Record Information |
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Version | 1.0 |
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Created at | 2022-09-07 00:36:22 UTC |
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Updated at | 2022-09-07 00:36:22 UTC |
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NP-MRD ID | NP0240716 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (1s,2r,3r,6s,7r,8s,11r,14s,15r,17r)-10-hydroxy-17-(hydroxymethyl)-1,5,6-trimethyl-8-(2-methylpropyl)-19-oxa-9-azapentacyclo[13.3.1.0²,¹⁴.0³,¹¹.0⁷,¹¹]nonadeca-4,9-dien-12-one |
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Description | 16-Hydroxymethylaspergillin PZ belongs to the class of organic compounds known as aspochalasins. These are cytochalasans with a structure in which the hydrogenated isoindole bears a 2-methylpropyl group. (1s,2r,3r,6s,7r,8s,11r,14s,15r,17r)-10-hydroxy-17-(hydroxymethyl)-1,5,6-trimethyl-8-(2-methylpropyl)-19-oxa-9-azapentacyclo[13.3.1.0²,¹⁴.0³,¹¹.0⁷,¹¹]nonadeca-4,9-dien-12-one is found in Westerdykella dispersa. It was first documented in 2022 (PMID: 36087890). Based on a literature review a significant number of articles have been published on 16-hydroxymethylaspergillin PZ (PMID: 36086484) (PMID: 36085917) (PMID: 36084381) (PMID: 36069270) (PMID: 36067517) (PMID: 36066812). |
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Structure | CC(C)C[C@@H]1N=C(O)[C@]23[C@H]1[C@H](C)C(C)=C[C@@H]2[C@@H]1[C@H](CC3=O)[C@H]2C[C@@H](CO)C[C@]1(C)O2 InChI=1S/C25H37NO4/c1-12(2)6-18-21-14(4)13(3)7-17-22-16(9-20(28)25(17,21)23(29)26-18)19-8-15(11-27)10-24(22,5)30-19/h7,12,14-19,21-22,27H,6,8-11H2,1-5H3,(H,26,29)/t14-,15-,16-,17-,18+,19-,21+,22+,24+,25-/m1/s1 |
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Synonyms | Not Available |
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Chemical Formula | C25H37NO4 |
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Average Mass | 415.5740 Da |
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Monoisotopic Mass | 415.27226 Da |
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IUPAC Name | (1S,2R,3R,6S,7R,8S,11R,14S,15R,17R)-10-hydroxy-17-(hydroxymethyl)-1,5,6-trimethyl-8-(2-methylpropyl)-19-oxa-9-azapentacyclo[13.3.1.0^{2,14}.0^{3,11}.0^{7,11}]nonadeca-4,9-dien-12-one |
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Traditional Name | (1S,2R,3R,6S,7R,8S,11R,14S,15R,17R)-10-hydroxy-17-(hydroxymethyl)-1,5,6-trimethyl-8-(2-methylpropyl)-19-oxa-9-azapentacyclo[13.3.1.0^{2,14}.0^{3,11}.0^{7,11}]nonadeca-4,9-dien-12-one |
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CAS Registry Number | Not Available |
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SMILES | CC(C)C[C@@H]1N=C(O)[C@]23[C@H]1[C@H](C)C(C)=C[C@@H]2[C@@H]1[C@H](CC3=O)[C@H]2C[C@@H](CO)C[C@]1(C)O2 |
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InChI Identifier | InChI=1S/C25H37NO4/c1-12(2)6-18-21-14(4)13(3)7-17-22-16(9-20(28)25(17,21)23(29)26-18)19-8-15(11-27)10-24(22,5)30-19/h7,12,14-19,21-22,27H,6,8-11H2,1-5H3,(H,26,29)/t14-,15-,16-,17-,18+,19-,21+,22+,24+,25-/m1/s1 |
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InChI Key | FNAWUKKMCPWLMR-UHRWYVDDSA-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 aspochalasins. These are cytochalasans with a structure in which the hydrogenated isoindole bears a 2-methylpropyl group. |
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Kingdom | Organic compounds |
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Super Class | Alkaloids and derivatives |
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Class | Cytochalasans |
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Sub Class | Aspochalasins |
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Direct Parent | Aspochalasins |
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Alternative Parents | |
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Substituents | - Aspochalasin skeleton
- Isoindolone
- Azaspirodecane
- Isoindole or derivatives
- Isoindoline
- 2-pyrrolidone
- Pyrrolidone
- Oxane
- Tetrahydrofuran
- Pyrrolidine
- Secondary carboxylic acid amide
- Lactam
- Ketone
- Carboxamide group
- Oxacycle
- Azacycle
- Organoheterocyclic compound
- Ether
- Dialkyl ether
- Carboxylic acid derivative
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Organic oxide
- Hydrocarbon derivative
- Primary alcohol
- Organooxygen compound
- Organonitrogen compound
- Carbonyl group
- Alcohol
- Aliphatic heteropolycyclic compound
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Molecular Framework | Aliphatic 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 | - Thakre N, Simao Gurge RM, Isoe J, Kivi H, Strickland J, Delacruz LR, Rodriguez AM, Haney R, Sadeghi R, Joy T, Chen M, Luckhart S, Riehle MA: Manipulation of pantothenate kinase in Anopheles stephensi suppresses pantothenate levels with minimal impacts on mosquito fitness. Insect Biochem Mol Biol. 2022 Oct;149:103834. doi: 10.1016/j.ibmb.2022.103834. Epub 2022 Sep 7. [PubMed:36087890 ]
- Toth J, Patel R, Arvaneh M: Electrophysiological Correlates of Response Time in a Vigilant Attention Task. Annu Int Conf IEEE Eng Med Biol Soc. 2022 Jul;2022:2340-2343. doi: 10.1109/EMBC48229.2022.9871442. [PubMed:36086484 ]
- Kumar H, Ganapathy N, Puthankattil SD, Swaminathan R: Assessment of emotional states in EEG signals using multi-frequency power spectrum and functional connectivity patterns. Annu Int Conf IEEE Eng Med Biol Soc. 2022 Jul;2022:280-283. doi: 10.1109/EMBC48229.2022.9871510. [PubMed:36085917 ]
- He Z, Du L, Wang P, Xia P, Liu Z, Song Y, Chen X, Fang Z: Single-channel EEG sleep staging based on data augmentation and cross-subject discrepancy alleviation. Comput Biol Med. 2022 Oct;149:106044. doi: 10.1016/j.compbiomed.2022.106044. Epub 2022 Aug 27. [PubMed:36084381 ]
- Herrera S, Rivero KI, Guzman A, Cedeno J, Miksovska J, Raptis RG: Mononuclear, hexanuclear and polymeric indium(III) pyrazolido complexes; structural characterization, dynamic solution studies and luminescent properties. Dalton Trans. 2022 Sep 26;51(37):14277-14286. doi: 10.1039/d2dt01901a. [PubMed:36069270 ]
- Bibik YS, Shova S, Rotaru A, Shylin SI, Fritsky IO, Lampeka RD, Gural'skiy IA: Cooperative Spin Crossover above Room Temperature in the Iron(II) Cyanoborohydride-Pyrazine Complex. Inorg Chem. 2022 Sep 19;61(37):14761-14769. doi: 10.1021/acs.inorgchem.2c02177. Epub 2022 Sep 6. [PubMed:36067517 ]
- Bakery HH, Allam GA, Abuelsaad ASA, Abdel-Latif M, Elkenawy AE, Khalil RG: Anti-inflammatory, antioxidant, anti-fibrotic and schistosomicidal properties of plumbagin in murine schistosomiasis. Parasite Immunol. 2022 Nov;44(11):e12945. doi: 10.1111/pim.12945. Epub 2022 Sep 6. [PubMed:36066812 ]
- Nakrak S, Tontiwachwuthikul P, Gao H, Liang Z, Sema T: Comprehensive mass transfer analysis of CO(2) absorption in high potential ternary AMP-PZ-MEA solvent using three-level factorial design. Environ Sci Pollut Res Int. 2023 Jan;30(4):10001-10023. doi: 10.1007/s11356-022-22819-x. Epub 2022 Sep 6. [PubMed:36066795 ]
- Wang L, Sun H, Yang M, Xu Y, Hou L, Yu H, Wang X, Zhang Z, Han J: Bidirectional regulatory effects of Cordyceps on arrhythmia: Clinical evaluations and network pharmacology. Front Pharmacol. 2022 Aug 19;13:948173. doi: 10.3389/fphar.2022.948173. eCollection 2022. [PubMed:36059969 ]
- Puthanakit T, Nantanee R, Jaru-Ampornpan P, Chantasrisawad N, Sophonphan J, Meepuksom T, Jupimai T, Sodsai P, Anugulruengkitt S, Hirankarn N: Heterologous Prime-boost of SARS-CoV-2 inactivated vaccine and mRNA BNT162b2 among Healthy Thai Adolescents. Vaccine X. 2022 Dec;12:100211. doi: 10.1016/j.jvacx.2022.100211. Epub 2022 Aug 29. [PubMed:36059600 ]
- LOTUS database [Link]
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