Record Information |
---|
Version | 1.0 |
---|
Created at | 2021-01-06 07:26:02 UTC |
---|
Updated at | 2021-07-15 17:38:27 UTC |
---|
NP-MRD ID | NP0022216 |
---|
Secondary Accession Numbers | None |
---|
Natural Product Identification |
---|
Common Name | Phevalin |
---|
Provided By | NPAtlas |
---|
Description | Phevalin is also known as aureusimine b. Phevalin 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. Phevalin is found in Streptomyces griseus and Streptomyces sp.. It was first documented in 1995 (PMID: 7490226). Based on a literature review a significant number of articles have been published on phevalin (PMID: 22808288) (PMID: 23070851) (PMID: 15896956) (PMID: 23302043). |
---|
Structure | [H]N1C(=O)C(=NC([H])=C1C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H])C([H])(C([H])([H])[H])C([H])([H])[H] InChI=1S/C14H16N2O/c1-10(2)13-14(17)16-12(9-15-13)8-11-6-4-3-5-7-11/h3-7,9-10H,8H2,1-2H3,(H,16,17) |
---|
Synonyms | Value | Source |
---|
3-(1-Methylethyl)-6-(phenylmethyl)-2(1H)-pyrazinone | ChEBI | 6-Benzyl-3-(propan-2-yl)-1,2-dihydropyrazin-2-one | ChEBI | 6-Benzyl-3-isopropyl-1H-pyrazin-2-one | ChEBI | 6-Benzyl-3-propan-2-yl-1H-pyrazin-2-one | ChEBI | Aureusimine b | ChEBI | Phevalin | MeSH | 6-Benzyl-3-isopropyl-2(1H)-pyrazinone | MeSH |
|
---|
Chemical Formula | C14H16N2O |
---|
Average Mass | 228.2950 Da |
---|
Monoisotopic Mass | 228.12626 Da |
---|
IUPAC Name | 6-benzyl-3-(propan-2-yl)-1,2-dihydropyrazin-2-one |
---|
Traditional Name | 6-benzyl-3-isopropyl-1H-pyrazin-2-one |
---|
CAS Registry Number | Not Available |
---|
SMILES | CC(C)C1=NC=C(CC2=CC=CC=C2)NC1=O |
---|
InChI Identifier | InChI=1S/C14H16N2O/c1-10(2)13-14(17)16-12(9-15-13)8-11-6-4-3-5-7-11/h3-7,9-10H,8H2,1-2H3,(H,16,17) |
---|
InChI Key | CZUORGWXUVRUMV-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 | This compound belongs to the class of organic compounds known as pyrazines. These are compounds containing a pyrazine ring, which is a six-member aromatic heterocycle, that consists of two nitrogen atoms (at positions 1 and 4) and four carbon atoms. |
---|
Kingdom | Organic compounds |
---|
Super Class | Organoheterocyclic compounds |
---|
Class | Diazines |
---|
Sub Class | Pyrazines |
---|
Direct Parent | Pyrazines |
---|
Alternative Parents | |
---|
Substituents | - Benzenoid
- Pyrazine
- Monocyclic benzene moiety
- Heteroaromatic compound
- Lactam
- Azacycle
- Organic nitrogen compound
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Organonitrogen compound
- Aromatic heteromonocyclic compound
|
---|
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 | - Alvarez ME, White CB, Gregory J, Kydd GC, Harris A, Sun HH, Gillum AM, Cooper R: Phevalin, a new calpain inhibitor, from a Streptomyces sp. J Antibiot (Tokyo). 1995 Oct;48(10):1165-7. doi: 10.7164/antibiotics.48.1165. [PubMed:7490226 ]
- Secor PR, Jennings LK, James GA, Kirker KR, Pulcini ED, McInnerney K, Gerlach R, Livinghouse T, Hilmer JK, Bothner B, Fleckman P, Olerud JE, Stewart PS: Phevalin (aureusimine B) production by Staphylococcus aureus biofilm and impacts on human keratinocyte gene expression. PLoS One. 2012;7(7):e40973. doi: 10.1371/journal.pone.0040973. Epub 2012 Jul 13. [PubMed:22808288 ]
- Wyatt MA, Mok MC, Junop M, Magarvey NA: Heterologous expression and structural characterisation of a pyrazinone natural product assembly line. Chembiochem. 2012 Nov 5;13(16):2408-15. doi: 10.1002/cbic.201200340. Epub 2012 Oct 15. [PubMed:23070851 ]
- Zeng Y, Li Q, Hanzlik RP, Aube J: Synthesis of a small library of diketopiperazines as potential inhibitors of calpain. Bioorg Med Chem Lett. 2005 Jun 15;15(12):3034-8. doi: 10.1016/j.bmcl.2005.04.031. [PubMed:15896956 ]
- Wilson DJ, Shi C, Teitelbaum AM, Gulick AM, Aldrich CC: Characterization of AusA: a dimodular nonribosomal peptide synthetase responsible for the production of aureusimine pyrazinones. Biochemistry. 2013 Feb 5;52(5):926-37. doi: 10.1021/bi301330q. Epub 2013 Jan 23. [PubMed:23302043 ]
|
---|