MiMeDB: Showing metabocard for Pestalofone E (MMDBc0005715)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-14 23:13:15 UTC

Update Date

2022-08-31 06:24:24 UTC

Metabolite ID

MMDBc0005715

Metabolite Identification

Common Name

Pestalofone E

Description

Pestalofone E belongs to the class of organic compounds known as 4-prenylated xanthones. These are organic compounds containing a C5-isoprenoid group linked to a xanthone moiety at the 4-position. Xanthone is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring that carries a ketone group. Based on a literature review very few articles have been published on Pestalofone E.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152101132D          

 48 52  0  0  1  0            999 V2000
   -0.5105    5.5126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7270    4.7981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2989    6.4311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1113    6.2878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7646    7.4675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5413   11.4870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7270    6.2271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5520    6.2271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5470    7.8383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3878    9.1612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1396    7.7540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7363    6.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3935    4.6876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3145    5.5126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0167    7.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6416    6.9198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6699    8.3860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3595    7.6951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4541    6.7766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5753    9.3045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6790    4.2751    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3272    7.8973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2060    5.3693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0450    8.6725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7022    8.1838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8898    8.3271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2325    8.8158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9844    7.4085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9645    4.6876    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2931   10.0798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6790    5.9251    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3935    5.5126    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9645    5.5126    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2042    7.3496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6790    3.4501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4881    4.5941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6076    9.1023    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9504    9.5910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4807   10.2230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6790    6.7501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6757    6.2878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4824    8.2427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8234   10.7117    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7969    7.2653    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2501    5.1001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9645    3.8626    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6790    5.1001    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8707    6.0901    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0  0  0  0
 14  1  1  0  0  0  0
 14  2  1  0  0  0  0
 14  7  2  0  0  0  0
 15  3  1  0  0  0  0
 15  9  1  0  0  0  0
 16  4  1  0  0  0  0
 17 10  2  0  0  0  0
 17 11  1  0  0  0  0
 18  9  1  0  0  0  0
 18 16  2  0  0  0  0
 19 12  1  0  0  0  0
 19 16  1  0  0  0  0
 20 10  1  0  0  0  0
 21 13  1  0  0  0  0
 22 11  2  0  0  0  0
 23 12  1  0  0  0  0
 24 20  2  0  0  0  0
 24 22  1  0  0  0  0
 26 18  1  0  0  0  0
 26 25  2  0  0  0  0
 27 24  1  0  0  0  0
 27 25  1  0  0  0  0
 28 19  2  0  0  0  0
 28 25  1  0  0  0  0
 29 21  1  0  0  0  0
 30 20  1  0  0  0  0
 32 13  1  0  0  0  0
 32 23  1  1  0  0  0
 32 31  1  0  0  0  0
 33  8  1  1  0  0  0
 33 29  1  0  0  0  0
 33 31  1  0  0  0  0
 34 15  2  0  0  0  0
 21 35  1  6  0  0  0
 36 23  2  0  0  0  0
 37 26  1  0  0  0  0
 38 27  2  0  0  0  0
 39 30  2  0  0  0  0
 31 40  1  6  0  0  0
 32 41  1  6  0  0  0
 42  5  1  0  0  0  0
 42 17  1  0  0  0  0
 43  6  1  0  0  0  0
 43 30  1  0  0  0  0
 44 22  1  0  0  0  0
 44 28  1  0  0  0  0
 45 29  1  0  0  0  0
 45 33  1  0  0  0  0
 21 46  1  1  0  0  0
 29 47  1  1  0  0  0
 31 48  1  1  0  0  0
M  END


  Mrv1652305152101132D          

 48 52  0  0  1  0            999 V2000
   -0.5105    5.5126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7270    4.7981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2989    6.4311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1113    6.2878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7646    7.4675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5413   11.4870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7270    6.2271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5520    6.2271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5470    7.8383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3878    9.1612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1396    7.7540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7363    6.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3935    4.6876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3145    5.5126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0167    7.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6416    6.9198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6699    8.3860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3595    7.6951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4541    6.7766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5753    9.3045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6790    4.2751    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3272    7.8973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2060    5.3693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0450    8.6725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7022    8.1838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8898    8.3271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2325    8.8158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9844    7.4085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9645    4.6876    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2931   10.0798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6790    5.9251    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3935    5.5126    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9645    5.5126    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2042    7.3496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6790    3.4501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4881    4.5941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6076    9.1023    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9504    9.5910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4807   10.2230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6790    6.7501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6757    6.2878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4824    8.2427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8234   10.7117    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7969    7.2653    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2501    5.1001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9645    3.8626    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6790    5.1001    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8707    6.0901    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0  0  0  0
 14  1  1  0  0  0  0
 14  2  1  0  0  0  0
 14  7  2  0  0  0  0
 15  3  1  0  0  0  0
 15  9  1  0  0  0  0
 16  4  1  0  0  0  0
 17 10  2  0  0  0  0
 17 11  1  0  0  0  0
 18  9  1  0  0  0  0
 18 16  2  0  0  0  0
 19 12  1  0  0  0  0
 19 16  1  0  0  0  0
 20 10  1  0  0  0  0
 21 13  1  0  0  0  0
 22 11  2  0  0  0  0
 23 12  1  0  0  0  0
 24 20  2  0  0  0  0
 24 22  1  0  0  0  0
 26 18  1  0  0  0  0
 26 25  2  0  0  0  0
 27 24  1  0  0  0  0
 27 25  1  0  0  0  0
 28 19  2  0  0  0  0
 28 25  1  0  0  0  0
 29 21  1  0  0  0  0
 30 20  1  0  0  0  0
 32 13  1  0  0  0  0
 32 23  1  1  0  0  0
 32 31  1  0  0  0  0
 33  8  1  1  0  0  0
 33 29  1  0  0  0  0
 33 31  1  0  0  0  0
 34 15  2  0  0  0  0
 21 35  1  6  0  0  0
 36 23  2  0  0  0  0
 37 26  1  0  0  0  0
 38 27  2  0  0  0  0
 39 30  2  0  0  0  0
 31 40  1  6  0  0  0
 32 41  1  6  0  0  0
 42  5  1  0  0  0  0
 42 17  1  0  0  0  0
 43  6  1  0  0  0  0
 43 30  1  0  0  0  0
 44 22  1  0  0  0  0
 44 28  1  0  0  0  0
 45 29  1  0  0  0  0
 45 33  1  0  0  0  0
 21 46  1  1  0  0  0
 29 47  1  1  0  0  0
 31 48  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0005715

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@]12O[C@]1(CC=C(C)C)[C@]([H])(O)[C@](O)(C[C@]2([H])O)C(=O)CC1=C2OC3=CC(OC)=CC(C(=O)OC)=C3C(=O)C2=C(O)C(CC(C)=O)=C1C

> <INCHI_IDENTIFIER>
InChI=1S/C33H36O12/c1-14(2)7-8-33-29(45-33)21(35)13-32(41,31(33)40)23(36)12-19-16(4)18(9-15(3)34)26(37)25-27(38)24-20(30(39)43-6)10-17(42-5)11-22(24)44-28(19)25/h7,10-11,21,29,31,35,37,40-41H,8-9,12-13H2,1-6H3/t21-,29-,31+,32-,33-/m0/s1

> <INCHI_KEY>
FYULFHVQQBWSCF-JRLFQTPXSA-N

> <FORMULA>
C33H36O12

> <MOLECULAR_WEIGHT>
624.639

> <EXACT_MASS>
624.220676599

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
63.75694613578222

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 8-hydroxy-3-methoxy-6-methyl-9-oxo-5-{2-oxo-2-[(1R,2R,3R,5S,6S)-2,3,5-trihydroxy-1-(3-methylbut-2-en-1-yl)-7-oxabicyclo[4.1.0]heptan-3-yl]ethyl}-7-(2-oxopropyl)-9H-xanthene-1-carboxylate

