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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:32:40 UTC

Update Date

2022-03-07 02:52:17 UTC

HMDB ID

HMDB0029791

Secondary Accession Numbers

HMDB29791

Metabolite Identification

Common Name

Dulciol D

Description

Dulciol D 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. Dulciol D is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review very few articles have been published on Dulciol D.

Structure

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

HMDB0029791
     RDKit          3D
Dulciol D
 41 44  0  0  0  0  0  0  0  0999 V2000
   -4.2132    2.7044    0.8524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5718    1.8765    0.0671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4576    0.4295    0.4258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4875    0.2415    1.9335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6107   -0.2915   -0.1971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1451   -0.0396   -0.0664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0037   -1.0484   -0.9797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7509   -1.4358   -1.3954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6002   -2.4607   -2.3236 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4035   -0.8309   -0.9150 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5959   -1.2409   -1.3477 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7101   -0.7107   -0.9321 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6526    0.3092   -0.0134 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8298    0.8663    0.4229 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0314    0.4058   -0.0557 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1121   -0.6206   -0.9815 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1589   -1.2570   -1.6095 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5462   -2.1993   -2.4222 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2460   -2.1197   -2.2802 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9234   -1.1713   -1.4114 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4199    0.7585    0.4567 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4225    1.6817    1.2853 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2611    0.1861    0.0057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9979    0.5892    0.4359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1566    1.5758    1.3300 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2995    3.7532    0.5983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6670    2.3762    1.7584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1150    2.2058   -0.8451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7377   -0.5473    2.2330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4658   -0.1541    2.2856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1745    1.1613    2.4339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6647   -0.0984   -1.2881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6048   -1.3779   -0.0199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5488    0.1167    0.2321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8530   -1.5738   -1.4053 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3056   -2.7605   -2.6418 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7867    1.6648    1.1420 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9909    0.8270    0.2704 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2064   -1.0751   -1.5030 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1071   -2.8786   -3.0624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5840    2.1626    1.8258 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  3  5  1  0
  3  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 13 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  2  0
 24 25  1  0
 24  6  1  0
 23 10  1  0
 20 12  1  0
 20 16  2  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  4 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  5 34  1  0
  7 35  1  0
  9 36  1  0
 14 37  1  0
 15 38  1  0
 17 39  1  0
 18 40  1  0
 25 41  1  0
M  END

  Mrv0541 02241217182D          

 25 28  0  0  0  0            999 V2000
   -3.0165    0.3992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0165   -0.4266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3023   -0.8394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5895   -0.4266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5895    0.3992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3023    0.8106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8753   -0.8394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1624   -0.4266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1624    0.3992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8753    0.8106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5519   -0.8394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2646   -0.4266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2646    0.3992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5519    0.8106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5519    1.6652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5519   -1.8303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0285    0.8394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8335    0.3757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6317    0.8367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6679    1.4656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4027    1.4877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8753    1.8303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6317   -0.9784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2986   -1.7339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4785   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  2 23  1  0  0  0  0
  3  4  2  0  0  0  0
  3 25  1  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  5  6  2  0  0  0  0
  5 10  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 11  1  0  0  0  0
  9 10  1  0  0  0  0
  9 14  1  0  0  0  0
 10 22  2  0  0  0  0
 11 12  2  0  0  0  0
 11 16  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 17  1  0  0  0  0
 14 15  1  0  0  0  0
 17 18  1  0  0  0  0
 17 20  1  0  0  0  0
 17 21  1  0  0  0  0
 18 19  2  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0029791

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)(C=C)C1=C(O)C2=C(OC3=C4OC=CC4=CC=C3C2=O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H16O5/c1-4-20(2,3)12-9-13(21)19-14(16(12)23)15(22)11-6-5-10-7-8-24-17(10)18(11)25-19/h4-9,21,23H,1H2,2-3H3

> <INCHI_KEY>
XYTVIOHQRFERMN-UHFFFAOYSA-N

> <FORMULA>
C20H16O5

> <MOLECULAR_WEIGHT>
336.338

> <EXACT_MASS>
336.099773622

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
35.22045962451248

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7,10-dihydroxy-8-(2-methylbut-3-en-2-yl)-6H-furo[3,2-c]xanthen-6-one

> <ALOGPS_LOGP>
4.62

> <JCHEM_LOGP>
4.847269927000001

> <ALOGPS_LOGS>
-3.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.107035771656216

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.302320154414664

> <JCHEM_PKA_STRONGEST_BASIC>
-4.073723813286441

> <JCHEM_POLAR_SURFACE_AREA>
79.89999999999999

> <JCHEM_REFRACTIVITY>
92.9302

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.09e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7,10-dihydroxy-8-(2-methylbut-3-en-2-yl)furo[3,2-c]xanthen-6-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0029791
     RDKit          3D
Dulciol D
 41 44  0  0  0  0  0  0  0  0999 V2000
   -4.2132    2.7044    0.8524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5718    1.8765    0.0671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4576    0.4295    0.4258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4875    0.2415    1.9335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6107   -0.2915   -0.1971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1451   -0.0396   -0.0664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0037   -1.0484   -0.9797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7509   -1.4358   -1.3954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6002   -2.4607   -2.3236 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4035   -0.8309   -0.9150 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5959   -1.2409   -1.3477 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7101   -0.7107   -0.9321 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6526    0.3092   -0.0134 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8298    0.8663    0.4229 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0314    0.4058   -0.0557 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1121   -0.6206   -0.9815 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1589   -1.2570   -1.6095 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5462   -2.1993   -2.4222 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2460   -2.1197   -2.2802 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9234   -1.1713   -1.4114 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4199    0.7585    0.4567 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4225    1.6817    1.2853 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2611    0.1861    0.0057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9979    0.5892    0.4359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1566    1.5758    1.3300 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2995    3.7532    0.5983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6670    2.3762    1.7584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1150    2.2058   -0.8451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7377   -0.5473    2.2330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4658   -0.1541    2.2856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1745    1.1613    2.4339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6647   -0.0984   -1.2881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6048   -1.3779   -0.0199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5488    0.1167    0.2321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8530   -1.5738   -1.4053 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3056   -2.7605   -2.6418 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7867    1.6648    1.1420 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9909    0.8270    0.2704 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2064   -1.0751   -1.5030 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1071   -2.8786   -3.0624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5840    2.1626    1.8258 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  3  5  1  0
  3  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 13 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  2  0
 24 25  1  0
 24  6  1  0
 23 10  1  0
 20 12  1  0
 20 16  2  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  4 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  5 34  1  0
  7 35  1  0
  9 36  1  0
 14 37  1  0
 15 38  1  0
 17 39  1  0
 18 40  1  0
 25 41  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -5.631   0.745   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.631  -0.796   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.298  -1.567   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.967  -0.796   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.967   0.745   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.298   1.513   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.634  -1.567   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.303  -0.796   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.303   0.745   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.634   1.513   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.030  -1.567   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.361  -0.796   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.361   0.745   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.030   1.513   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.030   3.108   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       1.030  -3.417   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       3.786   1.567   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.289   0.701   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.779   1.562   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.113   2.736   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.485   2.777   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.634   3.417   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -6.779  -1.826   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -6.157  -3.237   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -4.627  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   23                                                  
CONECT    3    2    4   25                                                  
CONECT    4    3    5    7                                                  
CONECT    5    4    6   10                                                  
CONECT    6    1    5                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10   14                                                  
CONECT   10    5    9   22                                                  
CONECT   11    8   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   17                                                  
CONECT   14    9   13   15                                                  
CONECT   15   14                                                            
CONECT   16   11                                                            
CONECT   17   13   18   20   21                                             
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   17                                                            
CONECT   21   17                                                            
CONECT   22   10                                                            
CONECT   23    2   24                                                       
CONECT   24   23   25                                                       
CONECT   25    3   24                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

COMPND    HMDB0029791
HETATM    1  C1  UNL     1      -4.213   2.704   0.852  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.572   1.877   0.067  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.458   0.429   0.426  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.488   0.241   1.934  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.611  -0.291  -0.197  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.145  -0.040  -0.066  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.004  -1.048  -0.980  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.751  -1.436  -1.395  1.00  0.00           C  
HETATM    9  O1  UNL     1      -0.600  -2.461  -2.324  1.00  0.00           O  
HETATM   10  C9  UNL     1       0.403  -0.831  -0.915  1.00  0.00           C  
HETATM   11  O2  UNL     1       1.596  -1.241  -1.348  1.00  0.00           O  
HETATM   12  C10 UNL     1       2.710  -0.711  -0.932  1.00  0.00           C  
HETATM   13  C11 UNL     1       2.653   0.309  -0.013  1.00  0.00           C  
HETATM   14  C12 UNL     1       3.830   0.866   0.423  1.00  0.00           C  
HETATM   15  C13 UNL     1       5.031   0.406  -0.056  1.00  0.00           C  
HETATM   16  C14 UNL     1       5.112  -0.621  -0.982  1.00  0.00           C  
HETATM   17  C15 UNL     1       6.159  -1.257  -1.609  1.00  0.00           C  
HETATM   18  C16 UNL     1       5.546  -2.199  -2.422  1.00  0.00           C  
HETATM   19  O3  UNL     1       4.246  -2.120  -2.280  1.00  0.00           O  
HETATM   20  C17 UNL     1       3.923  -1.171  -1.411  1.00  0.00           C  
HETATM   21  C18 UNL     1       1.420   0.758   0.457  1.00  0.00           C  
HETATM   22  O4  UNL     1       1.422   1.682   1.285  1.00  0.00           O  
HETATM   23  C19 UNL     1       0.261   0.186   0.006  1.00  0.00           C  
HETATM   24  C20 UNL     1      -0.998   0.589   0.436  1.00  0.00           C  
HETATM   25  O5  UNL     1      -1.157   1.576   1.330  1.00  0.00           O  
HETATM   26  H1  UNL     1      -4.299   3.753   0.598  1.00  0.00           H  
HETATM   27  H2  UNL     1      -4.667   2.376   1.758  1.00  0.00           H  
HETATM   28  H3  UNL     1      -3.115   2.206  -0.845  1.00  0.00           H  
HETATM   29  H4  UNL     1      -2.738  -0.547   2.233  1.00  0.00           H  
HETATM   30  H5  UNL     1      -4.466  -0.154   2.286  1.00  0.00           H  
HETATM   31  H6  UNL     1      -3.174   1.161   2.434  1.00  0.00           H  
HETATM   32  H7  UNL     1      -4.665  -0.098  -1.288  1.00  0.00           H  
HETATM   33  H8  UNL     1      -4.605  -1.378  -0.020  1.00  0.00           H  
HETATM   34  H9  UNL     1      -5.549   0.117   0.232  1.00  0.00           H  
HETATM   35  H10 UNL     1      -2.853  -1.574  -1.405  1.00  0.00           H  
HETATM   36  H11 UNL     1       0.306  -2.761  -2.642  1.00  0.00           H  
HETATM   37  H12 UNL     1       3.787   1.665   1.142  1.00  0.00           H  
HETATM   38  H13 UNL     1       5.991   0.827   0.270  1.00  0.00           H  
HETATM   39  H14 UNL     1       7.206  -1.075  -1.503  1.00  0.00           H  
HETATM   40  H15 UNL     1       6.107  -2.879  -3.062  1.00  0.00           H  
HETATM   41  H16 UNL     1      -0.584   2.163   1.826  1.00  0.00           H  
CONECT    1    2    2   26   27
CONECT    2    3   28
CONECT    3    4    5    6
CONECT    4   29   30   31
CONECT    5   32   33   34
CONECT    6    7    7   24
CONECT    7    8   35
CONECT    8    9   10   10
CONECT    9   36
CONECT   10   11   23
CONECT   11   12
CONECT   12   13   13   20
CONECT   13   14   21
CONECT   14   15   15   37
CONECT   15   16   38
CONECT   16   17   20   20
CONECT   17   18   18   39
CONECT   18   19   40
CONECT   19   20
CONECT   21   22   22   23
CONECT   23   24   24
CONECT   24   25
CONECT   25   41
END

HMDB0029791
     RDKit          3D
Dulciol D
 41 44  0  0  0  0  0  0  0  0999 V2000
   -4.2132    2.7044    0.8524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5718    1.8765    0.0671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4576    0.4295    0.4258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4875    0.2415    1.9335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6107   -0.2915   -0.1971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1451   -0.0396   -0.0664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0037   -1.0484   -0.9797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7509   -1.4358   -1.3954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6002   -2.4607   -2.3236 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4035   -0.8309   -0.9150 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5959   -1.2409   -1.3477 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7101   -0.7107   -0.9321 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6526    0.3092   -0.0134 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8298    0.8663    0.4229 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0314    0.4058   -0.0557 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1121   -0.6206   -0.9815 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1589   -1.2570   -1.6095 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5462   -2.1993   -2.4222 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2460   -2.1197   -2.2802 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9234   -1.1713   -1.4114 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4199    0.7585    0.4567 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4225    1.6817    1.2853 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2611    0.1861    0.0057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9979    0.5892    0.4359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1566    1.5758    1.3300 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2995    3.7532    0.5983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6670    2.3762    1.7584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1150    2.2058   -0.8451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7377   -0.5473    2.2330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4658   -0.1541    2.2856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1745    1.1613    2.4339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6647   -0.0984   -1.2881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6048   -1.3779   -0.0199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5488    0.1167    0.2321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8530   -1.5738   -1.4053 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3056   -2.7605   -2.6418 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7867    1.6648    1.1420 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9909    0.8270    0.2704 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2064   -1.0751   -1.5030 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1071   -2.8786   -3.0624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5840    2.1626    1.8258 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  3  5  1  0
  3  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 13 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  2  0
 24 25  1  0
 24  6  1  0
 23 10  1  0
 20 12  1  0
 20 16  2  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  4 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  5 34  1  0
  7 35  1  0
  9 36  1  0
 14 37  1  0
 15 38  1  0
 17 39  1  0
 18 40  1  0
 25 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₀H₁₆O₅

Average Molecular Weight

336.338

Monoisotopic Molecular Weight

336.099773622

IUPAC Name

7,10-dihydroxy-8-(2-methylbut-3-en-2-yl)-6H-furo[3,2-c]xanthen-6-one

Traditional Name

7,10-dihydroxy-8-(2-methylbut-3-en-2-yl)furo[3,2-c]xanthen-6-one

CAS Registry Number

175617-26-2

SMILES

CC(C)(C=C)C1=C(O)C2=C(OC3=C4OC=CC4=CC=C3C2=O)C(O)=C1

InChI Identifier

InChI=1S/C20H16O5/c1-4-20(2,3)12-9-13(21)19-14(16(12)23)15(22)11-6-5-10-7-8-24-17(10)18(11)25-19/h4-9,21,23H,1H2,2-3H3

InChI Key

XYTVIOHQRFERMN-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
Benzofuran
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Benzenoid
Pyran
Furan
Heteroaromatic compound
Vinylogous acid
Oxacycle
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

cyclic ketone (CHEBI:65948 )
organic heterotetracyclic compound (CHEBI:65948 )
polyphenol (CHEBI:65948 )
cyclic ether (CHEBI:65948 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0029791)
Cell membrane (HMDB: HMDB0029791)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0029791)

Source

Endogenous

Endogenous (HMDB: HMDB0029791)

Plant

Plant (HMDB: HMDB0029791)

Exogenous

Food

Food (HMDB: HMDB0029791)

Fruit

Fruits (FooDB: FOOD00871)

Exogenous (HMDB: HMDB0029791)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	194 - 196 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0066 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	0.041 g/L	ALOGPS
logP	4.62	ALOGPS
logP	4.85	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	8.3	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	79.9 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	92.93 m³·mol⁻¹	ChemAxon
Polarizability	35.22 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]+	178.14	31661259
DarkChem	[M-H]-	175.998	31661259
DeepCCS	[M+H]+	187.929	30932474
DeepCCS	[M-H]-	185.571	30932474
DeepCCS	[M-2H]-	219.478	30932474
DeepCCS	[M+Na]+	194.706	30932474
AllCCS	[M+H]+	179.0	32859911
AllCCS	[M+H-H2O]+	175.6	32859911
AllCCS	[M+NH4]+	182.1	32859911
AllCCS	[M+Na]+	183.0	32859911
AllCCS	[M-H]-	179.9	32859911
AllCCS	[M+Na-2H]-	179.0	32859911
AllCCS	[M+HCOO]-	178.2	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.	6.55 minutes	32390414
Predicted by Siyang on May 30, 2022	19.1336 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.87 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	29.6 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3139.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	576.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	252.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	334.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	519.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	752.2 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	1137.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	81.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1596.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	685.0 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	1953.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	506.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	582.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	446.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	327.5 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	13.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dulciol D	CC(C)(C=C)C1=C(O)C2=C(OC3=C4OC=CC4=CC=C3C2=O)C(O)=C1	3902.7	Standard polar	33892256
Dulciol D	CC(C)(C=C)C1=C(O)C2=C(OC3=C4OC=CC4=CC=C3C2=O)C(O)=C1	2902.5	Standard non polar	33892256
Dulciol D	CC(C)(C=C)C1=C(O)C2=C(OC3=C4OC=CC4=CC=C3C2=O)C(O)=C1	3087.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dulciol D,1TMS,isomer #1	C=CC(C)(C)C1=CC(O)=C2OC3=C(C=CC4=C3OC=C4)C(=O)C2=C1O[Si](C)(C)C	3312.8	Semi standard non polar	33892256
Dulciol D,1TMS,isomer #2	C=CC(C)(C)C1=CC(O[Si](C)(C)C)=C2OC3=C(C=CC4=C3OC=C4)C(=O)C2=C1O	3342.8	Semi standard non polar	33892256
Dulciol D,2TMS,isomer #1	C=CC(C)(C)C1=CC(O[Si](C)(C)C)=C2OC3=C(C=CC4=C3OC=C4)C(=O)C2=C1O[Si](C)(C)C	3308.8	Semi standard non polar	33892256
Dulciol D,1TBDMS,isomer #1	C=CC(C)(C)C1=CC(O)=C2OC3=C(C=CC4=C3OC=C4)C(=O)C2=C1O[Si](C)(C)C(C)(C)C	3537.6	Semi standard non polar	33892256
Dulciol D,1TBDMS,isomer #2	C=CC(C)(C)C1=CC(O[Si](C)(C)C(C)(C)C)=C2OC3=C(C=CC4=C3OC=C4)C(=O)C2=C1O	3574.9	Semi standard non polar	33892256
Dulciol D,2TBDMS,isomer #1	C=CC(C)(C)C1=CC(O[Si](C)(C)C(C)(C)C)=C2OC3=C(C=CC4=C3OC=C4)C(=O)C2=C1O[Si](C)(C)C(C)(C)C	3749.8	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 D GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-1219000000-21b42ca1b11bb1fb3f73	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dulciol D GC-MS (2 TMS) - 70eV, Positive	splash10-084i-5605900000-d3f0ab06784f64dbf27e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dulciol D 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 D 10V, Positive-QTOF	splash10-000i-0009000000-d4ef05a49401c647dfab	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dulciol D 20V, Positive-QTOF	splash10-014r-3019000000-d6f22f091747669180c0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dulciol D 40V, Positive-QTOF	splash10-02t9-9512000000-6fb73c27a79e35f6b4f9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dulciol D 10V, Negative-QTOF	splash10-000i-0009000000-471fb4f01511ac16f079	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dulciol D 20V, Negative-QTOF	splash10-000i-1029000000-1b3f06de4dede21b0356	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dulciol D 40V, Negative-QTOF	splash10-0a4i-2931000000-671064888c0860bca7fd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dulciol D 10V, Positive-QTOF	splash10-000i-0009000000-3885aaa300cc39c87daa	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dulciol D 20V, Positive-QTOF	splash10-052r-0019000000-b305c9cf852652598e97	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dulciol D 40V, Positive-QTOF	splash10-000i-8796000000-bf5d8b8b1b65ac213849	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dulciol D 10V, Negative-QTOF	splash10-000i-0009000000-dc81427ba733f47873d1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dulciol D 20V, Negative-QTOF	splash10-052r-0329000000-673b28b9cda502911833	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dulciol D 40V, Negative-QTOF	splash10-000i-0962000000-900504c700cc221ffa0a	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

FDB000998

KNApSAcK ID

C00053013

Chemspider ID

8580179

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10404741

PDB ID

Not Available

ChEBI ID

65948

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1811321

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 D (HMDB0029791)

MOL for HMDB0029791 (Dulciol D)

3D MOL for HMDB0029791 (Dulciol D)

3D SDF for HMDB0029791 (Dulciol D)

3D-SDF for HMDB0029791 (Dulciol D)

PDB for HMDB0029791 (Dulciol D)

3D PDB for HMDB0029791 (Dulciol D)

SMILES for HMDB0029791 (Dulciol D)

INCHI for HMDB0029791 (Dulciol D)

Structure for HMDB0029791 (Dulciol D)

3D Structure for HMDB0029791 (Dulciol D)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra