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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 22:50:55 UTC

Update Date

2021-09-26 23:17:43 UTC

HMDB ID

HMDB0259891

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Wedelolactone

Description

wedelolactone belongs to the class of organic compounds known as coumestans. These are polycyclic aromatic compounds containing a coumestan moiety, which consists of a benzoxole fused to a chromen-2-one to form 1-Benzoxolo[3,2-c]chromen-6-one. They are oxidation products of pterocarpan. Thus, wedelolactone is considered to be a flavonoid. wedelolactone 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 a significant number of articles have been published on wedelolactone. This compound has been identified in human blood as reported by (PMID: 31557052 ). Wedelolactone is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Wedelolactone is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0259891
     RDKit          3D
Wedelolactone
 33 36  0  0  0  0  0  0  0  0999 V2000
    5.9660    1.0397   -0.8014 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1405    0.8328    0.3169 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7773    0.6148    0.1818 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2131    0.5995   -1.0759 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8461    0.3766   -1.1428 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2501    0.3559   -2.3980 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0840    0.1793   -0.0092 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6493    0.1946    1.2501 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0256    0.4188    1.3200 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9385    0.0086    2.3382 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3563   -0.2032    2.2854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0232   -0.3798    3.3395 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0207   -0.2396    1.1000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3368   -0.4355    0.7360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5029   -0.6724    1.4293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7055   -0.8312    0.7716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9036   -1.0710    1.4258 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7080   -0.7449   -0.6177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9247   -0.9033   -1.3175 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5417   -0.5085   -1.3006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3518   -0.3524   -0.6359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1011   -0.1180   -1.0626 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2773   -0.0431   -0.0693 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0234    0.9799   -0.4311 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7423    2.0754   -1.1805 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7781    0.2777   -1.5874 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8283    0.7563   -1.9510 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7823    0.4971   -3.2428 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4640    0.4302    2.3046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4588   -0.7326    2.5109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8986   -1.1329    2.4319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8682   -0.8312   -2.3219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5296   -0.4378   -2.4022 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
  9  3  1  0
 23 13  2  0
 23  7  1  0
 21 14  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  6 28  1  0
  9 29  1  0
 15 30  1  0
 17 31  1  0
 19 32  1  0
 20 33  1  0
M  END


  Mrv1652309122100512D          

 23 26  0  0  0  0            999 V2000
    6.4435   -0.1829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9909    0.5068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1672    0.4596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7962   -0.2772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9726   -0.3244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5199    0.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8909    1.1022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7145    1.1494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4382    1.7920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6146    1.7448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1619    2.4345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2436    1.0079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6962    0.3182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1801   -0.3254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4085   -0.0335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6753   -0.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0188    0.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0204    0.8585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7537    1.2366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4477    0.7906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6736    1.3045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7521   -0.3437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6016   -1.0613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
  6 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 15 20  1  0  0  0  0
 12 20  1  0  0  0  0
 18 21  1  0  0  0  0
 17 22  1  0  0  0  0
  5 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0259891

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(O)=C2C3=C(C4=CC(O)=C(O)C=C4O3)C(=O)OC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H10O7/c1-21-6-2-10(19)14-12(3-6)23-16(20)13-7-4-8(17)9(18)5-11(7)22-15(13)14/h2-5,17-19H,1H3

> <INCHI_KEY>
XQDCKJKKMFWXGB-UHFFFAOYSA-N

> <FORMULA>
C16H10O7

> <MOLECULAR_WEIGHT>
314.249

> <EXACT_MASS>
314.042652662

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
30.381132205501746

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,13,14-trihydroxy-5-methoxy-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-1(10),2,4,6,11,13,15-heptaen-9-one

> <ALOGPS_LOGP>
2.78

> <JCHEM_LOGP>
1.936084735

> <ALOGPS_LOGS>
-2.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.312350670809035

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.625310228138843

> <JCHEM_PKA_STRONGEST_BASIC>
-3.058423482916905

> <JCHEM_POLAR_SURFACE_AREA>
109.36000000000001

> <JCHEM_REFRACTIVITY>
78.0636

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.24e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,13,14-trihydroxy-5-methoxy-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-1(10),2,4,6,11,13,15-heptaen-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0259891
     RDKit          3D
Wedelolactone
 33 36  0  0  0  0  0  0  0  0999 V2000
    5.9660    1.0397   -0.8014 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1405    0.8328    0.3169 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7773    0.6148    0.1818 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2131    0.5995   -1.0759 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8461    0.3766   -1.1428 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2501    0.3559   -2.3980 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0840    0.1793   -0.0092 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6493    0.1946    1.2501 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0256    0.4188    1.3200 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9385    0.0086    2.3382 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3563   -0.2032    2.2854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0232   -0.3798    3.3395 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0207   -0.2396    1.1000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3368   -0.4355    0.7360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5029   -0.6724    1.4293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7055   -0.8312    0.7716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9036   -1.0710    1.4258 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7080   -0.7449   -0.6177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9247   -0.9033   -1.3175 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5417   -0.5085   -1.3006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3518   -0.3524   -0.6359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1011   -0.1180   -1.0626 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2773   -0.0431   -0.0693 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0234    0.9799   -0.4311 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7423    2.0754   -1.1805 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7781    0.2777   -1.5874 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8283    0.7563   -1.9510 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7823    0.4971   -3.2428 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4640    0.4302    2.3046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4588   -0.7326    2.5109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8986   -1.1329    2.4319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8682   -0.8312   -2.3219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5296   -0.4378   -2.4022 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
  9  3  1  0
 23 13  2  0
 23  7  1  0
 21 14  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  6 28  1  0
  9 29  1  0
 15 30  1  0
 17 31  1  0
 19 32  1  0
 20 33  1  0
M  END

HEADER    PROTEIN                                 12-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-21         0                                  
HETATM    1  C   UNK     0      12.028  -0.341   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      11.183   0.946   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       9.645   0.858   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.953  -0.517   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.415  -0.606   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.570   0.682   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.263   2.057   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.800   2.146   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.418   3.345   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.881   3.257   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.036   4.544   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.188   1.881   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.033   0.594   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.070  -0.607   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.629  -0.063   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.260  -0.768   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.035   0.064   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.038   1.603   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.407   2.308   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.702   1.476   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.257   2.435   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -1.404  -0.641   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       6.723  -1.981   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   23                                                  
CONECT    6    5    7   13                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7    3                                                       
CONECT    9    7   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   20                                                  
CONECT   13   12    6   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19   15   12                                                  
CONECT   21   18                                                            
CONECT   22   17                                                            
CONECT   23    5                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

COMPND    HMDB0259891
HETATM    1  C1  UNL     1       5.966   1.040  -0.801  1.00  0.00           C  
HETATM    2  O1  UNL     1       5.140   0.833   0.317  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.777   0.615   0.182  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.213   0.600  -1.076  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.846   0.377  -1.143  1.00  0.00           C  
HETATM    6  O2  UNL     1       1.250   0.356  -2.398  1.00  0.00           O  
HETATM    7  C5  UNL     1       1.084   0.179  -0.009  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.649   0.195   1.250  1.00  0.00           C  
HETATM    9  C7  UNL     1       3.026   0.419   1.320  1.00  0.00           C  
HETATM   10  O3  UNL     1       0.939   0.009   2.338  1.00  0.00           O  
HETATM   11  C8  UNL     1      -0.356  -0.203   2.285  1.00  0.00           C  
HETATM   12  O4  UNL     1      -1.023  -0.380   3.340  1.00  0.00           O  
HETATM   13  C9  UNL     1      -1.021  -0.240   1.100  1.00  0.00           C  
HETATM   14  C10 UNL     1      -2.337  -0.435   0.736  1.00  0.00           C  
HETATM   15  C11 UNL     1      -3.503  -0.672   1.429  1.00  0.00           C  
HETATM   16  C12 UNL     1      -4.706  -0.831   0.772  1.00  0.00           C  
HETATM   17  O5  UNL     1      -5.904  -1.071   1.426  1.00  0.00           O  
HETATM   18  C13 UNL     1      -4.708  -0.745  -0.618  1.00  0.00           C  
HETATM   19  O6  UNL     1      -5.925  -0.903  -1.317  1.00  0.00           O  
HETATM   20  C14 UNL     1      -3.542  -0.509  -1.301  1.00  0.00           C  
HETATM   21  C15 UNL     1      -2.352  -0.352  -0.636  1.00  0.00           C  
HETATM   22  O7  UNL     1      -1.101  -0.118  -1.063  1.00  0.00           O  
HETATM   23  C16 UNL     1      -0.277  -0.043  -0.069  1.00  0.00           C  
HETATM   24  H1  UNL     1       7.023   0.980  -0.431  1.00  0.00           H  
HETATM   25  H2  UNL     1       5.742   2.075  -1.180  1.00  0.00           H  
HETATM   26  H3  UNL     1       5.778   0.278  -1.587  1.00  0.00           H  
HETATM   27  H4  UNL     1       3.828   0.756  -1.951  1.00  0.00           H  
HETATM   28  H5  UNL     1       1.782   0.497  -3.243  1.00  0.00           H  
HETATM   29  H6  UNL     1       3.464   0.430   2.305  1.00  0.00           H  
HETATM   30  H7  UNL     1      -3.459  -0.733   2.511  1.00  0.00           H  
HETATM   31  H8  UNL     1      -5.899  -1.133   2.432  1.00  0.00           H  
HETATM   32  H9  UNL     1      -5.868  -0.831  -2.322  1.00  0.00           H  
HETATM   33  H10 UNL     1      -3.530  -0.438  -2.402  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3
CONECT    3    4    4    9
CONECT    4    5   27
CONECT    5    6    7    7
CONECT    6   28
CONECT    7    8   23
CONECT    8    9    9   10
CONECT    9   29
CONECT   10   11
CONECT   11   12   12   13
CONECT   13   14   23   23
CONECT   14   15   15   21
CONECT   15   16   30
CONECT   16   17   18   18
CONECT   17   31
CONECT   18   19   20
CONECT   19   32
CONECT   20   21   21   33
CONECT   21   22
CONECT   22   23
END

HMDB0259891
     RDKit          3D
Wedelolactone
 33 36  0  0  0  0  0  0  0  0999 V2000
    5.9660    1.0397   -0.8014 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1405    0.8328    0.3169 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7773    0.6148    0.1818 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2131    0.5995   -1.0759 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8461    0.3766   -1.1428 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2501    0.3559   -2.3980 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0840    0.1793   -0.0092 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6493    0.1946    1.2501 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0256    0.4188    1.3200 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9385    0.0086    2.3382 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3563   -0.2032    2.2854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0232   -0.3798    3.3395 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0207   -0.2396    1.1000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3368   -0.4355    0.7360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5029   -0.6724    1.4293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7055   -0.8312    0.7716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9036   -1.0710    1.4258 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7080   -0.7449   -0.6177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9247   -0.9033   -1.3175 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5417   -0.5085   -1.3006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3518   -0.3524   -0.6359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1011   -0.1180   -1.0626 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2773   -0.0431   -0.0693 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0234    0.9799   -0.4311 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7423    2.0754   -1.1805 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7781    0.2777   -1.5874 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8283    0.7563   -1.9510 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7823    0.4971   -3.2428 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4640    0.4302    2.3046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4588   -0.7326    2.5109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8986   -1.1329    2.4319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8682   -0.8312   -2.3219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5296   -0.4378   -2.4022 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
  9  3  1  0
 23 13  2  0
 23  7  1  0
 21 14  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  6 28  1  0
  9 29  1  0
 15 30  1  0
 17 31  1  0
 19 32  1  0
 20 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,8,9-Trihydroxy-3-methoxycoumestan	ChEBI

Chemical Formula

C₁₆H₁₀O₇

Average Molecular Weight

314.249

Monoisotopic Molecular Weight

314.042652662

IUPAC Name

3,13,14-trihydroxy-5-methoxy-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-1(10),2,4,6,11,13,15-heptaen-9-one

