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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 17:53:58 UTC

Update Date

2022-03-07 02:53:36 UTC

HMDB ID

HMDB0033142

Secondary Accession Numbers

HMDB33142

Metabolite Identification

Common Name

Melilotocarpan A

Description

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

Structure

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

HMDB0033142
     RDKit          3D
Melilotocarpan A
 38 41  0  0  0  0  0  0  0  0999 V2000
    5.6762    2.4890   -0.3360 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5987    1.1723    0.1528 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4188    0.4562    0.2366 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4617   -0.8287    0.7326 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3188   -1.6193    0.8508 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0944   -1.0764    0.4485 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0502    0.2080   -0.0476 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1983    0.9754   -0.1561 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7203    0.5318   -0.3838 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0588   -0.7222   -0.6213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3805   -0.4935   -0.3968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1007    0.1507   -1.3815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4573    0.4067   -1.2538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1080    0.0065   -0.1097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4639    0.2290    0.0872 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2206    0.8906   -0.9159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3773   -0.6385    0.8715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0071   -1.0484    2.0258 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0288   -0.8931    0.7448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2831   -1.5425    1.7279 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1110   -1.3189    1.8114 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6983   -1.5770    0.4181 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7229    2.6234   -0.7236 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0045    2.5994   -1.2273 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4676    3.2453    0.4443 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4220   -1.2214    1.0355 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3557   -2.6289    1.2410 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1610    1.9941   -0.5498 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2847   -1.1161   -1.6148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6439    0.4885   -2.3025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0401    0.9098   -2.0130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1798    1.1886   -0.4357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7274    1.8368   -1.2473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4002    0.2426   -1.7876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0034   -0.8862    2.1730 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5459   -2.0638    2.5015 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3832   -0.3102    2.1212 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6689   -2.6594    0.1781 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
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
  8  3  1  0
 22 10  1  0
 22  6  1  0
 19 11  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
  8 28  1  0
 10 29  1  0
 12 30  1  0
 13 31  1  0
 16 32  1  0
 16 33  1  0
 16 34  1  0
 18 35  1  0
 21 36  1  0
 21 37  1  0
 22 38  1  0
M  END


  Mrv0541 05061306562D          

 22 25  0  0  0  0            999 V2000
    7.2186    1.9602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5894    0.8188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7521    1.2040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0188    0.8259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7999    2.3869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9763    2.3397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0972    2.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1579    0.3177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7913    2.0281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3248    1.2719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2526    1.6971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5289    1.0546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6053    1.6029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3640    2.0960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0579    0.9131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0762    1.7443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8816    0.9603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6869    0.1762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5246    2.4062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2184    1.5557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3343    0.2705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5923    2.3879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  6  5  2  0  0  0  0
  9  3  1  0  0  0  0
  9  7  2  0  0  0  0
 10  4  1  0  0  0  0
 11  5  1  0  0  0  0
 12  8  1  0  0  0  0
 12 10  1  0  0  0  0
 13  6  1  0  0  0  0
 14  7  1  0  0  0  0
 14 10  2  0  0  0  0
 15 13  2  0  0  0  0
 16 11  1  0  0  0  0
 16 12  1  0  0  0  0
 17 11  2  0  0  0  0
 17 15  1  0  0  0  0
 18 15  1  0  0  0  0
 19  1  1  0  0  0  0
 19  9  1  0  0  0  0
 20  2  1  0  0  0  0
 20 13  1  0  0  0  0
 21  8  1  0  0  0  0
 21 17  1  0  0  0  0
 22 14  1  0  0  0  0
 22 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033142

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=C(C=C1)C1COC3=C(C=CC(OC)=C3O)C1O2

> <INCHI_IDENTIFIER>
InChI=1S/C17H16O5/c1-19-9-3-4-10-12-8-21-17-11(16(12)22-14(10)7-9)5-6-13(20-2)15(17)18/h3-7,12,16,18H,8H2,1-2H3

> <INCHI_KEY>
YHSXPHNOIMTWTH-UHFFFAOYSA-N

> <FORMULA>
C17H16O5

> <MOLECULAR_WEIGHT>
300.3059

> <EXACT_MASS>
300.099773622

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
31.240742864184895

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <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-hexaen-6-ol

> <ALOGPS_LOGP>
2.82

> <JCHEM_LOGP>
2.3515521306666667

> <ALOGPS_LOGS>
-3.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.18722832376842

> <JCHEM_PKA_STRONGEST_BASIC>
-4.291168224484533

> <JCHEM_POLAR_SURFACE_AREA>
57.150000000000006

> <JCHEM_REFRACTIVITY>
79.52430000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.67e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,14-dimethoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaen-6-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033142
     RDKit          3D
Melilotocarpan A
 38 41  0  0  0  0  0  0  0  0999 V2000
    5.6762    2.4890   -0.3360 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5987    1.1723    0.1528 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4188    0.4562    0.2366 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4617   -0.8287    0.7326 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3188   -1.6193    0.8508 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0944   -1.0764    0.4485 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0502    0.2080   -0.0476 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1983    0.9754   -0.1561 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7203    0.5318   -0.3838 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0588   -0.7222   -0.6213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3805   -0.4935   -0.3968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1007    0.1507   -1.3815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4573    0.4067   -1.2538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1080    0.0065   -0.1097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4639    0.2290    0.0872 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2206    0.8906   -0.9159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3773   -0.6385    0.8715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0071   -1.0484    2.0258 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0288   -0.8931    0.7448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2831   -1.5425    1.7279 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1110   -1.3189    1.8114 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6983   -1.5770    0.4181 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7229    2.6234   -0.7236 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0045    2.5994   -1.2273 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4676    3.2453    0.4443 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4220   -1.2214    1.0355 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3557   -2.6289    1.2410 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1610    1.9941   -0.5498 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2847   -1.1161   -1.6148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6439    0.4885   -2.3025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0401    0.9098   -2.0130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1798    1.1886   -0.4357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7274    1.8368   -1.2473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4002    0.2426   -1.7876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0034   -0.8862    2.1730 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5459   -2.0638    2.5015 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3832   -0.3102    2.1212 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6689   -2.6594    0.1781 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
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
  8  3  1  0
 22 10  1  0
 22  6  1  0
 19 11  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
  8 28  1  0
 10 29  1  0
 12 30  1  0
 13 31  1  0
 16 32  1  0
 16 33  1  0
 16 34  1  0
 18 35  1  0
 21 36  1  0
 21 37  1  0
 22 38  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      13.475   3.659   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.100   1.528   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.737   2.247   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.368   1.542   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.360   4.456   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.822   4.367   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.515   4.618   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.895   0.593   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.810   3.786   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.073   2.374   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.205   3.168   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.587   1.969   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.130   2.992   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.146   3.913   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.975   1.704   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.742   3.256   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.512   1.793   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.282   0.329   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      12.179   4.492   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -0.408   2.904   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       4.357   0.505   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       6.706   4.457   0.000  0.00  0.00           O+0
CONECT    1   19                                                            
CONECT    2   20                                                            
CONECT    3    4    9                                                       
CONECT    4    3   10                                                       
CONECT    5    6   11                                                       
CONECT    6    5   13                                                       
CONECT    7    9   14                                                       
CONECT    8   12   21                                                       
CONECT    9    3    7   19                                                  
CONECT   10    4   12   14                                                  
CONECT   11    5   16   17                                                  
CONECT   12    8   10   16                                                  
CONECT   13    6   15   20                                                  
CONECT   14    7   10   22                                                  
CONECT   15   13   17   18                                                  
CONECT   16   11   12   22                                                  
CONECT   17   11   15   21                                                  
CONECT   18   15                                                            
CONECT   19    1    9                                                       
CONECT   20    2   13                                                       
CONECT   21    8   17                                                       
CONECT   22   14   16                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

COMPND    HMDB0033142
HETATM    1  C1  UNL     1       5.676   2.489  -0.336  1.00  0.00           C  
HETATM    2  O1  UNL     1       5.599   1.172   0.153  1.00  0.00           O  
HETATM    3  C2  UNL     1       4.419   0.456   0.237  1.00  0.00           C  
HETATM    4  C3  UNL     1       4.462  -0.829   0.733  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.319  -1.619   0.851  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.094  -1.076   0.448  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.050   0.208  -0.048  1.00  0.00           C  
HETATM    8  C7  UNL     1       3.198   0.975  -0.156  1.00  0.00           C  
HETATM    9  O2  UNL     1       0.720   0.532  -0.384  1.00  0.00           O  
HETATM   10  C8  UNL     1       0.059  -0.722  -0.621  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.380  -0.494  -0.397  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.101   0.151  -1.382  1.00  0.00           C  
HETATM   13  C11 UNL     1      -3.457   0.407  -1.254  1.00  0.00           C  
HETATM   14  C12 UNL     1      -4.108   0.007  -0.110  1.00  0.00           C  
HETATM   15  O3  UNL     1      -5.464   0.229   0.087  1.00  0.00           O  
HETATM   16  C13 UNL     1      -6.221   0.891  -0.916  1.00  0.00           C  
HETATM   17  C14 UNL     1      -3.377  -0.638   0.872  1.00  0.00           C  
HETATM   18  O4  UNL     1      -4.007  -1.048   2.026  1.00  0.00           O  
HETATM   19  C15 UNL     1      -2.029  -0.893   0.745  1.00  0.00           C  
HETATM   20  O5  UNL     1      -1.283  -1.542   1.728  1.00  0.00           O  
HETATM   21  C16 UNL     1       0.111  -1.319   1.811  1.00  0.00           C  
HETATM   22  C17 UNL     1       0.698  -1.577   0.418  1.00  0.00           C  
HETATM   23  H1  UNL     1       6.723   2.623  -0.724  1.00  0.00           H  
HETATM   24  H2  UNL     1       5.004   2.599  -1.227  1.00  0.00           H  
HETATM   25  H3  UNL     1       5.468   3.245   0.444  1.00  0.00           H  
HETATM   26  H4  UNL     1       5.422  -1.221   1.036  1.00  0.00           H  
HETATM   27  H5  UNL     1       3.356  -2.629   1.241  1.00  0.00           H  
HETATM   28  H6  UNL     1       3.161   1.994  -0.550  1.00  0.00           H  
HETATM   29  H7  UNL     1       0.285  -1.116  -1.615  1.00  0.00           H  
HETATM   30  H8  UNL     1      -1.644   0.488  -2.303  1.00  0.00           H  
HETATM   31  H9  UNL     1      -4.040   0.910  -2.013  1.00  0.00           H  
HETATM   32  H10 UNL     1      -7.180   1.189  -0.436  1.00  0.00           H  
HETATM   33  H11 UNL     1      -5.727   1.837  -1.247  1.00  0.00           H  
HETATM   34  H12 UNL     1      -6.400   0.243  -1.788  1.00  0.00           H  
HETATM   35  H13 UNL     1      -5.003  -0.886   2.173  1.00  0.00           H  
HETATM   36  H14 UNL     1       0.546  -2.064   2.502  1.00  0.00           H  
HETATM   37  H15 UNL     1       0.383  -0.310   2.121  1.00  0.00           H  
HETATM   38  H16 UNL     1       0.669  -2.659   0.178  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   26
CONECT    5    6    6   27
CONECT    6    7   22
CONECT    7    8    8    9
CONECT    8   28
CONECT    9   10
CONECT   10   11   22   29
CONECT   11   12   12   19
CONECT   12   13   30
CONECT   13   14   14   31
CONECT   14   15   17
CONECT   15   16
CONECT   16   32   33   34
CONECT   17   18   19   19
CONECT   18   35
CONECT   19   20
CONECT   20   21
CONECT   21   22   36   37
CONECT   22   38
END

HMDB0033142
     RDKit          3D
Melilotocarpan A
 38 41  0  0  0  0  0  0  0  0999 V2000
    5.6762    2.4890   -0.3360 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5987    1.1723    0.1528 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4188    0.4562    0.2366 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4617   -0.8287    0.7326 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3188   -1.6193    0.8508 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0944   -1.0764    0.4485 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0502    0.2080   -0.0476 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1983    0.9754   -0.1561 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7203    0.5318   -0.3838 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0588   -0.7222   -0.6213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3805   -0.4935   -0.3968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1007    0.1507   -1.3815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4573    0.4067   -1.2538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1080    0.0065   -0.1097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4639    0.2290    0.0872 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2206    0.8906   -0.9159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3773   -0.6385    0.8715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0071   -1.0484    2.0258 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0288   -0.8931    0.7448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2831   -1.5425    1.7279 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1110   -1.3189    1.8114 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6983   -1.5770    0.4181 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7229    2.6234   -0.7236 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0045    2.5994   -1.2273 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4676    3.2453    0.4443 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4220   -1.2214    1.0355 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3557   -2.6289    1.2410 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1610    1.9941   -0.5498 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2847   -1.1161   -1.6148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6439    0.4885   -2.3025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0401    0.9098   -2.0130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1798    1.1886   -0.4357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7274    1.8368   -1.2473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4002    0.2426   -1.7876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0034   -0.8862    2.1730 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5459   -2.0638    2.5015 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3832   -0.3102    2.1212 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6689   -2.6594    0.1781 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
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
  8  3  1  0
 22 10  1  0
 22  6  1  0
 19 11  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
  8 28  1  0
 10 29  1  0
 12 30  1  0
 13 31  1  0
 16 32  1  0
 16 33  1  0
 16 34  1  0
 18 35  1  0
 21 36  1  0
 21 37  1  0
 22 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-Hydroxy-3,9-dimethoxypterocarpan	HMDB
4-Hydroxyhomopterocarpin	HMDB

Chemical Formula

C₁₇H₁₆O₅

Average Molecular Weight

300.3059

Monoisotopic Molecular Weight

300.099773622

IUPAC Name

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

Traditional Name

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

CAS Registry Number

61135-95-3

SMILES

COC1=CC2=C(C=C1)C1COC3=C(C=CC(OC)=C3O)C1O2

InChI Identifier

InChI=1S/C17H16O5/c1-19-9-3-4-10-12-8-21-17-11(16(12)22-14(10)7-9)5-6-13(20-2)15(17)18/h3-7,12,16,18H,8H2,1-2H3

InChI Key

YHSXPHNOIMTWTH-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

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0033142)
Cell membrane (HMDB: HMDB0033142)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033142)

Source

Exogenous

Exogenous (HMDB: HMDB0033142)

Food

Food (HMDB: HMDB0033142)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Pulse

Pulses (FooDB: FOOD00867)

Endogenous

Plant

Plant (HMDB: HMDB0033142)
Fabaceae (HMDB: HMDB0033142)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033142)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	48 - 51 °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	0.097 g/L	ALOGPS
logP	2.82	ALOGPS
logP	2.35	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	9.19	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	57.15 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	79.52 m³·mol⁻¹	ChemAxon
Polarizability	31.24 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]+	171.873	31661259
DarkChem	[M-H]-	171.334	31661259
DeepCCS	[M+H]+	172.661	30932474
DeepCCS	[M-H]-	170.303	30932474
DeepCCS	[M-2H]-	203.964	30932474
DeepCCS	[M+Na]+	179.191	30932474
AllCCS	[M+H]+	171.0	32859911
AllCCS	[M+H-H2O]+	167.4	32859911
AllCCS	[M+NH4]+	174.3	32859911
AllCCS	[M+Na]+	175.2	32859911
AllCCS	[M-H]-	175.4	32859911
AllCCS	[M+Na-2H]-	174.8	32859911
AllCCS	[M+HCOO]-	174.3	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.	7.05 minutes	32390414
Predicted by Siyang on May 30, 2022	13.2395 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.87 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	24.5 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2106.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	317.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	181.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	189.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	155.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	604.4 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	581.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	137.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1223.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	460.8 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	1263.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	390.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	409.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	361.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	300.0 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	21.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Melilotocarpan A	COC1=CC2=C(C=C1)C1COC3=C(C=CC(OC)=C3O)C1O2	3771.7	Standard polar	33892256
Melilotocarpan A	COC1=CC2=C(C=C1)C1COC3=C(C=CC(OC)=C3O)C1O2	2494.6	Standard non polar	33892256
Melilotocarpan A	COC1=CC2=C(C=C1)C1COC3=C(C=CC(OC)=C3O)C1O2	2687.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Melilotocarpan A,1TMS,isomer #1	COC1=CC=C2C(=C1)OC1C3=CC=C(OC)C(O[Si](C)(C)C)=C3OCC21	2691.2	Semi standard non polar	33892256
Melilotocarpan A,1TBDMS,isomer #1	COC1=CC=C2C(=C1)OC1C3=CC=C(OC)C(O[Si](C)(C)C(C)(C)C)=C3OCC21	2938.0	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 A GC-MS (Non-derivatized) - 70eV, Positive	splash10-0079-0890000000-e84db6797a37ac28c1fd	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Melilotocarpan A GC-MS (1 TMS) - 70eV, Positive	splash10-0ab9-2139000000-b152124ba1f48f5aa04e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Melilotocarpan A 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 A 10V, Positive-QTOF	splash10-0udr-0619000000-844721337747e7ab2e31	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melilotocarpan A 20V, Positive-QTOF	splash10-0udr-0946000000-f90a23ca127ad2599dd6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melilotocarpan A 40V, Positive-QTOF	splash10-053r-8900000000-a1f903592c7be3fb4ec5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melilotocarpan A 10V, Negative-QTOF	splash10-0002-0090000000-e9f51ee649a094f87353	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melilotocarpan A 20V, Negative-QTOF	splash10-0002-0090000000-3d1e2dad59533c854511	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melilotocarpan A 40V, Negative-QTOF	splash10-0nu0-2960000000-730f14734fd6a8133b65	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melilotocarpan A 10V, Positive-QTOF	splash10-0udi-0009000000-7fd5921050e52686aed7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melilotocarpan A 20V, Positive-QTOF	splash10-0udi-0509000000-f9212a7266c0db474ac3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melilotocarpan A 40V, Positive-QTOF	splash10-03di-1920000000-6fe3ee2d8ed32e90a582	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melilotocarpan A 10V, Negative-QTOF	splash10-0002-0090000000-c8e04b941de97dd002f4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melilotocarpan A 20V, Negative-QTOF	splash10-0002-0090000000-7f305f9d4ab17528533f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melilotocarpan A 40V, Negative-QTOF	splash10-00kf-1290000000-49f30f7fe366c6aad6be	2021-09-22	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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

4484393

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 A → 6-({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)-3,4,5-trihydroxyoxane-2-carboxylic acid	details

Showing metabocard for Melilotocarpan A (HMDB0033142)

MOL for HMDB0033142 (Melilotocarpan A)

3D MOL for HMDB0033142 (Melilotocarpan A)

3D SDF for HMDB0033142 (Melilotocarpan A)

3D-SDF for HMDB0033142 (Melilotocarpan A)

PDB for HMDB0033142 (Melilotocarpan A)

3D PDB for HMDB0033142 (Melilotocarpan A)

SMILES for HMDB0033142 (Melilotocarpan A)

INCHI for HMDB0033142 (Melilotocarpan A)

Structure for HMDB0033142 (Melilotocarpan A)

3D Structure for HMDB0033142 (Melilotocarpan A)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

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