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Showing NP-Card for (1r,5r,6r)-1-chloro-6-[(1z)-1-chloroprop-1-en-1-yl]-5-hydroxy-4-methoxy-7-oxabicyclo[4.1.0]hept-3-en-2-one (NP0330860)

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Record Information
Version2.0
Created at2022-09-12 16:37:44 UTC
Updated at2022-09-12 16:37:44 UTC
NP-MRD IDNP0330860
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1r,5r,6r)-1-chloro-6-[(1z)-1-chloroprop-1-en-1-yl]-5-hydroxy-4-methoxy-7-oxabicyclo[4.1.0]hept-3-en-2-one
Description (1r,5r,6r)-1-chloro-6-[(1z)-1-chloroprop-1-en-1-yl]-5-hydroxy-4-methoxy-7-oxabicyclo[4.1.0]hept-3-en-2-one is found in Lachnum papyraceum. Based on a literature review very few articles have been published on (1R,5R,6R)-1-chloro-6-(1-chloroprop-1-en-1-yl)-5-hydroxy-4-methoxy-7-oxabicyclo[4.1.0]Hept-3-en-2-one.
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0330860 ((1r,5r,6r)-1-chloro-6-[(1z)-1-chloroprop-1-en-1-yl]-5-hydroxy-4-methoxy-7-oxabicyclo[4.1.0]hept-3-en-2-one)


  Mrv1652309122218372D          

 16 17  0  0  1  0            999 V2000
   -1.1737   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7612   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0638   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4763   -2.2539    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.4763   -0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2382   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4763   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0638    0.7145    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.1908    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1908    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9053   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9053   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6197   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3342   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1908   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1908   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  5  3  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
  5 15  1  0  0  0  0
 15 16  1  1  0  0  0
M  END
Download

3D MOL for NP0330860 ((1r,5r,6r)-1-chloro-6-[(1z)-1-chloroprop-1-en-1-yl]-5-hydroxy-4-methoxy-7-oxabicyclo[4.1.0]hept-3-en-2-one)

     RDKit          3D

 26 27  0  0  0  0  0  0  0  0999 V2000
    4.1762    0.6808   -0.2301 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8768    0.0655   -0.6952 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7505    0.2405   -0.0248 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8599    1.2277    1.4206 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.4465   -0.3348   -0.4272 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0670    0.3298   -1.7008 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1147   -1.1308   -1.4908 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1743   -1.9945   -2.6325 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.2582   -1.6784   -1.4841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5802   -2.7827   -2.0473 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3388   -0.9642   -0.8167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9834   -0.2650    0.2499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9961    0.4316    0.9075 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1632    1.8382    0.7018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5886   -0.2665    0.6660 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3593   -1.3832    1.5141 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8037    0.8524   -1.1072 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8655    1.6584    0.2420 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5816    0.0089    0.5268 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8866   -0.5165   -1.5835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3787   -0.9866   -1.1354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0114    2.1648    1.3150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4553    1.9744   -0.3635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2381    2.3917    0.8654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3769    0.6043    1.3639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8753   -2.1657    1.2188 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  1  0
 13 12  1  0
 12 11  2  0
 11  9  1  0
  9 10  2  0
  9  7  1  0
  7  8  1  6
  7  6  1  0
  6  5  1  0
  5 15  1  0
 15 16  1  0
  5  3  1  1
  3  4  1  0
  3  2  2  0
  2  1  1  0
 15 12  1  0
  5  7  1  0
 14 22  1  0
 14 23  1  0
 14 24  1  0
 11 21  1  0
 15 25  1  1
 16 26  1  0
  2 20  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
M  END
Download

3D SDF for NP0330860 ((1r,5r,6r)-1-chloro-6-[(1z)-1-chloroprop-1-en-1-yl]-5-hydroxy-4-methoxy-7-oxabicyclo[4.1.0]hept-3-en-2-one)


  Mrv1652309122218372D          

 16 17  0  0  1  0            999 V2000
   -1.1737   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7612   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0638   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4763   -2.2539    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.4763   -0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2382   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4763   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0638    0.7145    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.1908    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1908    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9053   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9053   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6197   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3342   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1908   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1908   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  5  3  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
  5 15  1  0  0  0  0
 15 16  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0330860

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=O)[C@@]2(Cl)O[C@]2([C@@H]1O)C(\Cl)=C\C

> <INCHI_IDENTIFIER>
InChI=1S/C10H10Cl2O4/c1-3-6(11)9-8(14)5(15-2)4-7(13)10(9,12)16-9/h3-4,8,14H,1-2H3/b6-3-/t8-,9+,10-/m1/s1

> <INCHI_KEY>
REDDCMGYPGBKPN-XHIPISRXSA-N

> <FORMULA>
C10H10Cl2O4

> <MOLECULAR_WEIGHT>
265.09

> <EXACT_MASS>
263.9956142

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
23.47782521363731

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,5R,6R)-1-chloro-6-[(1Z)-1-chloroprop-1-en-1-yl]-5-hydroxy-4-methoxy-7-oxabicyclo[4.1.0]hept-3-en-2-one

> <JCHEM_LOGP>
1.6594159793333332

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.151600545719925

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.030925022855483

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9021269004080894

> <JCHEM_POLAR_SURFACE_AREA>
59.06

> <JCHEM_REFRACTIVITY>
61.057300000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,5R,6R)-1-chloro-6-[(1Z)-1-chloroprop-1-en-1-yl]-5-hydroxy-4-methoxy-7-oxabicyclo[4.1.0]hept-3-en-2-one

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0330860 ((1r,5r,6r)-1-chloro-6-[(1z)-1-chloroprop-1-en-1-yl]-5-hydroxy-4-methoxy-7-oxabicyclo[4.1.0]hept-3-en-2-one)

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PDB for NP0330860 ((1r,5r,6r)-1-chloro-6-[(1z)-1-chloroprop-1-en-1-yl]-5-hydroxy-4-methoxy-7-oxabicyclo[4.1.0]hept-3-en-2-one)
HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.191  -4.207   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.421  -2.874   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.119  -2.874   0.000  0.00  0.00           C+0
HETATM    4 Cl   UNK     0       0.889  -4.207   0.000  0.00  0.00          Cl+0
HETATM    5  C   UNK     0       0.889  -1.540   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.445  -0.770   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.889  -0.000   0.000  0.00  0.00           C+0
HETATM    8 Cl   UNK     0       0.119   1.334   0.000  0.00  0.00          Cl+0
HETATM    9  C   UNK     0       2.223   0.770   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.223   2.310   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       3.556  -0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.556  -1.540   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.890  -2.310   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       6.224  -1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.223  -2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.223  -3.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7   15                                             
CONECT    6    5    7                                                       
CONECT    7    6    5    8    9                                             
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12    5   16                                                  
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

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3D PDB for NP0330860 ((1r,5r,6r)-1-chloro-6-[(1z)-1-chloroprop-1-en-1-yl]-5-hydroxy-4-methoxy-7-oxabicyclo[4.1.0]hept-3-en-2-one)
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SMILES for NP0330860 ((1r,5r,6r)-1-chloro-6-[(1z)-1-chloroprop-1-en-1-yl]-5-hydroxy-4-methoxy-7-oxabicyclo[4.1.0]hept-3-en-2-one)
COC1=CC(=O)[C@@]2(Cl)O[C@]2([C@@H]1O)C(\Cl)=C\C
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INCHI for NP0330860 ((1r,5r,6r)-1-chloro-6-[(1z)-1-chloroprop-1-en-1-yl]-5-hydroxy-4-methoxy-7-oxabicyclo[4.1.0]hept-3-en-2-one)
InChI=1S/C10H10Cl2O4/c1-3-6(11)9-8(14)5(15-2)4-7(13)10(9,12)16-9/h3-4,8,14H,1-2H3/b6-3-/t8-,9+,10-/m1/s1
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SynonymsNot Available
Chemical FormulaC10H10Cl2O4
Average Mass265.0900 Da
Monoisotopic Mass263.99561 Da
IUPAC Name(1R,5R,6R)-1-chloro-6-[(1Z)-1-chloroprop-1-en-1-yl]-5-hydroxy-4-methoxy-7-oxabicyclo[4.1.0]hept-3-en-2-one
Traditional Name(1R,5R,6R)-1-chloro-6-[(1Z)-1-chloroprop-1-en-1-yl]-5-hydroxy-4-methoxy-7-oxabicyclo[4.1.0]hept-3-en-2-one
CAS Registry NumberNot Available
SMILES
COC1=CC(=O)[C@@]2(Cl)O[C@]2([C@@H]1O)C(\Cl)=C\C
InChI Identifier
InChI=1S/C10H10Cl2O4/c1-3-6(11)9-8(14)5(15-2)4-7(13)10(9,12)16-9/h3-4,8,14H,1-2H3/b6-3-/t8-,9+,10-/m1/s1
InChI KeyREDDCMGYPGBKPN-XHIPISRXSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Lachnum papyraceumLOTUS 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
logP1.66ChemAxon
pKa (Strongest Acidic)12.03ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area59.06 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity61.06 m³·mol⁻¹ChemAxon
Polarizability23.48 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound163048780  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]