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Showing NP-Card for (+)-(S,R)-Epoxyartemidin (NP0078824)

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Record Information
Version1.0
Created at2022-04-28 23:54:58 UTC
Updated at2022-04-28 23:54:58 UTC
NP-MRD IDNP0078824
Secondary Accession NumbersNone
Natural Product Identification
Common Name(+)-(S,R)-Epoxyartemidin
Description(+)-(S,R)-epoxyartemidin belongs to the class of organic compounds known as isocoumarins and derivatives. These are polycyclic compounds containing an isochromane which bears a ketone at the carbon C1. (+)-(S,R)-Epoxyartemidin is found in Artemisia campestris and Artemisia dracunculus . It was first documented in 2004 (PMID: 14738379). Based on a literature review very few articles have been published on (+)-(S,R)-epoxyartemidin.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0078824 ((+)-(S,R)-Epoxyartemidin)


  Mrv1652304292201542D          

 16 18  0  0  1  0            999 V2000
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2704    0.7145    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2704    1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5559    1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
 12  8  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 13 16  1  0  0  0  0
 12 16  1  0  0  0  0
M  END
Download

3D MOL for NP0078824 ((+)-(S,R)-Epoxyartemidin)

     RDKit          3D

 28 30  0  0  0  0  0  0  0  0999 V2000
    4.9764    0.0057    0.3447 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8943   -0.9764   -0.0996 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5875   -0.2299   -0.0791 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3375    0.2512    1.3045 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4670   -0.6697    0.7219 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1258   -0.0969    0.3478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0048   -0.8198    0.6667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2336   -0.2695    0.3104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3996   -0.9527    0.6066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6062   -0.4007    0.2507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6693    0.8332   -0.4018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5120    1.4985   -0.6890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2839    0.9596   -0.3388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0882    1.6031   -0.6124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1205    2.7169   -1.2000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0596    1.0639   -0.2664 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1746    0.6772   -0.5334 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5270    0.6253    1.1397 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8976   -0.5240    0.6704 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0830   -1.3609   -1.1130 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8475   -1.8170    0.6154 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4670    0.6148   -0.7873 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4679   -1.7209    1.0739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9511   -1.7802    1.1748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3200   -1.9065    1.1125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5069   -0.9599    0.4959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6573    1.1850   -0.6405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5593    2.4504   -1.1922 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
  5  3  1  0
 16  6  1  0
 13  8  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  6
  5 23  1  1
  7 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 12 28  1  0
M  END
Download

3D SDF for NP0078824 ((+)-(S,R)-Epoxyartemidin)


  Mrv1652304292201542D          

 16 18  0  0  1  0            999 V2000
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2704    0.7145    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2704    1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5559    1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
 12  8  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 13 16  1  0  0  0  0
 12 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0078824

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@@H]1O[C@H]1C1=CC2=CC=CC=C2C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C13H12O3/c1-2-10-12(15-10)11-7-8-5-3-4-6-9(8)13(14)16-11/h3-7,10,12H,2H2,1H3/t10-,12+/m0/s1

> <INCHI_KEY>
VNEONZFLGNRQJT-CMPLNLGQSA-N

> <FORMULA>
C13H12O3

> <MOLECULAR_WEIGHT>
216.236

> <EXACT_MASS>
216.078644246

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
22.846101787397657

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-[(2R,3S)-3-ethyloxiran-2-yl]-1H-isochromen-1-one

> <ALOGPS_LOGP>
2.41

> <JCHEM_LOGP>
2.6790191246666666

> <ALOGPS_LOGS>
-3.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.250934582981559

> <JCHEM_POLAR_SURFACE_AREA>
38.83

> <JCHEM_REFRACTIVITY>
60.244000000000014

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.99e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[(2R,3S)-3-ethyloxiran-2-yl]isochromen-1-one

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0078824 ((+)-(S,R)-Epoxyartemidin)

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PDB for NP0078824 ((+)-(S,R)-Epoxyartemidin)
HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.105   1.334   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.105   2.874   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.771   3.644   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.875  -0.000   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8   10                                                       
CONECT   10    9    4   11                                                  
CONECT   11   10                                                            
CONECT   12    8   13   16                                                  
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   13   12                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   36    0
END

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3D PDB for NP0078824 ((+)-(S,R)-Epoxyartemidin)
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SMILES for NP0078824 ((+)-(S,R)-Epoxyartemidin)
CC[C@@H]1O[C@H]1C1=CC2=CC=CC=C2C(=O)O1
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INCHI for NP0078824 ((+)-(S,R)-Epoxyartemidin)
InChI=1S/C13H12O3/c1-2-10-12(15-10)11-7-8-5-3-4-6-9(8)13(14)16-11/h3-7,10,12H,2H2,1H3/t10-,12+/m0/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC13H12O3
Average Mass216.2360 Da
Monoisotopic Mass216.07864 Da
IUPAC Name3-[(2R,3S)-3-ethyloxiran-2-yl]-1H-isochromen-1-one
Traditional Name3-[(2R,3S)-3-ethyloxiran-2-yl]isochromen-1-one
CAS Registry NumberNot Available
SMILES
CC[C@@H]1O[C@H]1C1=CC2=CC=CC=C2C(=O)O1
InChI Identifier
InChI=1S/C13H12O3/c1-2-10-12(15-10)11-7-8-5-3-4-6-9(8)13(14)16-11/h3-7,10,12H,2H2,1H3/t10-,12+/m0/s1
InChI KeyVNEONZFLGNRQJT-CMPLNLGQSA-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
Artemisia campestrisLOTUS Database
Artemisia dracunculusPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as isocoumarins and derivatives. These are polycyclic compounds containing an isochromane which bears a ketone at the carbon C1.
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassIsocoumarins and derivatives  
Sub ClassNot Available
Direct ParentIsocoumarins and derivatives  
Alternative Parents
Substituents
  • Isocoumarin
    • 

  • Benzopyran
    • 

  • 2-benzopyran
    • 

  • Pyranone
    • 

  • Pyran
    • 

  • Benzenoid
    • 

  • Heteroaromatic compound
    • 

  • Lactone
    • 

  • Dialkyl ether
    • 

  • Oxirane
    • 

  • Ether
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Organic oxygen compound
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
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
logP2.41ALOGPS
logP2.68ChemAxon
logS-3ALOGPS
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area38.83 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity60.24 m³·mol⁻¹ChemAxon
Polarizability22.85 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID10192523  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound21580105  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Engelmeier D, Hadacek F, Hofer O, Lutz-Kutschera G, Nagl M, Wurz G, Greger H: Antifungal 3-butylisocoumarins from Asteraceae-Anthemideae. J Nat Prod. 2004 Jan;67(1):19-25. doi: 10.1021/np0301339. [PubMed:14738379  ]