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Record Information
Version1.0
Created at2021-01-06 06:30:40 UTC
Updated at2021-07-15 17:35:48 UTC
NP-MRD IDNP0021235
Secondary Accession NumbersNone
Natural Product Identification
Common NameAntifungal macrolide
Provided ByNPAtlasNPAtlas Logo
Description Antifungal macrolide is found in Streptomyces sp. It was first documented in 1986 (PMID: 3777909). Based on a literature review a significant number of articles have been published on Antifungal macrolide (PMID: 25871291) (PMID: 30206268) (PMID: 25558397) (PMID: 23007575).
Structure
Data?1624572077
SynonymsNot Available
Chemical FormulaC22H36O6
Average Mass396.5240 Da
Monoisotopic Mass396.25119 Da
IUPAC Name(1R,2R,5R,7R,10S,11R,14S,16S)-5,14-diethyl-2,11-dimethyl-4,13,19,20-tetraoxatricyclo[14.2.1.1^{7,10}]icosane-3,12-dione
Traditional Name(1R,2R,5R,7R,10S,11R,14S,16S)-5,14-diethyl-2,11-dimethyl-4,13,19,20-tetraoxatricyclo[14.2.1.1^{7,10}]icosane-3,12-dione
CAS Registry NumberNot Available
SMILES
CC[C@H]1C[C@@H]2CC[C@@H](O2)[C@@H](C)C(=O)O[C@H](CC)C[C@H]2CC[C@H](O2)C(C)C(=O)O1
InChI Identifier
InChI=1S/C22H36O6/c1-5-15-11-17-7-9-20(25-17)14(4)22(24)28-16(6-2)12-18-8-10-19(26-18)13(3)21(23)27-15/h13-20H,5-12H2,1-4H3/t13-,14?,15-,16+,17-,18+,19-,20+/m1/s1
InChI KeyVYGSEJPMQXVTNW-UPOFUFPUSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Streptomyces sp.NPAtlas
Chemical Taxonomy
ClassificationNot classified
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.55ALOGPS
logP3.76ChemAxon
logS-4.6ALOGPS
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area71.06 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity103.72 m³·mol⁻¹ChemAxon
Polarizability43.59 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
NPAtlas IDNPA002911
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID78436578
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound139583904
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Shishido TK, Humisto A, Jokela J, Liu L, Wahlsten M, Tamrakar A, Fewer DP, Permi P, Andreote AP, Fiore MF, Sivonen K: Antifungal compounds from cyanobacteria. Mar Drugs. 2015 Apr 13;13(4):2124-40. doi: 10.3390/md13042124. [PubMed:25871291 ]
  2. Jois HR, Sarkar A, Gurusiddaiah S: Antifungal macrodiolide from Streptomyces sp. Antimicrob Agents Chemother. 1986 Sep;30(3):458-64. doi: 10.1128/aac.30.3.458. [PubMed:3777909 ]
  3. Kim HJ, Han CY, Park JS, Oh SH, Kang SH, Choi SS, Kim JM, Kwak JH, Kim ES: Nystatin-like Pseudonocardia polyene B1, a novel disaccharide-containing antifungal heptaene antibiotic. Sci Rep. 2018 Sep 11;8(1):13584. doi: 10.1038/s41598-018-31801-y. [PubMed:30206268 ]
  4. Efimova SS, Schagina LV, Ostroumova OS: Investigation of channel-forming activity of polyene macrolide antibiotics in planar lipid bilayers in the presence of dipole modifiers. Acta Naturae. 2014 Oct;6(4):67-79. [PubMed:25558397 ]
  5. Dodurga Y, Avci CB, Susluer SY, Satiroglu Tufan NL, Gunduz C: The expression of URGCP gene in prostate cancer cell lines: correlation with rapamycin. Mol Biol Rep. 2012 Dec;39(12):10173-7. doi: 10.1007/s11033-012-1891-6. Epub 2012 Sep 25. [PubMed:23007575 ]