| Record Information |
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| Version | 2.0 |
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| Created at | 2022-09-12 14:13:54 UTC |
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| Updated at | 2022-09-12 14:13:55 UTC |
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| NP-MRD ID | NP0329650 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | (7s,10s,17s)-3,7,10,28-tetrahydroxy-14-methoxy-24,25-dimethyl-12,18,20-trioxa-25-azaheptacyclo[15.11.1.0²,¹⁵.0⁴,¹³.0⁶,¹¹.0²¹,²⁹.0²²,²⁷]nonacosa-1(29),2(15),3,6(11),13,21,23,27-octaene-5,26-dione |
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| Description | Simaomicin 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. (7s,10s,17s)-3,7,10,28-tetrahydroxy-14-methoxy-24,25-dimethyl-12,18,20-trioxa-25-azaheptacyclo[15.11.1.0²,¹⁵.0⁴,¹³.0⁶,¹¹.0²¹,²⁹.0²²,²⁷]nonacosa-1(29),2(15),3,6(11),13,21,23,27-octaene-5,26-dione is found in Actinomadura madurae. (7s,10s,17s)-3,7,10,28-tetrahydroxy-14-methoxy-24,25-dimethyl-12,18,20-trioxa-25-azaheptacyclo[15.11.1.0²,¹⁵.0⁴,¹³.0⁶,¹¹.0²¹,²⁹.0²²,²⁷]nonacosa-1(29),2(15),3,6(11),13,21,23,27-octaene-5,26-dione was first documented in 2004 (PMID: 15081413). Based on a literature review a small amount of articles have been published on Simaomicin (PMID: 17446697) (PMID: 24038677) (PMID: 19077005) (PMID: 18503207). |
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| Structure | COC1=C2OC3=C([C@@H](O)CC[C@@H]3O)C(=O)C2=C(O)C2=C1C[C@@H]1OCOC3=C4C=C(C)N(C)C(=O)C4=C(O)C2=C13 InChI=1S/C28H25NO10/c1-9-6-10-16(28(35)29(9)2)22(33)19-15-11(7-14-18(19)24(10)38-8-37-14)25(36-3)27-20(21(15)32)23(34)17-12(30)4-5-13(31)26(17)39-27/h6,12-14,30-33H,4-5,7-8H2,1-3H3/t12-,13-,14-/m0/s1 |
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| Synonyms | Not Available |
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| Chemical Formula | C28H25NO10 |
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| Average Mass | 535.5050 Da |
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| Monoisotopic Mass | 535.14785 Da |
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| IUPAC Name | (7S,10S,17S)-3,7,10,28-tetrahydroxy-14-methoxy-24,25-dimethyl-12,18,20-trioxa-25-azaheptacyclo[15.11.1.0^{2,15}.0^{4,13}.0^{6,11}.0^{21,29}.0^{22,27}]nonacosa-1(29),2(15),3,6(11),13,21,23,27-octaene-5,26-dione |
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| Traditional Name | (7S,10S,17S)-3,7,10,28-tetrahydroxy-14-methoxy-24,25-dimethyl-12,18,20-trioxa-25-azaheptacyclo[15.11.1.0^{2,15}.0^{4,13}.0^{6,11}.0^{21,29}.0^{22,27}]nonacosa-1(29),2(15),3,6(11),13,21,23,27-octaene-5,26-dione |
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| CAS Registry Number | Not Available |
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| SMILES | COC1=C2OC3=C([C@@H](O)CC[C@@H]3O)C(=O)C2=C(O)C2=C1C[C@@H]1OCOC3=C4C=C(C)N(C)C(=O)C4=C(O)C2=C13 |
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| InChI Identifier | InChI=1S/C28H25NO10/c1-9-6-10-16(28(35)29(9)2)22(33)19-15-11(7-14-18(19)24(10)38-8-37-14)25(36-3)27-20(21(15)32)23(34)17-12(30)4-5-13(31)26(17)39-27/h6,12-14,30-33H,4-5,7-8H2,1-3H3/t12-,13-,14-/m0/s1 |
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| InChI Key | DQPBSXMRMTWOAQ-IHRRRGAJSA-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 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
- Isoquinolone
- 1-naphthol
- Chromone
- Naphthalene
- Isoquinoline
- Anisole
- Methylpyridine
- Alkyl aryl ether
- Pyranone
- Pyridinone
- Pyran
- Benzenoid
- Pyridine
- Heteroaromatic compound
- Vinylogous acid
- Lactam
- Secondary alcohol
- Azacycle
- Oxacycle
- Acetal
- Ether
- Polyol
- Organooxygen compound
- Organonitrogen compound
- Alcohol
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Organic oxygen compound
- Organic nitrogen compound
- 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 | - Ui H, Ishiyama A, Sekiguchi H, Namatame M, Nishihara A, Takahashi Y, Shiomi K, Otoguro K, Omura S: Selective and potent in vitro antimalarial activities found in four microbial metabolites. J Antibiot (Tokyo). 2007 Mar;60(3):220-2. doi: 10.1038/ja.2007.27. [PubMed:17446697 ]
- Wang Y, Wang C, Butler JR, Ready JM: Dehydrogenative coupling to enable the enantioselective total synthesis of (-)-simaomicin alpha. Angew Chem Int Ed Engl. 2013 Oct 4;52(41):10796-9. doi: 10.1002/anie.201304812. Epub 2013 Aug 22. [PubMed:24038677 ]
- Koizumi Y, Tomoda H, Kumagai A, Zhou XP, Koyota S, Sugiyama T: Simaomicin alpha, a polycyclic xanthone, induces G(1) arrest with suppression of retinoblastoma protein phosphorylation. Cancer Sci. 2009 Feb;100(2):322-6. doi: 10.1111/j.1349-7006.2008.01033.x. [PubMed:19077005 ]
- Ishiyama A, Otoguro K, Namatame M, Nishihara A, Furusawa T, Takahashi Y, Masuma R, Shiomi K, Omura S: Simaomicin alpha: effects on the cell cycle of synchronized, cultured Plasmodium falciparum. J Antibiot (Tokyo). 2008 Apr;61(4):254-7. doi: 10.1038/ja.2008.38. [PubMed:18503207 ]
- Arai M, Sato H, Kobayashi H, Suganuma M, Kawabe T, Tomoda H, Omura S: Selective inhibition of bleomycin-induced G2 cell cycle checkpoint by simaomicin alpha. Biochem Biophys Res Commun. 2004 May 7;317(3):817-22. doi: 10.1016/j.bbrc.2004.03.117. [PubMed:15081413 ]
- LOTUS database [Link]
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