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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:30:57 UTC

Update Date

2022-03-07 02:52:11 UTC

HMDB ID

HMDB0029527

Secondary Accession Numbers

HMDB29527

Metabolite Identification

Common Name

Melilotocarpan B

Description

Melilotocarpan B belongs to the class of organic compounds known as pterocarpans. These are benzo-pyrano-furano-benzene compounds, containing the 6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids. Thus, melilotocarpan b is considered to be a flavonoid. Based on a literature review very few articles have been published on Melilotocarpan B.

Structure

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

HMDB0029527
     RDKit          3D
Melilotocarpan B
 35 38  0  0  0  0  0  0  0  0999 V2000
    6.1230    0.2295    0.2010 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9719    1.0223    0.0063 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6901    0.5085    0.1417 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4126   -0.8009    0.4733 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0969   -1.2278    0.5869 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0334   -0.3714    0.3756 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3093    0.9457    0.0420 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6122    1.3716   -0.0713 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8684    2.6751   -0.4013 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2190    1.7684   -0.1607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0115    1.6568    0.5075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2843    0.2714    1.0447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6073   -0.1429    0.5238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9309    0.0841    0.9064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9875   -0.4464    0.2001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7686   -1.2242   -0.9152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8245   -1.7779   -1.6547 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4560   -1.4446   -1.2878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3826   -0.9184   -0.5882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9878   -1.0103   -0.7805 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3675   -0.7733    0.4834 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2527   -0.4932   -0.6093 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9191   -0.3780    1.1264 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0256    0.8132    0.3684 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2588   -1.4559    0.6347 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9070   -2.2674    0.8500 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1118    3.3192   -0.5604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0856    2.3654    1.3577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8006    1.9956   -0.2183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2725    0.2764    2.1690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0538    0.7012    1.7889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9994   -0.2547    0.5183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2499   -1.2814   -2.4349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2924   -2.0558   -2.1638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4489   -1.6797    1.1166 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  7 10  1  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
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
  8  3  1  0
 21 12  1  0
 21  6  1  0
 19 13  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
  9 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 14 31  1  0
 15 32  1  0
 17 33  1  0
 18 34  1  0
 21 35  1  0
M  END


  Mrv0541 02241207452D          

 21 24  0  0  0  0            999 V2000
   -1.0340   -2.3086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0340   -1.4836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7490   -1.0711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7490   -0.2461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0340    0.1664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3204   -0.2461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3204   -1.0711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3945   -1.4836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1096   -1.0711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1096   -0.2461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3945    0.1664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5664    0.9735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1777    2.3086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6922    1.6404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0277    0.8869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5424    0.2200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7214    0.3052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3859    1.0602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8714    1.7271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4627   -1.4836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1777   -1.0711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  7  1  0  0  0  0
  3  4  1  0  0  0  0
  3 20  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6 11  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 17  1  0  0  0  0
 11 12  1  0  0  0  0
 12 18  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 19  2  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
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0029527

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C2=C(C=C1)C1OC3=C(C=CC(O)=C3)C1CO2

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O5/c1-19-12-5-4-10-15-11(7-20-16(10)14(12)18)9-3-2-8(17)6-13(9)21-15/h2-6,11,15,17-18H,7H2,1H3

> <INCHI_KEY>
QDFJNOVWEADTGJ-UHFFFAOYSA-N

> <FORMULA>
C16H14O5

> <MOLECULAR_WEIGHT>
286.2794

> <EXACT_MASS>
286.084123558

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
29.205453809118772

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaene-6,14-diol

> <ALOGPS_LOGP>
2.63

> <JCHEM_LOGP>
2.2056580746666663

> <ALOGPS_LOGS>
-3.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.708524670990863

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.0316346267296

> <JCHEM_PKA_STRONGEST_BASIC>
-4.438035927281741

> <JCHEM_POLAR_SURFACE_AREA>
68.15

> <JCHEM_REFRACTIVITY>
75.042

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.63e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
melilotocarpan B

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0029527
     RDKit          3D
Melilotocarpan B
 35 38  0  0  0  0  0  0  0  0999 V2000
    6.1230    0.2295    0.2010 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9719    1.0223    0.0063 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6901    0.5085    0.1417 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4126   -0.8009    0.4733 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0969   -1.2278    0.5869 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0334   -0.3714    0.3756 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3093    0.9457    0.0420 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6122    1.3716   -0.0713 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8684    2.6751   -0.4013 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2190    1.7684   -0.1607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0115    1.6568    0.5075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2843    0.2714    1.0447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6073   -0.1429    0.5238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9309    0.0841    0.9064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9875   -0.4464    0.2001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7686   -1.2242   -0.9152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8245   -1.7779   -1.6547 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4560   -1.4446   -1.2878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3826   -0.9184   -0.5882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9878   -1.0103   -0.7805 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3675   -0.7733    0.4834 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2527   -0.4932   -0.6093 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9191   -0.3780    1.1264 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0256    0.8132    0.3684 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2588   -1.4559    0.6347 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9070   -2.2674    0.8500 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1118    3.3192   -0.5604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0856    2.3654    1.3577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8006    1.9956   -0.2183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2725    0.2764    2.1690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0538    0.7012    1.7889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9994   -0.2547    0.5183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2499   -1.2814   -2.4349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2924   -2.0558   -2.1638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4489   -1.6797    1.1166 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  7 10  1  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
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
  8  3  1  0
 21 12  1  0
 21  6  1  0
 19 13  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
  9 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 14 31  1  0
 15 32  1  0
 17 33  1  0
 18 34  1  0
 21 35  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  O   UNK     0      -1.930  -4.309   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.930  -2.769   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.265  -1.999   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.265  -0.459   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.930   0.311   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.598  -0.459   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.598  -1.999   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.736  -2.769   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.071  -1.999   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.071  -0.459   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.736   0.311   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.057   1.817   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       5.932   4.309   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.025   3.062   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.652   1.656   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.746   0.411   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.213   0.570   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.587   1.979   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.493   3.224   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -4.597  -2.769   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -5.932  -1.999   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4   20                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    2    6    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   17                                                  
CONECT   11    6   10   12                                                  
CONECT   12   11   18                                                       
CONECT   13   14                                                            
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   10   16   18                                                  
CONECT   18   12   17   19                                                  
CONECT   19   14   18                                                       
CONECT   20    3   21                                                       
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

COMPND    HMDB0029527
HETATM    1  C1  UNL     1       6.123   0.229   0.201  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.972   1.022   0.006  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.690   0.509   0.142  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.413  -0.801   0.473  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.097  -1.228   0.587  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.033  -0.371   0.376  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.309   0.946   0.042  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.612   1.372  -0.071  1.00  0.00           C  
HETATM    9  O2  UNL     1       2.868   2.675  -0.401  1.00  0.00           O  
HETATM   10  O3  UNL     1       0.219   1.768  -0.161  1.00  0.00           O  
HETATM   11  C8  UNL     1      -1.012   1.657   0.507  1.00  0.00           C  
HETATM   12  C9  UNL     1      -1.284   0.271   1.045  1.00  0.00           C  
HETATM   13  C10 UNL     1      -2.607  -0.143   0.524  1.00  0.00           C  
HETATM   14  C11 UNL     1      -3.931   0.084   0.906  1.00  0.00           C  
HETATM   15  C12 UNL     1      -4.988  -0.446   0.200  1.00  0.00           C  
HETATM   16  C13 UNL     1      -4.769  -1.224  -0.915  1.00  0.00           C  
HETATM   17  O4  UNL     1      -5.825  -1.778  -1.655  1.00  0.00           O  
HETATM   18  C14 UNL     1      -3.456  -1.445  -1.288  1.00  0.00           C  
HETATM   19  C15 UNL     1      -2.383  -0.918  -0.588  1.00  0.00           C  
HETATM   20  O5  UNL     1      -0.988  -1.010  -0.780  1.00  0.00           O  
HETATM   21  C16 UNL     1      -0.368  -0.773   0.483  1.00  0.00           C  
HETATM   22  H1  UNL     1       6.253  -0.493  -0.609  1.00  0.00           H  
HETATM   23  H2  UNL     1       5.919  -0.378   1.126  1.00  0.00           H  
HETATM   24  H3  UNL     1       7.026   0.813   0.368  1.00  0.00           H  
HETATM   25  H4  UNL     1       4.259  -1.456   0.635  1.00  0.00           H  
HETATM   26  H5  UNL     1       1.907  -2.267   0.850  1.00  0.00           H  
HETATM   27  H6  UNL     1       2.112   3.319  -0.560  1.00  0.00           H  
HETATM   28  H7  UNL     1      -1.086   2.365   1.358  1.00  0.00           H  
HETATM   29  H8  UNL     1      -1.801   1.996  -0.218  1.00  0.00           H  
HETATM   30  H9  UNL     1      -1.273   0.276   2.169  1.00  0.00           H  
HETATM   31  H10 UNL     1      -4.054   0.701   1.789  1.00  0.00           H  
HETATM   32  H11 UNL     1      -5.999  -0.255   0.518  1.00  0.00           H  
HETATM   33  H12 UNL     1      -6.250  -1.281  -2.435  1.00  0.00           H  
HETATM   34  H13 UNL     1      -3.292  -2.056  -2.164  1.00  0.00           H  
HETATM   35  H14 UNL     1      -0.449  -1.680   1.117  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   25
CONECT    5    6    6   26
CONECT    6    7   21
CONECT    7    8    8   10
CONECT    8    9
CONECT    9   27
CONECT   10   11
CONECT   11   12   28   29
CONECT   12   13   21   30
CONECT   13   14   14   19
CONECT   14   15   31
CONECT   15   16   16   32
CONECT   16   17   18
CONECT   17   33
CONECT   18   19   19   34
CONECT   19   20
CONECT   20   21
CONECT   21   35
END

HMDB0029527
     RDKit          3D
Melilotocarpan B
 35 38  0  0  0  0  0  0  0  0999 V2000
    6.1230    0.2295    0.2010 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9719    1.0223    0.0063 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6901    0.5085    0.1417 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4126   -0.8009    0.4733 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0969   -1.2278    0.5869 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0334   -0.3714    0.3756 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3093    0.9457    0.0420 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6122    1.3716   -0.0713 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8684    2.6751   -0.4013 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2190    1.7684   -0.1607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0115    1.6568    0.5075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2843    0.2714    1.0447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6073   -0.1429    0.5238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9309    0.0841    0.9064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9875   -0.4464    0.2001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7686   -1.2242   -0.9152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8245   -1.7779   -1.6547 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4560   -1.4446   -1.2878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3826   -0.9184   -0.5882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9878   -1.0103   -0.7805 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3675   -0.7733    0.4834 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2527   -0.4932   -0.6093 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9191   -0.3780    1.1264 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0256    0.8132    0.3684 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2588   -1.4559    0.6347 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9070   -2.2674    0.8500 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1118    3.3192   -0.5604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0856    2.3654    1.3577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8006    1.9956   -0.2183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2725    0.2764    2.1690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0538    0.7012    1.7889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9994   -0.2547    0.5183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2499   -1.2814   -2.4349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2924   -2.0558   -2.1638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4489   -1.6797    1.1166 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  7 10  1  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
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
  8  3  1  0
 21 12  1  0
 21  6  1  0
 19 13  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
  9 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 14 31  1  0
 15 32  1  0
 17 33  1  0
 18 34  1  0
 21 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4,9-Dihydroxy-3-methoxypterocarpan	HMDB

Chemical Formula

C₁₆H₁₄O₅

Average Molecular Weight

286.2794

Monoisotopic Molecular Weight

286.084123558

IUPAC Name

5-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaene-6,14-diol

Traditional Name

melilotocarpan B

CAS Registry Number

83013-83-6

SMILES

COC1=C(O)C2=C(C=C1)C1OC3=C(C=CC(O)=C3)C1CO2

InChI Identifier

InChI=1S/C16H14O5/c1-19-12-5-4-10-15-11(7-20-16(10)14(12)18)9-3-2-8(17)6-13(9)21-15/h2-6,11,15,17-18H,7H2,1H3

InChI Key

QDFJNOVWEADTGJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pterocarpans. These are benzo-pyrano-furano-benzene compounds, containing the 6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Furanoisoflavonoids

Direct Parent

Pterocarpans

Alternative Parents

Substituents

Isoflavanol
Pterocarpan
Isoflavan
Chromane
Benzopyran
1-benzopyran
Benzofuran
Coumaran
Anisole
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Organoheterocyclic compound
Ether
Oxacycle
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Pterocarpans (LMPK12070077 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	173 - 175.5 °C	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
Water Solubility	0.26 g/L	ALOGPS
logP	2.63	ALOGPS
logP	2.21	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	9.03	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	68.15 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	75.04 m³·mol⁻¹	ChemAxon
Polarizability	29.21 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]+	165.688	31661259
DarkChem	[M-H]-	165.807	31661259
DeepCCS	[M+H]+	170.489	30932474
DeepCCS	[M-H]-	168.131	30932474
DeepCCS	[M-2H]-	201.017	30932474
DeepCCS	[M+Na]+	176.582	30932474
AllCCS	[M+H]+	166.8	32859911
AllCCS	[M+H-H2O]+	163.1	32859911
AllCCS	[M+NH4]+	170.2	32859911
AllCCS	[M+Na]+	171.2	32859911
AllCCS	[M-H]-	170.2	32859911
AllCCS	[M+Na-2H]-	169.5	32859911
AllCCS	[M+HCOO]-	168.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.0 minutes	32390414
Predicted by Siyang on May 30, 2022	11.6504 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.93 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	25.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1779.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	271.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	153.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	170.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	138.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	553.4 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	462.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	128.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	999.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	398.7 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	1197.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	339.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	349.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	416.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	246.4 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	73.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Melilotocarpan B	COC1=C(O)C2=C(C=C1)C1OC3=C(C=CC(O)=C3)C1CO2	3783.2	Standard polar	33892256
Melilotocarpan B	COC1=C(O)C2=C(C=C1)C1OC3=C(C=CC(O)=C3)C1CO2	2571.1	Standard non polar	33892256
Melilotocarpan B	COC1=C(O)C2=C(C=C1)C1OC3=C(C=CC(O)=C3)C1CO2	2801.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Melilotocarpan B,1TMS,isomer #1	COC1=CC=C2C(=C1O[Si](C)(C)C)OCC1C3=CC=C(O)C=C3OC21	2683.3	Semi standard non polar	33892256
Melilotocarpan B,1TMS,isomer #2	COC1=CC=C2C(=C1O)OCC1C3=CC=C(O[Si](C)(C)C)C=C3OC21	2738.2	Semi standard non polar	33892256
Melilotocarpan B,2TMS,isomer #1	COC1=CC=C2C(=C1O[Si](C)(C)C)OCC1C3=CC=C(O[Si](C)(C)C)C=C3OC21	2705.1	Semi standard non polar	33892256
Melilotocarpan B,1TBDMS,isomer #1	COC1=CC=C2C(=C1O[Si](C)(C)C(C)(C)C)OCC1C3=CC=C(O)C=C3OC21	2942.2	Semi standard non polar	33892256
Melilotocarpan B,1TBDMS,isomer #2	COC1=CC=C2C(=C1O)OCC1C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3OC21	3005.4	Semi standard non polar	33892256
Melilotocarpan B,2TBDMS,isomer #1	COC1=CC=C2C(=C1O[Si](C)(C)C(C)(C)C)OCC1C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3OC21	3190.4	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 - Melilotocarpan B GC-MS (Non-derivatized) - 70eV, Positive	splash10-059i-0490000000-339df8799be1aab5f4e4	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Melilotocarpan B GC-MS (2 TMS) - 70eV, Positive	splash10-014i-5149700000-2f02118a036234eb69dd	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Melilotocarpan B GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Melilotocarpan B 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 - Melilotocarpan B 10V, Positive-QTOF	splash10-000i-0590000000-2eedb9e50a93fccfd270	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melilotocarpan B 20V, Positive-QTOF	splash10-000i-0790000000-c8ae12f7942777e4fec5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melilotocarpan B 40V, Positive-QTOF	splash10-001i-9600000000-3f9ba7d7e74b17cbc5fa	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melilotocarpan B 10V, Negative-QTOF	splash10-000i-0090000000-0819975ba8e07288945d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melilotocarpan B 20V, Negative-QTOF	splash10-000i-0090000000-7edbebc8d2d5199da1c6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melilotocarpan B 40V, Negative-QTOF	splash10-00ls-2930000000-608e1c9ced70e7592dac	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melilotocarpan B 10V, Negative-QTOF	splash10-000i-0090000000-14912e1703be5edd027d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melilotocarpan B 20V, Negative-QTOF	splash10-000i-0190000000-f5f231717c607b9c521e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melilotocarpan B 40V, Negative-QTOF	splash10-03dr-3690000000-6eb54fe3322f6f14c04b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melilotocarpan B 10V, Positive-QTOF	splash10-000i-0090000000-b239d41c6032c85540b2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melilotocarpan B 20V, Positive-QTOF	splash10-000i-0490000000-589dcb73d78b023bbc5f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melilotocarpan B 40V, Positive-QTOF	splash10-0002-1930000000-f7eaa74f742661eeab8d	2021-09-24	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

FDB000667

KNApSAcK ID

C00009997

Chemspider ID

24843017

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44257459

PDB ID

Not Available

ChEBI ID

Not Available

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

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

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

Melilotocarpan B → 3,4,5-trihydroxy-6-({14-hydroxy-5-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaen-6-yl}oxy)oxane-2-carboxylic acid	details
Melilotocarpan B → 3,4,5-trihydroxy-6-({6-hydroxy-5-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaen-14-yl}oxy)oxane-2-carboxylic acid	details

Showing metabocard for Melilotocarpan B (HMDB0029527)

MOL for HMDB0029527 (Melilotocarpan B)

3D MOL for HMDB0029527 (Melilotocarpan B)

3D SDF for HMDB0029527 (Melilotocarpan B)

3D-SDF for HMDB0029527 (Melilotocarpan B)

PDB for HMDB0029527 (Melilotocarpan B)

3D PDB for HMDB0029527 (Melilotocarpan B)

SMILES for HMDB0029527 (Melilotocarpan B)

INCHI for HMDB0029527 (Melilotocarpan B)

Structure for HMDB0029527 (Melilotocarpan B)

3D Structure for HMDB0029527 (Melilotocarpan B)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions