NP-MRD: Showing NP-Card for chrysoxanthone D (NP0332933)

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Record Information

Version

2.0

Created at

2024-05-02 07:40:56 UTC

Updated at

2024-09-03 04:20:42 UTC

NP-MRD ID

NP0332933

Natural Product DOI

https://doi.org/10.57994/2214

Secondary Accession Numbers

None

Natural Product Identification

Common Name

chrysoxanthone D

Description

Chrysoxanthone D belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. chrysoxanthone D was first documented in 2024 (PMID: 38354306). Based on a literature review very few articles have been published on chrysoxanthone D.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01142310172D          

 47 52  0  0  1  0            999 V2000
    7.1447    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 C   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    0.8250    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
    5.8999   -1.0445    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0995   -1.8450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3999   -2.2822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7679   -1.7519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0769   -0.9869    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6398   -0.2873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3423   -3.1052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5776   -0.2851    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9605   -1.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7730   -0.9012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3033   -1.5332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6784   -1.8197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    1.2375    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    0.8250    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    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    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
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    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
    2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  1  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    0.8250    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    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    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    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2295   -1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   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
  4  5  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 10  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  1  6  0  0  0
  9 13  2  0  0  0  0
  7 14  1  6  0  0  0
  6 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 15 18  2  0  0  0  0
  6 19  1  6  0  0  0
 19 20  1  0  0  0  0
  3 20  1  0  0  0  0
 20 21  2  0  0  0  0
  4 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 23 29  1  0  0  0  0
 27 30  1  0  0  0  0
 31 30  1  0  0  0  0
 31 32  1  6  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 32 35  2  0  0  0  0
 36 31  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  1  0  0  0
 37 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 40 42  2  0  0  0  0
 31 42  1  0  0  0  0
 42 43  1  0  0  0  0
 26 43  1  0  0  0  0
 43 44  2  0  0  0  0
 36 45  1  6  0  0  0
 22 46  1  0  0  0  0
 46 47  2  0  0  0  0
  2 47  1  0  0  0  0
M  END


  Mrv2104 01142310172D          

 47 52  0  0  1  0            999 V2000
    7.1447    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 C   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    0.8250    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
    5.8999   -1.0445    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0995   -1.8450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3999   -2.2822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7679   -1.7519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0769   -0.9869    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6398   -0.2873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3423   -3.1052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5776   -0.2851    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9605   -1.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7730   -0.9012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3033   -1.5332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6784   -1.8197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    1.2375    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    0.8250    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    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    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
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    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
    2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  1  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    0.8250    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    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    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    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2295   -1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   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
  4  5  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 10  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  1  6  0  0  0
  9 13  2  0  0  0  0
  7 14  1  6  0  0  0
  6 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 15 18  2  0  0  0  0
  6 19  1  6  0  0  0
 19 20  1  0  0  0  0
  3 20  1  0  0  0  0
 20 21  2  0  0  0  0
  4 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 23 29  1  0  0  0  0
 27 30  1  0  0  0  0
 31 30  1  0  0  0  0
 31 32  1  6  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 32 35  2  0  0  0  0
 36 31  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  1  0  0  0
 37 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 40 42  2  0  0  0  0
 31 42  1  0  0  0  0
 42 43  1  0  0  0  0
 26 43  1  0  0  0  0
 43 44  2  0  0  0  0
 36 45  1  6  0  0  0
 22 46  1  0  0  0  0
 46 47  2  0  0  0  0
  2 47  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0332933

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

> <INCHI_KEY>
GHQRQPAIRKIZDP-AKBFVYQBSA-N

> <FORMULA>
C32H30O14

> <MOLECULAR_WEIGHT>
638.578

> <EXACT_MASS>
638.163555646

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
61.29209634115305

> <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-8-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>
8.409479084641145

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.455419553033514

> <JCHEM_PKA_STRONGEST_BASIC>
-3.493185660254414

> <JCHEM_POLAR_SURFACE_AREA>
212.41999999999996

> <JCHEM_REFRACTIVITY>
154.1781

> <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-8-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  O   UNK     0      13.337   4.620   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      10.669  -0.000   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.013  -1.950   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      11.386  -3.444   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      10.080  -4.260   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.900  -3.270   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.477  -1.842   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.661  -0.536   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       9.972  -5.796   0.000  0.00  0.00           O+0
HETATM   14  H   UNK     0      10.411  -0.532   0.000  0.00  0.00           H+0
HETATM   15  C   UNK     0      12.993  -1.950   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      14.510  -1.682   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      15.500  -2.862   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      12.466  -3.397   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      13.337  -0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.337   1.540   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      14.670   2.310   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.667  -1.540   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       5.335  -1.540   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0       0.428  -2.016   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   47                                                  
CONECT    3    2    4   20                                                  
CONECT    4    3    5   22                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   15   19                                             
CONECT    7    6    8   11   14                                             
CONECT    8    7    9                                                       
CONECT    9    8   10   13                                                  
CONECT   10    9   11                                                       
CONECT   11   10    7   12                                                  
CONECT   12   11                                                            
CONECT   13    9                                                            
CONECT   14    7                                                            
CONECT   15    6   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   15                                                            
CONECT   19    6   20                                                       
CONECT   20   19    3   21                                                  
CONECT   21   20                                                            
CONECT   22    4   23   46                                                  
CONECT   23   22   24   29                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   43                                                  
CONECT   27   26   28   30                                                  
CONECT   28   27   29                                                       
CONECT   29   28   23                                                       
CONECT   30   27   31                                                       
CONECT   31   30   32   36   42                                             
CONECT   32   31   33   35                                                  
CONECT   33   32   34                                                       
CONECT   34   33                                                            
CONECT   35   32                                                            
CONECT   36   31   37   45                                                  
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40                                                       
CONECT   40   39   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   31   43                                                  
CONECT   43   42   26   44                                                  
CONECT   44   43                                                            
CONECT   45   36                                                            
CONECT   46   22   47                                                       
CONECT   47   46    2                                                       
MASTER        0    0    0    0    0    0    0    0   47    0  104    0
END

View in JSmol

Synonyms

Not Available

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

InChI Key

GHQRQPAIRKIZDP-AKBFVYQBSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500 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

This compound belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpenoid
Diterpene lactone
Xanthone
Xanthene
Dibenzopyran
Fatty alcohol ester
Chromone
1-benzopyran
Benzopyran
Chromane
Tricarboxylic acid or derivatives
Aryl alkyl ketone
Aryl ketone
Gamma-keto acid
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Dihydropyranone
Beta-hydroxy acid
Alkyl aryl ether
Fatty acyl
Alpha-branched alpha,beta-unsaturated-ketone
Benzenoid
Pyran
Oxane
Monosaccharide
Keto acid
Hydroxy acid
Gamma butyrolactone
Beta-hydroxy ketone
Vinylogous acid
Alpha,beta-unsaturated ketone
Methyl ester
Tetrahydrofuran
Enone
Acryloyl-group
Secondary alcohol
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
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)	7.46	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	61.29 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

Not Available

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 D (NP0332933)

MOL for NP0332933 (chrysoxanthone D)

3D MOL for NP0332933 (chrysoxanthone D)

3D SDF for NP0332933 (chrysoxanthone D)

3D-SDF for NP0332933 (chrysoxanthone D)

PDB for NP0332933 (chrysoxanthone D)

3D PDB for NP0332933 (chrysoxanthone D)

SMILES for NP0332933 (chrysoxanthone D)

INCHI for NP0332933 (chrysoxanthone D)

Structure for NP0332933 (chrysoxanthone D)

3D Structure for NP0332933 (chrysoxanthone D)