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Record Information
Version1.0
Created at2020-12-09 00:42:06 UTC
Updated at2021-07-15 16:46:26 UTC
NP-MRD IDNP0003452
Secondary Accession NumbersNone
Natural Product Identification
Common NameSB 253518
Provided ByNPAtlasNPAtlas Logo
Description SB 253518 is found in Pseudomonas fluorescens and Pseudomonas fluorescens DSM 11579. It was first documented in 2000 (PMID: 10994818). Based on a literature review very few articles have been published on (3R)-N-{2-[(1E,7aR)-3-oxo-hexahydropyrrolo[1,2-c][1,3]oxazol-1-ylidene]acetyl}-3-{[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}hexadec-4-enimidic acid.
Structure
Thumb
Synonyms
ValueSource
(3R)-N-{2-[(1E,7ar)-3-oxo-hexahydropyrrolo[1,2-c][1,3]oxazol-1-ylidene]acetyl}-3-{[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}hexadec-4-enimidateGenerator
Chemical FormulaC30H48N2O9
Average Mass580.7190 Da
Monoisotopic Mass580.33598 Da
IUPAC Name(3R,4E)-N-{2-[(1E,7aR)-3-oxo-hexahydropyrrolo[1,2-c][1,3]oxazol-1-ylidene]acetyl}-3-{[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}hexadec-4-enamide
Traditional Name(3R,4E)-N-{2-[(1E,7aR)-3-oxo-tetrahydropyrrolo[1,2-c][1,3]oxazol-1-ylidene]acetyl}-3-{[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}hexadec-4-enamide
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCC\C=C\[C@@H](CC(=O)NC(=O)\C=C1\OC(=O)N2CCC[C@H]12)O[C@@H]1O[C@@H](C)[C@H](O)[C@@H](O)[C@H]1O
InChI Identifier
InChI=1S/C30H48N2O9/c1-3-4-5-6-7-8-9-10-11-12-13-15-21(40-29-28(37)27(36)26(35)20(2)39-29)18-24(33)31-25(34)19-23-22-16-14-17-32(22)30(38)41-23/h13,15,19-22,26-29,35-37H,3-12,14,16-18H2,1-2H3,(H,31,33,34)/b15-13+,23-19+/t20-,21-,22+,26-,27+,28+,29-/m0/s1
InChI KeyLVTDKRIMXLJUAE-JTQWKVPKSA-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
Pseudomonas fluorescensNPAtlas
Pseudomonas fluorescens DSM 11579Bacteria
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
logP3.91ALOGPS
logP3.48ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)11.64ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area154.86 ŲChemAxon
Rotatable Bond Count16ChemAxon
Refractivity152.38 m³·mol⁻¹ChemAxon
Polarizability64.03 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
NPAtlas IDNPA019403
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID78442781
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound139588501
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Thirkettle J: SB-253514 and analogues; novel inhibitors of lipoprotein associated phospholipase A2 produced by Pseudomonas fluorescens DSM 11579. III. Biotransformation using naringinase. J Antibiot (Tokyo). 2000 Jul;53(7):733-5. doi: 10.7164/antibiotics.53.733. [PubMed:10994818 ]