Traditional Name

3,13,14-trihydroxy-5-methoxy-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-1(10),2,4,6,11,13,15-heptaen-9-one

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=C2C3=C(C4=CC(O)=C(O)C=C4O3)C(=O)OC2=C1

InChI Identifier

InChI=1S/C16H10O7/c1-21-6-2-10(19)14-12(3-6)23-16(20)13-7-4-8(17)9(18)5-11(7)22-15(13)14/h2-5,17-19H,1H3

InChI Key

XQDCKJKKMFWXGB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumestans. These are polycyclic aromatic compounds containing a coumestan moiety, which consists of a benzoxole fused to a chromen-2-one to form 1-Benzoxolo[3,2-c]chromen-6-one. They are oxidation products of pterocarpan.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Coumestans

Direct Parent

Coumestans

Alternative Parents

Substituents

Coumestan
Furanocoumarin
Angular furanocoumarin
Coumarin
1-benzopyran
Benzopyran
Furopyran
Benzofuran
Anisole
Pyranone
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Pyran
Benzenoid
Heteroaromatic compound
Furan
Lactone
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

aromatic ether (CHEBI:10037 )
polyphenol (CHEBI:10037 )
delta-lactone (CHEBI:10037 )
coumestans (CHEBI:10037 )
Coumestan flavonoids (C10541 )
Coumestanes (C10541 )
Coumestan flavonoids (LMPK12090046 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

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	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.78	ALOGPS
logP	1.94	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	6.63	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	109.36 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	78.06 m³·mol⁻¹	ChemAxon
Polarizability	30.38 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
AllCCS	[M+H]+	170.27	32859911
AllCCS	[M+H-H2O]+	166.716	32859911
AllCCS	[M+Na]+	174.513	32859911
AllCCS	[M+NH4]+	173.566	32859911
AllCCS	[M-H]-	171.081	32859911
AllCCS	[M+Na-2H]-	170.073	32859911
AllCCS	[M+HCOO]-	169.105	32859911
DeepCCS	[M+H]+	176.697	30932474
DeepCCS	[M-H]-	174.339	30932474
DeepCCS	[M-2H]-	208.502	30932474
DeepCCS	[M+Na]+	184.034	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Wedelolactone	COC1=CC(O)=C2C3=C(C4=CC(O)=C(O)C=C4O3)C(=O)OC2=C1	4733.6	Standard polar	33892256
Wedelolactone	COC1=CC(O)=C2C3=C(C4=CC(O)=C(O)C=C4O3)C(=O)OC2=C1	3094.5	Standard non polar	33892256
Wedelolactone	COC1=CC(O)=C2C3=C(C4=CC(O)=C(O)C=C4O3)C(=O)OC2=C1	3209.2	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 - Wedelolactone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0019-0491000000-213664832fc21092ede7	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Wedelolactone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Wedelolactone GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Wedelolactone GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Wedelolactone GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Wedelolactone GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Wedelolactone GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Wedelolactone GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Wedelolactone GC-MS (TMS_3_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Wedelolactone GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Wedelolactone GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Wedelolactone GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Wedelolactone GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Wedelolactone GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Wedelolactone GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Wedelolactone GC-MS (TBDMS_3_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

KNApSAcK ID

C00002585

Chemspider ID

4445124

KEGG Compound ID

C10541

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Wedelolactone

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

10037

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Wedelolactone (HMDB0259891)

MOL for HMDB0259891 (Wedelolactone)

3D MOL for HMDB0259891 (Wedelolactone)

3D SDF for HMDB0259891 (Wedelolactone)

3D-SDF for HMDB0259891 (Wedelolactone)

PDB for HMDB0259891 (Wedelolactone)

3D PDB for HMDB0259891 (Wedelolactone)

SMILES for HMDB0259891 (Wedelolactone)

INCHI for HMDB0259891 (Wedelolactone)

Structure for HMDB0259891 (Wedelolactone)

3D Structure for HMDB0259891 (Wedelolactone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra