Record Information |
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Version | 1.0 |
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Created at | 2022-09-07 15:19:21 UTC |
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Updated at | 2022-09-07 15:19:22 UTC |
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NP-MRD ID | NP0251962 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (3r,6s,9s,13s)-9-benzyl-13-[(2s)-hexan-2-yl]-5,8,11-trihydroxy-6-methyl-3-(2-methylpropyl)-1-oxa-4,7,10-triazacyclotrideca-4,7,10-trien-2-one |
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Description | Beauveriolide I belongs to the class of organic compounds known as cyclic depsipeptides. These are natural or synthetic compounds having sequences of amino and hydroxy carboxylic acid residues (usually α-amino and α-hydroxy acids) connected in a ring. The residues are commonly but not necessarily regularly alternating. Beauveriolide I is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. It was first documented in 2002 (PMID: 12617514). Based on a literature review a significant number of articles have been published on beauveriolide I (PMID: 36099392) (PMID: 35412727) (PMID: 31661213) (PMID: 31593386) (PMID: 17803269) (PMID: 31926180). |
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Structure | CCCC[C@H](C)[C@@H]1CC(O)=N[C@@H](CC2=CC=CC=C2)C(O)=N[C@@H](C)C(O)=N[C@H](CC(C)C)C(=O)O1 InChI=1S/C27H41N3O5/c1-6-7-11-18(4)23-16-24(31)29-21(15-20-12-9-8-10-13-20)26(33)28-19(5)25(32)30-22(14-17(2)3)27(34)35-23/h8-10,12-13,17-19,21-23H,6-7,11,14-16H2,1-5H3,(H,28,33)(H,29,31)(H,30,32)/t18-,19-,21-,22+,23-/m0/s1 |
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Synonyms | Not Available |
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Chemical Formula | C27H41N3O5 |
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Average Mass | 487.6410 Da |
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Monoisotopic Mass | 487.30462 Da |
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IUPAC Name | (3R,6S,9S,13S)-9-benzyl-13-[(2S)-hexan-2-yl]-5,8,11-trihydroxy-6-methyl-3-(2-methylpropyl)-1-oxa-4,7,10-triazacyclotrideca-4,7,10-trien-2-one |
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Traditional Name | (3R,6S,9S,13S)-9-benzyl-13-[(2S)-hexan-2-yl]-5,8,11-trihydroxy-6-methyl-3-(2-methylpropyl)-1-oxa-4,7,10-triazacyclotrideca-4,7,10-trien-2-one |
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CAS Registry Number | Not Available |
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SMILES | CCCC[C@H](C)[C@@H]1CC(O)=N[C@@H](CC2=CC=CC=C2)C(O)=N[C@@H](C)C(O)=N[C@H](CC(C)C)C(=O)O1 |
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InChI Identifier | InChI=1S/C27H41N3O5/c1-6-7-11-18(4)23-16-24(31)29-21(15-20-12-9-8-10-13-20)26(33)28-19(5)25(32)30-22(14-17(2)3)27(34)35-23/h8-10,12-13,17-19,21-23H,6-7,11,14-16H2,1-5H3,(H,28,33)(H,29,31)(H,30,32)/t18-,19-,21-,22+,23-/m0/s1 |
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InChI Key | ZKSLFHXTWGEITF-JIORRVSTSA-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 cyclic depsipeptides. These are natural or synthetic compounds having sequences of amino and hydroxy carboxylic acid residues (usually α-amino and α-hydroxy acids) connected in a ring. The residues are commonly but not necessarily regularly alternating. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Peptidomimetics |
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Sub Class | Depsipeptides |
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Direct Parent | Cyclic depsipeptides |
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Alternative Parents | |
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Substituents | - Cyclic depsipeptide
- Macrolide lactam
- Alpha-amino acid ester
- Macrolactam
- Macrolide
- Alpha-amino acid or derivatives
- Monocyclic benzene moiety
- Benzenoid
- Carboxamide group
- Carboxylic acid ester
- Lactam
- Lactone
- Secondary carboxylic acid amide
- Carboxylic acid derivative
- Oxacycle
- Azacycle
- Organoheterocyclic compound
- Monocarboxylic acid or derivatives
- Organic oxygen compound
- Hydrocarbon derivative
- Organic nitrogen compound
- Organic oxide
- Organopnictogen compound
- Organooxygen compound
- Organonitrogen compound
- Carbonyl group
- Aromatic heteromonocyclic compound
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Molecular Framework | Aromatic heteromonocyclic 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 | - Freebody J: "The Root of All Evil is Inactivity": The Response of French Psychiatrists to New Approaches to Patient Work and Occupation, 1918-1939. 2021. [PubMed:36099392 ]
- Authors unspecified: Childhood Pulmonary Inflammatory Myofibroblastic Tumors Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:35412727 ]
- Authors unspecified: Childhood Adrenocortical Carcinoma Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:31661213 ]
- Authors unspecified: Childhood Breast Tumors Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:31593386 ]
- Tomoda H, Doi T: Discovery and combinatorial synthesis of fungal metabolites beauveriolides, novel antiatherosclerotic agents. Acc Chem Res. 2008 Jan;41(1):32-9. doi: 10.1021/ar700117b. Epub 2007 Sep 6. [PubMed:17803269 ]
- Wang X, Gao YL, Zhang ML, Zhang HD, Huang JZ, Li L: Genome mining and biosynthesis of the Acyl-CoA:cholesterol acyltransferase inhibitor beauveriolide I and III in Cordyceps militaris. J Biotechnol. 2020 Feb 10;309:85-91. doi: 10.1016/j.jbiotec.2020.01.002. Epub 2020 Jan 8. [PubMed:31926180 ]
- Huang HJ, Jian YR, Chen CY: Traditional Chinese medicine application in HIV: an in silico study. J Biomol Struct Dyn. 2014;32(1):1-12. doi: 10.1080/07391102.2012.745168. Epub 2012 Dec 20. [PubMed:23252879 ]
- Nakaya S, Mizuno S, Ishigami H, Yamakawa Y, Kawagishi H, Ushimaru T: New rapid screening method for anti-aging compounds using budding yeast and identification of beauveriolide I as a potent active compound. Biosci Biotechnol Biochem. 2012;76(6):1226-8. doi: 10.1271/bbb.110872. Epub 2012 Jun 7. [PubMed:22790951 ]
- Witter DP, Chen Y, Rogel JK, Boldt GE, Wentworth P Jr: The natural products beauveriolide I and III: a new class of beta-amyloid-lowering compounds. Chembiochem. 2009 May 25;10(8):1344-7. doi: 10.1002/cbic.200900139. [PubMed:19396893 ]
- Namatame I, Matsuda D, Tomoda H, Yamaguchi Y, Masuma R, Kobayashi S, Omura S: Selective production of fungal beauveriolide I or III by fermentation in amino acid-supplemented media. J Antibiot (Tokyo). 2002 Dec;55(12):1048-52. doi: 10.7164/antibiotics.55.1048. [PubMed:12617514 ]
- LOTUS database [Link]
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