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Record Information
Version1.0
Created at2020-12-09 00:31:12 UTC
Updated at2021-07-15 16:45:37 UTC
NP-MRD IDNP0003143
Secondary Accession NumbersNone
Natural Product Identification
Common NameFlagranone B
Provided ByNPAtlasNPAtlas Logo
Description Flagranone B is found in Arthrobotrys flagrans. It was first documented in 1999 (PMID: 10656575). Based on a literature review very few articles have been published on (2E,4E)-1-{4-[(acetyloxy)methyl]-2,5-dioxo-7-oxabicyclo[4.1.0]Hept-3-en-1-yl}-3-methyl-6-oxohexa-2,4-dien-1-yl acetate.
Structure
Data?1624573741
Synonyms
ValueSource
(2E,4E)-1-{4-[(acetyloxy)methyl]-2,5-dioxo-7-oxabicyclo[4.1.0]hept-3-en-1-yl}-3-methyl-6-oxohexa-2,4-dien-1-yl acetic acidGenerator
Chemical FormulaC18H18O8
Average Mass362.3340 Da
Monoisotopic Mass362.10017 Da
IUPAC Name(1S,2E,4E)-1-[(1S,6R)-4-[(acetyloxy)methyl]-2,5-dioxo-7-oxabicyclo[4.1.0]hept-3-en-1-yl]-3-methyl-6-oxohexa-2,4-dien-1-yl acetate
Traditional Name(1S,2E,4E)-1-[(1S,6R)-4-[(acetyloxy)methyl]-2,5-dioxo-7-oxabicyclo[4.1.0]hept-3-en-1-yl]-3-methyl-6-oxohexa-2,4-dien-1-yl acetate
CAS Registry NumberNot Available
SMILES
CC(=O)OCC1=CC(=O)C2(OC2C1=O)C(OC(C)=O)\C=C(/C)\C=C\C=O
InChI Identifier
InChI=1S/C18H18O8/c1-10(5-4-6-19)7-15(25-12(3)21)18-14(22)8-13(9-24-11(2)20)16(23)17(18)26-18/h4-8,15,17H,9H2,1-3H3/b5-4+,10-7+
InChI KeySVNKMLNHRUIBIV-YIORLJKJSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
Species NameSourceReference
Arthrobotrys flagrans
Species Where Detected
Species NameSourceReference
Duddingtonia flagransKNApSAcK Database
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
logP1.73ALOGPS
logP0.61ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)14.99ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area116.34 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity89.64 m³·mol⁻¹ChemAxon
Polarizability36.05 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
NPAtlas IDNPA002154
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID8888990
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10713650
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Anderson MG, Rickards RW, Lacey E: Structures of flagranones A, B and C, cyclohexenoxide antibiotics from the nematode-trapping fungus Duddingtonia flagrans. J Antibiot (Tokyo). 1999 Nov;52(11):1023-8. doi: 10.7164/antibiotics.52.1023. [PubMed:10656575 ]