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Record Information
Version1.0
Created at2020-12-09 03:31:47 UTC
Updated at2021-07-15 16:55:06 UTC
NP-MRD IDNP0006543
Secondary Accession NumbersNone
Natural Product Identification
Common NameRhizoxin D3
Provided ByNPAtlasNPAtlas Logo
Description Rhizoxin D3 is found in Burkholderia. It was first documented in 2006 (PMID: 16939276).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC34H47NO8
Average Mass597.7490 Da
Monoisotopic Mass597.33017 Da
IUPAC Name2-[(3Z,6R,8R,9R,10Z,12Z,14S)-8,14-dihydroxy-16-[(2R,3R,4E,6E,8E)-3-hydroxy-4,8-dimethyl-9-(2-methyl-1,3-oxazol-4-yl)nona-4,6,8-trien-2-yl]-9,13-dimethyl-2-oxo-1-oxacyclohexadeca-3,10,12-trien-6-yl]acetic acid
Traditional Name[(3Z,6R,8R,9R,10Z,12Z,14S)-8,14-dihydroxy-16-[(2R,3R,4E,6E,8E)-3-hydroxy-4,8-dimethyl-9-(2-methyl-1,3-oxazol-4-yl)nona-4,6,8-trien-2-yl]-9,13-dimethyl-2-oxo-1-oxacyclohexadeca-3,10,12-trien-6-yl]acetic acid
CAS Registry NumberNot Available
SMILES
C[C@H]([C@@H](O)C(\C)=C\C=C\C(\C)=C\C1=COC(C)=N1)[C@@H]1C[C@H](O)\C(C)=C/C=C\[C@@H](C)[C@H](O)C[C@H](CC(O)=O)C\C=C/C(=O)O1
InChI Identifier
InChI=1S/C34H47NO8/c1-21(16-28-20-42-26(6)35-28)10-7-13-24(4)34(41)25(5)31-19-30(37)23(3)12-8-11-22(2)29(36)17-27(18-32(38)39)14-9-15-33(40)43-31/h7-13,15-16,20,22,25,27,29-31,34,36-37,41H,14,17-19H2,1-6H3,(H,38,39)/b10-7+,11-8-,15-9-,21-16+,23-12-,24-13+/t22-,25+,27-,29-,30+,31+,34+/m1/s1
InChI KeyRUSPDHDYUAUHKZ-UIZWKYEWSA-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
BurkholderiaNPAtlas
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
logP4.51ALOGPS
logP4.02ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)4.33ChemAxon
pKa (Strongest Basic)0.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area150.32 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity170.71 m³·mol⁻¹ChemAxon
Polarizability67.61 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
External LinksNot Available
References
General References
  1. Scherlach K, Partida-Martinez LP, Dahse HM, Hertweck C: Antimitotic rhizoxin derivatives from a cultured bacterial endosymbiont of the rice pathogenic fungus Rhizopus microsporus. J Am Chem Soc. 2006 Sep 6;128(35):11529-36. doi: 10.1021/ja062953o. [PubMed:16939276 ]