NP-MRD: Showing NP-Card for chrysoxanthone E (NP0332934)

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Record Information

Version

1.0

Created at

2024-05-02 07:41:26 UTC

Updated at

2024-05-02 08:06:19 UTC

NP-MRD ID

NP0332934

Secondary Accession Numbers

None

Natural Product Identification

Common Name

chrysoxanthone E

Description

Methyl (3S,4R,4aS)-1,4,8-trihydroxy-7-[(2S)-5-hydroxy-2-(methoxycarbonyl)-2-[(2S,3S)-3-methyl-5-oxooxolan-2-yl]-4-oxo-3,4-dihydro-2H-1-benzopyran-6-yl]-3-methyl-9-oxo-3,4,4a,9-tetrahydro-2H-xanthene-4a-carboxylate belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring. Based on a literature review very few articles have been published on methyl (3S,4R,4aS)-1,4,8-trihydroxy-7-[(2S)-5-hydroxy-2-(methoxycarbonyl)-2-[(2S,3S)-3-methyl-5-oxooxolan-2-yl]-4-oxo-3,4-dihydro-2H-1-benzopyran-6-yl]-3-methyl-9-oxo-3,4,4a,9-tetrahydro-2H-xanthene-4a-carboxylate.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01142310182D          

 47 52  0  0  1  0            999 V2000
    0.7145   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   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
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.7124    0.3627    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8936    0.2622    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5054    0.5901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5342    1.4146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7590    1.6968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2511    1.0467    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4266    1.0755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2182    1.8760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2427   -0.5558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7730    0.0762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5855   -0.0670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5249   -1.3310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   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
   -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 O   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 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3356   -4.0537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  6  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 22 21  1  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  1  0  0  0
 20 24  2  0  0  0  0
 16 25  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 25 28  2  0  0  0  0
 16 29  1  1  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 14 32  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  2  0  0  0  0
 11 33  1  0  0  0  0
 33 34  1  0  0  0  0
 10 35  1  0  0  0  0
 35 36  2  0  0  0  0
  6 36  1  0  0  0  0
 37  4  1  0  0  0  0
 37 38  1  6  0  0  0
 37 39  1  0  0  0  0
 39 40  1  1  0  0  0
 39 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 42 44  2  0  0  0  0
  4 44  1  0  0  0  0
 44 45  1  0  0  0  0
  7 45  1  0  0  0  0
 45 46  2  0  0  0  0
  3 47  2  0  0  0  0
M  END


  Mrv2104 01142310182D          

 47 52  0  0  1  0            999 V2000
    0.7145   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   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
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.7124    0.3627    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8936    0.2622    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5054    0.5901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5342    1.4146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7590    1.6968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2511    1.0467    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4266    1.0755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2182    1.8760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2427   -0.5558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7730    0.0762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5855   -0.0670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5249   -1.3310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   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
   -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 O   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 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3356   -4.0537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  6  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 22 21  1  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  1  0  0  0
 20 24  2  0  0  0  0
 16 25  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 25 28  2  0  0  0  0
 16 29  1  1  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 14 32  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  2  0  0  0  0
 11 33  1  0  0  0  0
 33 34  1  0  0  0  0
 10 35  1  0  0  0  0
 35 36  2  0  0  0  0
  6 36  1  0  0  0  0
 37  4  1  0  0  0  0
 37 38  1  6  0  0  0
 37 39  1  0  0  0  0
 39 40  1  1  0  0  0
 39 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 42 44  2  0  0  0  0
  4 44  1  0  0  0  0
 44 45  1  0  0  0  0
  7 45  1  0  0  0  0
 45 46  2  0  0  0  0
  3 47  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0332934

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(OC(=O)C[C@@H]1C)[C@]1(CC(=O)C2=C(O)C(=CC=C2O1)C1=C(O)C2=C(O[C@]3([C@H](O)[C@@H](C)CC(O)=C3C2=O)C(=O)OC)C=C1)C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C32H30O14/c1-12-9-16(33)23-26(38)22-19(46-32(23,27(12)39)30(41)43-4)8-6-15(25(22)37)14-5-7-18-21(24(14)36)17(34)11-31(45-18,29(40)42-3)28-13(2)10-20(35)44-28/h5-8,12-13,27-28,33,36-37,39H,9-11H2,1-4H3/t12-,13-,27+,28-,31+,32+/m0/s1

> <INCHI_KEY>
MLEYBVBRIZGXRW-AKBFVYQBSA-N

> <FORMULA>
C32H30O14

> <MOLECULAR_WEIGHT>
638.578

> <EXACT_MASS>
638.163555646

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
62.471145264780354

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (3S,4R,4aR)-1,4,8-trihydroxy-7-[(2R)-5-hydroxy-2-(methoxycarbonyl)-2-[(2S,3S)-3-methyl-5-oxooxolan-2-yl]-4-oxo-3,4-dihydro-2H-1-benzopyran-6-yl]-3-methyl-9-oxo-3,4,4a,9-tetrahydro-2H-xanthene-4a-carboxylate

> <JCHEM_LOGP>
2.9331879353333337

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.57374109868784

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.425490382527418

> <JCHEM_PKA_STRONGEST_BASIC>
-3.493185660254414

> <JCHEM_POLAR_SURFACE_AREA>
212.41999999999996

> <JCHEM_REFRACTIVITY>
154.17810000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
methyl (3S,4R,4aR)-1,4,8-trihydroxy-7-[(2R)-5-hydroxy-2-(methoxycarbonyl)-2-[(2S,3S)-3-methyl-5-oxooxolan-2-yl]-4-oxo-3H-1-benzopyran-6-yl]-3-methyl-9-oxo-3,4-dihydro-2H-xanthene-4a-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 14-JAN-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   14-JAN-23         0                                  
HETATM    1  C   UNK     0       1.334  -8.470   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.000  -6.160   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      10.669   0.000   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.530   0.677   0.000  0.00  0.00           C+0
HETATM   18  H   UNK     0      11.001   0.489   0.000  0.00  0.00           H+0
HETATM   19  O   UNK     0      14.010   1.102   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      14.064   2.641   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.617   3.167   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.669   1.954   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.130   2.008   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      15.341   3.502   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      13.520  -1.037   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      14.510   0.142   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      16.026  -0.125   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      14.046  -2.485   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      10.669  -4.620   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0      -0.626  -7.567   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   47                                                  
CONECT    4    3    5   37   44                                             
CONECT    5    4    6                                                       
CONECT    6    5    7   36                                                  
CONECT    7    6    8   45                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   35                                                  
CONECT   11   10   12   33                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   32                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   25   29                                             
CONECT   17   16   18   19   22                                             
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   24                                                  
CONECT   21   20   22                                                       
CONECT   22   21   17   23                                                  
CONECT   23   22                                                            
CONECT   24   20                                                            
CONECT   25   16   26   28                                                  
CONECT   26   25   27                                                       
CONECT   27   26                                                            
CONECT   28   25                                                            
CONECT   29   16   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   14   30   33                                                  
CONECT   33   32   11   34                                                  
CONECT   34   33                                                            
CONECT   35   10   36                                                       
CONECT   36   35    6                                                       
CONECT   37    4   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   42                                                       
CONECT   42   41   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42    4   45                                                  
CONECT   45   44    7   46                                                  
CONECT   46   45                                                            
CONECT   47    3                                                            
MASTER        0    0    0    0    0    0    0    0   47    0  104    0
END

View in JSmol

Synonyms

Value	Source
Methyl (3S,4R,4as)-1,4,8-trihydroxy-7-[(2S)-5-hydroxy-2-(methoxycarbonyl)-2-[(2S,3S)-3-methyl-5-oxooxolan-2-yl]-4-oxo-3,4-dihydro-2H-1-benzopyran-6-yl]-3-methyl-9-oxo-3,4,4a,9-tetrahydro-2H-xanthene-4a-carboxylic acid	Generator

Chemical Formula

C₃₂H₃₀O₁₄

Average Mass

638.5780 Da

Monoisotopic Mass

638.16356 Da

IUPAC Name

methyl (3S,4R,4aR)-1,4,8-trihydroxy-7-[(2R)-5-hydroxy-2-(methoxycarbonyl)-2-[(2S,3S)-3-methyl-5-oxooxolan-2-yl]-4-oxo-3,4-dihydro-2H-1-benzopyran-6-yl]-3-methyl-9-oxo-3,4,4a,9-tetrahydro-2H-xanthene-4a-carboxylate

Traditional Name

methyl (3S,4R,4aR)-1,4,8-trihydroxy-7-[(2R)-5-hydroxy-2-(methoxycarbonyl)-2-[(2S,3S)-3-methyl-5-oxooxolan-2-yl]-4-oxo-3H-1-benzopyran-6-yl]-3-methyl-9-oxo-3,4-dihydro-2H-xanthene-4a-carboxylate

CAS Registry Number

Not Available

SMILES

[H][C@@]1(OC(=O)C[C@@H]1C)[C@]1(CC(=O)C2=C(O)C(=CC=C2O1)C1=C(O)C2=C(O[C@]3([C@H](O)[C@@H](C)CC(O)=C3C2=O)C(=O)OC)C=C1)C(=O)OC

InChI Identifier

InChI=1S/C32H30O14/c1-12-9-16(33)23-26(38)22-19(46-32(23,27(12)39)30(41)43-4)8-6-15(25(22)37)14-5-7-18-21(24(14)36)17(34)11-31(45-18,29(40)42-3)28-13(2)10-20(35)44-28/h5-8,12-13,27-28,33,36-37,39H,9-11H2,1-4H3/t12-,13-,27+,28-,31+,32+/m0/s1

InChI Key

MLEYBVBRIZGXRW-AKBFVYQBSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, CDCl3, experimental)	1994762426@qq.com	Nanjing University of Chinese Medicine	Jing Guan	2024-05-02	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
chrysogenum		Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Xanthones

Alternative Parents

Substituents

Xanthone
Chromone
Tricarboxylic acid or derivatives
Aryl alkyl ketone
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
Beta-hydroxy acid
Alkyl aryl ether
Benzenoid
Hydroxy acid
Gamma butyrolactone
Vinylogous acid
Methyl ester
Tetrahydrofuran
Secondary alcohol
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Polyol
Ether
Enol
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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	2.93	ChemAxon
pKa (Strongest Acidic)	7.43	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	212.42 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	154.18 m³·mol⁻¹	ChemAxon
Polarizability	62.47 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

71048850

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Guan J, Zhang PP, Wang XH, Guo YT, Zhang ZJ, Li P, Lin LP: Structure-Guided Discovery of Diverse Cytotoxic Dimeric Xanthones/Chromanones from Penicillium chrysogenum C-7-2-1 and Their Interconversion Properties. J Nat Prod. 2024 Feb 23;87(2):238-251. doi: 10.1021/acs.jnatprod.3c00907. Epub 2024 Feb 14. [PubMed:38354306 ]

Showing NP-Card for chrysoxanthone E (NP0332934)

MOL for NP0332934 (chrysoxanthone E)

3D MOL for NP0332934 (chrysoxanthone E)

3D SDF for NP0332934 (chrysoxanthone E)

3D-SDF for NP0332934 (chrysoxanthone E)

PDB for NP0332934 (chrysoxanthone E)

3D PDB for NP0332934 (chrysoxanthone E)

SMILES for NP0332934 (chrysoxanthone E)

INCHI for NP0332934 (chrysoxanthone E)

Structure for NP0332934 (chrysoxanthone E)

3D Structure for NP0332934 (chrysoxanthone E)