Record Information |
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Version | 1.0 |
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Created at | 2022-09-12 10:56:45 UTC |
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Updated at | 2022-09-12 10:56:45 UTC |
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NP-MRD ID | NP0327928 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (1r,3e,5s,7r)-3-[(3,4-dihydroxyphenyl)(hydroxy)methylidene]-7-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-6,6-dimethyl-1,5-bis(3-methylbut-2-en-1-yl)bicyclo[3.3.1]nonane-2,4,9-trione |
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Description | Oblongifolin B belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. (1r,3e,5s,7r)-3-[(3,4-dihydroxyphenyl)(hydroxy)methylidene]-7-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-6,6-dimethyl-1,5-bis(3-methylbut-2-en-1-yl)bicyclo[3.3.1]nonane-2,4,9-trione is found in Garcinia oblongifolia. It was first documented in 2013 (PMID: 24273863). Based on a literature review a significant number of articles have been published on Oblongifolin B (PMID: 32354180) (PMID: 29461053) (PMID: 34086414) (PMID: 33390942). |
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Structure | CC(C)=CCC\C(C)=C\C[C@@H]1C[C@@]2(CC=C(C)C)C(=O)\C(=C(/O)C3=CC=C(O)C(O)=C3)C(=O)[C@](CC=C(C)C)(C2=O)C1(C)C InChI=1S/C38H50O6/c1-23(2)11-10-12-26(7)13-15-28-22-37(19-17-24(3)4)33(42)31(32(41)27-14-16-29(39)30(40)21-27)34(43)38(35(37)44,36(28,8)9)20-18-25(5)6/h11,13-14,16-18,21,28,39-41H,10,12,15,19-20,22H2,1-9H3/b26-13+,32-31+/t28-,37+,38-/m1/s1 |
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Synonyms | Not Available |
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Chemical Formula | C38H50O6 |
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Average Mass | 602.8120 Da |
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Monoisotopic Mass | 602.36074 Da |
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IUPAC Name | (1R,3E,5S,7R)-3-[(3,4-dihydroxyphenyl)(hydroxy)methylidene]-7-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-6,6-dimethyl-1,5-bis(3-methylbut-2-en-1-yl)bicyclo[3.3.1]nonane-2,4,9-trione |
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Traditional Name | (1R,3E,5S,7R)-3-[(3,4-dihydroxyphenyl)(hydroxy)methylidene]-7-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-6,6-dimethyl-1,5-bis(3-methylbut-2-en-1-yl)bicyclo[3.3.1]nonane-2,4,9-trione |
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CAS Registry Number | Not Available |
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SMILES | CC(C)=CCC\C(C)=C\C[C@@H]1C[C@@]2(CC=C(C)C)C(=O)\C(=C(/O)C3=CC=C(O)C(O)=C3)C(=O)[C@](CC=C(C)C)(C2=O)C1(C)C |
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InChI Identifier | InChI=1S/C38H50O6/c1-23(2)11-10-12-26(7)13-15-28-22-37(19-17-24(3)4)33(42)31(32(41)27-14-16-29(39)30(40)21-27)34(43)38(35(37)44,36(28,8)9)20-18-25(5)6/h11,13-14,16-18,21,28,39-41H,10,12,15,19-20,22H2,1-9H3/b26-13+,32-31+/t28-,37+,38-/m1/s1 |
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InChI Key | CVCIGXIQAYQNTE-KQQVVUIOSA-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 sesquiterpenoids. These are terpenes with three consecutive 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 | Sesquiterpenoids |
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Direct Parent | Sesquiterpenoids |
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Alternative Parents | |
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Substituents | - Sesquiterpenoid
- Catechol
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Monocyclic benzene moiety
- Benzenoid
- Vinylogous acid
- Ketone
- Enol
- Hydrocarbon derivative
- Organic oxide
- Carbonyl group
- Organic oxygen compound
- Organooxygen compound
- 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 | - Ccana-Ccapatinta GV, Mejia JAA, Tanimoto MH, Groppo M, Carvalho JCAS, Bastos JK: Dalbergia ecastaphyllum (L.) Taub. and Symphonia globulifera L.f.: The Botanical Sources of Isoflavonoids and Benzophenones in Brazilian Red Propolis. Molecules. 2020 Apr 28;25(9). pii: molecules25092060. doi: 10.3390/molecules25092060. [PubMed:32354180 ]
- Yang XW, Grossman RB, Xu G: Research Progress of Polycyclic Polyprenylated Acylphloroglucinols. Chem Rev. 2018 Apr 11;118(7):3508-3558. doi: 10.1021/acs.chemrev.7b00551. Epub 2018 Feb 20. [PubMed:29461053 ]
- de Souza Silva T, Silva JMB, Braun GH, Mejia JAA, Ccapatinta GVC, Santos MFC, Tanimoto MH, Bastos JK, Parreira RLT, Orenha RP, Borges A, Berretta AA, Veneziani RCS, Martins CHG, Ambrosio SR: Green and Red Brazilian Propolis: Antimicrobial Potential and Anti-Virulence against ATCC and Clinically Isolated Multidrug-Resistant Bacteria. Chem Biodivers. 2021 Aug;18(8):e2100307. doi: 10.1002/cbdv.202100307. Epub 2021 Jun 22. [PubMed:34086414 ]
- Han L, Xu D, Xi Z, Wu M, Nik Nabil WN, Zhang J, Sui H, Fu W, Zhou H, Lao Y, Xu G, Guo C, Xu H: The Natural Compound Oblongifolin C Exhibits Anticancer Activity by Inhibiting HSPA8 and Cathepsin B In Vitro. Front Pharmacol. 2020 Dec 17;11:564833. doi: 10.3389/fphar.2020.564833. eCollection 2020. [PubMed:33390942 ]
- Ito C, Matsui T, Noda E, Ruangrungsi N, Itoigawa M: Biphenyl derivatives from Garcinia schomburgkiana and the cytotoxicity of the isolated compounds. Nat Prod Commun. 2013 Sep;8(9):1265-7. [PubMed:24273863 ]
- LOTUS database [Link]
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