NP-MRD: Showing NP-Card for (2R,3R)-2,5-diacetoxy-7-methoxyspiro[2H-1-benzopyran-3(4H),5'(6'H)-cyclob+ (NP0042606)

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Record Information

Version

2.0

Created at

2021-06-21 00:13:51 UTC

Updated at

2021-06-30 00:17:47 UTC

NP-MRD ID

NP0042606

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2R,3R)-2,5-diacetoxy-7-methoxyspiro[2H-1-benzopyran-3(4H),5'(6'H)-cyclob+

Provided By

JEOL Database JEOL Logo

Description

(2R,3R)-2,5-diacetoxy-7-methoxyspiro[2H-1-benzopyran-3(4H),5'(6'H)-cyclob+ is found in Ledebouria ovatifolia and Ledebouria socialis. (2R,3R)-2,5-diacetoxy-7-methoxyspiro[2H-1-benzopyran-3(4H),5'(6'H)-cyclob+ was first documented in 2013 (Waller, C. P., et al.).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212102133D          

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     RDKit          3D

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  4  3  2  0  0  0  0
 19 20  1  0  0  0  0
 21 20  1  0  0  0  0
 30 10  1  0  0  0  0
  6  7  1  0  0  0  0
 11 13  1  0  0  0  0
  7  8  1  0  0  0  0
 12  3  1  0  0  0  0
  7  9  2  0  0  0  0
 11 10  1  0  0  0  0
 14 15  1  0  0  0  0
 19 26  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 30 31  2  0  0  0  0
 16 18  2  0  0  0  0
 24 23  1  0  0  0  0
 14 19  1  0  0  0  0
  5  6  1  0  0  0  0
 14 13  1  0  0  0  0
  3  2  1  0  0  0  0
 19 30  1  1  0  0  0
 23 29  1  0  0  0  0
 29 28  1  0  0  0  0
 28 27  1  0  0  0  0
 27 24  1  0  0  0  0
 14 40  1  6  0  0  0
  4 35  1  0  0  0  0
 12 39  1  0  0  0  0
 22 46  1  0  0  0  0
 25 47  1  0  0  0  0
  1 32  1  0  0  0  0
  1 33  1  0  0  0  0
  1 34  1  0  0  0  0
 20 44  1  0  0  0  0
 20 45  1  0  0  0  0
  8 36  1  0  0  0  0
  8 37  1  0  0  0  0
  8 38  1  0  0  0  0
 17 41  1  0  0  0  0
 17 42  1  0  0  0  0
 17 43  1  0  0  0  0
 28 48  1  0  0  0  0
 28 49  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0042606

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C1=C2OC([H])([H])OC2=C([H])C2=C1C([H])([H])[C@@]21C(=O)C2=C(OC(=O)C([H])([H])[H])C([H])=C(OC([H])([H])[H])C([H])=C2O[C@]1([H])OC(=O)C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H18O9/c1-10(23)29-17-5-13(26-3)6-18-19(17)20(25)22(21(31-18)30-11(2)24)8-12-4-15-16(7-14(12)22)28-9-27-15/h4-7,21H,8-9H2,1-3H3/t21-,22-/m0/s1

> <INCHI_KEY>
MSDXBYMGBSBBTO-VXKWHMMOSA-N

> <FORMULA>
C22H18O9

> <MOLECULAR_WEIGHT>
426.377

> <EXACT_MASS>
426.09508216

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
42.516220456216814

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3R)-2-(acetyloxy)-7-methoxy-4-oxo-2,4-dihydro-9',11'-dioxaspiro[1-benzopyran-3,4'-tricyclo[6.3.0.0^{3,6}]undecane]-1',3'(6'),7'-trien-5-yl acetate

> <ALOGPS_LOGP>
2.46

> <JCHEM_LOGP>
2.299219847666667

> <ALOGPS_LOGS>
-4.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.391217299765775

> <JCHEM_POLAR_SURFACE_AREA>
106.59

> <JCHEM_REFRACTIVITY>
102.4167

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.16e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R)-2-(acetyloxy)-7-methoxy-4-oxo-2H-9',11'-dioxaspiro[1-benzopyran-3,4'-tricyclo[6.3.0.0^{3,6}]undecane]-1',3'(6'),7'-trien-5-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 49 53  0  0  0  0  0  0  0  0999 V2000
    0.0051    4.2259   -4.7571 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2280    4.1085   -4.0394 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2638    3.1997   -3.0189 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4800    3.1345   -2.3383 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6445    2.2432   -1.2740 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8958    2.2375   -0.6538 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8702    2.8616    0.5893 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2178    2.7229    1.2314 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9207    3.4538    1.0889 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6111    1.3798   -0.8940 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3829    1.4789   -1.5536 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2150    2.3704   -2.6213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7200    0.7245   -1.2464 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7755    0.2923    0.1244 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8935    1.4011    1.0346 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1263    1.9667    1.0936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1008    3.1502    2.0116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1195    1.5740    0.5003 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4882   -0.4831    0.4744 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4379   -1.2152    1.8746 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4918   -2.5044    1.1061 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5046   -3.8755    1.2398 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5763   -4.5789    0.0533 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6310   -3.9494   -1.1815 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6175   -2.5747   -1.3123 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5472   -1.8755   -0.1249 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6950   -4.8386   -2.2096 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6856   -6.0900   -1.4916 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6006   -5.9349   -0.0598 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7690    0.3332    0.1489 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8703    0.1467    0.6710 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1426    4.9891   -5.5290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2493    3.2864   -5.2588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8068    4.5574   -4.1013 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2997    3.7836   -2.6363 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4791    1.6656    1.3224 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1868    3.1581    2.2343 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9661    3.2555    0.6395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7517    2.3976   -3.1151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6547   -0.3577    0.2278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0899    3.6166    2.0293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8473    2.8279    3.0245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3775    3.8849    1.6486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4756   -1.0434    2.4559 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2912   -1.0144    2.5324 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4659   -4.3697    2.2008 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6584   -2.0899   -2.2784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1730   -6.6810   -1.8307 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6046   -6.6377   -1.7306 H   0  0  0  0  0  0  0  0  0  0  0  0
 26 21  2  0
 11 12  2  0
 21 22  1  0
 22 23  2  0
 10  5  2  0
 24 25  2  0
 25 26  1  0
  5  4  1  0
  2  1  1  0
  4  3  2  0
 19 20  1  0
 21 20  1  0
 30 10  1  0
  6  7  1  0
 11 13  1  0
  7  8  1  0
 12  3  1  0
  7  9  2  0
 11 10  1  0
 14 15  1  0
 19 26  1  0
 15 16  1  0
 16 17  1  0
 30 31  2  0
 16 18  2  0
 24 23  1  0
 14 19  1  0
  5  6  1  0
 14 13  1  0
  3  2  1  0
 19 30  1  1
 23 29  1  0
 29 28  1  0
 28 27  1  0
 27 24  1  0
 14 40  1  6
  4 35  1  0
 12 39  1  0
 22 46  1  0
 25 47  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
 20 44  1  0
 20 45  1  0
  8 36  1  0
  8 37  1  0
  8 38  1  0
 17 41  1  0
 17 42  1  0
 17 43  1  0
 28 48  1  0
 28 49  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0       0.005   4.226  -4.757  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.228   4.109  -4.039  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.264   3.200  -3.019  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.480   3.135  -2.338  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.644   2.243  -1.274  0.00  0.00           C+0
HETATM    6  O   UNK     0       3.896   2.237  -0.654  0.00  0.00           O+0
HETATM    7  C   UNK     0       3.870   2.862   0.589  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.218   2.723   1.231  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.921   3.454   1.089  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.611   1.380  -0.894  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.383   1.479  -1.554  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.215   2.370  -2.621  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.720   0.725  -1.246  0.00  0.00           O+0
HETATM   14  C   UNK     0      -0.776   0.292   0.124  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.894   1.401   1.035  0.00  0.00           O+0
HETATM   16  C   UNK     0      -2.126   1.967   1.094  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.101   3.150   2.012  0.00  0.00           C+0
HETATM   18  O   UNK     0      -3.119   1.574   0.500  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.488  -0.483   0.474  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.438  -1.215   1.875  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.492  -2.504   1.106  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.505  -3.876   1.240  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.576  -4.579   0.053  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.631  -3.949  -1.182  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.618  -2.575  -1.312  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.547  -1.876  -0.125  0.00  0.00           C+0
HETATM   27  O   UNK     0       0.695  -4.839  -2.210  0.00  0.00           O+0
HETATM   28  C   UNK     0       0.686  -6.090  -1.492  0.00  0.00           C+0
HETATM   29  O   UNK     0       0.601  -5.935  -0.060  0.00  0.00           O+0
HETATM   30  C   UNK     0       1.769   0.333   0.149  0.00  0.00           C+0
HETATM   31  O   UNK     0       2.870   0.147   0.671  0.00  0.00           O+0
HETATM   32  H   UNK     0       0.143   4.989  -5.529  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.249   3.286  -5.259  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.807   4.557  -4.101  0.00  0.00           H+0
HETATM   35  H   UNK     0       3.300   3.784  -2.636  0.00  0.00           H+0
HETATM   36  H   UNK     0       5.479   1.666   1.322  0.00  0.00           H+0
HETATM   37  H   UNK     0       5.187   3.158   2.234  0.00  0.00           H+0
HETATM   38  H   UNK     0       5.966   3.256   0.640  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.752   2.398  -3.115  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.655  -0.358   0.228  0.00  0.00           H+0
HETATM   41  H   UNK     0      -3.090   3.617   2.029  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.847   2.828   3.025  0.00  0.00           H+0
HETATM   43  H   UNK     0      -1.377   3.885   1.649  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.476  -1.043   2.456  0.00  0.00           H+0
HETATM   45  H   UNK     0       1.291  -1.014   2.532  0.00  0.00           H+0
HETATM   46  H   UNK     0       0.466  -4.370   2.201  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.658  -2.090  -2.278  0.00  0.00           H+0
HETATM   48  H   UNK     0      -0.173  -6.681  -1.831  0.00  0.00           H+0
HETATM   49  H   UNK     0       1.605  -6.638  -1.731  0.00  0.00           H+0
CONECT    1    2   32   33   34                                             
CONECT    2    1    3                                                       
CONECT    3    4   12    2                                                  
CONECT    4    5    3   35                                                  
CONECT    5   10    4    6                                                  
CONECT    6    7    5                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7   36   37   38                                             
CONECT    9    7                                                            
CONECT   10    5   30   11                                                  
CONECT   11   12   13   10                                                  
CONECT   12   11    3   39                                                  
CONECT   13   11   14                                                       
CONECT   14   15   19   13   40                                             
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16   41   42   43                                             
CONECT   18   16                                                            
CONECT   19   20   26   14   30                                             
CONECT   20   19   21   44   45                                             
CONECT   21   26   22   20                                                  
CONECT   22   21   23   46                                                  
CONECT   23   22   24   29                                                  
CONECT   24   25   23   27                                                  
CONECT   25   24   26   47                                                  
CONECT   26   21   25   19                                                  
CONECT   27   28   24                                                       
CONECT   28   29   27   48   49                                             
CONECT   29   23   28                                                       
CONECT   30   10   31   19                                                  
CONECT   31   30                                                            
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    4                                                            
CONECT   36    8                                                            
CONECT   37    8                                                            
CONECT   38    8                                                            
CONECT   39   12                                                            
CONECT   40   14                                                            
CONECT   41   17                                                            
CONECT   42   17                                                            
CONECT   43   17                                                            
CONECT   44   20                                                            
CONECT   45   20                                                            
CONECT   46   22                                                            
CONECT   47   25                                                            
CONECT   48   28                                                            
CONECT   49   28                                                            
MASTER        0    0    0    0    0    0    0    0   49    0  106    0
END

RDKit          3D

49 53  0  0  0  0  0  0  0  0999 V2000
    0.0051    4.2259   -4.7571 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2280    4.1085   -4.0394 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2638    3.1997   -3.0189 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4800    3.1345   -2.3383 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6445    2.2432   -1.2740 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8958    2.2375   -0.6538 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8702    2.8616    0.5893 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2178    2.7229    1.2314 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9207    3.4538    1.0889 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6111    1.3798   -0.8940 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3829    1.4789   -1.5536 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2150    2.3704   -2.6213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7200    0.7245   -1.2464 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7755    0.2923    0.1244 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8935    1.4011    1.0346 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1263    1.9667    1.0936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1008    3.1502    2.0116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1195    1.5740    0.5003 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4882   -0.4831    0.4744 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4379   -1.2152    1.8746 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4918   -2.5044    1.1061 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5046   -3.8755    1.2398 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5763   -4.5789    0.0533 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6310   -3.9494   -1.1815 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6175   -2.5747   -1.3123 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5472   -1.8755   -0.1249 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6950   -4.8386   -2.2096 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6856   -6.0900   -1.4916 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6006   -5.9349   -0.0598 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7690    0.3332    0.1489 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8703    0.1467    0.6710 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1426    4.9891   -5.5290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2493    3.2864   -5.2588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8068    4.5574   -4.1013 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2997    3.7836   -2.6363 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4791    1.6656    1.3224 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1868    3.1581    2.2343 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9661    3.2555    0.6395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7517    2.3976   -3.1151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6547   -0.3577    0.2278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0899    3.6166    2.0293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8473    2.8279    3.0245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3775    3.8849    1.6486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4756   -1.0434    2.4559 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2912   -1.0144    2.5324 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4659   -4.3697    2.2008 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6584   -2.0899   -2.2784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1730   -6.6810   -1.8307 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6046   -6.6377   -1.7306 H   0  0  0  0  0  0  0  0  0  0  0  0
 26 21  2  0
 11 12  2  0
 21 22  1  0
 22 23  2  0
 10  5  2  0
 24 25  2  0
 25 26  1  0
  5  4  1  0
  2  1  1  0
  4  3  2  0
 19 20  1  0
 21 20  1  0
 30 10  1  0
  6  7  1  0
 11 13  1  0
  7  8  1  0
 12  3  1  0
  7  9  2  0
 11 10  1  0
 14 15  1  0
 19 26  1  0
 15 16  1  0
 16 17  1  0
 30 31  2  0
 16 18  2  0
 24 23  1  0
 14 19  1  0
  5  6  1  0
 14 13  1  0
  3  2  1  0
 19 30  1  1
 23 29  1  0
 29 28  1  0
 28 27  1  0
 27 24  1  0
 14 40  1  6
  4 35  1  0
 12 39  1  0
 22 46  1  0
 25 47  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
 20 44  1  0
 20 45  1  0
  8 36  1  0
  8 37  1  0
  8 38  1  0
 17 41  1  0
 17 42  1  0
 17 43  1  0
 28 48  1  0
 28 49  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Not Available

Chemical Formula

C₂₂H₁₈O₉

Average Mass

426.3770 Da

Monoisotopic Mass

426.09508 Da

IUPAC Name

(2R,3R)-2-(acetyloxy)-7-methoxy-4-oxo-2,4-dihydro-9',11'-dioxaspiro[1-benzopyran-3,4'-tricyclo[6.3.0.0^{3,6}]undecane]-1',3'(6'),7'-trien-5-yl acetate

Traditional Name

(2R,3R)-2-(acetyloxy)-7-methoxy-4-oxo-2H-9',11'-dioxaspiro[1-benzopyran-3,4'-tricyclo[6.3.0.0^{3,6}]undecane]-1',3'(6'),7'-trien-5-yl acetate

CAS Registry Number

Not Available

SMILES

[H]C1=C2OC([H])([H])OC2=C([H])C2=C1C([H])([H])[C@@]21C(=O)C2=C(OC(=O)C([H])([H])[H])C([H])=C(OC([H])([H])[H])C([H])=C2O[C@]1([H])OC(=O)C([H])([H])[H]

InChI Identifier

InChI=1S/C22H18O9/c1-10(23)29-17-5-13(26-3)6-18-19(17)20(25)22(21(31-18)30-11(2)24)8-12-4-15-16(7-14(12)22)28-9-27-15/h4-7,21H,8-9H2,1-3H3/t21-,22-/m0/s1

InChI Key

MSDXBYMGBSBBTO-VXKWHMMOSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ledebouria ovatifolia	JEOL database	Waller, C. P., et al, Phytochem. 95, 284 (2013)
Ledebouria socialis	JEOL database	Waller, C. P., et al, Phytochem. 95, 284 (2013)

Chemical Taxonomy

Classification

Not classified

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.46	ALOGPS
logP	2.3	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	106.59 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	102.42 m³·mol⁻¹	ChemAxon
Polarizability	42.52 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

Not Available

References

General References

Waller, C. P., et al. (2013). Waller, C. P., et al, Phytochem. 95, 284 (2013). Phytochem..

Showing NP-Card for (2R,3R)-2,5-diacetoxy-7-methoxyspiro[2H-1-benzopyran-3(4H),5'(6'H)-cyclob+ (NP0042606)

MOL for NP0042606 ((2R,3R)-2,5-diacetoxy-7-methoxyspiro[2H-1-benzopyran-3(4H),5'(6'H)-cyclob+)

3D MOL for NP0042606 ((2R,3R)-2,5-diacetoxy-7-methoxyspiro[2H-1-benzopyran-3(4H),5'(6'H)-cyclob+)

3D SDF for NP0042606 ((2R,3R)-2,5-diacetoxy-7-methoxyspiro[2H-1-benzopyran-3(4H),5'(6'H)-cyclob+)

3D-SDF for NP0042606 ((2R,3R)-2,5-diacetoxy-7-methoxyspiro[2H-1-benzopyran-3(4H),5'(6'H)-cyclob+)

PDB for NP0042606 ((2R,3R)-2,5-diacetoxy-7-methoxyspiro[2H-1-benzopyran-3(4H),5'(6'H)-cyclob+)

3D PDB for NP0042606 ((2R,3R)-2,5-diacetoxy-7-methoxyspiro[2H-1-benzopyran-3(4H),5'(6'H)-cyclob+)

SMILES for NP0042606 ((2R,3R)-2,5-diacetoxy-7-methoxyspiro[2H-1-benzopyran-3(4H),5'(6'H)-cyclob+)

INCHI for NP0042606 ((2R,3R)-2,5-diacetoxy-7-methoxyspiro[2H-1-benzopyran-3(4H),5'(6'H)-cyclob+)

Structure for NP0042606 ((2R,3R)-2,5-diacetoxy-7-methoxyspiro[2H-1-benzopyran-3(4H),5'(6'H)-cyclob+)

3D Structure for NP0042606 ((2R,3R)-2,5-diacetoxy-7-methoxyspiro[2H-1-benzopyran-3(4H),5'(6'H)-cyclob+)