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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 12:43:36 UTC

Update Date

2021-09-26 23:07:18 UTC

HMDB ID

HMDB0253835

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Kushenin

Description

Kushenin 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, kushenin is considered to be a flavonoid. Based on a literature review a significant number of articles have been published on Kushenin. This compound has been identified in human blood as reported by (PMID: 31557052 ). Kushenin is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Kushenin is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0253835
     RDKit          3D
Kushenin
 35 38  0  0  0  0  0  0  0  0999 V2000
    2.8930   -0.8854    3.3327 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5202   -1.9189    2.4257 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0223   -1.5695    1.1879 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8773   -0.2503    0.8067 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3788    0.0995   -0.4322 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0091   -0.8859   -1.3298 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1518   -2.2072   -0.9543 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6581   -2.5583    0.3039 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7682   -3.9089    0.5989 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5372   -0.2670   -2.5073 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0128    0.9994   -2.0600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2972    0.8647   -1.4473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3287    0.2709   -2.1416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5951    0.1217   -1.5924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8569    0.5658   -0.3311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1199    0.4194    0.2218 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8111    1.1708    0.3800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5711    1.3091   -0.1764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5583    1.9149    0.5606 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5905    2.3619   -0.1008 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1168    1.3920   -1.1090 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.2168    2.8080 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0074   -0.2870    3.6439 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3186   -1.3303    4.2569 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1556    0.5346    1.4817 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8686   -2.9936   -1.6413 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1248   -4.1933    1.4845 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0333    1.6469   -2.9630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1436   -0.0884   -3.1420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3749   -0.3578   -2.1893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8405    1.1135    0.1285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0306    1.5180    1.3769 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3855    2.4837    0.6903 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4841    3.3610   -0.5690 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0118    1.7706   -1.6453 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
  6 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
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
  8  3  1  0
 21 11  1  0
 21  5  1  0
 18 12  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  7 26  1  0
  9 27  1  0
 11 28  1  0
 13 29  1  0
 14 30  1  0
 16 31  1  0
 17 32  1  0
 20 33  1  0
 20 34  1  0
 21 35  1  0
M  END


  Mrv1533004161516112D          

 21 24  0  0  0  0            999 V2000
    1.6271   -1.0648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3604   -0.6867    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0545   -1.1327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7877   -0.7546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4818   -1.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2776   -0.9832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6486   -0.2464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4723   -0.1992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9249   -0.8889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7486   -0.8418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2012   -1.5315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0249   -1.4844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8302   -2.2684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0066   -2.3156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5539   -1.6258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7303   -1.6730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2142   -2.3166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4426   -2.0247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7093   -2.4027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0152   -1.9568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2820   -2.3348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
  9 15  1  0  0  0  0
 15 16  1  0  0  0  0
  6 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  5 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
  3 20  1  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0253835

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=C(OC3C2COC2=CC(O)=CC=C32)C=C1O

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

> <INCHI_KEY>
NYGZYUAVZPIKBZ-UHFFFAOYSA-N

> <FORMULA>
C16H14O5

> <MOLECULAR_WEIGHT>
286.283

> <EXACT_MASS>
286.084123551

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
29.117916950597674

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
13-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2,4,6,11(16),12,14-hexaene-5,14-diol

> <ALOGPS_LOGP>
2.63

> <JCHEM_LOGP>
2.2056580746666663

> <ALOGPS_LOGS>
-3.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.07730037979556

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.31255746465356

> <JCHEM_PKA_STRONGEST_BASIC>
-4.403463914043713

> <JCHEM_POLAR_SURFACE_AREA>
68.15

> <JCHEM_REFRACTIVITY>
75.042

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.29e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
kushenin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0253835
     RDKit          3D
Kushenin
 35 38  0  0  0  0  0  0  0  0999 V2000
    2.8930   -0.8854    3.3327 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5202   -1.9189    2.4257 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0223   -1.5695    1.1879 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8773   -0.2503    0.8067 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3788    0.0995   -0.4322 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0091   -0.8859   -1.3298 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1518   -2.2072   -0.9543 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6581   -2.5583    0.3039 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7682   -3.9089    0.5989 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5372   -0.2670   -2.5073 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0128    0.9994   -2.0600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2972    0.8647   -1.4473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3287    0.2709   -2.1416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5951    0.1217   -1.5924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8569    0.5658   -0.3311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1199    0.4194    0.2218 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8111    1.1708    0.3800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5711    1.3091   -0.1764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5583    1.9149    0.5606 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5905    2.3619   -0.1008 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1168    1.3920   -1.1090 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.2168    2.8080 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0074   -0.2870    3.6439 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3186   -1.3303    4.2569 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1556    0.5346    1.4817 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8686   -2.9936   -1.6413 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1248   -4.1933    1.4845 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0333    1.6469   -2.9630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1436   -0.0884   -3.1420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3749   -0.3578   -2.1893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8405    1.1135    0.1285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0306    1.5180    1.3769 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3855    2.4837    0.6903 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4841    3.3610   -0.5690 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0118    1.7706   -1.6453 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
  6 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
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
  8  3  1  0
 21 11  1  0
 21  5  1  0
 18 12  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  7 26  1  0
  9 27  1  0
 11 28  1  0
 13 29  1  0
 14 30  1  0
 16 31  1  0
 17 32  1  0
 20 33  1  0
 20 34  1  0
 21 35  1  0
M  END

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       3.037  -1.988   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.406  -1.282   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.702  -2.114   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.070  -1.409   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.366  -2.241   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.852  -1.835   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.544  -0.460   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      12.082  -0.372   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      12.927  -1.659   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.464  -1.571   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      15.309  -2.859   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      16.846  -2.771   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      14.616  -4.234   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.079  -4.322   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.234  -3.035   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.697  -3.123   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       9.733  -4.324   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       8.293  -3.779   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.924  -4.485   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.628  -3.653   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       4.260  -4.358   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   20                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   18                                                  
CONECT    6    5    7   16                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   15                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14    9   16                                                  
CONECT   16   15    6   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17    5   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19    3   21                                                  
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

COMPND    HMDB0253835
HETATM    1  C1  UNL     1       2.893  -0.885   3.333  1.00  0.00           C  
HETATM    2  O1  UNL     1       2.520  -1.919   2.426  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.022  -1.569   1.188  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.877  -0.250   0.807  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.379   0.099  -0.432  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.009  -0.886  -1.330  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.152  -2.207  -0.954  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.658  -2.558   0.304  1.00  0.00           C  
HETATM    9  O2  UNL     1       1.768  -3.909   0.599  1.00  0.00           O  
HETATM   10  O3  UNL     1       0.537  -0.267  -2.507  1.00  0.00           O  
HETATM   11  C8  UNL     1       0.013   0.999  -2.060  1.00  0.00           C  
HETATM   12  C9  UNL     1      -1.297   0.865  -1.447  1.00  0.00           C  
HETATM   13  C10 UNL     1      -2.329   0.271  -2.142  1.00  0.00           C  
HETATM   14  C11 UNL     1      -3.595   0.122  -1.592  1.00  0.00           C  
HETATM   15  C12 UNL     1      -3.857   0.566  -0.331  1.00  0.00           C  
HETATM   16  O4  UNL     1      -5.120   0.419   0.222  1.00  0.00           O  
HETATM   17  C13 UNL     1      -2.811   1.171   0.380  1.00  0.00           C  
HETATM   18  C14 UNL     1      -1.571   1.309  -0.176  1.00  0.00           C  
HETATM   19  O5  UNL     1      -0.558   1.915   0.561  1.00  0.00           O  
HETATM   20  C15 UNL     1       0.590   2.362  -0.101  1.00  0.00           C  
HETATM   21  C16 UNL     1       1.117   1.392  -1.109  1.00  0.00           C  
HETATM   22  H1  UNL     1       3.602  -0.217   2.808  1.00  0.00           H  
HETATM   23  H2  UNL     1       2.007  -0.287   3.644  1.00  0.00           H  
HETATM   24  H3  UNL     1       3.319  -1.330   4.257  1.00  0.00           H  
HETATM   25  H4  UNL     1       2.156   0.535   1.482  1.00  0.00           H  
HETATM   26  H5  UNL     1       0.869  -2.994  -1.641  1.00  0.00           H  
HETATM   27  H6  UNL     1       2.125  -4.193   1.484  1.00  0.00           H  
HETATM   28  H7  UNL     1       0.033   1.647  -2.963  1.00  0.00           H  
HETATM   29  H8  UNL     1      -2.144  -0.088  -3.142  1.00  0.00           H  
HETATM   30  H9  UNL     1      -4.375  -0.358  -2.189  1.00  0.00           H  
HETATM   31  H10 UNL     1      -5.841   1.113   0.128  1.00  0.00           H  
HETATM   32  H11 UNL     1      -3.031   1.518   1.377  1.00  0.00           H  
HETATM   33  H12 UNL     1       1.385   2.484   0.690  1.00  0.00           H  
HETATM   34  H13 UNL     1       0.484   3.361  -0.569  1.00  0.00           H  
HETATM   35  H14 UNL     1       2.012   1.771  -1.645  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   25
CONECT    5    6    6   21
CONECT    6    7   10
CONECT    7    8    8   26
CONECT    8    9
CONECT    9   27
CONECT   10   11
CONECT   11   12   21   28
CONECT   12   13   13   18
CONECT   13   14   29
CONECT   14   15   15   30
CONECT   15   16   17
CONECT   16   31
CONECT   17   18   18   32
CONECT   18   19
CONECT   19   20
CONECT   20   21   33   34
CONECT   21   35
END

HMDB0253835
     RDKit          3D
Kushenin
 35 38  0  0  0  0  0  0  0  0999 V2000
    2.8930   -0.8854    3.3327 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5202   -1.9189    2.4257 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0223   -1.5695    1.1879 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8773   -0.2503    0.8067 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3788    0.0995   -0.4322 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0091   -0.8859   -1.3298 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1518   -2.2072   -0.9543 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6581   -2.5583    0.3039 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7682   -3.9089    0.5989 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5372   -0.2670   -2.5073 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0128    0.9994   -2.0600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2972    0.8647   -1.4473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3287    0.2709   -2.1416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5951    0.1217   -1.5924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8569    0.5658   -0.3311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1199    0.4194    0.2218 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8111    1.1708    0.3800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5711    1.3091   -0.1764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5583    1.9149    0.5606 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5905    2.3619   -0.1008 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1168    1.3920   -1.1090 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.2168    2.8080 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0074   -0.2870    3.6439 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3186   -1.3303    4.2569 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1556    0.5346    1.4817 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8686   -2.9936   -1.6413 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1248   -4.1933    1.4845 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0333    1.6469   -2.9630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1436   -0.0884   -3.1420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3749   -0.3578   -2.1893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8405    1.1135    0.1285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0306    1.5180    1.3769 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3855    2.4837    0.6903 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4841    3.3610   -0.5690 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0118    1.7706   -1.6453 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
  6 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
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
  8  3  1  0
 21 11  1  0
 21  5  1  0
 18 12  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  7 26  1  0
  9 27  1  0
 11 28  1  0
 13 29  1  0
 14 30  1  0
 16 31  1  0
 17 32  1  0
 20 33  1  0
 20 34  1  0
 21 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₆H₁₄O₅

Average Molecular Weight

286.283

Monoisotopic Molecular Weight

286.084123551

IUPAC Name

13-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2,4,6,11(16),12,14-hexaene-5,14-diol

Traditional Name

kushenin

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(OC3C2COC2=CC(O)=CC=C32)C=C1O

InChI Identifier

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

InChI Key

NYGZYUAVZPIKBZ-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-2-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 (LMPK12070055 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	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
logP	2.63	ALOGPS
logP	2.21	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	9.31	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	68.15 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	75.04 m³·mol⁻¹	ChemAxon
Polarizability	29.12 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
DeepCCS	[M-2H]-	196.278	30932474
DeepCCS	[M+Na]+	171.689	30932474
AllCCS	[M+H]+	166.7	32859911
AllCCS	[M+H-H2O]+	163.0	32859911
AllCCS	[M+NH4]+	170.1	32859911
AllCCS	[M+Na]+	171.1	32859911
AllCCS	[M-H]-	170.2	32859911
AllCCS	[M+Na-2H]-	169.5	32859911
AllCCS	[M+HCOO]-	168.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Kushenin	COC1=CC2=C(OC3C2COC2=CC(O)=CC=C32)C=C1O	3840.6	Standard polar	33892256
Kushenin	COC1=CC2=C(OC3C2COC2=CC(O)=CC=C32)C=C1O	2621.2	Standard non polar	33892256
Kushenin	COC1=CC2=C(OC3C2COC2=CC(O)=CC=C32)C=C1O	2830.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Kushenin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ab9-0590000000-9e1f28896dcbc901a383	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Kushenin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Kushenin GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Kushenin GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Kushenin GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Kushenin GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Kushenin GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Kushenin GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-04	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 - Kushenin 10V, Positive-QTOF	splash10-000i-0090000000-b239d41c6032c85540b2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kushenin 20V, Positive-QTOF	splash10-000i-0490000000-c023c0b5e003962b65fd	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kushenin 40V, Positive-QTOF	splash10-02ti-3980000000-3dd85421a065600113d5	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kushenin 10V, Negative-QTOF	splash10-000i-0090000000-14912e1703be5edd027d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kushenin 20V, Negative-QTOF	splash10-000i-0090000000-5e901ef6c268fc3decca	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kushenin 40V, Negative-QTOF	splash10-000i-0590000000-f9db5f76f252c3bfeac9	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

KNApSAcK ID

C00009994

Chemspider ID

4477346

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Kushenin

METLIN ID

Not Available

PubChem Compound

5318889

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Kushenin (HMDB0253835)

MOL for HMDB0253835 (Kushenin)

3D MOL for HMDB0253835 (Kushenin)

3D SDF for HMDB0253835 (Kushenin)

3D-SDF for HMDB0253835 (Kushenin)

PDB for HMDB0253835 (Kushenin)

3D PDB for HMDB0253835 (Kushenin)

SMILES for HMDB0253835 (Kushenin)

INCHI for HMDB0253835 (Kushenin)

Structure for HMDB0253835 (Kushenin)

3D Structure for HMDB0253835 (Kushenin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra