Record Information |
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Version | 1.0 |
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Created at | 2022-09-02 11:03:38 UTC |
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Updated at | 2022-09-02 11:03:38 UTC |
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NP-MRD ID | NP0154273 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (2r,3r,9r)-5-acetyl-4-hydroxy-8,8-dimethyl-7,16-diazapentacyclo[9.6.1.0²,⁹.0³,⁷.0¹⁵,¹⁸]octadeca-1(17),4,11(18),12,14-pentaen-6-one |
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Description | Iso-alpha-cyclopiazonic acid, also known as iso-a-cyclopiazonate, belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position. It was first documented in 2014 (PMID: 24983640). Based on a literature review a significant number of articles have been published on Iso-alpha-cyclopiazonic acid (PMID: 26460559) (PMID: 36055769) (PMID: 36055768) (PMID: 36055767) (PMID: 36055766) (PMID: 36055765). |
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Structure | CC(=O)C1=C(O)[C@H]2[C@@H]3[C@@H](CC4=C5C(NC=C35)=CC=C4)C(C)(C)N2C1=O InChI=1S/C20H20N2O3/c1-9(23)14-18(24)17-16-11-8-21-13-6-4-5-10(15(11)13)7-12(16)20(2,3)22(17)19(14)25/h4-6,8,12,16-17,21,24H,7H2,1-3H3/t12-,16+,17-/m1/s1 |
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Synonyms | Value | Source |
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Iso-a-cyclopiazonate | Generator | Iso-a-cyclopiazonic acid | Generator | Iso-alpha-cyclopiazonate | Generator | Iso-α-cyclopiazonate | Generator | Iso-α-cyclopiazonic acid | Generator |
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Chemical Formula | C20H20N2O3 |
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Average Mass | 336.3910 Da |
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Monoisotopic Mass | 336.14739 Da |
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IUPAC Name | (2R,3R,9R)-5-acetyl-4-hydroxy-8,8-dimethyl-7,16-diazapentacyclo[9.6.1.0^{2,9}.0^{3,7}.0^{15,18}]octadeca-1(17),4,11(18),12,14-pentaen-6-one |
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Traditional Name | (2R,3R,9R)-5-acetyl-4-hydroxy-8,8-dimethyl-7,16-diazapentacyclo[9.6.1.0^{2,9}.0^{3,7}.0^{15,18}]octadeca-1(17),4,11(18),12,14-pentaen-6-one |
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CAS Registry Number | Not Available |
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SMILES | CC(=O)C1=C(O)[C@H]2[C@@H]3[C@@H](CC4=C5C(NC=C35)=CC=C4)C(C)(C)N2C1=O |
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InChI Identifier | InChI=1S/C20H20N2O3/c1-9(23)14-18(24)17-16-11-8-21-13-6-4-5-10(15(11)13)7-12(16)20(2,3)22(17)19(14)25/h4-6,8,12,16-17,21,24H,7H2,1-3H3/t12-,16+,17-/m1/s1 |
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InChI Key | SZINUGQCTHLQAZ-OAUYIBNBSA-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 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Indoles and derivatives |
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Sub Class | Indoles |
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Direct Parent | 3-alkylindoles |
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Alternative Parents | |
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Substituents | - 3-alkylindole
- Isoindole or derivatives
- Isoindoline
- Pyrrolizine
- Benzenoid
- Heteroaromatic compound
- Vinylogous acid
- Tertiary carboxylic acid amide
- Pyrroline
- Pyrrolidine
- Pyrrole
- Lactam
- Ketone
- Carboxamide group
- Azacycle
- Enol
- Carboxylic acid derivative
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Organonitrogen 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 | - Sun K, Li Y, Guo L, Wang Y, Liu P, Zhu W: Indole diterpenoids and isocoumarin from the fungus, Aspergillus flavus, isolated from the prawn, Penaeus vannamei. Mar Drugs. 2014 Jun 30;12(7):3970-81. doi: 10.3390/md12073970. [PubMed:24983640 ]
- Zhu H, Chen C, Wang J, Li XN, Wei G, Guo Y, Yao G, Luo Z, Zhang J, Xue Y, Zhang Y: Penicamedine A, a Highly Oxygenated Hexacyclic Indole Alkaloid from Penicillium camemberti. Chem Biodivers. 2015 Oct;12(10):1547-53. doi: 10.1002/cbdv.201400412. [PubMed:26460559 ]
- Pays E, Radwanska M, Magez S: The Pathogenesis of African Trypanosomiasis. Annu Rev Pathol. 2022 Sep 2. doi: 10.1146/annurev-pathmechdis-031621-025153. [PubMed:36055769 ]
- Khan K, Van Aken O: The colonisation of land was a likely driving force for the evolution of mitochondrial retrograde signalling in plants. J Exp Bot. 2022 Sep 3. pii: 6687801. doi: 10.1093/jxb/erac351. [PubMed:36055768 ]
- Authors unspecified: Erratum. Br J Dermatol. 2022 Sep;187(3):451. doi: 10.1111/bjd.21748. [PubMed:36055767 ]
- Authors unspecified: BAD and BPG guidelines for narrowband ultraviolet B phototherapy 2022. Br J Dermatol. 2022 Sep;187(3):vi. doi: 10.1111/bjd.21734. [PubMed:36055766 ]
- Sprecher E: What do rare and common have in common? Br J Dermatol. 2022 Sep;187(3):279-280. doi: 10.1111/bjd.21632. [PubMed:36055765 ]
- Dias BGC, Santos FAP, Meschiatti M, Brixner BM, Almeida AA, Queiroz O, Cappellozza BI: Effects of feeding different probiotic types on metabolic, performance, and carcass responses of Bos indicus feedlot cattle offered a high-concentrate diet. J Anim Sci. 2022 Oct 1;100(10). pii: 6687795. doi: 10.1093/jas/skac289. [PubMed:36055763 ]
- Authors unspecified: Revolutionizing Atopic Dermatitis, 9-11 April 2022. Br J Dermatol. 2022 Sep;187(3):e80-e155. doi: 10.1111/bjd.21666. [PubMed:36055764 ]
- Wang B, Lv R, Zhang Z, Yang C, Xun H, Liu B, Gong L: Homoeologous exchange enables rapid evolution of tolerance to salinity and hyper-osmotic stresses in a synthetic allotetraploid wheat. J Exp Bot. 2022 Dec 8;73(22):7488-7502. doi: 10.1093/jxb/erac355. [PubMed:36055762 ]
- LOTUS database [Link]
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