Record Information |
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Version | 1.0 |
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Created at | 2022-09-04 06:33:15 UTC |
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Updated at | 2022-09-04 06:33:15 UTC |
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NP-MRD ID | NP0189963 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | α-conidendrin |
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Description | Alpha-Conidendrin, also known as α-conidendrin, belongs to the class of organic compounds known as lignan lactones. These are lignans that contain a lactone moiety. They include 1-aryltetralin lactones, dibenzylbutyrolactone lignans, and podophyllotoxins, among others. α-conidendrin is found in Abies holophylla, Dolomiaea souliei, Taxus mairei, Taxus wallichiana and Tsuga heterophylla. It was first documented in 2012 (PMID: 22949834). Alpha-Conidendrin is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 32552421) (PMID: 31971313) (PMID: 30920215) (PMID: 27774796). |
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Structure | [H][C@]12COC(=O)[C@]1([H])CC1=CC(OC)=C(O)C=C1[C@@H]2C1=CC(OC)=C(O)C=C1 InChI=1S/C20H20O6/c1-24-17-6-10(3-4-15(17)21)19-12-8-16(22)18(25-2)7-11(12)5-13-14(19)9-26-20(13)23/h3-4,6-8,13-14,19,21-22H,5,9H2,1-2H3/t13-,14+,19+/m1/s1 |
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Synonyms | Value | Source |
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a-Conidendrin | Generator | Α-conidendrin | Generator | Conidendrin | MeSH | alpha-Conidendrin | PhytoBank | (-)-alpha-Conidendrin | PhytoBank | (-)-α-Conidendrin | PhytoBank |
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Chemical Formula | C20H20O6 |
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Average Mass | 356.3740 Da |
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Monoisotopic Mass | 356.12599 Da |
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IUPAC Name | (3aR,4S,9aR)-6-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-7-methoxy-1H,3H,3aH,4H,9H,9aH-naphtho[2,3-c]furan-1-one |
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Traditional Name | (3aR,4S,9aR)-6-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-7-methoxy-3H,3aH,4H,9H,9aH-naphtho[2,3-c]furan-1-one |
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CAS Registry Number | Not Available |
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SMILES | [H][C@]12COC(=O)[C@]1([H])CC1=CC(OC)=C(O)C=C1[C@@H]2C1=CC(OC)=C(O)C=C1 |
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InChI Identifier | InChI=1S/C20H20O6/c1-24-17-6-10(3-4-15(17)21)19-12-8-16(22)18(25-2)7-11(12)5-13-14(19)9-26-20(13)23/h3-4,6-8,13-14,19,21-22H,5,9H2,1-2H3/t13-,14+,19+/m1/s1 |
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InChI Key | CAYMSCGTKZIVTN-TYILLQQXSA-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 lignan lactones. These are lignans that contain a lactone moiety. They include 1-aryltetralin lactones, dibenzylbutyrolactone lignans, and podophyllotoxins, among others. |
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Kingdom | Organic compounds |
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Super Class | Lignans, neolignans and related compounds |
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Class | Lignan lactones |
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Sub Class | Not Available |
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Direct Parent | Lignan lactones |
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Alternative Parents | |
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Substituents | - Lignan lactone
- 1-aryltetralin lignan
- Naphthofuran
- Methoxyphenol
- Tetralin
- Phenoxy compound
- Anisole
- Methoxybenzene
- Phenol ether
- 1-hydroxy-2-unsubstituted benzenoid
- Alkyl aryl ether
- Phenol
- Monocyclic benzene moiety
- Gamma butyrolactone
- Benzenoid
- Tetrahydrofuran
- Lactone
- Carboxylic acid ester
- Carboxylic acid derivative
- Oxacycle
- Ether
- Organoheterocyclic compound
- Monocarboxylic acid or derivatives
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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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 | - Shirakata H, Nishiwaki H, Yamauchi S: Syntheses of all eight stereoisomers of conidendrin. Biosci Biotechnol Biochem. 2020 Oct;84(10):1986-1996. doi: 10.1080/09168451.2020.1777081. Epub 2020 Jun 17. [PubMed:32552421 ]
- Hafezi K, Hemmati AA, Abbaszadeh H, Valizadeh A, Makvandi M: Anticancer activity and molecular mechanisms of alpha-conidendrin, a polyphenolic compound present in Taxus yunnanensis, on human breast cancer cell lines. Phytother Res. 2020 Jun;34(6):1397-1408. doi: 10.1002/ptr.6613. Epub 2020 Jan 23. [PubMed:31971313 ]
- Hartmann P, Lazzarotto M, Steiner L, Cigan E, Poschenrieder S, Sagmeister P, Fuchs M: TRIP-Catalyzed Asymmetric Synthesis of (+)-Yatein, (-)-alpha-Conidendrin, (+)-Isostegane, and (+)-Neoisostegane. J Org Chem. 2019 May 3;84(9):5831-5837. doi: 10.1021/acs.joc.9b00065. Epub 2019 Apr 5. [PubMed:30920215 ]
- Hu CL, Xiong J, Xu P, Cheng KJ, Yang GX, Hu JF: Lignans from the shed trunk barks of the critically endangered plant Abies beshanzuensis and their anti-neuroinflammatory activities. Nat Prod Res. 2017 Jun;31(12):1358-1364. doi: 10.1080/14786419.2016.1247082. Epub 2016 Oct 23. [PubMed:27774796 ]
- Sandberg T, Eklund P, Hotokka M: Conformational solvation studies of LIGNOLs with molecular dynamics and conductor-like screening model. Int J Mol Sci. 2012;13(8):9845-9863. doi: 10.3390/ijms13089845. Epub 2012 Aug 7. [PubMed:22949834 ]
- LOTUS database [Link]
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