Record Information |
---|
Version | 1.0 |
---|
Created at | 2020-12-09 06:35:06 UTC |
---|
Updated at | 2021-07-15 17:02:26 UTC |
---|
NP-MRD ID | NP0009144 |
---|
Secondary Accession Numbers | None |
---|
Natural Product Identification |
---|
Common Name | Marinopyrrole A |
---|
Provided By | NPAtlas |
---|
Description | (-)-Marinopyrrole A, also known as maritoclax, belongs to the class of organic compounds known as aryl-phenylketones. These are aromatic compounds containing a ketone substituted by one aryl group, and a phenyl group (-)-Marinopyrrole A 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. Marinopyrrole A is found in Streptomyces sp. CNQ-418. It was first documented in 2008 (PMID: 18205372). Based on a literature review a significant number of articles have been published on (-)-Marinopyrrole A (PMID: 20405892) (PMID: 19673475) (PMID: 21499535) (PMID: 21502631). |
---|
Structure | [H]OC1=C([H])C([H])=C([H])C([H])=C1C(=O)C1=C([H])C(Cl)=C(Cl)N1C1=C(N([H])C(Cl)=C1Cl)C(=O)C1=C([H])C([H])=C([H])C([H])=C1O[H] InChI=1S/C22H12Cl4N2O4/c23-12-9-13(19(31)10-5-1-3-7-14(10)29)28(22(12)26)18-16(24)21(25)27-17(18)20(32)11-6-2-4-8-15(11)30/h1-9,27,29-30H |
---|
Synonyms | Value | Source |
---|
Maritoclax | HMDB |
|
---|
Chemical Formula | C22H12Cl4N2O4 |
---|
Average Mass | 510.1500 Da |
---|
Monoisotopic Mass | 507.95512 Da |
---|
IUPAC Name | 2-[2,3,4',5'-tetrachloro-5-(2-hydroxybenzoyl)-1'H-[1,3'-bipyrrole]-2'-carbonyl]phenol |
---|
Traditional Name | 2-[2,3,4',5'-tetrachloro-5-(2-hydroxybenzoyl)-1'H-[1,3'-bipyrrole]-2'-carbonyl]phenol |
---|
CAS Registry Number | Not Available |
---|
SMILES | OC1=CC=CC=C1C(=O)C1=CC(Cl)=C(Cl)N1C1=C(NC(Cl)=C1Cl)C(=O)C1=CC=CC=C1O |
---|
InChI Identifier | InChI=1S/C22H12Cl4N2O4/c23-12-9-13(19(31)10-5-1-3-7-14(10)29)28(22(12)26)18-16(24)21(25)27-17(18)20(32)11-6-2-4-8-15(11)30/h1-9,27,29-30H |
---|
InChI Key | QYPJBTMRYKRTFG-UHFFFAOYSA-N |
---|
Experimental Spectra |
---|
|
| Not Available | Predicted Spectra |
---|
|
| Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
---|
1D NMR | 13C NMR Spectrum (1D, 25 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Chemical Shift Submissions |
---|
|
| Not Available | Species |
---|
Species of Origin | |
---|
Species Where Detected | |
---|
Chemical Taxonomy |
---|
Description | Belongs to the class of organic compounds known as aryl-phenylketones. These are aromatic compounds containing a ketone substituted by one aryl group, and a phenyl group. |
---|
Kingdom | Organic compounds |
---|
Super Class | Organic oxygen compounds |
---|
Class | Organooxygen compounds |
---|
Sub Class | Carbonyl compounds |
---|
Direct Parent | Aryl-phenylketones |
---|
Alternative Parents | Not Available |
---|
Substituents | Not Available |
---|
Molecular Framework | Aromatic heteromonocyclic compounds |
---|
External Descriptors | Not Available |
---|
Physical Properties |
---|
State | Not Available |
---|
Experimental Properties | Property | Value | Reference |
---|
Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
|
---|
Predicted Properties | |
---|
General References | - Hughes CC, Kauffman CA, Jensen PR, Fenical W: Structures, reactivities, and antibiotic properties of the marinopyrroles A-F. J Org Chem. 2010 May 21;75(10):3240-50. doi: 10.1021/jo1002054. [PubMed:20405892 ]
- Hughes CC, Prieto-Davo A, Jensen PR, Fenical W: The marinopyrroles, antibiotics of an unprecedented structure class from a marine Streptomyces sp. Org Lett. 2008 Feb 21;10(4):629-31. doi: 10.1021/ol702952n. Epub 2008 Jan 19. [PubMed:18205372 ]
- Hughes CC, Yang YL, Liu WT, Dorrestein PC, La Clair JJ, Fenical W: Marinopyrrole A target elucidation by acyl dye transfer. J Am Chem Soc. 2009 Sep 2;131(34):12094-6. doi: 10.1021/ja903149u. [PubMed:19673475 ]
- Nicolaou KC, Simmons NL, Chen JS, Haste NM, Nizet V: Total synthesis and biological evaluation of marinopyrrole A and analogues. Tetrahedron Lett. 2011 Apr 27;52(17):2041-2043. doi: 10.1016/j.tetlet.2010.09.059. [PubMed:21499535 ]
- Haste NM, Hughes CC, Tran DN, Fenical W, Jensen PR, Nizet V, Hensler ME: Pharmacological properties of the marine natural product marinopyrrole A against methicillin-resistant Staphylococcus aureus. Antimicrob Agents Chemother. 2011 Jul;55(7):3305-12. doi: 10.1128/AAC.01211-10. Epub 2011 Apr 18. [PubMed:21502631 ]
|
---|