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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:54:42 UTC

Update Date

2022-03-07 02:53:59 UTC

HMDB ID

HMDB0034116

Secondary Accession Numbers

HMDB34116

Metabolite Identification

Common Name

Homopisatin

Description

Homopisatin 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. Homopisatin has been detected, but not quantified in, several different foods, such as red tea, teas (Camellia sinensis), herbs and spices, black tea, and green tea. This could make homopisatin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Homopisatin.

Structure

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

HMDB0034116
     RDKit          3D
Homopisatin
 38 41  0  0  0  0  0  0  0  0999 V2000
   -6.2411    0.6883    1.5291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6406    0.3162    0.3128 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2650    0.0899    0.2775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4955    0.2279    1.4206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1365    0.0135    1.4260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5161   -0.3466    0.2762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2782   -0.4920   -0.8941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6401   -0.2780   -0.9035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6803   -0.8614   -2.1005 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2602   -0.7976   -2.2988 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2940    0.0586   -1.2259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2611    1.3358   -1.2771 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7433    0.0970   -1.0825 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8163    0.1169   -1.9448 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1124    0.1573   -1.4745 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3935    0.1794   -0.1245 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7119    0.2204    0.3440 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9485    0.2417    1.7397 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3176    0.1593    0.7396 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0038    0.1185    0.2738 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7754    0.0922    0.9713 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0875   -0.6112    0.1086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3238    0.8835    1.3799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1581   -0.2013    2.2158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7247    1.5265    2.0026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9828    0.5162    2.3476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5432    0.1224    2.3187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2488   -0.3843   -1.7949 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1442   -1.8275   -2.2243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0132   -0.3536   -3.2849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0102    1.7279   -2.1375 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6619    0.1010   -3.0351 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9493    0.1727   -2.1628 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5428    1.1750    2.1820 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3841   -0.5958    2.2458 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9973    0.0896    1.9947 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5497    0.1771    1.8027 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1612   -1.6821    0.0569 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  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 16 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
  8  3  1  0
 22 11  1  0
 22  6  1  0
 20 13  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
 10 30  1  0
 12 31  1  0
 14 32  1  0
 15 33  1  0
 18 34  1  0
 18 35  1  0
 18 36  1  0
 19 37  1  0
 22 38  1  0
M  END

  Mrv0541 05061307352D          

 22 25  0  0  0  0            999 V2000
    6.8689   -1.1420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2842   -3.5534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3033   -2.6629    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
    4.4796   -2.7100    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
    5.2216   -1.2363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1823   -2.7972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1217   -0.6408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6743   -1.9260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4883   -2.3512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0270   -2.0203    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
    4.3980   -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
    3.2033   -2.0674    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
    2.2284   -0.7391    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4979   -1.8789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2450   -2.7293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9453   -0.5937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6872   -2.7111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  2  0  0  0  0
  6  4  2  0  0  0  0
 10  3  1  0  0  0  0
 10  7  2  0  0  0  0
 11  4  1  0  0  0  0
 11  8  2  0  0  0  0
 12  5  1  0  0  0  0
 13  6  1  0  0  0  0
 14  7  1  0  0  0  0
 14 12  2  0  0  0  0
 15  8  1  0  0  0  0
 15 13  2  0  0  0  0
 16 12  1  0  0  0  0
 17  9  1  0  0  0  0
 17 13  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19  1  1  0  0  0  0
 19 10  1  0  0  0  0
 20  2  1  0  0  0  0
 20 11  1  0  0  0  0
 21  9  1  0  0  0  0
 21 14  1  0  0  0  0
 22 15  1  0  0  0  0
 22 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034116

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=C(C=C1)C1(O)COC3=C(C=CC(OC)=C3)C1O2

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

> <INCHI_KEY>
VVPGAJNPGZZNBM-UHFFFAOYSA-N

> <FORMULA>
C17H16O5

> <MOLECULAR_WEIGHT>
300.3059

> <EXACT_MASS>
300.099773622

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
31.158946868537612

> <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-10-ol

> <ALOGPS_LOGP>
2.82

> <JCHEM_LOGP>
1.9999370703333335

> <ALOGPS_LOGS>
-3.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.036948329184675

> <JCHEM_PKA_STRONGEST_BASIC>
-4.094838800814622

> <JCHEM_POLAR_SURFACE_AREA>
57.150000000000006

> <JCHEM_REFRACTIVITY>
78.63130000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.48e-01 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-10-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034116
     RDKit          3D
Homopisatin
 38 41  0  0  0  0  0  0  0  0999 V2000
   -6.2411    0.6883    1.5291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6406    0.3162    0.3128 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2650    0.0899    0.2775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4955    0.2279    1.4206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1365    0.0135    1.4260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5161   -0.3466    0.2762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2782   -0.4920   -0.8941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6401   -0.2780   -0.9035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6803   -0.8614   -2.1005 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2602   -0.7976   -2.2988 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2940    0.0586   -1.2259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2611    1.3358   -1.2771 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7433    0.0970   -1.0825 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8163    0.1169   -1.9448 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1124    0.1573   -1.4745 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3935    0.1794   -0.1245 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7119    0.2204    0.3440 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9485    0.2417    1.7397 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3176    0.1593    0.7396 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0038    0.1185    0.2738 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7754    0.0922    0.9713 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0875   -0.6112    0.1086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3238    0.8835    1.3799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1581   -0.2013    2.2158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7247    1.5265    2.0026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9828    0.5162    2.3476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5432    0.1224    2.3187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2488   -0.3843   -1.7949 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1442   -1.8275   -2.2243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0132   -0.3536   -3.2849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0102    1.7279   -2.1375 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6619    0.1010   -3.0351 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9493    0.1727   -2.1628 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5428    1.1750    2.1820 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3841   -0.5958    2.2458 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9973    0.0896    1.9947 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5497    0.1771    1.8027 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1612   -1.6821    0.0569 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  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 16 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
  8  3  1  0
 22 11  1  0
 22  6  1  0
 20 13  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
 10 30  1  0
 12 31  1  0
 14 32  1  0
 15 33  1  0
 18 34  1  0
 18 35  1  0
 18 36  1  0
 19 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      12.822  -2.132   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.531  -6.633   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.899  -4.971   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.985  -2.851   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.362  -5.059   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.353  -2.145   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.747  -2.308   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.207  -5.221   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.827  -1.196   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.592  -3.595   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       7.517  -3.771   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.649  -2.978   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.210  -2.396   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.576  -4.516   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.979  -3.859   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.135  -2.572   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.160  -1.380   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      12.129  -3.507   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -0.457  -5.095   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       7.365  -1.108   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       5.016  -5.061   0.000  0.00  0.00           O+0
CONECT    1   19                                                            
CONECT    2   20                                                            
CONECT    3    5   10                                                       
CONECT    4    6   11                                                       
CONECT    5    3   12                                                       
CONECT    6    4   13                                                       
CONECT    7   10   14                                                       
CONECT    8   11   15                                                       
CONECT    9   17   21                                                       
CONECT   10    3    7   19                                                  
CONECT   11    4    8   20                                                  
CONECT   12    5   14   16                                                  
CONECT   13    6   15   17                                                  
CONECT   14    7   12   21                                                  
CONECT   15    8   13   22                                                  
CONECT   16   12   17   22                                                  
CONECT   17    9   13   16   18                                             
CONECT   18   17                                                            
CONECT   19    1   10                                                       
CONECT   20    2   11                                                       
CONECT   21    9   14                                                       
CONECT   22   15   16                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

COMPND    HMDB0034116
HETATM    1  C1  UNL     1      -6.241   0.688   1.529  1.00  0.00           C  
HETATM    2  O1  UNL     1      -5.641   0.316   0.313  1.00  0.00           O  
HETATM    3  C2  UNL     1      -4.265   0.090   0.278  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.495   0.228   1.421  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.136   0.013   1.426  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.516  -0.347   0.276  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.278  -0.492  -0.894  1.00  0.00           C  
HETATM    8  C7  UNL     1      -3.640  -0.278  -0.903  1.00  0.00           C  
HETATM    9  O2  UNL     1      -1.680  -0.861  -2.100  1.00  0.00           O  
HETATM   10  C8  UNL     1      -0.260  -0.798  -2.299  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.294   0.059  -1.226  1.00  0.00           C  
HETATM   12  O3  UNL     1      -0.261   1.336  -1.277  1.00  0.00           O  
HETATM   13  C10 UNL     1       1.743   0.097  -1.083  1.00  0.00           C  
HETATM   14  C11 UNL     1       2.816   0.117  -1.945  1.00  0.00           C  
HETATM   15  C12 UNL     1       4.112   0.157  -1.474  1.00  0.00           C  
HETATM   16  C13 UNL     1       4.394   0.179  -0.125  1.00  0.00           C  
HETATM   17  O4  UNL     1       5.712   0.220   0.344  1.00  0.00           O  
HETATM   18  C14 UNL     1       5.949   0.242   1.740  1.00  0.00           C  
HETATM   19  C15 UNL     1       3.318   0.159   0.740  1.00  0.00           C  
HETATM   20  C16 UNL     1       2.004   0.118   0.274  1.00  0.00           C  
HETATM   21  O5  UNL     1       0.775   0.092   0.971  1.00  0.00           O  
HETATM   22  C17 UNL     1      -0.087  -0.611   0.109  1.00  0.00           C  
HETATM   23  H1  UNL     1      -7.324   0.883   1.380  1.00  0.00           H  
HETATM   24  H2  UNL     1      -6.158  -0.201   2.216  1.00  0.00           H  
HETATM   25  H3  UNL     1      -5.725   1.526   2.003  1.00  0.00           H  
HETATM   26  H4  UNL     1      -3.983   0.516   2.348  1.00  0.00           H  
HETATM   27  H5  UNL     1      -1.543   0.122   2.319  1.00  0.00           H  
HETATM   28  H6  UNL     1      -4.249  -0.384  -1.795  1.00  0.00           H  
HETATM   29  H7  UNL     1       0.144  -1.828  -2.224  1.00  0.00           H  
HETATM   30  H8  UNL     1      -0.013  -0.354  -3.285  1.00  0.00           H  
HETATM   31  H9  UNL     1      -0.010   1.728  -2.138  1.00  0.00           H  
HETATM   32  H10 UNL     1       2.662   0.101  -3.035  1.00  0.00           H  
HETATM   33  H11 UNL     1       4.949   0.173  -2.163  1.00  0.00           H  
HETATM   34  H12 UNL     1       5.543   1.175   2.182  1.00  0.00           H  
HETATM   35  H13 UNL     1       5.384  -0.596   2.246  1.00  0.00           H  
HETATM   36  H14 UNL     1       6.997   0.090   1.995  1.00  0.00           H  
HETATM   37  H15 UNL     1       3.550   0.177   1.803  1.00  0.00           H  
HETATM   38  H16 UNL     1       0.161  -1.682   0.057  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   29   30
CONECT   11   12   13   22
CONECT   12   31
CONECT   13   14   14   20
CONECT   14   15   32
CONECT   15   16   16   33
CONECT   16   17   19
CONECT   17   18
CONECT   18   34   35   36
CONECT   19   20   20   37
CONECT   20   21
CONECT   21   22
CONECT   22   38
END

HMDB0034116
     RDKit          3D
Homopisatin
 38 41  0  0  0  0  0  0  0  0999 V2000
   -6.2411    0.6883    1.5291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6406    0.3162    0.3128 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2650    0.0899    0.2775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4955    0.2279    1.4206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1365    0.0135    1.4260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5161   -0.3466    0.2762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2782   -0.4920   -0.8941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6401   -0.2780   -0.9035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6803   -0.8614   -2.1005 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2602   -0.7976   -2.2988 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2940    0.0586   -1.2259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2611    1.3358   -1.2771 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7433    0.0970   -1.0825 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8163    0.1169   -1.9448 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1124    0.1573   -1.4745 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3935    0.1794   -0.1245 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7119    0.2204    0.3440 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9485    0.2417    1.7397 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3176    0.1593    0.7396 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0038    0.1185    0.2738 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7754    0.0922    0.9713 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0875   -0.6112    0.1086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3238    0.8835    1.3799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1581   -0.2013    2.2158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7247    1.5265    2.0026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9828    0.5162    2.3476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5432    0.1224    2.3187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2488   -0.3843   -1.7949 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1442   -1.8275   -2.2243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0132   -0.3536   -3.2849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0102    1.7279   -2.1375 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6619    0.1010   -3.0351 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9493    0.1727   -2.1628 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5428    1.1750    2.1820 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3841   -0.5958    2.2458 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9973    0.0896    1.9947 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5497    0.1771    1.8027 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1612   -1.6821    0.0569 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  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 16 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
  8  3  1  0
 22 11  1  0
 22  6  1  0
 20 13  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
 10 30  1  0
 12 31  1  0
 14 32  1  0
 15 33  1  0
 18 34  1  0
 18 35  1  0
 18 36  1  0
 19 37  1  0
 22 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
6a-Hydroxy-3,9-dimethoxypterocarpan	HMDB
Variabilin?	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-10-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-10-ol

CAS Registry Number

3187-52-8

SMILES

COC1=CC2=C(C=C1)C1(O)COC3=C(C=CC(OC)=C3)C1O2

InChI Identifier

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

InChI Key

VVPGAJNPGZZNBM-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
Alkyl aryl ether
Benzenoid
Tertiary alcohol
Oxacycle
Organoheterocyclic compound
Ether
Alcohol
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0034116)
Cell membrane (HMDB: HMDB0034116)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034116)

Source

Exogenous

Exogenous (HMDB: HMDB0034116)

Food

Food (HMDB: HMDB0034116)

Pulse

Lentil

Lentils (FooDB: FOOD00098)

Pulses (FooDB: FOOD00867)

Tea

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0034116)
Fabaceae (HMDB: HMDB0034116)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0034116)

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
Water Solubility	0.15 g/L	ALOGPS
logP	2.82	ALOGPS
logP	2	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	12.04	ChemAxon
pKa (Strongest Basic)	-4.1	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	78.63 m³·mol⁻¹	ChemAxon
Polarizability	31.16 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]+	169.522	31661259
DarkChem	[M-H]-	171.854	31661259
DeepCCS	[M+H]+	172.416	30932474
DeepCCS	[M-H]-	170.058	30932474
DeepCCS	[M-2H]-	204.014	30932474
DeepCCS	[M+Na]+	179.229	30932474
AllCCS	[M+H]+	171.0	32859911
AllCCS	[M+H-H2O]+	167.4	32859911
AllCCS	[M+NH4]+	174.3	32859911
AllCCS	[M+Na]+	175.3	32859911
AllCCS	[M-H]-	175.4	32859911
AllCCS	[M+Na-2H]-	174.8	32859911
AllCCS	[M+HCOO]-	174.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Homopisatin	COC1=CC2=C(C=C1)C1(O)COC3=C(C=CC(OC)=C3)C1O2	3756.2	Standard polar	33892256
Homopisatin	COC1=CC2=C(C=C1)C1(O)COC3=C(C=CC(OC)=C3)C1O2	2458.6	Standard non polar	33892256
Homopisatin	COC1=CC2=C(C=C1)C1(O)COC3=C(C=CC(OC)=C3)C1O2	2596.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Homopisatin,1TMS,isomer #1	COC1=CC=C2C(=C1)OCC1(O[Si](C)(C)C)C3=CC=C(OC)C=C3OC21	2598.3	Semi standard non polar	33892256
Homopisatin,1TBDMS,isomer #1	COC1=CC=C2C(=C1)OCC1(O[Si](C)(C)C(C)(C)C)C3=CC=C(OC)C=C3OC21	2879.2	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 - Homopisatin GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-0970000000-599cdfc4a3c01c558955	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Homopisatin GC-MS (1 TMS) - 70eV, Positive	splash10-05g0-7329000000-befe2f33f5106b6164be	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Homopisatin 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 - Homopisatin 10V, Positive-QTOF	splash10-0udi-0129000000-1e6eab5222ba9cca6a5c	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Homopisatin 20V, Positive-QTOF	splash10-0udi-0169000000-42045439cdf23df3c1d0	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Homopisatin 40V, Positive-QTOF	splash10-0pec-9620000000-8f9fd0e017ab22bddaaf	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Homopisatin 10V, Negative-QTOF	splash10-0002-0090000000-e5486b5dc42104dd206c	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Homopisatin 20V, Negative-QTOF	splash10-0002-0090000000-fac81af0b80a88289e52	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Homopisatin 40V, Negative-QTOF	splash10-0ue9-1190000000-6cbec964c4ed7b9f3e80	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Homopisatin 10V, Positive-QTOF	splash10-0udi-0009000000-7fd5921050e52686aed7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Homopisatin 20V, Positive-QTOF	splash10-0udi-0209000000-8110ad6bf2d203cfbe46	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Homopisatin 40V, Positive-QTOF	splash10-0adi-4910000000-d592054a99f8e3eaaf06	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Homopisatin 10V, Negative-QTOF	splash10-0002-0090000000-c8e04b941de97dd002f4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Homopisatin 20V, Negative-QTOF	splash10-0002-0090000000-ddd549bcb0367aea7715	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Homopisatin 40V, Negative-QTOF	splash10-052f-2390000000-f6e0efa0366c55a6311d	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

FDB012384

KNApSAcK ID

C00002582

Chemspider ID

544745

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

627142

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.. .

Showing metabocard for Homopisatin (HMDB0034116)

MOL for HMDB0034116 (Homopisatin)

3D MOL for HMDB0034116 (Homopisatin)

3D SDF for HMDB0034116 (Homopisatin)

3D-SDF for HMDB0034116 (Homopisatin)

PDB for HMDB0034116 (Homopisatin)

3D PDB for HMDB0034116 (Homopisatin)

SMILES for HMDB0034116 (Homopisatin)

INCHI for HMDB0034116 (Homopisatin)

Structure for HMDB0034116 (Homopisatin)

3D Structure for HMDB0034116 (Homopisatin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra