Record Information |
---|
Version | 1.0 |
---|
Created at | 2022-09-03 06:27:24 UTC |
---|
Updated at | 2022-09-03 06:27:24 UTC |
---|
NP-MRD ID | NP0170313 |
---|
Secondary Accession Numbers | None |
---|
Natural Product Identification |
---|
Common Name | (r)-{[(2s,3s,4s)-2-amino-1,4-dihydroxy-4-(5-hydroxypyridin-2-yl)-3-methylbutylidene]amino}[(2r,3s,4r,5r)-3,4-dihydroxy-5-(4-hydroxy-2-oxopyrimidin-1-yl)oxolan-2-yl]acetic acid |
---|
Description | Nikkomycin z, also known as neopolyoxin C, belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. (r)-{[(2s,3s,4s)-2-amino-1,4-dihydroxy-4-(5-hydroxypyridin-2-yl)-3-methylbutylidene]amino}[(2r,3s,4r,5r)-3,4-dihydroxy-5-(4-hydroxy-2-oxopyrimidin-1-yl)oxolan-2-yl]acetic acid is found in Streptomyces tendae. It was first documented in 2022 (PMID: 35893139). Based on a literature review a significant number of articles have been published on nikkomycin z (PMID: 35788183) (PMID: 35648145) (PMID: 35601106) (PMID: 35533026). |
---|
Structure | C[C@@H]([C@H](N)C(O)=N[C@H]([C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(O)=NC1=O)C(O)=O)[C@H](O)C1=CC=C(O)C=N1 InChI=1S/C20H25N5O10/c1-7(13(28)9-3-2-8(26)6-22-9)11(21)17(31)24-12(19(32)33)16-14(29)15(30)18(35-16)25-5-4-10(27)23-20(25)34/h2-7,11-16,18,26,28-30H,21H2,1H3,(H,24,31)(H,32,33)(H,23,27,34)/t7-,11-,12+,13-,14-,15+,16+,18+/m0/s1 |
---|
Synonyms | Value | Source |
---|
Neopolyoxin C | MeSH | Nikkomycin | MeSH |
|
---|
Chemical Formula | C20H25N5O10 |
---|
Average Mass | 495.4450 Da |
---|
Monoisotopic Mass | 495.16014 Da |
---|
IUPAC Name | (2R)-2-{[(2S,3S,4S)-2-amino-1,4-dihydroxy-4-(5-hydroxypyridin-2-yl)-3-methylbutylidene]amino}-2-[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-hydroxy-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]acetic acid |
---|
Traditional Name | (R)-{[(2S,3S,4S)-2-amino-1,4-dihydroxy-4-(5-hydroxypyridin-2-yl)-3-methylbutylidene]amino}[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-hydroxy-2-oxopyrimidin-1-yl)oxolan-2-yl]acetic acid |
---|
CAS Registry Number | Not Available |
---|
SMILES | C[C@@H]([C@H](N)C(O)=N[C@H]([C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(O)=NC1=O)C(O)=O)[C@H](O)C1=CC=C(O)C=N1 |
---|
InChI Identifier | InChI=1S/C20H25N5O10/c1-7(13(28)9-3-2-8(26)6-22-9)11(21)17(31)24-12(19(32)33)16-14(29)15(30)18(35-16)25-5-4-10(27)23-20(25)34/h2-7,11-16,18,26,28-30H,21H2,1H3,(H,24,31)(H,32,33)(H,23,27,34)/t7-,11-,12+,13-,14-,15+,16+,18+/m0/s1 |
---|
InChI Key | WWJFFVUVFNBJTN-JKEIIPFCSA-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, 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 |
---|
|
| Not Available | Species |
---|
Species of Origin | |
---|
Chemical Taxonomy |
---|
Description | Belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. |
---|
Kingdom | Organic compounds |
---|
Super Class | Organic acids and derivatives |
---|
Class | Carboxylic acids and derivatives |
---|
Sub Class | Amino acids, peptides, and analogues |
---|
Direct Parent | Dipeptides |
---|
Alternative Parents | |
---|
Substituents | - Alpha-dipeptide
- 5'-deoxyribonucleoside
- N-acyl-alpha-amino acid
- N-acyl-alpha amino acid or derivatives
- Alpha-amino acid amide
- Glycosyl compound
- N-glycosyl compound
- Alpha-amino acid or derivatives
- Hydroxypyridine
- Pyrimidone
- Aralkylamine
- Fatty amide
- Hydropyrimidine
- N-acyl-amine
- Pyridine
- Pyrimidine
- Fatty acyl
- Oxolane
- Vinylogous amide
- Heteroaromatic compound
- 1,3-aminoalcohol
- Secondary carboxylic acid amide
- Secondary alcohol
- Amino acid or derivatives
- Urea
- Carboxamide group
- Lactam
- Amino acid
- Oxacycle
- Azacycle
- Organoheterocyclic compound
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Amine
- Alcohol
- Organic oxide
- Primary aliphatic amine
- Organic nitrogen compound
- Hydrocarbon derivative
- Carbonyl group
- Organonitrogen compound
- Aromatic alcohol
- Organooxygen compound
- Primary amine
- Organic oxygen 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 | - Poester VR, Munhoz LS, Benelli JL, Melo AM, Al-Hatmi AMS, Larwood DJ, Martinez M, Stevens DA, Xavier MO: Initial Results of the International Efforts in Screening New Agents against Candida auris. J Fungi (Basel). 2022 Jul 25;8(8):771. doi: 10.3390/jof8080771. [PubMed:35893139 ]
- Ren Z, Chhetri A, Guan Z, Suo Y, Yokoyama K, Lee SY: Structural basis for inhibition and regulation of a chitin synthase from Candida albicans. Nat Struct Mol Biol. 2022 Jul;29(7):653-664. doi: 10.1038/s41594-022-00791-x. Epub 2022 Jul 4. [PubMed:35788183 ]
- Khatoon R, Sharma S, Prasad R, Lynn AM, Prakash A, Banerjee A: Genome-wide analysis of PTR transporters in Candida species and their functional characterization in Candida auris. Appl Microbiol Biotechnol. 2022 Jun;106(11):4223-4235. doi: 10.1007/s00253-022-11998-9. Epub 2022 Jun 1. [PubMed:35648145 ]
- Brandt P, Gerwien F, Wagner L, Kruger T, Ramirez-Zavala B, Mirhakkak MH, Schauble S, Kniemeyer O, Panagiotou G, Brakhage AA, Morschhauser J, Vylkova S: Candida albicans SR-Like Protein Kinases Regulate Different Cellular Processes: Sky1 Is Involved in Control of Ion Homeostasis, While Sky2 Is Important for Dipeptide Utilization. Front Cell Infect Microbiol. 2022 May 6;12:850531. doi: 10.3389/fcimb.2022.850531. eCollection 2022. [PubMed:35601106 ]
- Khalfe Y, Rosen T: Future Fungal Fighters in Dermatology: Novel Antifungal Drug Pipeline. J Drugs Dermatol. 2022 May 1;21(5):496-501. doi: 10.36849/JDD.6373. [PubMed:35533026 ]
- LOTUS database [Link]
|
---|