolum]. Zhongguo Zhong Yao Za Zhi. 2016 Mar;41(6):1075-1080. doi: 10.4268/cjcmm20160617. [PubMed:28875673 ]
- Zhou S, Tang Q, Tang C, Liu Y, Ma F, Zhang X, Zhang JS: Triterpenes and Soluble Polysaccharide Changes in Lingzhi or Reishi Medicinal Mushroom, Ganoderma lucidum (Agaricomycetes), During Fruiting Growth. Int J Med Mushrooms. 2018;20(9):859-871. doi: 10.1615/IntJMedMushrooms.2018027357. [PubMed:30317980 ]
- Dong Q, Li Y, Liu G, Zhang Z, Zhou H, Yang H: High Oxygen Treatments Enhance the Contents of Phenolic Compound and Ganoderic Acid, and the Antioxidant and DNA Damage Protective Activities of Ganoderma lingzhi Fruiting Body. Front Microbiol. 2019 Oct 18;10:2363. doi: 10.3389/fmicb.2019.02363. eCollection 2019. [PubMed:31681225 ]
- Liu DL, Li YJ, Yang DH, Wang CR, Xu J, Yao N, Zhang XQ, Chen ZS, Ye WC, Zhang DM: Ganoderma lucidum derived ganoderenic acid B reverses ABCB1-mediated multidrug resistance in HepG2/ADM cells. Int J Oncol. 2015 May;46(5):2029-38. doi: 10.3892/ijo.2015.2925. Epub 2015 Mar 12. [PubMed:25779097 ]
- LOTUS database [Link]
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