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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:42:47 UTC

Update Date

2022-03-07 02:52:57 UTC

HMDB ID

HMDB0031385

Secondary Accession Numbers

HMDB31385

Metabolite Identification

Common Name

(±)-Dulciol E

Description

(±)-Dulciol E 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 (±)-Dulciol E.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0031385
     RDKit          3D
(±)-Dulciol E
 39 42  0  0  0  0  0  0  0  0999 V2000
   -3.8773    1.9304    0.4175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8357    1.0201   -0.1562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5190    1.4137    0.1847 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7230    0.2760    0.0741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5016   -0.8623    0.1201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9024   -2.0894    0.0266 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4631   -2.2059   -0.1125 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0420   -3.4579   -0.2047 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2663   -1.0743   -0.1611 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5819   -1.1827   -0.2950 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3403   -0.1063   -0.3407 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7065   -0.2126   -0.4795 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2949   -1.4568   -0.5724 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5114    0.9072   -0.5287 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9691    2.1756   -0.4397 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6144    2.2905   -0.3017 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8122    1.1675   -0.2530 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4551    1.2972   -0.1144 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8853    2.4088   -0.0270 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6645    0.1593   -0.0672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9215   -0.3919    0.2743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8434   -1.1500   -0.6487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3138   -0.6309    1.6824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4121    2.4407    1.3037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8261    1.4474    0.6481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0845    2.7332   -0.3215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8744    1.0368   -1.2842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5059   -2.9873    0.0618 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0454   -3.5602   -0.3073 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7205   -2.2836   -0.5381 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5846    0.8167   -0.6379 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5570    3.0821   -0.4731 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1611    3.2874   -0.2291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8055   -0.6805   -1.6572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5224   -2.1966   -0.6539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8605   -1.1024   -0.2068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4814   -0.6287    2.4111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1071    0.0386    2.0644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7580   -1.6686    1.7428 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
  5 21  1  0
 21 22  1  0
 21 23  1  0
 21  2  1  0
 20  4  1  0
 20  9  2  0
 17 11  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  6 28  1  0
  8 29  1  0
 13 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
 22 34  1  0
 22 35  1  0
 22 36  1  0
 23 37  1  0
 23 38  1  0
 23 39  1  0
M  END


  Mrv0541 05061305552D          

 23 26  0  0  0  0            999 V2000
    1.6569    0.3314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3686   -0.8676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9141   -1.8275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0117   -0.0886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2059    0.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2613   -0.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1753   -2.1717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2662   -0.2248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6497   -0.5209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9257   -1.3854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7051   -1.4843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9811   -2.3488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2877   -0.9531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8439   -0.3438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8993   -1.3072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4820   -0.7761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5373   -1.7395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1744   -1.0447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9546   -2.2706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2306   -3.1351    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5944    0.4425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0744   -0.0588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3431   -1.9165    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  6  4  1  0  0  0  0
  8  1  1  0  0  0  0
  9  5  1  0  0  0  0
 10  7  2  0  0  0  0
 11  6  2  0  0  0  0
 12  7  1  0  0  0  0
 14  9  1  0  0  0  0
 14 13  1  0  0  0  0
 15  9  2  0  0  0  0
 15 11  1  0  0  0  0
 16 10  1  0  0  0  0
 16 13  2  0  0  0  0
 17 12  2  0  0  0  0
 17 13  1  0  0  0  0
 18  2  1  0  0  0  0
 18  3  1  0  0  0  0
 18  8  1  0  0  0  0
 18 10  1  0  0  0  0
 19 11  1  0  0  0  0
 20 12  1  0  0  0  0
 21 14  2  0  0  0  0
 22  8  1  0  0  0  0
 22 16  1  0  0  0  0
 23 15  1  0  0  0  0
 23 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0031385

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1OC2=C3C(=O)C4=C(OC3=C(O)C=C2C1(C)C)C(O)=CC=C4

> <INCHI_IDENTIFIER>
InChI=1S/C18H16O5/c1-8-18(2,3)10-7-12(20)17-13(16(10)22-8)14(21)9-5-4-6-11(19)15(9)23-17/h4-8,19-20H,1-3H3

> <INCHI_KEY>
WJPITGSTUAHZBK-UHFFFAOYSA-N

> <FORMULA>
C18H16O5

> <MOLECULAR_WEIGHT>
312.3166

> <EXACT_MASS>
312.099773622

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
32.71834543230394

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7-dihydroxy-2,3,3-trimethyl-2H,3H,11H-furo[2,3-a]xanthen-11-one

> <ALOGPS_LOGP>
4.16

> <JCHEM_LOGP>
3.394275518666667

> <ALOGPS_LOGS>
-3.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.515262951402928

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.741434736903474

> <JCHEM_PKA_STRONGEST_BASIC>
-4.911044464396932

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
83.8394

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.20e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,7-dihydroxy-2,3,3-trimethyl-2H-furo[2,3-a]xanthen-11-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0031385
     RDKit          3D
(±)-Dulciol E
 39 42  0  0  0  0  0  0  0  0999 V2000
   -3.8773    1.9304    0.4175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8357    1.0201   -0.1562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5190    1.4137    0.1847 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7230    0.2760    0.0741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5016   -0.8623    0.1201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9024   -2.0894    0.0266 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4631   -2.2059   -0.1125 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0420   -3.4579   -0.2047 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2663   -1.0743   -0.1611 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5819   -1.1827   -0.2950 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3403   -0.1063   -0.3407 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7065   -0.2126   -0.4795 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2949   -1.4568   -0.5724 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5114    0.9072   -0.5287 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9691    2.1756   -0.4397 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6144    2.2905   -0.3017 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8122    1.1675   -0.2530 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4551    1.2972   -0.1144 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8853    2.4088   -0.0270 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6645    0.1593   -0.0672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9215   -0.3919    0.2743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8434   -1.1500   -0.6487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3138   -0.6309    1.6824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4121    2.4407    1.3037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8261    1.4474    0.6481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0845    2.7332   -0.3215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8744    1.0368   -1.2842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5059   -2.9873    0.0618 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0454   -3.5602   -0.3073 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7205   -2.2836   -0.5381 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5846    0.8167   -0.6379 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5570    3.0821   -0.4731 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1611    3.2874   -0.2291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8055   -0.6805   -1.6572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5224   -2.1966   -0.6539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8605   -1.1024   -0.2068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4814   -0.6287    2.4111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1071    0.0386    2.0644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7580   -1.6686    1.7428 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
  5 21  1  0
 21 22  1  0
 21 23  1  0
 21  2  1  0
 20  4  1  0
 20  9  2  0
 17 11  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  6 28  1  0
  8 29  1  0
 13 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
 22 34  1  0
 22 35  1  0
 22 36  1  0
 23 37  1  0
 23 38  1  0
 23 39  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       3.093   0.619   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.555  -1.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.573  -3.411   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.089  -0.165   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.584   0.165   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.554  -1.633   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.927  -4.054   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.230  -0.420   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.546  -0.972   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.461  -2.586   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.516  -2.771   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.431  -4.384   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.004  -1.779   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.042  -0.642   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.012  -2.440   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.500  -1.449   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.470  -3.247   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.059  -1.950   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      12.982  -4.238   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       7.897  -5.852   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       8.576   0.826   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       5.739  -0.110   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       9.974  -3.577   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2   18                                                            
CONECT    3   18                                                            
CONECT    4    5    6                                                       
CONECT    5    4    9                                                       
CONECT    6    4   11                                                       
CONECT    7   10   12                                                       
CONECT    8    1   18   22                                                  
CONECT    9    5   14   15                                                  
CONECT   10    7   16   18                                                  
CONECT   11    6   15   19                                                  
CONECT   12    7   17   20                                                  
CONECT   13   14   16   17                                                  
CONECT   14    9   13   21                                                  
CONECT   15    9   11   23                                                  
CONECT   16   10   13   22                                                  
CONECT   17   12   13   23                                                  
CONECT   18    2    3    8   10                                             
CONECT   19   11                                                            
CONECT   20   12                                                            
CONECT   21   14                                                            
CONECT   22    8   16                                                       
CONECT   23   15   17                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

COMPND    HMDB0031385
HETATM    1  C1  UNL     1      -3.877   1.930   0.417  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.836   1.020  -0.156  1.00  0.00           C  
HETATM    3  O1  UNL     1      -1.519   1.414   0.185  1.00  0.00           O  
HETATM    4  C3  UNL     1      -0.723   0.276   0.074  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.502  -0.862   0.120  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.902  -2.089   0.027  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.463  -2.206  -0.112  1.00  0.00           C  
HETATM    8  O2  UNL     1       1.042  -3.458  -0.205  1.00  0.00           O  
HETATM    9  C7  UNL     1       1.266  -1.074  -0.161  1.00  0.00           C  
HETATM   10  O3  UNL     1       2.582  -1.183  -0.295  1.00  0.00           O  
HETATM   11  C8  UNL     1       3.340  -0.106  -0.341  1.00  0.00           C  
HETATM   12  C9  UNL     1       4.707  -0.213  -0.480  1.00  0.00           C  
HETATM   13  O4  UNL     1       5.295  -1.457  -0.572  1.00  0.00           O  
HETATM   14  C10 UNL     1       5.511   0.907  -0.529  1.00  0.00           C  
HETATM   15  C11 UNL     1       4.969   2.176  -0.440  1.00  0.00           C  
HETATM   16  C12 UNL     1       3.614   2.290  -0.302  1.00  0.00           C  
HETATM   17  C13 UNL     1       2.812   1.168  -0.253  1.00  0.00           C  
HETATM   18  C14 UNL     1       1.455   1.297  -0.114  1.00  0.00           C  
HETATM   19  O5  UNL     1       0.885   2.409  -0.027  1.00  0.00           O  
HETATM   20  C15 UNL     1       0.665   0.159  -0.067  1.00  0.00           C  
HETATM   21  C16 UNL     1      -2.921  -0.392   0.274  1.00  0.00           C  
HETATM   22  C17 UNL     1      -3.843  -1.150  -0.649  1.00  0.00           C  
HETATM   23  C18 UNL     1      -3.314  -0.631   1.682  1.00  0.00           C  
HETATM   24  H1  UNL     1      -3.412   2.441   1.304  1.00  0.00           H  
HETATM   25  H2  UNL     1      -4.826   1.447   0.648  1.00  0.00           H  
HETATM   26  H3  UNL     1      -4.084   2.733  -0.322  1.00  0.00           H  
HETATM   27  H4  UNL     1      -2.874   1.037  -1.284  1.00  0.00           H  
HETATM   28  H5  UNL     1      -1.506  -2.987   0.062  1.00  0.00           H  
HETATM   29  H6  UNL     1       2.045  -3.560  -0.307  1.00  0.00           H  
HETATM   30  H7  UNL     1       4.721  -2.284  -0.538  1.00  0.00           H  
HETATM   31  H8  UNL     1       6.585   0.817  -0.638  1.00  0.00           H  
HETATM   32  H9  UNL     1       5.557   3.082  -0.473  1.00  0.00           H  
HETATM   33  H10 UNL     1       3.161   3.287  -0.229  1.00  0.00           H  
HETATM   34  H11 UNL     1      -3.805  -0.681  -1.657  1.00  0.00           H  
HETATM   35  H12 UNL     1      -3.522  -2.197  -0.654  1.00  0.00           H  
HETATM   36  H13 UNL     1      -4.860  -1.102  -0.207  1.00  0.00           H  
HETATM   37  H14 UNL     1      -2.481  -0.629   2.411  1.00  0.00           H  
HETATM   38  H15 UNL     1      -4.107   0.039   2.064  1.00  0.00           H  
HETATM   39  H16 UNL     1      -3.758  -1.669   1.743  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3   21   27
CONECT    3    4
CONECT    4    5    5   20
CONECT    5    6   21
CONECT    6    7    7   28
CONECT    7    8    9
CONECT    8   29
CONECT    9   10   20   20
CONECT   10   11
CONECT   11   12   12   17
CONECT   12   13   14
CONECT   13   30
CONECT   14   15   15   31
CONECT   15   16   32
CONECT   16   17   17   33
CONECT   17   18
CONECT   18   19   19   20
CONECT   21   22   23
CONECT   22   34   35   36
CONECT   23   37   38   39
END

HMDB0031385
     RDKit          3D
(±)-Dulciol E
 39 42  0  0  0  0  0  0  0  0999 V2000
   -3.8773    1.9304    0.4175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8357    1.0201   -0.1562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5190    1.4137    0.1847 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7230    0.2760    0.0741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5016   -0.8623    0.1201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9024   -2.0894    0.0266 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4631   -2.2059   -0.1125 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0420   -3.4579   -0.2047 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2663   -1.0743   -0.1611 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5819   -1.1827   -0.2950 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3403   -0.1063   -0.3407 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7065   -0.2126   -0.4795 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2949   -1.4568   -0.5724 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5114    0.9072   -0.5287 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9691    2.1756   -0.4397 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6144    2.2905   -0.3017 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8122    1.1675   -0.2530 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4551    1.2972   -0.1144 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8853    2.4088   -0.0270 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6645    0.1593   -0.0672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9215   -0.3919    0.2743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8434   -1.1500   -0.6487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3138   -0.6309    1.6824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4121    2.4407    1.3037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8261    1.4474    0.6481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0845    2.7332   -0.3215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8744    1.0368   -1.2842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5059   -2.9873    0.0618 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0454   -3.5602   -0.3073 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7205   -2.2836   -0.5381 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5846    0.8167   -0.6379 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5570    3.0821   -0.4731 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1611    3.2874   -0.2291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8055   -0.6805   -1.6572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5224   -2.1966   -0.6539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8605   -1.1024   -0.2068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4814   -0.6287    2.4111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1071    0.0386    2.0644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7580   -1.6686    1.7428 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
  5 21  1  0
 21 22  1  0
 21 23  1  0
 21  2  1  0
 20  4  1  0
 20  9  2  0
 17 11  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  6 28  1  0
  8 29  1  0
 13 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
 22 34  1  0
 22 35  1  0
 22 36  1  0
 23 37  1  0
 23 38  1  0
 23 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₈H₁₆O₅

Average Molecular Weight

312.3166

Monoisotopic Molecular Weight

312.099773622

IUPAC Name

5,7-dihydroxy-2,3,3-trimethyl-2H,3H,11H-furo[2,3-a]xanthen-11-one

Traditional Name

5,7-dihydroxy-2,3,3-trimethyl-2H-furo[2,3-a]xanthen-11-one

CAS Registry Number

175617-27-3

SMILES

CC1OC2=C3C(=O)C4=C(OC3=C(O)C=C2C1(C)C)C(O)=CC=C4

InChI Identifier

InChI=1S/C18H16O5/c1-8-18(2,3)10-7-12(20)17-13(16(10)22-8)14(21)9-5-4-6-11(19)15(9)23-17/h4-8,19-20H,1-3H3

InChI Key

WJPITGSTUAHZBK-UHFFFAOYSA-N

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
Coumaran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous ester
Ether
Oxacycle
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0031385)
Cell membrane (HMDB: HMDB0031385)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031385)

Source

Endogenous

Endogenous (HMDB: HMDB0031385)

Plant

Plant (HMDB: HMDB0031385)

Exogenous

Food

Food (HMDB: HMDB0031385)

Fruit

Fruits (FooDB: FOOD00871)

Exogenous (HMDB: HMDB0031385)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.3 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.042 g/L	ALOGPS
logP	4.16	ALOGPS
logP	3.39	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	7.74	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	83.84 m³·mol⁻¹	ChemAxon
Polarizability	32.72 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	173.259	31661259
DarkChem	[M-H]-	174.379	31661259
DeepCCS	[M+H]+	177.669	30932474
DeepCCS	[M-H]-	175.312	30932474
DeepCCS	[M-2H]-	209.313	30932474
DeepCCS	[M+Na]+	184.54	30932474
AllCCS	[M+H]+	171.3	32859911
AllCCS	[M+H-H2O]+	167.8	32859911
AllCCS	[M+NH4]+	174.6	32859911
AllCCS	[M+Na]+	175.5	32859911
AllCCS	[M-H]-	177.4	32859911
AllCCS	[M+Na-2H]-	176.6	32859911
AllCCS	[M+HCOO]-	175.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.17 minutes	32390414
Predicted by Siyang on May 30, 2022	15.4866 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.21 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2527.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	401.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	197.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	214.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	378.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	728.5 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	895.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	77.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1177.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	557.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1700.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	459.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	464.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	351.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	302.0 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	20.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(??)-Dulciol E	CC1OC2=C3C(=O)C4=C(OC3=C(O)C=C2C1(C)C)C(O)=CC=C4	3748.2	Standard polar	33892256
(??)-Dulciol E	CC1OC2=C3C(=O)C4=C(OC3=C(O)C=C2C1(C)C)C(O)=CC=C4	2644.8	Standard non polar	33892256
(??)-Dulciol E	CC1OC2=C3C(=O)C4=C(OC3=C(O)C=C2C1(C)C)C(O)=CC=C4	2795.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(??)-Dulciol E,1TMS,isomer #1	CC1OC2=C(C=C(O[Si](C)(C)C)C3=C2C(=O)C2=CC=CC(O)=C2O3)C1(C)C	2989.1	Semi standard non polar	33892256
(??)-Dulciol E,1TMS,isomer #2	CC1OC2=C(C=C(O)C3=C2C(=O)C2=CC=CC(O[Si](C)(C)C)=C2O3)C1(C)C	2970.8	Semi standard non polar	33892256
(??)-Dulciol E,2TMS,isomer #1	CC1OC2=C(C=C(O[Si](C)(C)C)C3=C2C(=O)C2=CC=CC(O[Si](C)(C)C)=C2O3)C1(C)C	3063.3	Semi standard non polar	33892256
(??)-Dulciol E,1TBDMS,isomer #1	CC1OC2=C(C=C(O[Si](C)(C)C(C)(C)C)C3=C2C(=O)C2=CC=CC(O)=C2O3)C1(C)C	3238.0	Semi standard non polar	33892256
(??)-Dulciol E,1TBDMS,isomer #2	CC1OC2=C(C=C(O)C3=C2C(=O)C2=CC=CC(O[Si](C)(C)C(C)(C)C)=C2O3)C1(C)C	3207.0	Semi standard non polar	33892256
(??)-Dulciol E,2TBDMS,isomer #1	CC1OC2=C(C=C(O[Si](C)(C)C(C)(C)C)C3=C2C(=O)C2=CC=CC(O[Si](C)(C)C(C)(C)C)=C2O3)C1(C)C	3529.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (±)-Dulciol E GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-0290000000-cd91827cfa3cd0a0904a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (±)-Dulciol E GC-MS (2 TMS) - 70eV, Positive	splash10-007o-5359600000-f9c5f0024e09255ad076	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (±)-Dulciol E GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Dulciol E 10V, Positive-QTOF	splash10-03di-0019000000-19ccbd960377f36e4a0a	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Dulciol E 20V, Positive-QTOF	splash10-03di-0096000000-3321a93535dc24d1262e	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Dulciol E 40V, Positive-QTOF	splash10-014r-9570000000-58205266091a7704faa7	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Dulciol E 10V, Negative-QTOF	splash10-03di-0009000000-c2274bc14e035f01aa93	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Dulciol E 20V, Negative-QTOF	splash10-03di-0019000000-814c4184765d99f03aaa	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Dulciol E 40V, Negative-QTOF	splash10-00kr-7970000000-2296b2a2da53a95e3b02	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Dulciol E 10V, Negative-QTOF	splash10-03di-0009000000-a968dea78994eb63447d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Dulciol E 20V, Negative-QTOF	splash10-03di-0029000000-5e6eff905389f4060f26	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Dulciol E 40V, Negative-QTOF	splash10-00kg-2390000000-a917eb022f7c792d9cc0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Dulciol E 10V, Positive-QTOF	splash10-03di-0009000000-0c9c5e8761c67e87c624	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Dulciol E 20V, Positive-QTOF	splash10-03di-0039000000-6d78268c99f601b9f287	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Dulciol E 40V, Positive-QTOF	splash10-000i-0190000000-3b407c7fdeaccbcea7a2	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB003452

KNApSAcK ID

Not Available

Chemspider ID

8909200

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10733867

PDB ID

Not Available

ChEBI ID

173262

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1826051

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for (±)-Dulciol E (HMDB0031385)

MOL for HMDB0031385 ((±)-Dulciol E)

3D MOL for HMDB0031385 ((±)-Dulciol E)

3D SDF for HMDB0031385 ((±)-Dulciol E)

3D-SDF for HMDB0031385 ((±)-Dulciol E)

PDB for HMDB0031385 ((±)-Dulciol E)

3D PDB for HMDB0031385 ((±)-Dulciol E)

SMILES for HMDB0031385 ((±)-Dulciol E)

INCHI for HMDB0031385 ((±)-Dulciol E)

Structure for HMDB0031385 ((±)-Dulciol E)

3D Structure for HMDB0031385 ((±)-Dulciol E)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra