Record Information |
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Version | 2.0 |
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Created at | 2022-09-12 00:03:26 UTC |
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Updated at | 2022-09-12 00:03:26 UTC |
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NP-MRD ID | NP0321702 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (2s,3s)-n-[(s)-[(4r,6r)-6-[(2s,3r)-3-[(3s)-6,8-dihydroxy-5-methyl-1-oxo-3,4-dihydro-2-benzopyran-3-yl]-2-hydroxybutyl]-4-hydroxy-5,5-dimethyloxan-2-yl](methoxy)methyl]-2-hydroxy-3-methoxy-5-methylhex-5-enimidic acid |
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Description | IRCINIASTATIN belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups. It was first documented in 2015 (PMID: 26544018). Based on a literature review a significant number of articles have been published on IRCINIASTATIN (PMID: 34058326) (PMID: 31063392) (PMID: 26879056) (PMID: 26027837). |
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Structure | CO[C@@H](CC(C)=C)[C@H](O)C(O)=N[C@@H](OC)C1C[C@@H](O)C(C)(C)[C@@H](C[C@H](O)[C@@H](C)[C@@H]2CC3=C(C)C(O)=CC(O)=C3C(=O)O2)O1 InChI=1S/C31H47NO11/c1-14(2)9-22(40-7)27(37)28(38)32-29(41-8)23-13-24(36)31(5,6)25(42-23)12-19(34)16(4)21-10-17-15(3)18(33)11-20(35)26(17)30(39)43-21/h11,16,19,21-25,27,29,33-37H,1,9-10,12-13H2,2-8H3,(H,32,38)/t16-,19+,21+,22+,23?,24-,25-,27+,29+/m1/s1 |
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Synonyms | Not Available |
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Chemical Formula | C31H47NO11 |
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Average Mass | 609.7130 Da |
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Monoisotopic Mass | 609.31491 Da |
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IUPAC Name | (2S,3S)-N-[(S)-[(4R,6R)-6-[(2S,3R)-3-[(3S)-6,8-dihydroxy-5-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-3-yl]-2-hydroxybutyl]-4-hydroxy-5,5-dimethyloxan-2-yl](methoxy)methyl]-2-hydroxy-3-methoxy-5-methylhex-5-enimidic acid |
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Traditional Name | (2S,3S)-N-[(S)-[(4R,6R)-6-[(2S,3R)-3-[(3S)-6,8-dihydroxy-5-methyl-1-oxo-3,4-dihydro-2-benzopyran-3-yl]-2-hydroxybutyl]-4-hydroxy-5,5-dimethyloxan-2-yl](methoxy)methyl]-2-hydroxy-3-methoxy-5-methylhex-5-enimidic acid |
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CAS Registry Number | Not Available |
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SMILES | CO[C@@H](CC(C)=C)[C@H](O)C(O)=N[C@@H](OC)C1C[C@@H](O)C(C)(C)[C@@H](C[C@H](O)[C@@H](C)[C@@H]2CC3=C(C)C(O)=CC(O)=C3C(=O)O2)O1 |
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InChI Identifier | InChI=1S/C31H47NO11/c1-14(2)9-22(40-7)27(37)28(38)32-29(41-8)23-13-24(36)31(5,6)25(42-23)12-19(34)16(4)21-10-17-15(3)18(33)11-20(35)26(17)30(39)43-21/h11,16,19,21-25,27,29,33-37H,1,9-10,12-13H2,2-8H3,(H,32,38)/t16-,19+,21+,22+,23?,24-,25-,27+,29+/m1/s1 |
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InChI Key | BNNIEBYABSNREN-FKNVEFDBSA-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 hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Benzene and substituted derivatives |
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Sub Class | Benzoic acids and derivatives |
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Direct Parent | Hydroxybenzoic acid derivatives |
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Alternative Parents | |
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Substituents | - Dihydroxybenzoic acid
- Benzopyran
- Isochromane
- 2-benzopyran
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Fatty amide
- Monosaccharide
- Fatty acyl
- N-acyl-amine
- Oxane
- Vinylogous acid
- Carboxamide group
- Carboxylic acid ester
- Lactone
- Secondary carboxylic acid amide
- Secondary alcohol
- Oxacycle
- Ether
- Dialkyl ether
- Carboxylic acid derivative
- Organoheterocyclic compound
- Organic nitrogen compound
- Hydrocarbon derivative
- Organic oxide
- Alcohol
- Organonitrogen compound
- Organooxygen compound
- Organic oxygen compound
- Carbonyl group
- 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 | - Burgers LD, Furst R: Natural products as drugs and tools for influencing core processes of eukaryotic mRNA translation. Pharmacol Res. 2021 Aug;170:105535. doi: 10.1016/j.phrs.2021.105535. Epub 2021 May 29. [PubMed:34058326 ]
- Yu J, Yang M, Guo Y, Ye T: Total Synthesis of Psymberin (Irciniastatin A). Org Lett. 2019 May 17;21(10):3670-3673. doi: 10.1021/acs.orglett.9b01113. Epub 2019 May 7. [PubMed:31063392 ]
- Liu Q, An C, TenDyke K, Cheng H, Shen YY, Hoye AT, Smith AB 3rd: Design, Synthesis, and Evaluation of Irciniastatin Analogues: Simplification of the Tetrahydropyran Core and the C(11) Substituents. J Org Chem. 2016 Mar 4;81(5):1930-42. doi: 10.1021/acs.joc.5b02771. Epub 2016 Feb 16. [PubMed:26879056 ]
- Uesugi S, Watanabe T, Imaizumi T, Ota Y, Yoshida K, Ebisu H, Chinen T, Nagumo Y, Shibuya M, Kanoh N, Usui T, Iwabuchi Y: Total Synthesis and Biological Evaluation of Irciniastatin A (a.k.a. Psymberin) and Irciniastatin B. J Org Chem. 2015 Dec 18;80(24):12333-50. doi: 10.1021/acs.joc.5b02256. Epub 2015 Nov 16. [PubMed:26544018 ]
- Quach HT, Hirano S, Fukuhara S, Watanabe T, Kanoh N, Iwabuchi Y, Usui T, Kataoka T: Irciniastatin A induces potent and sustained activation of extracellular signal-regulated kinase and thereby promotes ectodomain shedding of tumor necrosis factor receptor 1 in human lung carcinoma A549 cells. Biol Pharm Bull. 2015;38(6):941-6. doi: 10.1248/bpb.b15-00078. [PubMed:26027837 ]
- LOTUS database [Link]
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