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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:26:53 UTC

Update Date

2022-03-07 02:53:49 UTC

HMDB ID

HMDB0033692

Secondary Accession Numbers

HMDB33692

Metabolite Identification

Common Name

Melilotocarpan D

Description

Melilotocarpan D 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 D is considered to be a flavonoid. Melilotocarpan D has been detected, but not quantified in, herbs and spices and pulses. This could make melilotocarpan D a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Melilotocarpan D.

Structure

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

HMDB0033692
     RDKit          3D
Melilotocarpan D
 39 42  0  0  0  0  0  0  0  0999 V2000
    6.5116   -0.6997   -1.0258 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2545   -1.0937   -1.5397 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1003   -0.6768   -0.8952 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1708    0.1107    0.2310 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0651    0.5539    0.9116 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8113    0.2069    0.4653 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7209   -0.5813   -0.6619 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8373   -1.0246   -1.3426 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7552   -1.8279   -2.4904 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3505   -0.8143   -0.9426 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2739    0.3633   -0.4725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6947    0.2477   -0.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5023   -0.5572   -0.9300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8665   -0.6586   -0.6173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3712    0.0482    0.4529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7320   -0.0608    0.7548 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5725   -0.8716   -0.0120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5216    0.8423    1.1953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0783    1.5228    2.2487 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1685    0.9690    0.9186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3187    1.7808    1.6837 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1041    1.7578    1.4772 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4272    0.4494    0.8874 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3376   -1.2220   -1.5522 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6299   -0.9463    0.0513 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6361    0.4185   -1.0903 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1680    0.3880    0.5877 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1429    1.1800    1.8059 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5801   -2.1446   -2.9775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0067    1.2474   -1.0813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0916   -1.0983   -1.7572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5285   -1.2847   -1.2052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5629   -0.9145    0.4860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1248   -1.8949   -0.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6568   -0.4658   -1.0538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5043    2.1096    2.8148 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5577    1.8792    2.4974 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3952    2.6227    0.8622 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0194   -0.3544    1.5342 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  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 15 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
  8  3  1  0
 23 11  1  0
 23  6  1  0
 20 12  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  5 28  1  0
  9 29  1  0
 11 30  1  0
 13 31  1  0
 14 32  1  0
 17 33  1  0
 17 34  1  0
 17 35  1  0
 19 36  1  0
 22 37  1  0
 22 38  1  0
 23 39  1  0
M  END


  Mrv0541 05061307172D          

 23 26  0  0  0  0            999 V2000
    6.8689   -1.1420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2842   -3.5534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2608   -1.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4796   -2.7100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5275   -1.5272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3033   -2.6629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1217   -0.6408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9548   -1.5951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0270   -2.0203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7507   -1.3777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6743   -1.9260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4883   -2.3512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2216   -1.2363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1823   -2.7972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2033   -2.0674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3980   -1.2834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9156   -2.4191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5926   -0.4994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1431   -3.6213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4979   -1.8789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2450   -2.7293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9453   -0.5937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6872   -2.7111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  2  0  0  0  0
  6  4  2  0  0  0  0
  8  3  1  0  0  0  0
  9  4  1  0  0  0  0
 10  7  1  0  0  0  0
 10  8  1  0  0  0  0
 11  6  1  0  0  0  0
 12  5  1  0  0  0  0
 13 11  2  0  0  0  0
 14 12  2  0  0  0  0
 15  9  1  0  0  0  0
 15 10  1  0  0  0  0
 16  9  2  0  0  0  0
 16 13  1  0  0  0  0
 17  8  2  0  0  0  0
 17 14  1  0  0  0  0
 18 13  1  0  0  0  0
 19 14  1  0  0  0  0
 20  1  1  0  0  0  0
 20 11  1  0  0  0  0
 21  2  1  0  0  0  0
 21 12  1  0  0  0  0
 22  7  1  0  0  0  0
 22 16  1  0  0  0  0
 23 15  1  0  0  0  0
 23 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033692

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C2=C(C=C1)C1COC3=C(C=CC(OC)=C3O)C1O2

> <INCHI_IDENTIFIER>
InChI=1S/C17H16O6/c1-20-11-6-4-9-15-10(7-22-16(9)13(11)18)8-3-5-12(21-2)14(19)17(8)23-15/h3-6,10,15,18-19H,7H2,1-2H3

> <INCHI_KEY>
TYCXZCXHNKDQCZ-UHFFFAOYSA-N

> <FORMULA>
C17H16O6

> <MOLECULAR_WEIGHT>
316.3053

> <EXACT_MASS>
316.094688244

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
32.06215622718356

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,14-dimethoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaene-6,15-diol

> <ALOGPS_LOGP>
2.49

> <JCHEM_LOGP>
2.047986809

> <ALOGPS_LOGS>
-3.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.54487719494592

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.936264300856363

> <JCHEM_PKA_STRONGEST_BASIC>
-4.325013987561282

> <JCHEM_POLAR_SURFACE_AREA>
77.38000000000001

> <JCHEM_REFRACTIVITY>
81.50520000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.67e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
melilotocarpan D

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033692
     RDKit          3D
Melilotocarpan D
 39 42  0  0  0  0  0  0  0  0999 V2000
    6.5116   -0.6997   -1.0258 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2545   -1.0937   -1.5397 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1003   -0.6768   -0.8952 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1708    0.1107    0.2310 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0651    0.5539    0.9116 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8113    0.2069    0.4653 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7209   -0.5813   -0.6619 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8373   -1.0246   -1.3426 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7552   -1.8279   -2.4904 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3505   -0.8143   -0.9426 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2739    0.3633   -0.4725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6947    0.2477   -0.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5023   -0.5572   -0.9300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8665   -0.6586   -0.6173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3712    0.0482    0.4529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7320   -0.0608    0.7548 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5725   -0.8716   -0.0120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5216    0.8423    1.1953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0783    1.5228    2.2487 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1685    0.9690    0.9186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3187    1.7808    1.6837 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1041    1.7578    1.4772 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4272    0.4494    0.8874 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3376   -1.2220   -1.5522 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6299   -0.9463    0.0513 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6361    0.4185   -1.0903 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1680    0.3880    0.5877 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1429    1.1800    1.8059 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5801   -2.1446   -2.9775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0067    1.2474   -1.0813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0916   -1.0983   -1.7572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5285   -1.2847   -1.2052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5629   -0.9145    0.4860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1248   -1.8949   -0.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6568   -0.4658   -1.0538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5043    2.1096    2.8148 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5577    1.8792    2.4974 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3952    2.6227    0.8622 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0194   -0.3544    1.5342 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  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 15 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
  8  3  1  0
 23 11  1  0
 23  6  1  0
 20 12  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  5 28  1  0
  9 29  1  0
 11 30  1  0
 13 31  1  0
 14 32  1  0
 17 33  1  0
 17 34  1  0
 17 35  1  0
 19 36  1  0
 22 37  1  0
 22 38  1  0
 23 39  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      12.822  -2.132   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.531  -6.633   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.353  -2.145   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.362  -5.059   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.985  -2.851   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.899  -4.971   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.827  -1.196   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.649  -2.978   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.517  -3.771   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.135  -2.572   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.592  -3.595   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.911  -4.389   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.747  -2.308   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.207  -5.221   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.979  -3.859   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.210  -2.396   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.576  -4.516   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      10.440  -0.932   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.134  -6.760   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      12.129  -3.507   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -0.457  -5.095   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       7.365  -1.108   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       5.016  -5.061   0.000  0.00  0.00           O+0
CONECT    1   20                                                            
CONECT    2   21                                                            
CONECT    3    5    8                                                       
CONECT    4    6    9                                                       
CONECT    5    3   12                                                       
CONECT    6    4   11                                                       
CONECT    7   10   22                                                       
CONECT    8    3   10   17                                                  
CONECT    9    4   15   16                                                  
CONECT   10    7    8   15                                                  
CONECT   11    6   13   20                                                  
CONECT   12    5   14   21                                                  
CONECT   13   11   16   18                                                  
CONECT   14   12   17   19                                                  
CONECT   15    9   10   23                                                  
CONECT   16    9   13   22                                                  
CONECT   17    8   14   23                                                  
CONECT   18   13                                                            
CONECT   19   14                                                            
CONECT   20    1   11                                                       
CONECT   21    2   12                                                       
CONECT   22    7   16                                                       
CONECT   23   15   17                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

COMPND    HMDB0033692
HETATM    1  C1  UNL     1       6.512  -0.700  -1.026  1.00  0.00           C  
HETATM    2  O1  UNL     1       5.255  -1.094  -1.540  1.00  0.00           O  
HETATM    3  C2  UNL     1       4.100  -0.677  -0.895  1.00  0.00           C  
HETATM    4  C3  UNL     1       4.171   0.111   0.231  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.065   0.554   0.912  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.811   0.207   0.465  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.721  -0.581  -0.662  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.837  -1.025  -1.343  1.00  0.00           C  
HETATM    9  O2  UNL     1       2.755  -1.828  -2.490  1.00  0.00           O  
HETATM   10  O3  UNL     1       0.351  -0.814  -0.943  1.00  0.00           O  
HETATM   11  C8  UNL     1      -0.274   0.363  -0.473  1.00  0.00           C  
HETATM   12  C9  UNL     1      -1.695   0.248  -0.160  1.00  0.00           C  
HETATM   13  C10 UNL     1      -2.502  -0.557  -0.930  1.00  0.00           C  
HETATM   14  C11 UNL     1      -3.866  -0.659  -0.617  1.00  0.00           C  
HETATM   15  C12 UNL     1      -4.371   0.048   0.453  1.00  0.00           C  
HETATM   16  O4  UNL     1      -5.732  -0.061   0.755  1.00  0.00           O  
HETATM   17  C13 UNL     1      -6.573  -0.872  -0.012  1.00  0.00           C  
HETATM   18  C14 UNL     1      -3.522   0.842   1.195  1.00  0.00           C  
HETATM   19  O5  UNL     1      -4.078   1.523   2.249  1.00  0.00           O  
HETATM   20  C15 UNL     1      -2.169   0.969   0.919  1.00  0.00           C  
HETATM   21  O6  UNL     1      -1.319   1.781   1.684  1.00  0.00           O  
HETATM   22  C16 UNL     1       0.104   1.758   1.477  1.00  0.00           C  
HETATM   23  C17 UNL     1       0.427   0.449   0.887  1.00  0.00           C  
HETATM   24  H1  UNL     1       7.338  -1.222  -1.552  1.00  0.00           H  
HETATM   25  H2  UNL     1       6.630  -0.946   0.051  1.00  0.00           H  
HETATM   26  H3  UNL     1       6.636   0.418  -1.090  1.00  0.00           H  
HETATM   27  H4  UNL     1       5.168   0.388   0.588  1.00  0.00           H  
HETATM   28  H5  UNL     1       3.143   1.180   1.806  1.00  0.00           H  
HETATM   29  H6  UNL     1       3.580  -2.145  -2.978  1.00  0.00           H  
HETATM   30  H7  UNL     1      -0.007   1.247  -1.081  1.00  0.00           H  
HETATM   31  H8  UNL     1      -2.092  -1.098  -1.757  1.00  0.00           H  
HETATM   32  H9  UNL     1      -4.528  -1.285  -1.205  1.00  0.00           H  
HETATM   33  H10 UNL     1      -7.563  -0.914   0.486  1.00  0.00           H  
HETATM   34  H11 UNL     1      -6.125  -1.895  -0.059  1.00  0.00           H  
HETATM   35  H12 UNL     1      -6.657  -0.466  -1.054  1.00  0.00           H  
HETATM   36  H13 UNL     1      -3.504   2.110   2.815  1.00  0.00           H  
HETATM   37  H14 UNL     1       0.558   1.879   2.497  1.00  0.00           H  
HETATM   38  H15 UNL     1       0.395   2.623   0.862  1.00  0.00           H  
HETATM   39  H16 UNL     1       0.019  -0.354   1.534  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   27
CONECT    5    6    6   28
CONECT    6    7   23
CONECT    7    8    8   10
CONECT    8    9
CONECT    9   29
CONECT   10   11
CONECT   11   12   23   30
CONECT   12   13   13   20
CONECT   13   14   31
CONECT   14   15   15   32
CONECT   15   16   18
CONECT   16   17
CONECT   17   33   34   35
CONECT   18   19   20   20
CONECT   19   36
CONECT   20   21
CONECT   21   22
CONECT   22   23   37   38
CONECT   23   39
END

HMDB0033692
     RDKit          3D
Melilotocarpan D
 39 42  0  0  0  0  0  0  0  0999 V2000
    6.5116   -0.6997   -1.0258 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2545   -1.0937   -1.5397 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1003   -0.6768   -0.8952 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1708    0.1107    0.2310 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0651    0.5539    0.9116 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8113    0.2069    0.4653 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7209   -0.5813   -0.6619 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8373   -1.0246   -1.3426 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7552   -1.8279   -2.4904 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3505   -0.8143   -0.9426 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2739    0.3633   -0.4725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6947    0.2477   -0.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5023   -0.5572   -0.9300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8665   -0.6586   -0.6173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3712    0.0482    0.4529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7320   -0.0608    0.7548 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5725   -0.8716   -0.0120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5216    0.8423    1.1953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0783    1.5228    2.2487 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1685    0.9690    0.9186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3187    1.7808    1.6837 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1041    1.7578    1.4772 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4272    0.4494    0.8874 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3376   -1.2220   -1.5522 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6299   -0.9463    0.0513 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6361    0.4185   -1.0903 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1680    0.3880    0.5877 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1429    1.1800    1.8059 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5801   -2.1446   -2.9775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0067    1.2474   -1.0813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0916   -1.0983   -1.7572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5285   -1.2847   -1.2052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5629   -0.9145    0.4860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1248   -1.8949   -0.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6568   -0.4658   -1.0538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5043    2.1096    2.8148 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5577    1.8792    2.4974 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3952    2.6227    0.8622 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0194   -0.3544    1.5342 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  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 15 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
  8  3  1  0
 23 11  1  0
 23  6  1  0
 20 12  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  5 28  1  0
  9 29  1  0
 11 30  1  0
 13 31  1  0
 14 32  1  0
 17 33  1  0
 17 34  1  0
 17 35  1  0
 19 36  1  0
 22 37  1  0
 22 38  1  0
 23 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4,10-Dihydroxy-3,10-dimethoxypterocarpan	HMDB
4,10-Dihydroxy-3,9-dimethoxypterocarpan	HMDB

Chemical Formula

C₁₇H₁₆O₆

Average Molecular Weight

316.3053

Monoisotopic Molecular Weight

316.094688244

IUPAC Name

5,14-dimethoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaene-6,15-diol

Traditional Name

melilotocarpan D

CAS Registry Number

83013-81-4

SMILES

COC1=C(O)C2=C(C=C1)C1COC3=C(C=CC(OC)=C3O)C1O2

InChI Identifier

InChI=1S/C17H16O6/c1-20-11-6-4-9-15-10(7-22-16(9)13(11)18)8-3-5-12(21-2)14(19)17(8)23-15/h3-6,10,15,18-19H,7H2,1-2H3

InChI Key

TYCXZCXHNKDQCZ-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

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Pterocarpans (LMPK12070084 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0033692)
Cytoplasm (HMDB: HMDB0033692)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033692)

Source

Exogenous

Exogenous (HMDB: HMDB0033692)

Food

Food (HMDB: HMDB0033692)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Pulse

Pulses (FooDB: FOOD00867)

Endogenous

Plant

Plant (HMDB: HMDB0033692)
Fabaceae (HMDB: HMDB0033692)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033692)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	161 - 162.5 °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	0.27 g/L	ALOGPS
logP	2.49	ALOGPS
logP	2.05	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	8.94	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	77.38 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	81.51 m³·mol⁻¹	ChemAxon
Polarizability	32.06 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]+	171.676	31661259
DarkChem	[M-H]-	172.955	31661259
DeepCCS	[M+H]+	177.369	30932474
DeepCCS	[M-H]-	175.011	30932474
DeepCCS	[M-2H]-	209.064	30932474
DeepCCS	[M+Na]+	184.291	30932474
AllCCS	[M+H]+	174.2	32859911
AllCCS	[M+H-H2O]+	170.8	32859911
AllCCS	[M+NH4]+	177.4	32859911
AllCCS	[M+Na]+	178.3	32859911
AllCCS	[M-H]-	177.6	32859911
AllCCS	[M+Na-2H]-	177.1	32859911
AllCCS	[M+HCOO]-	176.6	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.	5.96 minutes	32390414
Predicted by Siyang on May 30, 2022	11.4141 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.95 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	26.3 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1871.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	240.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	151.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	170.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	99.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	549.2 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	462.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	136.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	970.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	390.2 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	1149.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	317.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	376.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	406.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	264.3 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	82.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Melilotocarpan D	COC1=C(O)C2=C(C=C1)C1COC3=C(C=CC(OC)=C3O)C1O2	3986.7	Standard polar	33892256
Melilotocarpan D	COC1=C(O)C2=C(C=C1)C1COC3=C(C=CC(OC)=C3O)C1O2	2634.8	Standard non polar	33892256
Melilotocarpan D	COC1=C(O)C2=C(C=C1)C1COC3=C(C=CC(OC)=C3O)C1O2	2871.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Melilotocarpan D,1TMS,isomer #1	COC1=CC=C2C(=C1O)OCC1C3=CC=C(OC)C(O[Si](C)(C)C)=C3OC21	2902.5	Semi standard non polar	33892256
Melilotocarpan D,1TMS,isomer #2	COC1=CC=C2C(=C1O)OC1C3=CC=C(OC)C(O[Si](C)(C)C)=C3OCC21	2865.8	Semi standard non polar	33892256
Melilotocarpan D,2TMS,isomer #1	COC1=CC=C2C(=C1O[Si](C)(C)C)OC1C3=CC=C(OC)C(O[Si](C)(C)C)=C3OCC21	2813.3	Semi standard non polar	33892256
Melilotocarpan D,1TBDMS,isomer #1	COC1=CC=C2C(=C1O)OCC1C3=CC=C(OC)C(O[Si](C)(C)C(C)(C)C)=C3OC21	3144.4	Semi standard non polar	33892256
Melilotocarpan D,1TBDMS,isomer #2	COC1=CC=C2C(=C1O)OC1C3=CC=C(OC)C(O[Si](C)(C)C(C)(C)C)=C3OCC21	3103.3	Semi standard non polar	33892256
Melilotocarpan D,2TBDMS,isomer #1	COC1=CC=C2C(=C1O[Si](C)(C)C(C)(C)C)OC1C3=CC=C(OC)C(O[Si](C)(C)C(C)(C)C)=C3OCC21	3277.6	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 D GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-0694000000-780f31fda8468544d0a1	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Melilotocarpan D GC-MS (2 TMS) - 70eV, Positive	splash10-00kk-3069800000-f343c9a18af7bf95ad02	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Melilotocarpan D GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Melilotocarpan D GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melilotocarpan D 10V, Positive-QTOF	splash10-014r-0609000000-16ff61d5c1e379454542	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melilotocarpan D 20V, Positive-QTOF	splash10-00kr-0937000000-517febdba007c12453a8	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melilotocarpan D 40V, Positive-QTOF	splash10-001i-8900000000-389fabdb5390a2c80202	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melilotocarpan D 10V, Negative-QTOF	splash10-014i-0009000000-7eb5483294da2784c0fe	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melilotocarpan D 20V, Negative-QTOF	splash10-014i-0196000000-79a4394f4ba150e2f3f4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melilotocarpan D 40V, Negative-QTOF	splash10-02or-1960000000-62e05c3bd055871dfa18	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melilotocarpan D 10V, Positive-QTOF	splash10-014i-0009000000-9d41b4964537964e8e8b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melilotocarpan D 20V, Positive-QTOF	splash10-014i-0319000000-df4b841c5597407d8080	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melilotocarpan D 40V, Positive-QTOF	splash10-004r-2910000000-d26e388fcc1c7d3ba3f7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melilotocarpan D 10V, Negative-QTOF	splash10-014i-0009000000-a5811c0f9e3fc0f9d174	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melilotocarpan D 20V, Negative-QTOF	splash10-014i-0096000000-6072561d9d3c9d22c24d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melilotocarpan D 40V, Negative-QTOF	splash10-0avl-1290000000-20936662c25cdf7ef46e	2021-09-24	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

FDB011798

KNApSAcK ID

C00009998

Chemspider ID

4477662

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5319351

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 D → 3,4,5-trihydroxy-6-({6-hydroxy-5,14-dimethoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaen-15-yl}oxy)oxane-2-carboxylic acid	details
Melilotocarpan D → 3,4,5-trihydroxy-6-({15-hydroxy-5,14-dimethoxy-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

Showing metabocard for Melilotocarpan D (HMDB0033692)

MOL for HMDB0033692 (Melilotocarpan D)

3D MOL for HMDB0033692 (Melilotocarpan D)

3D SDF for HMDB0033692 (Melilotocarpan D)

3D-SDF for HMDB0033692 (Melilotocarpan D)

PDB for HMDB0033692 (Melilotocarpan D)

3D PDB for HMDB0033692 (Melilotocarpan D)

SMILES for HMDB0033692 (Melilotocarpan D)

INCHI for HMDB0033692 (Melilotocarpan D)

Structure for HMDB0033692 (Melilotocarpan D)

3D Structure for HMDB0033692 (Melilotocarpan D)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions