Record Information |
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Version | 1.0 |
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Created at | 2022-09-02 15:27:10 UTC |
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Updated at | 2022-09-02 15:27:10 UTC |
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NP-MRD ID | NP0157947 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (2r,11s,13r)-22-chloro-2,5,28-trihydroxy-21-methoxy-7-methyl-14,16,19-trioxa-6-azaheptacyclo[15.11.1.0²,¹¹.0⁴,⁹.0¹³,²⁹.0¹⁸,²⁷.0²⁰,²⁵]nonacosa-1(29),4,6,8,17,20,22,24,27-nonaene-3,10,26-trione |
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Description | Xantholipin belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring. It was first documented in 2020 (PMID: 32651204). Based on a literature review a significant number of articles have been published on Xantholipin (PMID: 35512262) (PMID: 34962769) (PMID: 34564766) (PMID: 32649177). |
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Structure | COC1=C2OC3=C4OCO[C@@H]5C[C@@H]6C(=O)C7=CC(C)=NC(O)=C7C(=O)[C@]6(O)C(C(O)=C3C(=O)C2=CC=C1Cl)=C45 InChI=1S/C27H18ClNO10/c1-8-5-10-14(26(34)29-8)25(33)27(35)11(18(10)30)6-13-15-17(27)20(32)16-19(31)9-3-4-12(28)22(36-2)21(9)39-24(16)23(15)38-7-37-13/h3-5,11,13,32,35H,6-7H2,1-2H3,(H,29,34)/t11-,13-,27-/m1/s1 |
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Synonyms | Not Available |
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Chemical Formula | C27H18ClNO10 |
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Average Mass | 551.8900 Da |
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Monoisotopic Mass | 551.06192 Da |
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IUPAC Name | (2R,11S,13R)-22-chloro-2,5,28-trihydroxy-21-methoxy-7-methyl-14,16,19-trioxa-6-azaheptacyclo[15.11.1.0^{2,11}.0^{4,9}.0^{13,29}.0^{18,27}.0^{20,25}]nonacosa-1(29),4(9),5,7,17,20(25),21,23,27-nonaene-3,10,26-trione |
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Traditional Name | (2R,11S,13R)-22-chloro-2,5,28-trihydroxy-21-methoxy-7-methyl-14,16,19-trioxa-6-azaheptacyclo[15.11.1.0^{2,11}.0^{4,9}.0^{13,29}.0^{18,27}.0^{20,25}]nonacosa-1(29),4(9),5,7,17,20(25),21,23,27-nonaene-3,10,26-trione |
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CAS Registry Number | Not Available |
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SMILES | COC1=C2OC3=C4OCO[C@@H]5C[C@@H]6C(=O)C7=CC(C)=NC(O)=C7C(=O)[C@]6(O)C(C(O)=C3C(=O)C2=CC=C1Cl)=C45 |
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InChI Identifier | InChI=1S/C27H18ClNO10/c1-8-5-10-14(26(34)29-8)25(33)27(35)11(18(10)30)6-13-15-17(27)20(32)16-19(31)9-3-4-12(28)22(36-2)21(9)39-24(16)23(15)38-7-37-13/h3-5,11,13,32,35H,6-7H2,1-2H3,(H,29,34)/t11-,13-,27-/m1/s1 |
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InChI Key | HSVRTPZWHMWONP-JUEDDRGBSA-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 xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Benzopyrans |
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Sub Class | 1-benzopyrans |
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Direct Parent | Xanthones |
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Alternative Parents | |
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Substituents | - Xanthone
- Naphthopyranone
- Phenanthrene
- Naphthopyran
- Chromone
- Isoquinolone
- Naphthalene
- Tetralin
- Anisole
- Aryl alkyl ketone
- Aryl ketone
- Methylpyridine
- Alkyl aryl ether
- Pyranone
- Pyridinone
- Pyridine
- Pyran
- Benzenoid
- Aryl halide
- Aryl chloride
- Heteroaromatic compound
- Vinylogous amide
- Vinylogous acid
- Tertiary alcohol
- Ketone
- Lactam
- Ether
- Acetal
- Oxacycle
- Azacycle
- Organochloride
- Organic nitrogen compound
- Organic oxygen compound
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Organohalogen compound
- Organooxygen compound
- Organonitrogen compound
- Alcohol
- 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 | - Leetanasaksakul K, Koomsiri W, Suga T, Matsuo H, Hokari R, Wattana-Amorn P, Takahashi YK, Shiomi K, Nakashima T, Inahashi Y, Thamchaipenet A: Sattahipmycin, a Hexacyclic Xanthone Produced by a Marine-Derived Streptomyces. J Nat Prod. 2022 May 27;85(5):1211-1217. doi: 10.1021/acs.jnatprod.1c00870. Epub 2022 May 5. [PubMed:35512262 ]
- Toplak M, Teufel R: Three Rings to Rule Them All: How Versatile Flavoenzymes Orchestrate the Structural Diversification of Natural Products. Biochemistry. 2022 Jan 18;61(2):47-56. doi: 10.1021/acs.biochem.1c00763. Epub 2021 Dec 28. [PubMed:34962769 ]
- Vela Gurovic MS, Diaz ML, Gallo CA, Dietrich J: Phylogenomics, CAZyome and core secondary metabolome of Streptomyces albus species. Mol Genet Genomics. 2021 Nov;296(6):1299-1311. doi: 10.1007/s00438-021-01823-9. Epub 2021 Sep 26. [PubMed:34564766 ]
- Kong L, Wang Q, Deng Z, You D: Flavin Adenine Dinucleotide-Dependent Halogenase XanH and Engineering of Multifunctional Fusion Halogenases. Appl Environ Microbiol. 2020 Sep 1;86(18):e01225-20. doi: 10.1128/AEM.01225-20. Print 2020 Sep 1. [PubMed:32651204 ]
- Kong L, Wang Q, Yang W, Shen J, Li Y, Zheng X, Wang L, Chu Y, Deng Z, Chooi YH, You D: Three Recently Diverging Duplicated Methyltransferases Exhibit Substrate-Dependent Regioselectivity Essential for Xantholipin Biosynthesis. ACS Chem Biol. 2020 Aug 21;15(8):2107-2115. doi: 10.1021/acschembio.0c00296. Epub 2020 Jul 23. [PubMed:32649177 ]
- LOTUS database [Link]
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