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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:37:24 UTC

Update Date

2022-03-07 02:52:35 UTC

HMDB ID

HMDB0030521

Secondary Accession Numbers

HMDB30521

Metabolite Identification

Common Name

Sativan

Description

Sativan, also known as sativin, belongs to the class of organic compounds known as 4'-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C4' atom of the isoflavonoid backbone. Isoflavonoids are natural products derived from 3-phenylchromen-4-one. Sativan has been detected, but not quantified in, several different foods, such as bayberries (Myrica), deerberries (Vaccinium stamineum), cherry tomatoes (Solanum lycopersicum var. cerasiforme), wakames (Undaria pinnatifida), and pepper (capsicum). This could make sativan a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Sativan.

Structure

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

HMDB0030521
     RDKit          3D
Sativan
 39 41  0  0  0  0  0  0  0  0999 V2000
    5.8567   -1.3355    0.2293 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1163   -0.1322    0.1580 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7545   -0.1655   -0.0313 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0612   -1.3740   -0.1591 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6853   -1.3846   -0.3497 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0242   -0.1855   -0.4098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4327   -0.1675   -0.6002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9259   -1.5640   -0.8918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2811   -1.4102   -1.3534 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1462   -0.8131   -0.4504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5253   -1.0401   -0.4755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3697   -0.4435    0.4231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7228   -0.6780    0.3838 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8636    0.3994    1.3764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5060    0.6287    1.4085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6190    0.0327    0.5025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1691    0.3369    0.6152 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6958    1.0349   -0.2847 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9981    2.2362   -0.3497 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7080    3.4459   -0.2194 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0614    1.0135   -0.0961 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6818   -2.0032   -0.6361 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5676   -1.9217    1.1371 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9357   -1.1424    0.3237 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6117   -2.2925   -0.1069 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2359   -2.3629   -0.4330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6820    0.5356   -1.4263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3184   -2.0736   -1.6665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9051   -2.1650    0.0266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8827   -1.7197   -1.2536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4024   -0.1661   -0.1273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5205    0.8940    2.1150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1275    1.3070    2.1807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7390   -0.0725    1.5707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0908    1.4456    0.7223 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1664    3.4355    0.8004 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0115    4.3074   -0.2218 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4491    3.6211   -0.9992 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6086    1.9386    0.0041 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  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
  6 18  1  0
 18 19  1  0
 19 20  1  0
 18 21  2  0
 21  3  1  0
 17  7  1  0
 16 10  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
 11 30  1  0
 13 31  1  0
 14 32  1  0
 15 33  1  0
 17 34  1  0
 17 35  1  0
 20 36  1  0
 20 37  1  0
 20 38  1  0
 21 39  1  0
M  END


  Mrv0541 05061305182D          

 21 23  0  0  0  0            999 V2000
    7.1447    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    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
 11  3  1  0  0  0  0
 11  7  1  0  0  0  0
 12  7  1  0  0  0  0
 12 10  1  0  0  0  0
 13  4  1  0  0  0  0
 13  8  2  0  0  0  0
 14  5  1  0  0  0  0
 14  9  2  0  0  0  0
 15  6  1  0  0  0  0
 15 12  1  0  0  0  0
 16  8  1  0  0  0  0
 16 11  2  0  0  0  0
 17  9  1  0  0  0  0
 17 15  2  0  0  0  0
 18 13  1  0  0  0  0
 19  1  1  0  0  0  0
 19 14  1  0  0  0  0
 20  2  1  0  0  0  0
 20 17  1  0  0  0  0
 21 10  1  0  0  0  0
 21 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030521

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(OC)=C(C=C1)C1COC2=C(C1)C=CC(O)=C2

> <INCHI_IDENTIFIER>
InChI=1S/C17H18O4/c1-19-14-5-6-15(17(9-14)20-2)12-7-11-3-4-13(18)8-16(11)21-10-12/h3-6,8-9,12,18H,7,10H2,1-2H3

> <INCHI_KEY>
TUXCLJQCYVCGDW-UHFFFAOYSA-N

> <FORMULA>
C17H18O4

> <MOLECULAR_WEIGHT>
286.3224

> <EXACT_MASS>
286.120509064

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
31.235274754844795

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(2,4-dimethoxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-ol

> <ALOGPS_LOGP>
3.13

> <JCHEM_LOGP>
3.179900667666667

> <ALOGPS_LOGS>
-4.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.781761268372893

> <JCHEM_PKA_STRONGEST_BASIC>
-4.365104800019207

> <JCHEM_POLAR_SURFACE_AREA>
47.92

> <JCHEM_REFRACTIVITY>
79.90570000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.48e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(2,4-dimethoxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030521
     RDKit          3D
Sativan
 39 41  0  0  0  0  0  0  0  0999 V2000
    5.8567   -1.3355    0.2293 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1163   -0.1322    0.1580 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7545   -0.1655   -0.0313 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0612   -1.3740   -0.1591 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6853   -1.3846   -0.3497 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0242   -0.1855   -0.4098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4327   -0.1675   -0.6002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9259   -1.5640   -0.8918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2811   -1.4102   -1.3534 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1462   -0.8131   -0.4504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5253   -1.0401   -0.4755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3697   -0.4435    0.4231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7228   -0.6780    0.3838 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8636    0.3994    1.3764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5060    0.6287    1.4085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6190    0.0327    0.5025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1691    0.3369    0.6152 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6958    1.0349   -0.2847 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9981    2.2362   -0.3497 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7080    3.4459   -0.2194 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0614    1.0135   -0.0961 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6818   -2.0032   -0.6361 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5676   -1.9217    1.1371 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9357   -1.1424    0.3237 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6117   -2.2925   -0.1069 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2359   -2.3629   -0.4330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6820    0.5356   -1.4263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3184   -2.0736   -1.6665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9051   -2.1650    0.0266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8827   -1.7197   -1.2536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4024   -0.1661   -0.1273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5205    0.8940    2.1150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1275    1.3070    2.1807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7390   -0.0725    1.5707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0908    1.4456    0.7223 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1664    3.4355    0.8004 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0115    4.3074   -0.2218 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4491    3.6211   -0.9992 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6086    1.9386    0.0041 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  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
  6 18  1  0
 18 19  1  0
 19 20  1  0
 18 21  2  0
 21  3  1  0
 17  7  1  0
 16 10  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
 11 30  1  0
 13 31  1  0
 14 32  1  0
 15 33  1  0
 17 34  1  0
 17 35  1  0
 20 36  1  0
 20 37  1  0
 20 38  1  0
 21 39  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      13.337   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      12.003   2.310   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
CONECT    1   19                                                            
CONECT    2   20                                                            
CONECT    3    4   11                                                       
CONECT    4    3   13                                                       
CONECT    5    6   14                                                       
CONECT    6    5   15                                                       
CONECT    7   11   12                                                       
CONECT    8   13   16                                                       
CONECT    9   14   17                                                       
CONECT   10   12   21                                                       
CONECT   11    3    7   16                                                  
CONECT   12    7   10   15                                                  
CONECT   13    4    8   18                                                  
CONECT   14    5    9   19                                                  
CONECT   15    6   12   17                                                  
CONECT   16    8   11   21                                                  
CONECT   17    9   15   20                                                  
CONECT   18   13                                                            
CONECT   19    1   14                                                       
CONECT   20    2   17                                                       
CONECT   21   10   16                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0030521
HETATM    1  C1  UNL     1       5.857  -1.336   0.229  1.00  0.00           C  
HETATM    2  O1  UNL     1       5.116  -0.132   0.158  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.755  -0.166  -0.031  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.061  -1.374  -0.159  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.685  -1.385  -0.350  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.024  -0.186  -0.410  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.433  -0.167  -0.600  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.926  -1.564  -0.892  1.00  0.00           C  
HETATM    9  O2  UNL     1      -2.281  -1.410  -1.353  1.00  0.00           O  
HETATM   10  C8  UNL     1      -3.146  -0.813  -0.450  1.00  0.00           C  
HETATM   11  C9  UNL     1      -4.525  -1.040  -0.475  1.00  0.00           C  
HETATM   12  C10 UNL     1      -5.370  -0.443   0.423  1.00  0.00           C  
HETATM   13  O3  UNL     1      -6.723  -0.678   0.384  1.00  0.00           O  
HETATM   14  C11 UNL     1      -4.864   0.399   1.376  1.00  0.00           C  
HETATM   15  C12 UNL     1      -3.506   0.629   1.408  1.00  0.00           C  
HETATM   16  C13 UNL     1      -2.619   0.033   0.502  1.00  0.00           C  
HETATM   17  C14 UNL     1      -1.169   0.337   0.615  1.00  0.00           C  
HETATM   18  C15 UNL     1       1.696   1.035  -0.285  1.00  0.00           C  
HETATM   19  O4  UNL     1       0.998   2.236  -0.350  1.00  0.00           O  
HETATM   20  C16 UNL     1       1.708   3.446  -0.219  1.00  0.00           C  
HETATM   21  C17 UNL     1       3.061   1.013  -0.096  1.00  0.00           C  
HETATM   22  H1  UNL     1       5.682  -2.003  -0.636  1.00  0.00           H  
HETATM   23  H2  UNL     1       5.568  -1.922   1.137  1.00  0.00           H  
HETATM   24  H3  UNL     1       6.936  -1.142   0.324  1.00  0.00           H  
HETATM   25  H4  UNL     1       3.612  -2.292  -0.107  1.00  0.00           H  
HETATM   26  H5  UNL     1       1.236  -2.363  -0.433  1.00  0.00           H  
HETATM   27  H6  UNL     1      -0.682   0.536  -1.426  1.00  0.00           H  
HETATM   28  H7  UNL     1      -0.318  -2.074  -1.666  1.00  0.00           H  
HETATM   29  H8  UNL     1      -0.905  -2.165   0.027  1.00  0.00           H  
HETATM   30  H9  UNL     1      -4.883  -1.720  -1.254  1.00  0.00           H  
HETATM   31  H10 UNL     1      -7.402  -0.166  -0.127  1.00  0.00           H  
HETATM   32  H11 UNL     1      -5.521   0.894   2.115  1.00  0.00           H  
HETATM   33  H12 UNL     1      -3.128   1.307   2.181  1.00  0.00           H  
HETATM   34  H13 UNL     1      -0.739  -0.072   1.571  1.00  0.00           H  
HETATM   35  H14 UNL     1      -1.091   1.446   0.722  1.00  0.00           H  
HETATM   36  H15 UNL     1       2.166   3.436   0.800  1.00  0.00           H  
HETATM   37  H16 UNL     1       1.012   4.307  -0.222  1.00  0.00           H  
HETATM   38  H17 UNL     1       2.449   3.621  -0.999  1.00  0.00           H  
HETATM   39  H18 UNL     1       3.609   1.939   0.004  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3
CONECT    3    4    4   21
CONECT    4    5   25
CONECT    5    6    6   26
CONECT    6    7   18
CONECT    7    8   17   27
CONECT    8    9   28   29
CONECT    9   10
CONECT   10   11   11   16
CONECT   11   12   30
CONECT   12   13   14   14
CONECT   13   31
CONECT   14   15   32
CONECT   15   16   16   33
CONECT   16   17
CONECT   17   34   35
CONECT   18   19   21   21
CONECT   19   20
CONECT   20   36   37   38
CONECT   21   39
END

HMDB0030521
     RDKit          3D
Sativan
 39 41  0  0  0  0  0  0  0  0999 V2000
    5.8567   -1.3355    0.2293 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1163   -0.1322    0.1580 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7545   -0.1655   -0.0313 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0612   -1.3740   -0.1591 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6853   -1.3846   -0.3497 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0242   -0.1855   -0.4098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4327   -0.1675   -0.6002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9259   -1.5640   -0.8918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2811   -1.4102   -1.3534 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1462   -0.8131   -0.4504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5253   -1.0401   -0.4755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3697   -0.4435    0.4231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7228   -0.6780    0.3838 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8636    0.3994    1.3764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5060    0.6287    1.4085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6190    0.0327    0.5025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1691    0.3369    0.6152 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6958    1.0349   -0.2847 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9981    2.2362   -0.3497 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7080    3.4459   -0.2194 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0614    1.0135   -0.0961 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6818   -2.0032   -0.6361 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5676   -1.9217    1.1371 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9357   -1.1424    0.3237 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6117   -2.2925   -0.1069 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2359   -2.3629   -0.4330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6820    0.5356   -1.4263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3184   -2.0736   -1.6665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9051   -2.1650    0.0266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8827   -1.7197   -1.2536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4024   -0.1661   -0.1273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5205    0.8940    2.1150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1275    1.3070    2.1807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7390   -0.0725    1.5707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0908    1.4456    0.7223 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1664    3.4355    0.8004 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0115    4.3074   -0.2218 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4491    3.6211   -0.9992 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6086    1.9386    0.0041 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  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
  6 18  1  0
 18 19  1  0
 19 20  1  0
 18 21  2  0
 21  3  1  0
 17  7  1  0
 16 10  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
 11 30  1  0
 13 31  1  0
 14 32  1  0
 15 33  1  0
 17 34  1  0
 17 35  1  0
 20 36  1  0
 20 37  1  0
 20 38  1  0
 21 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(-)-Sativan	HMDB
2'-O-Methylvestitol	HMDB
7-Hydroxy-2',4'-dimethoxyisoflavan	HMDB
Sativin	HMDB
Sativin (alfalfa)	HMDB
Sativan	MeSH

Chemical Formula

C₁₇H₁₈O₄

Average Molecular Weight

286.3224

Monoisotopic Molecular Weight

286.120509064

IUPAC Name

3-(2,4-dimethoxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-ol

Traditional Name

3-(2,4-dimethoxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-ol

CAS Registry Number

41743-86-6

SMILES

COC1=CC(OC)=C(C=C1)C1COC2=C(C1)C=CC(O)=C2

InChI Identifier

InChI=1S/C17H18O4/c1-19-14-5-6-15(17(9-14)20-2)12-7-11-3-4-13(18)8-16(11)21-10-12/h3-6,8-9,12,18H,7,10H2,1-2H3

InChI Key

TUXCLJQCYVCGDW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 4'-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C4' atom of the isoflavonoid backbone. Isoflavonoids are natural products derived from 3-phenylchromen-4-one.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

O-methylated isoflavonoids

Direct Parent

4'-O-methylated isoflavonoids

Alternative Parents

Substituents

2p-methoxyisoflavonoid-skeleton
4p-methoxyisoflavonoid
Hydroxyisoflavonoid
Isoflavanol
Isoflavan
Chromane
Benzopyran
M-dimethoxybenzene
Dimethoxybenzene
1-benzopyran
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Oxacycle
Ether
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

a flavonoid (CPD-9367 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0030521)

Source

Exogenous

Exogenous (HMDB: HMDB0030521)

Food

Pulse

Pulses (FooDB: FOOD00867)

Endogenous

Endogenous (HMDB: HMDB0030521)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	128 - 129 °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	0.015 g/L	ALOGPS
logP	3.13	ALOGPS
logP	3.18	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	9.78	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	47.92 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	79.91 m³·mol⁻¹	ChemAxon
Polarizability	31.24 Å³	ChemAxon
Number of Rings	3	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]+	169.993	31661259
DarkChem	[M-H]-	169.238	31661259
DeepCCS	[M+H]+	171.326	30932474
DeepCCS	[M-H]-	168.968	30932474
DeepCCS	[M-2H]-	201.854	30932474
DeepCCS	[M+Na]+	177.419	30932474
AllCCS	[M+H]+	167.8	32859911
AllCCS	[M+H-H2O]+	164.1	32859911
AllCCS	[M+NH4]+	171.2	32859911
AllCCS	[M+Na]+	172.2	32859911
AllCCS	[M-H]-	172.6	32859911
AllCCS	[M+Na-2H]-	172.1	32859911
AllCCS	[M+HCOO]-	171.8	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.	7.6 minutes	32390414
Predicted by Siyang on May 30, 2022	14.4101 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.26 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2102.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	368.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	191.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	200.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	288.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	666.2 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	600.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	132.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1358.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	508.2 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1382.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	433.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	416.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	359.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	287.6 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	11.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Sativan	COC1=CC(OC)=C(C=C1)C1COC2=C(C1)C=CC(O)=C2	3564.5	Standard polar	33892256
Sativan	COC1=CC(OC)=C(C=C1)C1COC2=C(C1)C=CC(O)=C2	2517.7	Standard non polar	33892256
Sativan	COC1=CC(OC)=C(C=C1)C1COC2=C(C1)C=CC(O)=C2	2711.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Sativan,1TMS,isomer #1	COC1=CC=C(C2COC3=CC(O[Si](C)(C)C)=CC=C3C2)C(OC)=C1	2540.7	Semi standard non polar	33892256
Sativan,1TBDMS,isomer #1	COC1=CC=C(C2COC3=CC(O[Si](C)(C)C(C)(C)C)=CC=C3C2)C(OC)=C1	2802.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Sativan GC-MS (Non-derivatized) - 70eV, Positive	splash10-0kmr-0490000000-6b04e8d084537d989653	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sativan GC-MS (1 TMS) - 70eV, Positive	splash10-006x-3539000000-b1ea81d564557fa1a5e5	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sativan 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 - Sativan 10V, Positive-QTOF	splash10-0079-0790000000-b7ab2d4a8dde58970e46	2015-05-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sativan 20V, Positive-QTOF	splash10-00di-0950000000-bc22f47561d65f8a4744	2015-05-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sativan 40V, Positive-QTOF	splash10-05fr-2920000000-0cadcfa4b764b4a16ae8	2015-05-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sativan 10V, Negative-QTOF	splash10-000i-0390000000-4e24e908ea01c0359c7d	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sativan 20V, Negative-QTOF	splash10-000i-0690000000-0e475e25503c9eb8fb18	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sativan 40V, Negative-QTOF	splash10-05g0-3950000000-6b150d88620333f6ef7d	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sativan 10V, Negative-QTOF	splash10-000i-0090000000-03e53c541e9b60a095ae	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sativan 20V, Negative-QTOF	splash10-000i-0290000000-dbae0c5223648a9fb628	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sativan 40V, Negative-QTOF	splash10-000l-2690000000-152d36a273dad8e6e908	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sativan 10V, Positive-QTOF	splash10-000i-0980000000-2c817385f79fb460e783	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sativan 20V, Positive-QTOF	splash10-000i-0970000000-97d2a52de0e8782853fc	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sativan 40V, Positive-QTOF	splash10-0kmr-0910000000-f63d928bc349749930a0	2021-09-23	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

596401

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 Sativan (HMDB0030521)

MOL for HMDB0030521 (Sativan)

3D MOL for HMDB0030521 (Sativan)

3D SDF for HMDB0030521 (Sativan)

3D-SDF for HMDB0030521 (Sativan)

PDB for HMDB0030521 (Sativan)

3D PDB for HMDB0030521 (Sativan)

SMILES for HMDB0030521 (Sativan)

INCHI for HMDB0030521 (Sativan)

Structure for HMDB0030521 (Sativan)

3D Structure for HMDB0030521 (Sativan)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra