Record Information |
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Version | 2.0 |
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Created at | 2022-09-12 05:31:15 UTC |
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Updated at | 2022-09-12 05:31:15 UTC |
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NP-MRD ID | NP0325054 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (1s,2r,3r,4s)-2,3-bis({[(4-bromo-1h-pyrrol-2-yl)formamido]methyl})-4-(2-imino-1,3-dihydroimidazol-4-yl)cyclobutane-1-carboxylic acid |
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Description | Nakamuric acid, also known as nakamate, belongs to the class of organic compounds known as gamma amino acids and derivatives. These are amino acids having a (-NH2) group attached to the gamma carbon atom. (1s,2r,3r,4s)-2,3-bis({[(4-bromo-1h-pyrrol-2-yl)formamido]methyl})-4-(2-imino-1,3-dihydroimidazol-4-yl)cyclobutane-1-carboxylic acid is found in Agelas nakamurai. It was first documented in 2007 (PMID: 17375928). Based on a literature review a significant number of articles have been published on nakamuric acid (PMID: 32585891) (PMID: 36130844) (PMID: 36130843) (PMID: 36130842) (PMID: 36130841) (PMID: 36130840). |
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Structure | OC(=O)[C@H]1[C@H](CNC(=O)C2=CC(Br)=CN2)[C@@H](CNC(=O)C2=CC(Br)=CN2)[C@@H]1C1=CNC(=N)N1 InChI=1S/C20H21Br2N7O4/c21-8-1-12(24-3-8)17(30)26-5-10-11(6-27-18(31)13-2-9(22)4-25-13)16(19(32)33)15(10)14-7-28-20(23)29-14/h1-4,7,10-11,15-16,24-25H,5-6H2,(H,26,30)(H,27,31)(H,32,33)(H3,23,28,29)/t10-,11-,15-,16+/m1/s1 |
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Synonyms | Value | Source |
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Nakamate | Generator | Nakamic acid | Generator |
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Chemical Formula | C20H21Br2N7O4 |
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Average Mass | 583.2410 Da |
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Monoisotopic Mass | 581.00218 Da |
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IUPAC Name | (1S,2R,3R,4S)-2,3-bis({[(4-bromo-1H-pyrrol-2-yl)formamido]methyl})-4-(2-imino-2,3-dihydro-1H-imidazol-4-yl)cyclobutane-1-carboxylic acid |
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Traditional Name | (1S,2R,3R,4S)-2,3-bis({[(4-bromo-1H-pyrrol-2-yl)formamido]methyl})-4-(2-imino-1,3-dihydroimidazol-4-yl)cyclobutane-1-carboxylic acid |
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CAS Registry Number | Not Available |
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SMILES | OC(=O)[C@H]1[C@H](CNC(=O)C2=CC(Br)=CN2)[C@@H](CNC(=O)C2=CC(Br)=CN2)[C@@H]1C1=CNC(=N)N1 |
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InChI Identifier | InChI=1S/C20H21Br2N7O4/c21-8-1-12(24-3-8)17(30)26-5-10-11(6-27-18(31)13-2-9(22)4-25-13)16(19(32)33)15(10)14-7-28-20(23)29-14/h1-4,7,10-11,15-16,24-25H,5-6H2,(H,26,30)(H,27,31)(H,32,33)(H3,23,28,29)/t10-,11-,15-,16+/m1/s1 |
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InChI Key | SJXLCFWCEINREE-WVATUKLVSA-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 gamma amino acids and derivatives. These are amino acids having a (-NH2) group attached to the gamma carbon atom. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboxylic acids and derivatives |
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Sub Class | Amino acids, peptides, and analogues |
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Direct Parent | Gamma amino acids and derivatives |
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Alternative Parents | |
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Substituents | - Gamma amino acid or derivatives
- 2-heteroaryl carboxamide
- Pyrrole-2-carboxylic acid or derivatives
- Pyrrole-2-carboxamide
- Imidazolyl carboxylic acid derivative
- Aminoimidazole
- Aryl bromide
- Aryl halide
- Substituted pyrrole
- Azole
- Heteroaromatic compound
- Pyrrole
- Imidazole
- Amino acid
- Carboxamide group
- Secondary carboxylic acid amide
- Azacycle
- Carboxylic acid
- Organoheterocyclic compound
- Monocarboxylic acid or derivatives
- Organooxygen compound
- Primary amine
- Organic nitrogen compound
- Amine
- Carbonyl group
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen compound
- Organohalogen compound
- Organobromide
- Organonitrogen compound
- 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 | - Pech-Puch D, Perez-Povedano M, Martinez-Guitian M, Lasarte-Monterrubio C, Vazquez-Ucha JC, Bou G, Rodriguez J, Beceiro A, Jimenez C: In Vitro and In Vivo Assessment of the Efficacy of Bromoageliferin, an Alkaloid Isolated from the Sponge Agelas dilatata, against Pseudomonas aeruginosa. Mar Drugs. 2020 Jun 23;18(6). pii: md18060326. doi: 10.3390/md18060326. [PubMed:32585891 ]
- O'Malley DP, Li K, Maue M, Zografos AL, Baran PS: Total synthesis of dimeric pyrrole-imidazole alkaloids: sceptrin, ageliferin, nagelamide e, oxysceptrin, nakamuric acid, and the axinellamine carbon skeleton. J Am Chem Soc. 2007 Apr 18;129(15):4762-75. doi: 10.1021/ja069035a. Epub 2007 Mar 22. [PubMed:17375928 ]
- Cani I, Righini M, Cenni P, Foschi M: Teaching NeuroImage: Partially Reversible Widespread Leukoencephalopathy Associated With Atypical Hemolytic Uremic Syndrome. Neurology. 2022 Sep 21. pii: WNL.0000000000201378. doi: 10.1212/WNL.0000000000201378. [PubMed:36130844 ]
- Sasaki R, Morimoto S, Ozawa F, Okano H, Yoshida M, Ishiura H, Tsuji S, Kuzuhara S, Kokubo Y: APOE Alleles With Tau and Abeta Pathology In Patients With Amyotrophic Lateral Sclerosis and Parkinsonism-Dementia Complex in the Kii Peninsula. Neurology. 2022 Sep 21. pii: WNL.0000000000201156. doi: 10.1212/WNL.0000000000201156. [PubMed:36130843 ]
- Zhang Z, Wang M, Gill D, Liu X: Genetically Predicted Smoking and Alcohol Consumption and Functional Outcome After Ischemic Stroke. Neurology. 2022 Sep 21. pii: WNL.0000000000201291. doi: 10.1212/WNL.0000000000201291. [PubMed:36130842 ]
- Khamis S, Mitakidou MR, Champion M, Goyal S, Jones RL, Siddiqui A, Sabanathan S, Hedderly T, Lin JP, Jungbluth H, Papandreou A: Clinical Reasoning: A Teenage Girl With Progressive Hyperkinetic Movements, Seizures, and Encephalopathy. Neurology. 2022 Sep 21. pii: WNL.0000000000201385. doi: 10.1212/WNL.0000000000201385. [PubMed:36130841 ]
- Rosenberg A, Ohlund-Wistbacka U, Hall A, Bonnard A, Hagman G, Ryden M, Thunborg C, Wiggenraad F, Sandebring-Matton A, Solomon A, Kivipelto M: beta-Amyloid, Tau, Neurodegeneration Classification and Eligibility for Anti-amyloid Treatment in a Memory Clinic Population. Neurology. 2022 Sep 21. pii: WNL.0000000000201043. doi: 10.1212/WNL.0000000000201043. [PubMed:36130840 ]
- Yu H, Cai G, Wu J, Li Q: Clinical Phenotypic Variability and Significance of Pneumolabyrinth After Tympanum-Penetrating Injury. Ear Nose Throat J. 2022 Sep 21:1455613221128132. doi: 10.1177/01455613221128132. [PubMed:36130836 ]
- Bedford J, Martin P, Crowe S, Wagstaff D, Santos C, Singleton G, Baumber R, Vindrola-Padros C, Vohra R, Swart M, Oliver CM, Dorey J, Leeman I, Moonesinghe SR: Development and internal validation of a model for postoperative morbidity in adults undergoing major elective colorectal surgery: the peri-operative quality improvement programme (PQIP) colorectal risk model. Anaesthesia. 2022 Sep 21. doi: 10.1111/anae.15858. [PubMed:36130834 ]
- Silverman A, Beres S: Child Neurology: Horner Syndrome in an Otherwise Well-Appearing Infant. Neurology. 2022 Sep 21. pii: WNL.0000000000201377. doi: 10.1212/WNL.0000000000201377. [PubMed:36130839 ]
- Harada Y, Wang SH, Juel VC: Clinical Reasoning: A 36-Year-Old Man With Asymmetric Muscle Weakness. Neurology. 2022 Sep 21. pii: WNL.0000000000201379. doi: 10.1212/WNL.0000000000201379. [PubMed:36130838 ]
- Guest O, Memon AA, Chukweubuka A, Zaheer M, Siddiqi N: Robotic low anterior resection for locally advanced rectal cancer - A video vignette. Colorectal Dis. 2022 Sep 21. doi: 10.1111/codi.16345. [PubMed:36130837 ]
- Pellicori P, Kalra PR, Clark AL, Friday JM, Cleland JGF: Chronic kidney disease (CKD) and CKD-ism in heart failure - what a mess! Eur J Heart Fail. 2022 Sep 21. doi: 10.1002/ejhf.2696. [PubMed:36130835 ]
- Wang X, Gao Y, Ma Z, Rodriguez RA, Yu ZX, Chen C: Syntheses of Sceptrins and Nakamuric Acid and Insights into the Biosyntheses of Pyrrole-Imidazole Dimers. Org Chem Front. 2015 Aug 1;2(8):978-984. doi: 10.1039/C5QO00165J. [PubMed:26328059 ]
- Wang X, Chen C: An approach for the synthesis of nakamuric acid. Tetrahedron. 2015 Jun 3;71(22):3690-3693. doi: 10.1016/j.tet.2014.10.027. [PubMed:25983349 ]
- LOTUS database [Link]
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