Record Information |
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Version | 1.0 |
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Created at | 2023-05-05 12:00:10 UTC |
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Updated at | 2024-05-11 04:52:26 UTC |
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NP-MRD ID | NP0331610 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (−)-versicolamide B |
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Description | (+)-Notoamide B belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position. It was first documented in 2015 (PMID: 25767298). Based on a literature review a significant number of articles have been published on (+)-Notoamide B (PMID: 32672903) (PMID: 30016097) (PMID: 29632911) (PMID: 29622844). |
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Structure | CC1(C)[C@H]2C[C@@]34CCCN3C(=O)[C@]2(C[C@]11C(O)=NC2=C1C=CC1=C2C=CC(C)(C)O1)N=C4O InChI=1S/C26H29N3O4/c1-22(2)10-8-14-16(33-22)7-6-15-18(14)27-20(31)25(15)13-26-17(23(25,3)4)12-24(19(30)28-26)9-5-11-29(24)21(26)32/h6-8,10,17H,5,9,11-13H2,1-4H3,(H,27,31)(H,28,30)/t17-,24-,25+,26-/m1/s1 |
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Synonyms | Not Available |
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Chemical Formula | C26H29N3O4 |
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Average Mass | 447.5350 Da |
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Monoisotopic Mass | 447.21581 Da |
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IUPAC Name | (1'R,3S,3'R,7'R)-2,13'-dihydroxy-4',4',7,7-tetramethyl-7H-9',14'-diazaspiro[chromeno[5,6-b]pyrrole-3,5'-tetracyclo[5.5.2.0^{1,9}.0^{3,7}]tetradecan]-13'-en-8'-one |
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Traditional Name | (1'R,3S,3'R,7'R)-2,13'-dihydroxy-4',4',7,7-tetramethyl-9',14'-diazaspiro[chromeno[5,6-b]pyrrole-3,5'-tetracyclo[5.5.2.0^{1,9}.0^{3,7}]tetradecan]-13'-en-8'-one |
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CAS Registry Number | Not Available |
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SMILES | CC1(C)[C@H]2C[C@@]34CCCN3C(=O)[C@]2(C[C@]11C(O)=NC2=C1C=CC1=C2C=CC(C)(C)O1)N=C4O |
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InChI Identifier | InChI=1S/C26H29N3O4/c1-22(2)10-8-14-16(33-22)7-6-15-18(14)27-20(31)25(15)13-26-17(23(25,3)4)12-24(19(30)28-26)9-5-11-29(24)21(26)32/h6-8,10,17H,5,9,11-13H2,1-4H3,(H,27,31)(H,28,30)/t17-,24-,25+,26-/m1/s1 |
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InChI Key | RNWRZMCJFWSZOX-UVZSNKINSA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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| 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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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 1H NMR Spectrum (1D, 400, C3D6O, simulated) | zhangcuixian@gzucm.edu.cn | guangzhou university of Chinese medicine | zhangcuixian | 2024-05-11 | View Spectrum |
| 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 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position. |
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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 | 2,2-dimethyl-1-benzopyrans |
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Alternative Parents | |
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Substituents | - 2,2-dimethyl-1-benzopyran
- Alpha-amino acid or derivatives
- 3-alkylindole
- Indole or derivatives
- Indolizidine
- Alkyl aryl ether
- Delta-lactam
- Piperidinone
- Tetrahydropyridine
- Piperidine
- Benzenoid
- Cyclic carboximidic acid
- Tertiary carboxylic acid amide
- Pyrrolidine
- Carboxamide group
- Lactam
- Carboxylic acid derivative
- Ether
- Oxacycle
- Azacycle
- Organic 1,3-dipolar compound
- Propargyl-type 1,3-dipolar organic compound
- Hydrocarbon derivative
- Organic oxygen compound
- Organic oxide
- Carbonyl group
- Organonitrogen compound
- Organooxygen compound
- Organopnictogen 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 | - Gao S, Tian WJ, Liao ZJ, Wang GH, Zeng DQ, Liu XZ, Wang XY, Zhou H, Chen HF, Lin T: Chemical Constituents from Endophytic Fungus Annulohypoxylon cf. stygium in Leaves of Anoectochilus roxburghii. Chem Biodivers. 2020 Sep;17(9):e2000424. doi: 10.1002/cbdv.202000424. Epub 2020 Aug 31. [PubMed:32672903 ]
- Li H, Sun W, Deng M, Zhou Q, Wang J, Liu J, Chen C, Qi C, Luo Z, Xue Y, Zhu H, Zhang Y: Asperversiamides, Linearly Fused Prenylated Indole Alkaloids from the Marine-Derived Fungus Aspergillus versicolor. J Org Chem. 2018 Aug 3;83(15):8483-8492. doi: 10.1021/acs.joc.8b01087. Epub 2018 Jul 25. [PubMed:30016097 ]
- Klas KR, Kato H, Frisvad JC, Yu F, Newmister SA, Fraley AE, Sherman DH, Tsukamoto S, Williams RM: Structural and stereochemical diversity in prenylated indole alkaloids containing the bicyclo[2.2.2]diazaoctane ring system from marine and terrestrial fungi. Nat Prod Rep. 2018 Jun 20;35(6):532-558. doi: 10.1039/c7np00042a. [PubMed:29632911 ]
- Sugimoto K, Sadahiro Y, Kagiyama I, Kato H, Sherman DH, Williams RM, Tsukamoto S: Isolation of amoenamide A and five antipodal prenylated alkaloids from Aspergillus amoenus NRRL 35600. Tetrahedron Lett. 2017 Jul 19;58(29):2797-2800. doi: 10.1016/j.tetlet.2017.05.057. Epub 2017 May 18. [PubMed:29622844 ]
- Kato H, Nakahara T, Yamaguchi M, Kagiyama I, Finefield JM, Sunderhaus JD, Sherman DH, Williams RM, Tsukamoto S: Bioconversion of 6-epi-Notoamide T Produces Metabolites of Unprecedented Structures in a Marine-derived Aspergillus sp. Tetrahedron Lett. 2015 Jan 1;56(1):247-251. doi: 10.1016/j.tetlet.2014.11.083. [PubMed:25767298 ]
- Hu JS, He YP, Zhou FG, Wu PP, Chen LY, Ni C, Zhang ZK, Xiao XJ, An LK, He XX, Zhang CX: New Indole Diketopiperazine Alkaloids from Soft Coral-Associated Epiphytic Fungus Aspergillus versicolor CGF 9-1-2. Chem Biodivers. 2023 Jun;20(6):e202300301. doi: 10.1002/cbdv.202300301. Epub 2023 May 17. [PubMed:37097072 ]
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