> <ALOGPS_LOGP>
1.93

> <JCHEM_LOGP>
3.173190391666666

> <ALOGPS_LOGS>
-3.90

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.635619973952908

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.253322053150788

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2428811174882846

> <JCHEM_POLAR_SURFACE_AREA>
189.41999999999996

> <JCHEM_REFRACTIVITY>
160.4556

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.89e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 8-hydroxy-3-methoxy-6-methyl-9-oxo-5-{2-oxo-2-[(1R,2R,3R,5S,6S)-2,3,5-trihydroxy-1-(3-methylbut-2-en-1-yl)-7-oxabicyclo[4.1.0]heptan-3-yl]ethyl}-7-(2-oxopropyl)xanthene-1-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-MAY-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-MAY-21         0                                  
HETATM    1  C   UNK     0      -0.953  10.290   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.357   8.956   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.291  12.005   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.808  11.737   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      16.361  13.939   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.210  21.442   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.357  11.624   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.897  11.624   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.754  14.632   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.790  17.101   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.327  14.474   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.841  11.202   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.335   8.750   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.587  10.290   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.764  13.452   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.798  12.917   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.317  15.654   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.271  14.364   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.314  12.650   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.274  17.368   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.001   7.980   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.811  14.742   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.851  10.023   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.284  16.189   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.777  15.276   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.261  15.544   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.767  16.456   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.304  13.829   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.667   8.750   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      11.747  18.816   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.001  11.060   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.335  10.290   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.667  10.290   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       2.248  13.719   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       5.001   6.440   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       8.378   8.576   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       6.734  16.991   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       9.241  17.903   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      10.231  19.083   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0       5.001  12.600   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0       6.861  11.737   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      15.834  15.386   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0      12.737  19.995   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0      10.821  13.562   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0       2.333   9.520   0.000  0.00  0.00           O+0
HETATM   46  H   UNK     0       3.667   7.210   0.000  0.00  0.00           H+0
HETATM   47  H   UNK     0       5.001   9.520   0.000  0.00  0.00           H+0
HETATM   48  H   UNK     0       3.492  11.368   0.000  0.00  0.00           H+0
CONECT    1   14                                                            
CONECT    2   14                                                            
CONECT    3   15                                                            
CONECT    4   16                                                            
CONECT    5   42                                                            
CONECT    6   43                                                            
CONECT    7    8   14                                                       
CONECT    8    7   33                                                       
CONECT    9   15   18                                                       
CONECT   10   17   20                                                       
CONECT   11   17   22                                                       
CONECT   12   19   23                                                       
CONECT   13   21   32                                                       
CONECT   14    1    2    7                                                  
CONECT   15    3    9   34                                                  
CONECT   16    4   18   19                                                  
CONECT   17   10   11   42                                                  
CONECT   18    9   16   26                                                  
CONECT   19   12   16   28                                                  
CONECT   20   10   24   30                                                  
CONECT   21   13   29   35   46                                             
CONECT   22   11   24   44                                                  
CONECT   23   12   32   36                                                  
CONECT   24   20   22   27                                                  
CONECT   25   26   27   28                                                  
CONECT   26   18   25   37                                                  
CONECT   27   24   25   38                                                  
CONECT   28   19   25   44                                                  
CONECT   29   21   33   45   47                                             
CONECT   30   20   39   43                                                  
CONECT   31   32   33   40   48                                             
CONECT   32   13   23   31   41                                             
CONECT   33    8   29   31   45                                             
CONECT   34   15                                                            
CONECT   35   21                                                            
CONECT   36   23                                                            
CONECT   37   26                                                            
CONECT   38   27                                                            
CONECT   39   30                                                            
CONECT   40   31                                                            
CONECT   41   32                                                            
CONECT   42    5   17                                                       
CONECT   43    6   30                                                       
CONECT   44   22   28                                                       
CONECT   45   29   33                                                       
CONECT   46   21                                                            
CONECT   47   29                                                            
CONECT   48   31                                                            
MASTER        0    0    0    0    0    0    0    0   48    0  104    0
END

Synonyms

Not Available

Molecular Formula

C₃₃H₃₆O₁₂

Average Mass

624.639

Monoisotopic Mass

624.220676599

IUPAC Name

methyl 8-hydroxy-3-methoxy-6-methyl-9-oxo-5-{2-oxo-2-[(1R,2R,3R,5S,6S)-2,3,5-trihydroxy-1-(3-methylbut-2-en-1-yl)-7-oxabicyclo[4.1.0]heptan-3-yl]ethyl}-7-(2-oxopropyl)-9H-xanthene-1-carboxylate

Traditional Name

methyl 8-hydroxy-3-methoxy-6-methyl-9-oxo-5-{2-oxo-2-[(1R,2R,3R,5S,6S)-2,3,5-trihydroxy-1-(3-methylbut-2-en-1-yl)-7-oxabicyclo[4.1.0]heptan-3-yl]ethyl}-7-(2-oxopropyl)xanthene-1-carboxylate

CAS Registry Number

Not Available

SMILES

[H][C@@]12O[C@]1(CC=C(C)C)[C@]([H])(O)[C@](O)(C[C@]2([H])O)C(=O)CC1=C2OC3=CC(OC)=CC(C(=O)OC)=C3C(=O)C2=C(O)C(CC(C)=O)=C1C

InChI Identifier

InChI=1S/C33H36O12/c1-14(2)7-8-33-29(45-33)21(35)13-32(41,31(33)40)23(36)12-19-16(4)18(9-15(3)34)26(37)25-27(38)24-20(30(39)43-6)10-17(42-5)11-22(24)44-28(19)25/h7,10-11,21,29,31,35,37,40-41H,8-9,12-13H2,1-6H3/t21-,29-,31+,32-,33-/m0/s1

InChI Key

FYULFHVQQBWSCF-JRLFQTPXSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 4-prenylated xanthones. These are organic compounds containing a C5-isoprenoid group linked to a xanthone moiety at the 4-position. Xanthone is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring that carries a ketone group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

4-prenylated xanthones

Alternative Parents

Substituents

4-prenylated xanthone
Chromone
M-methoxybenzoic acid or derivatives
Anisole
Alkyl aryl ether
Pyranone
Oxepane
Cyclitol or derivatives
Benzenoid
Pyran
Alpha-hydroxy ketone
Heteroaromatic compound
Vinylogous acid
Methyl ester
Tertiary alcohol
Cyclic alcohol
Carboxylic acid ester
Secondary alcohol
Ketone
Ether
Oxirane
Dialkyl ether
Polyol
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Organic oxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.079 g/L	ALOGPS
logP	1.93	ALOGPS
logP	3.17	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	8.25	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	189.42 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	160.46 m³·mol⁻¹	ChemAxon
Polarizability	63.76 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_17) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-10	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-18	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces	Metabolic reconstruction

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

23334663

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

42609855

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

van Santen JA, Poynton EF, Iskakova D, McMann E, Alsup TA, Clark TN, Fergusson CH, Fewer DP, Hughes AH, McCadden CA, Parra J, Soldatou S, Rudolf JD, Janssen EM, Duncan KR, Linington RG: The Natural Products Atlas 2.0: a database of microbially-derived natural products. Nucleic Acids Res. 2022 Jan 7;50(D1):D1317-D1323. doi: 10.1093/nar/gkab941. [PubMed:34718710 ]

Showing metabocard for Pestalofone E (MMDBc0005715)

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3D Structure for #<Metabolite:0x00007fecae503348>