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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:36:21 UTC

Update Date

2022-03-07 02:53:52 UTC

HMDB ID

HMDB0033831

Secondary Accession Numbers

HMDB33831

Metabolite Identification

Common Name

Medicagol

Description

Medicagol 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, medicagol is considered to be a flavonoid. Medicagol has been detected, but not quantified in, several different foods, such as breakfast cereal, green tea, pulses, black tea, and teas (Camellia sinensis). This could make medicagol a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Medicagol.

Structure

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

HMDB0033831
     RDKit          3D
Medicagol
 30 34  0  0  0  0  0  0  0  0999 V2000
    0.7029    2.2739    2.0460 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1258    1.5038    1.1328 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3933    1.5062    0.7612 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8125    0.6913   -0.1966 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1498    0.6935   -0.5891 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6362   -0.1321   -1.5778 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9921   -0.1052   -1.9504 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7320   -0.9777   -2.1765 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4162   -1.0185   -1.8299 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9661   -0.1715   -0.8301 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6280   -0.1799   -0.4437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4003   -0.8657   -0.8422 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4864   -0.5170   -0.1647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7942   -0.9478   -0.2197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7556   -0.3914    0.6336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4308    0.5925    1.5448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1093    1.0100    1.5821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1517    0.4717    0.7486 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1978    0.6682    0.5514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5962    0.9197    2.2235 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7037    0.4553    1.4405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1095   -0.6430    0.7759 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8348    1.3664   -0.1024 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5823   -0.7533   -1.4197 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0812   -1.6508   -2.9686 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6817   -1.6859   -2.2963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0778   -1.7152   -0.9215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8031    1.7764    2.2763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9601    1.2793    0.7305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5541    0.1678    2.0820 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 16 20  1  0
 20 21  1  0
 21 22  1  0
 19  2  1  0
 10  4  1  0
 19 11  2  0
 18 13  1  0
 22 15  1  0
  5 23  1  0
  7 24  1  0
  8 25  1  0
  9 26  1  0
 14 27  1  0
 17 28  1  0
 21 29  1  0
 21 30  1  0
M  END


  Mrv0541 05061307232D          

 22 26  0  0  0  0            999 V2000
   -0.4612   -0.1409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3618   -0.0836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3618   -1.5664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5998   -1.6045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6578    0.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6116   -0.8497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8230   -0.8824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8230   -0.7676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9003   -1.1671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4612   -1.5091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9293   -0.3426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3283   -1.2173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3573   -0.3928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1072   -1.3943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6460   -0.7103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7454   -2.1358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6460   -0.9397    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2065   -2.8198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1035   -1.4996    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1504   -0.1656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1541   -0.0603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9224   -2.1931    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  7  1  1  0  0  0  0
  7  3  2  0  0  0  0
  8  2  1  0  0  0  0
  9  4  2  0  0  0  0
 10  3  1  0  0  0  0
 10  8  2  0  0  0  0
 11  5  2  0  0  0  0
 11  9  1  0  0  0  0
 12  4  1  0  0  0  0
 13  5  1  0  0  0  0
 13 12  2  0  0  0  0
 14  9  1  0  0  0  0
 15  8  1  0  0  0  0
 15 14  2  0  0  0  0
 16 14  1  0  0  0  0
 17  7  1  0  0  0  0
 18 16  2  0  0  0  0
 19  6  1  0  0  0  0
 19 12  1  0  0  0  0
 20  6  1  0  0  0  0
 20 13  1  0  0  0  0
 21 11  1  0  0  0  0
 21 15  1  0  0  0  0
 22 10  1  0  0  0  0
 22 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033831

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC2=C(C=C1)C1=C(C3=CC4=C(OCO4)C=C3O1)C(=O)O2

> <INCHI_IDENTIFIER>
InChI=1S/C16H8O6/c17-7-1-2-8-10(3-7)22-16(18)14-9-4-12-13(20-6-19-12)5-11(9)21-15(8)14/h1-5,17H,6H2

> <INCHI_KEY>
URMVEUAWRUQHON-UHFFFAOYSA-N

> <FORMULA>
C16H8O6

> <MOLECULAR_WEIGHT>
296.2311

> <EXACT_MASS>
296.032087988

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
29.02475642612746

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
16-hydroxy-5,7,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-1(12),2,4(8),9,13(18),14,16-heptaen-20-one

> <ALOGPS_LOGP>
2.45

> <JCHEM_LOGP>
2.324120111666666

> <ALOGPS_LOGS>
-2.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.117088387657561

> <JCHEM_PKA_STRONGEST_BASIC>
-4.198783131496715

> <JCHEM_POLAR_SURFACE_AREA>
78.13000000000001

> <JCHEM_REFRACTIVITY>
73.4055

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.68e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
medicagol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033831
     RDKit          3D
Medicagol
 30 34  0  0  0  0  0  0  0  0999 V2000
    0.7029    2.2739    2.0460 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1258    1.5038    1.1328 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3933    1.5062    0.7612 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8125    0.6913   -0.1966 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1498    0.6935   -0.5891 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6362   -0.1321   -1.5778 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9921   -0.1052   -1.9504 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7320   -0.9777   -2.1765 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4162   -1.0185   -1.8299 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9661   -0.1715   -0.8301 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6280   -0.1799   -0.4437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4003   -0.8657   -0.8422 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4864   -0.5170   -0.1647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7942   -0.9478   -0.2197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7556   -0.3914    0.6336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4308    0.5925    1.5448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1093    1.0100    1.5821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1517    0.4717    0.7486 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1978    0.6682    0.5514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5962    0.9197    2.2235 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7037    0.4553    1.4405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1095   -0.6430    0.7759 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8348    1.3664   -0.1024 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5823   -0.7533   -1.4197 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0812   -1.6508   -2.9686 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6817   -1.6859   -2.2963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0778   -1.7152   -0.9215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8031    1.7764    2.2763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9601    1.2793    0.7305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5541    0.1678    2.0820 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 16 20  1  0
 20 21  1  0
 21 22  1  0
 19  2  1  0
 10  4  1  0
 19 11  2  0
 18 13  1  0
 22 15  1  0
  5 23  1  0
  7 24  1  0
  8 25  1  0
  9 26  1  0
 14 27  1  0
 17 28  1  0
 21 29  1  0
 21 30  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      -0.861  -0.263   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.675  -0.156   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.675  -2.924   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.720  -2.995   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.828   0.083   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.475  -1.586   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.536  -1.647   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.536  -1.433   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.414  -2.179   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.861  -2.817   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.468  -0.640   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.079  -2.272   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.134  -0.733   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.933  -2.603   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.073  -1.326   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.258  -3.987   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -3.073  -1.754   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       4.119  -5.264   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       9.527  -2.799   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       9.614  -0.309   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       4.021  -0.113   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       1.722  -4.094   0.000  0.00  0.00           O+0
CONECT    1    2    7                                                       
CONECT    2    1    8                                                       
CONECT    3    7   10                                                       
CONECT    4    9   12                                                       
CONECT    5   11   13                                                       
CONECT    6   19   20                                                       
CONECT    7    1    3   17                                                  
CONECT    8    2   10   15                                                  
CONECT    9    4   11   14                                                  
CONECT   10    3    8   22                                                  
CONECT   11    5    9   21                                                  
CONECT   12    4   13   19                                                  
CONECT   13    5   12   20                                                  
CONECT   14    9   15   16                                                  
CONECT   15    8   14   21                                                  
CONECT   16   14   18   22                                                  
CONECT   17    7                                                            
CONECT   18   16                                                            
CONECT   19    6   12                                                       
CONECT   20    6   13                                                       
CONECT   21   11   15                                                       
CONECT   22   10   16                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   52    0
END

COMPND    HMDB0033831
HETATM    1  O1  UNL     1       0.703   2.274   2.046  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.126   1.504   1.133  1.00  0.00           C  
HETATM    3  O2  UNL     1       2.393   1.506   0.761  1.00  0.00           O  
HETATM    4  C2  UNL     1       2.812   0.691  -0.197  1.00  0.00           C  
HETATM    5  C3  UNL     1       4.150   0.694  -0.589  1.00  0.00           C  
HETATM    6  C4  UNL     1       4.636  -0.132  -1.578  1.00  0.00           C  
HETATM    7  O3  UNL     1       5.992  -0.105  -1.950  1.00  0.00           O  
HETATM    8  C5  UNL     1       3.732  -0.978  -2.177  1.00  0.00           C  
HETATM    9  C6  UNL     1       2.416  -1.018  -1.830  1.00  0.00           C  
HETATM   10  C7  UNL     1       1.966  -0.172  -0.830  1.00  0.00           C  
HETATM   11  C8  UNL     1       0.628  -0.180  -0.444  1.00  0.00           C  
HETATM   12  O4  UNL     1      -0.400  -0.866  -0.842  1.00  0.00           O  
HETATM   13  C9  UNL     1      -1.486  -0.517  -0.165  1.00  0.00           C  
HETATM   14  C10 UNL     1      -2.794  -0.948  -0.220  1.00  0.00           C  
HETATM   15  C11 UNL     1      -3.756  -0.391   0.634  1.00  0.00           C  
HETATM   16  C12 UNL     1      -3.431   0.592   1.545  1.00  0.00           C  
HETATM   17  C13 UNL     1      -2.109   1.010   1.582  1.00  0.00           C  
HETATM   18  C14 UNL     1      -1.152   0.472   0.749  1.00  0.00           C  
HETATM   19  C15 UNL     1       0.198   0.668   0.551  1.00  0.00           C  
HETATM   20  O5  UNL     1      -4.596   0.920   2.223  1.00  0.00           O  
HETATM   21  C16 UNL     1      -5.704   0.455   1.441  1.00  0.00           C  
HETATM   22  O6  UNL     1      -5.110  -0.643   0.776  1.00  0.00           O  
HETATM   23  H1  UNL     1       4.835   1.366  -0.102  1.00  0.00           H  
HETATM   24  H2  UNL     1       6.582  -0.753  -1.420  1.00  0.00           H  
HETATM   25  H3  UNL     1       4.081  -1.651  -2.969  1.00  0.00           H  
HETATM   26  H4  UNL     1       1.682  -1.686  -2.296  1.00  0.00           H  
HETATM   27  H5  UNL     1      -3.078  -1.715  -0.921  1.00  0.00           H  
HETATM   28  H6  UNL     1      -1.803   1.776   2.276  1.00  0.00           H  
HETATM   29  H7  UNL     1      -5.960   1.279   0.731  1.00  0.00           H  
HETATM   30  H8  UNL     1      -6.554   0.168   2.082  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   19
CONECT    3    4
CONECT    4    5    5   10
CONECT    5    6   23
CONECT    6    7    8    8
CONECT    7   24
CONECT    8    9   25
CONECT    9   10   10   26
CONECT   10   11
CONECT   11   12   19   19
CONECT   12   13
CONECT   13   14   14   18
CONECT   14   15   27
CONECT   15   16   16   22
CONECT   16   17   20
CONECT   17   18   18   28
CONECT   18   19
CONECT   20   21
CONECT   21   22   29   30
END

HMDB0033831
     RDKit          3D
Medicagol
 30 34  0  0  0  0  0  0  0  0999 V2000
    0.7029    2.2739    2.0460 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1258    1.5038    1.1328 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3933    1.5062    0.7612 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8125    0.6913   -0.1966 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1498    0.6935   -0.5891 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6362   -0.1321   -1.5778 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9921   -0.1052   -1.9504 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7320   -0.9777   -2.1765 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4162   -1.0185   -1.8299 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9661   -0.1715   -0.8301 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6280   -0.1799   -0.4437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4003   -0.8657   -0.8422 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4864   -0.5170   -0.1647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7942   -0.9478   -0.2197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7556   -0.3914    0.6336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4308    0.5925    1.5448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1093    1.0100    1.5821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1517    0.4717    0.7486 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1978    0.6682    0.5514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5962    0.9197    2.2235 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7037    0.4553    1.4405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1095   -0.6430    0.7759 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8348    1.3664   -0.1024 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5823   -0.7533   -1.4197 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0812   -1.6508   -2.9686 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6817   -1.6859   -2.2963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0778   -1.7152   -0.9215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8031    1.7764    2.2763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9601    1.2793    0.7305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5541    0.1678    2.0820 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 16 20  1  0
 20 21  1  0
 21 22  1  0
 19  2  1  0
 10  4  1  0
 19 11  2  0
 18 13  1  0
 22 15  1  0
  5 23  1  0
  7 24  1  0
  8 25  1  0
  9 26  1  0
 14 27  1  0
 17 28  1  0
 21 29  1  0
 21 30  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-Hydroxy-6H-[1,3]dioxolo[5,6]benzofuro[3,2-c][1]-benzopyran-6-one, 9ci	HMDB
3-Hydroxy-8,9-methylenedioxycoumestan	HMDB
7-Hydroxy-11,12-methylenedioxycoumestan	HMDB
7-Hydroxy-5',6'-methylenedioxybenzofurano[3',2':3,4]coumarin	HMDB

Chemical Formula

C₁₆H₈O₆

Average Molecular Weight

296.2311

Monoisotopic Molecular Weight

296.032087988

IUPAC Name

16-hydroxy-5,7,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-1(12),2,4(8),9,13(18),14,16-heptaen-20-one

Traditional Name

medicagol

CAS Registry Number

1983-72-8

SMILES

OC1=CC2=C(C=C1)C1=C(C3=CC4=C(OCO4)C=C3O1)C(=O)O2

InChI Identifier

InChI=1S/C16H8O6/c17-7-1-2-8-10(3-7)22-16(18)14-9-4-12-13(20-6-19-12)5-11(9)21-15(8)14/h1-5,17H,6H2

InChI Key

URMVEUAWRUQHON-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
Angular furanocoumarin
Furanocoumarin
Coumarin
Benzopyran
1-benzopyran
Benzodioxole
Benzofuran
Furopyran
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Furan
Lactone
Acetal
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Coumestan flavonoids (LMPK12090025 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0033831)
Cytoplasm (HMDB: HMDB0033831)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033831)

Source

Exogenous

Exogenous (HMDB: HMDB0033831)

Food

Food (HMDB: HMDB0033831)

Herb and spice

Herb

Alfalfa (FooDB: FOOD00286)

Herbs and Spices (FooDB: FOOD00866)

Cereal and cereal product

Cereal product

Breakfast cereal (FooDB: FOOD00270)

Cereals and cereal products (FooDB: FOOD00858)

Pulse

Pea

Chickpea (FooDB: FOOD00047)

Pulses (FooDB: FOOD00867)

Not Available

Nutrient (HMDB: HMDB0033831)
Anti ulcer (HMDB: HMDB0033831)

Industrial application

Agriculture

Pesticide

Fungicide (HMDB: HMDB0033831)

Pesticide (HMDB: HMDB0033831)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	324 - 325 °C	Not Available
Boiling Point	552.00 to 553.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	59.59 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.706 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.37 g/L	ALOGPS
logP	2.45	ALOGPS
logP	2.32	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	7.12	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	78.13 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	73.41 m³·mol⁻¹	ChemAxon
Polarizability	29.02 Å³	ChemAxon
Number of Rings	5	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]+	165.544	31661259
DarkChem	[M-H]-	167.887	31661259
DeepCCS	[M+H]+	169.663	30932474
DeepCCS	[M-H]-	167.305	30932474
DeepCCS	[M-2H]-	200.787	30932474
DeepCCS	[M+Na]+	176.014	30932474
AllCCS	[M+H]+	166.3	32859911
AllCCS	[M+H-H2O]+	162.6	32859911
AllCCS	[M+NH4]+	169.8	32859911
AllCCS	[M+Na]+	170.8	32859911
AllCCS	[M-H]-	168.7	32859911
AllCCS	[M+Na-2H]-	167.4	32859911
AllCCS	[M+HCOO]-	166.0	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.	6.36 minutes	32390414
Predicted by Siyang on May 30, 2022	14.6496 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.2 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	30.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2219.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	452.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	182.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	259.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	260.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	552.0 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	597.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	104.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1228.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	470.9 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	1565.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	423.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	352.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	411.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	375.0 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	81.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Medicagol	OC1=CC2=C(C=C1)C1=C(C3=CC4=C(OCO4)C=C3O1)C(=O)O2	4323.2	Standard polar	33892256
Medicagol	OC1=CC2=C(C=C1)C1=C(C3=CC4=C(OCO4)C=C3O1)C(=O)O2	2936.2	Standard non polar	33892256
Medicagol	OC1=CC2=C(C=C1)C1=C(C3=CC4=C(OCO4)C=C3O1)C(=O)O2	3115.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Medicagol,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C2C(=C1)OC(=O)C1=C2OC2=CC3=C(C=C21)OCO3	3159.5	Semi standard non polar	33892256
Medicagol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)OC(=O)C1=C2OC2=CC3=C(C=C21)OCO3	3362.7	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 - Medicagol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-0090000000-a27156413a82b2896b34	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Medicagol GC-MS (1 TMS) - 70eV, Positive	splash10-00di-5239000000-a9c7b2d5e4247055cf19	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Medicagol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Medicagol 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 - Medicagol 10V, Positive-QTOF	splash10-0002-0090000000-9e260f2a78964c96d248	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Medicagol 20V, Positive-QTOF	splash10-0002-0090000000-f3ea38dbbb02ebbaa19d	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Medicagol 40V, Positive-QTOF	splash10-0uxr-0090000000-66fc3c899f2a8ff81a72	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Medicagol 10V, Negative-QTOF	splash10-0002-0090000000-07cbe8cbbe681a4d18ed	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Medicagol 20V, Negative-QTOF	splash10-0002-0090000000-12c8d5ab4a4d80ea5677	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Medicagol 40V, Negative-QTOF	splash10-0002-1090000000-b9e2a75b068f0418b327	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Medicagol 10V, Negative-QTOF	splash10-0002-0090000000-f8e22b439b39dc395389	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Medicagol 20V, Negative-QTOF	splash10-0002-0090000000-f8e22b439b39dc395389	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Medicagol 40V, Negative-QTOF	splash10-00kb-0090000000-583929b0bf872bdc92fc	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Medicagol 10V, Positive-QTOF	splash10-0002-0090000000-8ea6aa97400e7e22a923	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Medicagol 20V, Positive-QTOF	splash10-0002-0090000000-8ea6aa97400e7e22a923	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Medicagol 40V, Positive-QTOF	splash10-0002-0090000000-15c5acd3c3d21df7c434	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB011998

KNApSAcK ID

C00009760

Chemspider ID

4477641

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5319322

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1398761

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 Medicagol (HMDB0033831)

MOL for HMDB0033831 (Medicagol)

3D MOL for HMDB0033831 (Medicagol)

3D SDF for HMDB0033831 (Medicagol)

3D-SDF for HMDB0033831 (Medicagol)

PDB for HMDB0033831 (Medicagol)

3D PDB for HMDB0033831 (Medicagol)

SMILES for HMDB0033831 (Medicagol)

INCHI for HMDB0033831 (Medicagol)

Structure for HMDB0033831 (Medicagol)

3D Structure for HMDB0033831 (Medicagol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra