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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 18:26:16 UTC

Update Date

2022-03-07 02:53:49 UTC

HMDB ID

HMDB0033683

Secondary Accession Numbers

HMDB33683

Metabolite Identification

Common Name

Melilotocarpan E

Description

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

Structure

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

HMDB0033683
     RDKit          3D
Melilotocarpan E
 39 42  0  0  0  0  0  0  0  0999 V2000
    5.8472    1.8445    0.4143 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3330    0.6044    0.0051 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9912    0.3328    0.1693 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1813    1.2890    0.7339 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8451    0.9944    0.8874 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3250   -0.2069    0.4955 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1229   -1.1994   -0.0817 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4588   -0.8960   -0.2315 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3229   -1.8264   -0.7966 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5748   -2.4174   -0.4747 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1525   -2.6235   -0.5539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4662   -1.2828   -0.6454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9172   -1.1930   -0.5805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9883   -1.9307   -1.0583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2767   -1.5387   -0.8090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5418   -0.4008   -0.0767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8583   -0.0429    0.1504 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4972    0.3615    0.4171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7904    1.5028    1.1513 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9560    2.7778    0.6100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1984   -0.0560    0.1517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9870    0.5493    0.5461 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0926   -0.5407    0.6492 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4042    2.6374   -0.2312 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5844    2.1019    1.4627 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9462    1.8085    0.2693 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5911    2.2618    1.0536 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1856    1.7184    1.3244 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2984   -1.6368   -0.9192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1114   -3.3295   -1.3549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1200   -3.0769    0.4300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0823   -0.6805   -1.4926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7931   -2.8206   -1.6310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1269   -2.1213   -1.1864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0712    0.7853    0.6833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6730    2.7559   -0.2320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3175    3.4420    1.4352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0250    3.2339    0.2403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2741   -1.1807    1.5202 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  1  0
 19 20  1  0
 18 21  2  0
 21 22  1  0
 22 23  1  0
  8  3  1  0
 23 12  1  0
 23  6  1  0
 21 13  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
 11 31  1  0
 12 32  1  0
 14 33  1  0
 15 34  1  0
 17 35  1  0
 20 36  1  0
 20 37  1  0
 20 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
    1.8372   -4.0673    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
    0.4883   -2.3512    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
    5.2216   -1.2363    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
    1.1823   -2.7972    0.0000 C   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
    5.5926   -0.4994    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
    1.1431   -3.6213    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  5  1  0  0  0  0
 12  6  1  0  0  0  0
 13 12  2  0  0  0  0
 14  9  1  0  0  0  0
 14 10  1  0  0  0  0
 15  9  2  0  0  0  0
 15 13  1  0  0  0  0
 16  8  2  0  0  0  0
 17 11  2  0  0  0  0
 17 16  1  0  0  0  0
 18 11  1  0  0  0  0
 19 13  1  0  0  0  0
 20  1  1  0  0  0  0
 20 12  1  0  0  0  0
 21  2  1  0  0  0  0
 21 17  1  0  0  0  0
 22  7  1  0  0  0  0
 22 15  1  0  0  0  0
 23 14  1  0  0  0  0
 23 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033683

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C2=C(C=C1)C1OC3=C(C=CC(O)=C3OC)C1CO2

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

> <INCHI_KEY>
AHWUIMDBTDTTRI-UHFFFAOYSA-N

> <FORMULA>
C17H16O6

> <MOLECULAR_WEIGHT>
316.3053

> <EXACT_MASS>
316.094688244

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
31.791664772875663

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,15-dimethoxy-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>
2.52

> <JCHEM_LOGP>
2.047986809

> <ALOGPS_LOGS>
-3.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.1396849039631

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.13584321244658

> <JCHEM_PKA_STRONGEST_BASIC>
-4.340787967668605

> <JCHEM_POLAR_SURFACE_AREA>
77.38000000000001

> <JCHEM_REFRACTIVITY>
81.50520000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.52e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
melilotocarpan E

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033683
     RDKit          3D
Melilotocarpan E
 39 42  0  0  0  0  0  0  0  0999 V2000
    5.8472    1.8445    0.4143 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3330    0.6044    0.0051 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9912    0.3328    0.1693 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1813    1.2890    0.7339 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8451    0.9944    0.8874 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3250   -0.2069    0.4955 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1229   -1.1994   -0.0817 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4588   -0.8960   -0.2315 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3229   -1.8264   -0.7966 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5748   -2.4174   -0.4747 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1525   -2.6235   -0.5539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4662   -1.2828   -0.6454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9172   -1.1930   -0.5805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9883   -1.9307   -1.0583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2767   -1.5387   -0.8090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5418   -0.4008   -0.0767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8583   -0.0429    0.1504 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4972    0.3615    0.4171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7904    1.5028    1.1513 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9560    2.7778    0.6100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1984   -0.0560    0.1517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9870    0.5493    0.5461 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0926   -0.5407    0.6492 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4042    2.6374   -0.2312 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5844    2.1019    1.4627 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9462    1.8085    0.2693 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5911    2.2618    1.0536 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1856    1.7184    1.3244 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2984   -1.6368   -0.9192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1114   -3.3295   -1.3549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1200   -3.0769    0.4300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0823   -0.6805   -1.4926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7931   -2.8206   -1.6310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1269   -2.1213   -1.1864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0712    0.7853    0.6833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6730    2.7559   -0.2320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3175    3.4420    1.4352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0250    3.2339    0.2403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2741   -1.1807    1.5202 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  1  0
 19 20  1  0
 18 21  2  0
 21 22  1  0
 22 23  1  0
  8  3  1  0
 23 12  1  0
 23  6  1  0
 21 13  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
 11 31  1  0
 12 32  1  0
 14 33  1  0
 15 34  1  0
 17 35  1  0
 20 36  1  0
 20 37  1  0
 20 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       3.429  -7.592   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       0.911  -4.389   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.592  -3.595   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       5.979  -3.859   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.210  -2.396   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.576  -4.516   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.207  -5.221   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.457  -5.095   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      10.440  -0.932   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       2.134  -6.760   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   11                                                       
CONECT    6    4   12                                                       
CONECT    7   10   22                                                       
CONECT    8    3   10   16                                                  
CONECT    9    4   14   15                                                  
CONECT   10    7    8   14                                                  
CONECT   11    5   17   18                                                  
CONECT   12    6   13   20                                                  
CONECT   13   12   15   19                                                  
CONECT   14    9   10   23                                                  
CONECT   15    9   13   22                                                  
CONECT   16    8   17   23                                                  
CONECT   17   11   16   21                                                  
CONECT   18   11                                                            
CONECT   19   13                                                            
CONECT   20    1   12                                                       
CONECT   21    2   17                                                       
CONECT   22    7   15                                                       
CONECT   23   14   16                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

COMPND    HMDB0033683
HETATM    1  C1  UNL     1       5.847   1.844   0.414  1.00  0.00           C  
HETATM    2  O1  UNL     1       5.333   0.604   0.005  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.991   0.333   0.169  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.181   1.289   0.734  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.845   0.994   0.887  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.325  -0.207   0.496  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.123  -1.199  -0.082  1.00  0.00           C  
HETATM    8  C7  UNL     1       3.459  -0.896  -0.231  1.00  0.00           C  
HETATM    9  O2  UNL     1       4.323  -1.826  -0.797  1.00  0.00           O  
HETATM   10  O3  UNL     1       1.575  -2.417  -0.475  1.00  0.00           O  
HETATM   11  C8  UNL     1       0.152  -2.624  -0.554  1.00  0.00           C  
HETATM   12  C9  UNL     1      -0.466  -1.283  -0.645  1.00  0.00           C  
HETATM   13  C10 UNL     1      -1.917  -1.193  -0.581  1.00  0.00           C  
HETATM   14  C11 UNL     1      -2.988  -1.931  -1.058  1.00  0.00           C  
HETATM   15  C12 UNL     1      -4.277  -1.539  -0.809  1.00  0.00           C  
HETATM   16  C13 UNL     1      -4.542  -0.401  -0.077  1.00  0.00           C  
HETATM   17  O4  UNL     1      -5.858  -0.043   0.150  1.00  0.00           O  
HETATM   18  C14 UNL     1      -3.497   0.361   0.417  1.00  0.00           C  
HETATM   19  O5  UNL     1      -3.790   1.503   1.151  1.00  0.00           O  
HETATM   20  C15 UNL     1      -3.956   2.778   0.610  1.00  0.00           C  
HETATM   21  C16 UNL     1      -2.198  -0.056   0.152  1.00  0.00           C  
HETATM   22  O6  UNL     1      -0.987   0.549   0.546  1.00  0.00           O  
HETATM   23  C17 UNL     1      -0.093  -0.541   0.649  1.00  0.00           C  
HETATM   24  H1  UNL     1       5.404   2.637  -0.231  1.00  0.00           H  
HETATM   25  H2  UNL     1       5.584   2.102   1.463  1.00  0.00           H  
HETATM   26  H3  UNL     1       6.946   1.809   0.269  1.00  0.00           H  
HETATM   27  H4  UNL     1       3.591   2.262   1.054  1.00  0.00           H  
HETATM   28  H5  UNL     1       1.186   1.718   1.324  1.00  0.00           H  
HETATM   29  H6  UNL     1       5.298  -1.637  -0.919  1.00  0.00           H  
HETATM   30  H7  UNL     1      -0.111  -3.329  -1.355  1.00  0.00           H  
HETATM   31  H8  UNL     1      -0.120  -3.077   0.430  1.00  0.00           H  
HETATM   32  H9  UNL     1      -0.082  -0.681  -1.493  1.00  0.00           H  
HETATM   33  H10 UNL     1      -2.793  -2.821  -1.631  1.00  0.00           H  
HETATM   34  H11 UNL     1      -5.127  -2.121  -1.186  1.00  0.00           H  
HETATM   35  H12 UNL     1      -6.071   0.785   0.683  1.00  0.00           H  
HETATM   36  H13 UNL     1      -4.673   2.756  -0.232  1.00  0.00           H  
HETATM   37  H14 UNL     1      -4.317   3.442   1.435  1.00  0.00           H  
HETATM   38  H15 UNL     1      -3.025   3.234   0.240  1.00  0.00           H  
HETATM   39  H16 UNL     1      -0.274  -1.181   1.520  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   30   31
CONECT   12   13   23   32
CONECT   13   14   14   21
CONECT   14   15   33
CONECT   15   16   16   34
CONECT   16   17   18
CONECT   17   35
CONECT   18   19   21   21
CONECT   19   20
CONECT   20   36   37   38
CONECT   21   22
CONECT   22   23
CONECT   23   39
END

HMDB0033683
     RDKit          3D
Melilotocarpan E
 39 42  0  0  0  0  0  0  0  0999 V2000
    5.8472    1.8445    0.4143 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3330    0.6044    0.0051 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9912    0.3328    0.1693 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1813    1.2890    0.7339 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8451    0.9944    0.8874 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3250   -0.2069    0.4955 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1229   -1.1994   -0.0817 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4588   -0.8960   -0.2315 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3229   -1.8264   -0.7966 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5748   -2.4174   -0.4747 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1525   -2.6235   -0.5539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4662   -1.2828   -0.6454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9172   -1.1930   -0.5805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9883   -1.9307   -1.0583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2767   -1.5387   -0.8090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5418   -0.4008   -0.0767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8583   -0.0429    0.1504 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4972    0.3615    0.4171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7904    1.5028    1.1513 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9560    2.7778    0.6100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1984   -0.0560    0.1517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9870    0.5493    0.5461 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0926   -0.5407    0.6492 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4042    2.6374   -0.2312 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5844    2.1019    1.4627 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9462    1.8085    0.2693 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5911    2.2618    1.0536 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1856    1.7184    1.3244 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2984   -1.6368   -0.9192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1114   -3.3295   -1.3549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1200   -3.0769    0.4300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0823   -0.6805   -1.4926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7931   -2.8206   -1.6310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1269   -2.1213   -1.1864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0712    0.7853    0.6833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6730    2.7559   -0.2320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3175    3.4420    1.4352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0250    3.2339    0.2403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2741   -1.1807    1.5202 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  1  0
 19 20  1  0
 18 21  2  0
 21 22  1  0
 22 23  1  0
  8  3  1  0
 23 12  1  0
 23  6  1  0
 21 13  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
 11 31  1  0
 12 32  1  0
 14 33  1  0
 15 34  1  0
 17 35  1  0
 20 36  1  0
 20 37  1  0
 20 38  1  0
 23 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

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

Chemical Formula

C₁₇H₁₆O₆

Average Molecular Weight

316.3053

Monoisotopic Molecular Weight

316.094688244

IUPAC Name

5,15-dimethoxy-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 E

CAS Registry Number

83013-80-3

SMILES

COC1=C(O)C2=C(C=C1)C1OC3=C(C=CC(O)=C3OC)C1CO2

InChI Identifier

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

InChI Key

AHWUIMDBTDTTRI-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 (LMPK12070085 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0033683)
Cell membrane (HMDB: HMDB0033683)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033683)

Source

Exogenous

Exogenous (HMDB: HMDB0033683)

Food

Food (HMDB: HMDB0033683)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Pulse

Pulses (FooDB: FOOD00867)

Endogenous

Plant

Plant (HMDB: HMDB0033683)
Fabaceae (HMDB: HMDB0033683)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033683)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	197 - 199 °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	0.25 g/L	ALOGPS
logP	2.52	ALOGPS
logP	2.05	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	9.14	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	31.79 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]+	171.639	31661259
DarkChem	[M-H]-	172.796	31661259
DeepCCS	[M+H]+	177.681	30932474
DeepCCS	[M-H]-	175.323	30932474
DeepCCS	[M-2H]-	208.519	30932474
DeepCCS	[M+Na]+	183.774	30932474
AllCCS	[M+H]+	173.8	32859911
AllCCS	[M+H-H2O]+	170.3	32859911
AllCCS	[M+NH4]+	177.0	32859911
AllCCS	[M+Na]+	177.9	32859911
AllCCS	[M-H]-	177.4	32859911
AllCCS	[M+Na-2H]-	176.9	32859911
AllCCS	[M+HCOO]-	176.4	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.	5.54 minutes	32390414
Predicted by Siyang on May 30, 2022	11.1927 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	26.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1837.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	235.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	148.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	167.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	94.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	537.5 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	456.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	137.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	931.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	380.1 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	1120.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	309.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	348.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	408.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	271.8 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	85.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Melilotocarpan E	COC1=C(O)C2=C(C=C1)C1OC3=C(C=CC(O)=C3OC)C1CO2	4111.5	Standard polar	33892256
Melilotocarpan E	COC1=C(O)C2=C(C=C1)C1OC3=C(C=CC(O)=C3OC)C1CO2	2677.7	Standard non polar	33892256
Melilotocarpan E	COC1=C(O)C2=C(C=C1)C1OC3=C(C=CC(O)=C3OC)C1CO2	2777.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Melilotocarpan E,1TMS,isomer #1	COC1=CC=C2C(=C1O[Si](C)(C)C)OCC1C3=CC=C(O)C(OC)=C3OC21	2811.7	Semi standard non polar	33892256
Melilotocarpan E,1TMS,isomer #2	COC1=CC=C2C(=C1O)OCC1C3=CC=C(O[Si](C)(C)C)C(OC)=C3OC21	2876.8	Semi standard non polar	33892256
Melilotocarpan E,2TMS,isomer #1	COC1=CC=C2C(=C1O[Si](C)(C)C)OCC1C3=CC=C(O[Si](C)(C)C)C(OC)=C3OC21	2795.1	Semi standard non polar	33892256
Melilotocarpan E,1TBDMS,isomer #1	COC1=CC=C2C(=C1O[Si](C)(C)C(C)(C)C)OCC1C3=CC=C(O)C(OC)=C3OC21	3042.2	Semi standard non polar	33892256
Melilotocarpan E,1TBDMS,isomer #2	COC1=CC=C2C(=C1O)OCC1C3=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C3OC21	3107.6	Semi standard non polar	33892256
Melilotocarpan E,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(OC)=C3OC21	3234.0	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 E GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-0893000000-acd27951d0bd9d5bdd2f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Melilotocarpan E GC-MS (2 TMS) - 70eV, Positive	splash10-0072-3458900000-efaef0c720ba0797396e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Melilotocarpan E 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 E 10V, Positive-QTOF	splash10-014r-0509000000-39264f421766fca820a0	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melilotocarpan E 20V, Positive-QTOF	splash10-00kr-0749000000-809861f7282c3e405971	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melilotocarpan E 40V, Positive-QTOF	splash10-001i-9810000000-593d1f0563565cb7bbe8	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melilotocarpan E 10V, Negative-QTOF	splash10-014i-0009000000-ec3dc277bcf4d3b211b5	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melilotocarpan E 20V, Negative-QTOF	splash10-014i-0096000000-73b663032b6dae5a31ee	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melilotocarpan E 40V, Negative-QTOF	splash10-07fr-0690000000-ba84aa6d9746bdee432d	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melilotocarpan E 10V, Positive-QTOF	splash10-014i-0009000000-9d41b4964537964e8e8b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melilotocarpan E 20V, Positive-QTOF	splash10-014i-0309000000-dc1376bf4757359943ce	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melilotocarpan E 40V, Positive-QTOF	splash10-00os-0931000000-3cfb2a60a01170d282f9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melilotocarpan E 10V, Negative-QTOF	splash10-014i-0009000000-a5811c0f9e3fc0f9d174	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melilotocarpan E 20V, Negative-QTOF	splash10-014i-0096000000-45ee2cf8b53cc960c851	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melilotocarpan E 40V, Negative-QTOF	splash10-01bc-0590000000-f892cdc1b22adc09c782	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

FDB011786

KNApSAcK ID

C00009999

Chemspider ID

24843020

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44257462

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 E → 3,4,5-trihydroxy-6-({6-hydroxy-5,15-dimethoxy-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
Melilotocarpan E → 3,4,5-trihydroxy-6-({14-hydroxy-5,15-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 E (HMDB0033683)

MOL for HMDB0033683 (Melilotocarpan E)

3D MOL for HMDB0033683 (Melilotocarpan E)

3D SDF for HMDB0033683 (Melilotocarpan E)

3D-SDF for HMDB0033683 (Melilotocarpan E)

PDB for HMDB0033683 (Melilotocarpan E)

3D PDB for HMDB0033683 (Melilotocarpan E)

SMILES for HMDB0033683 (Melilotocarpan E)

INCHI for HMDB0033683 (Melilotocarpan E)

Structure for HMDB0033683 (Melilotocarpan E)

3D Structure for HMDB0033683 (Melilotocarpan E)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions