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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:28:47 UTC

Update Date

2022-03-07 02:53:50 UTC

HMDB ID

HMDB0033722

Secondary Accession Numbers

HMDB33722

Metabolite Identification

Common Name

Sativol

Description

6alpha-Hydroxymaackiain, also known as 6a-hydroxyinermin, 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, 6alpha-hydroxymaackiain is considered to be a flavonoid lipid molecule. 6alpha-Hydroxymaackiain is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 6alpha-Hydroxymaackiain has been detected, but not quantified in, several different foods, such as common pea, herbs and spices, pulses, and tea. This could make 6alpha-hydroxymaackiain a potential biomarker for the consumption of these foods.

Structure

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

HMDB0033722
     RDKit          3D
Sativol
 32 35  0  0  0  0  0  0  0  0999 V2000
    5.8542    0.1594   -0.0965 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8609   -0.3525   -0.9633 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5345   -0.1653   -0.6153 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1765    0.5067    0.5531 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8529    0.6725    0.8640 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8814    0.1821    0.0340 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2343   -0.4876   -1.1304 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3061   -0.9617   -1.9331 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9735   -0.8466   -1.7107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8135   -1.3215   -2.5163 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3598   -0.1877   -0.5644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5973    0.1120   -0.0235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8925   -0.1481   -0.4494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9489    0.2816    0.3130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7150    0.9693    1.4977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7843    1.4188    2.2946 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4437    1.2409    1.9440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3903    0.8020    1.1658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0879    0.9072    1.3238 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4475    0.3414    0.3338 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5628   -0.6604   -1.4535 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9566   -1.3212   -2.6033 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8605    1.2740   -0.0695 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8715   -0.2424   -0.3650 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6715   -0.2113    0.9545 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9725    0.8913    1.2036 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5841    1.1888    1.7616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0012   -0.6872   -1.3795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9513    0.0751   -0.0258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7365    1.2383    1.9999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2743    1.7754    2.8650 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2373   -1.6792   -3.2090 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  2  0
  9 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
  7 21  2  0
 21 22  1  0
 21  3  1  0
 20  6  1  0
 20 11  2  0
 18 12  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
 13 28  1  0
 14 29  1  0
 16 30  1  0
 17 31  1  0
 22 32  1  0
M  END


  Mrv0541 05061307192D          

 22 25  0  0  0  0            999 V2000
   -2.7328    1.2437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6087    0.8585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8754    1.2366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3435   -0.3244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1671   -0.2772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9538   -0.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6479    0.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1813    0.7906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1092    0.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5381    0.4596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2205   -0.0335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3855    1.0079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0855    1.1494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9328    0.3182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2618    1.1022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0145    1.7448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3811   -0.3437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4565    1.8863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4671    2.4345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3618    0.5068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4489   -0.3254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1908    1.7920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  5  4  2  0  0  0  0
  7  2  1  0  0  0  0
  7  6  2  0  0  0  0
  8  3  1  0  0  0  0
  9  4  1  0  0  0  0
 10  5  1  0  0  0  0
 11  6  1  0  0  0  0
 11  8  2  0  0  0  0
 12  8  1  0  0  0  0
 13 10  2  0  0  0  0
 14  9  1  0  0  0  0
 14 12  2  0  0  0  0
 15  9  2  0  0  0  0
 15 13  1  0  0  0  0
 16 12  1  0  0  0  0
 17  7  1  0  0  0  0
 18 13  1  0  0  0  0
 19 16  2  0  0  0  0
 20  1  1  0  0  0  0
 20 10  1  0  0  0  0
 21 11  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>
HMDB0033722

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C2=C(C=C1)C1=C(C3=C(O1)C=C(O)C=C3)C(=O)O2

> <INCHI_IDENTIFIER>
InChI=1S/C16H10O6/c1-20-10-5-4-9-14-12(16(19)22-15(9)13(10)18)8-3-2-7(17)6-11(8)21-14/h2-6,17-18H,1H3

> <INCHI_KEY>
YLRNDYZYIUVEDH-UHFFFAOYSA-N

> <FORMULA>
C16H10O6

> <MOLECULAR_WEIGHT>
298.247

> <EXACT_MASS>
298.047738052

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
29.444644119224495

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6,14-dihydroxy-5-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-9-one

> <ALOGPS_LOGP>
2.48

> <JCHEM_LOGP>
2.889650056666666

> <ALOGPS_LOGS>
-2.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.412767405241457

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.084498110042784

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5074163181426234

> <JCHEM_POLAR_SURFACE_AREA>
89.13000000000001

> <JCHEM_REFRACTIVITY>
76.0827

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.10e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6,14-dihydroxy-5-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033722
     RDKit          3D
Sativol
 32 35  0  0  0  0  0  0  0  0999 V2000
    5.8542    0.1594   -0.0965 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8609   -0.3525   -0.9633 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5345   -0.1653   -0.6153 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1765    0.5067    0.5531 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8529    0.6725    0.8640 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8814    0.1821    0.0340 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2343   -0.4876   -1.1304 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3061   -0.9617   -1.9331 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9735   -0.8466   -1.7107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8135   -1.3215   -2.5163 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3598   -0.1877   -0.5644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5973    0.1120   -0.0235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8925   -0.1481   -0.4494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9489    0.2816    0.3130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7150    0.9693    1.4977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7843    1.4188    2.2946 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4437    1.2409    1.9440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3903    0.8020    1.1658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0879    0.9072    1.3238 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4475    0.3414    0.3338 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5628   -0.6604   -1.4535 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9566   -1.3212   -2.6033 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8605    1.2740   -0.0695 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8715   -0.2424   -0.3650 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6715   -0.2113    0.9545 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9725    0.8913    1.2036 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5841    1.1888    1.7616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0012   -0.6872   -1.3795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9513    0.0751   -0.0258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7365    1.2383    1.9999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2743    1.7754    2.8650 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2373   -1.6792   -3.2090 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  2  0
  9 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
  7 21  2  0
 21 22  1  0
 21  3  1  0
 20  6  1  0
 20 11  2  0
 18 12  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
 13 28  1  0
 14 29  1  0
 16 30  1  0
 17 31  1  0
 22 32  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      -5.101   2.322   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.736   1.603   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.367   2.308   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.641  -0.606   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.179  -0.517   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.514  -0.768   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.809   0.064   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.072   1.476   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.204   0.682   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.871   0.858   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.145  -0.063   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.586   1.881   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.026   2.146   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.741   0.594   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.489   2.057   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.894   3.257   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.178  -0.642   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -2.719   3.521   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.739   4.544   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -4.409   0.946   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       2.705  -0.607   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       0.356   3.345   0.000  0.00  0.00           O+0
CONECT    1   20                                                            
CONECT    2    3    7                                                       
CONECT    3    2    8                                                       
CONECT    4    5    9                                                       
CONECT    5    4   10                                                       
CONECT    6    7   11                                                       
CONECT    7    2    6   17                                                  
CONECT    8    3   11   12                                                  
CONECT    9    4   14   15                                                  
CONECT   10    5   13   20                                                  
CONECT   11    6    8   21                                                  
CONECT   12    8   14   16                                                  
CONECT   13   10   15   18                                                  
CONECT   14    9   12   21                                                  
CONECT   15    9   13   22                                                  
CONECT   16   12   19   22                                                  
CONECT   17    7                                                            
CONECT   18   13                                                            
CONECT   19   16                                                            
CONECT   20    1   10                                                       
CONECT   21   11   14                                                       
CONECT   22   15   16                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

COMPND    HMDB0033722
HETATM    1  C1  UNL     1       5.854   0.159  -0.096  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.861  -0.352  -0.963  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.535  -0.165  -0.615  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.177   0.507   0.553  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.853   0.672   0.864  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.881   0.182   0.034  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.234  -0.488  -1.130  1.00  0.00           C  
HETATM    8  O2  UNL     1       0.306  -0.962  -1.933  1.00  0.00           O  
HETATM    9  C7  UNL     1      -0.974  -0.847  -1.711  1.00  0.00           C  
HETATM   10  O3  UNL     1      -1.813  -1.321  -2.516  1.00  0.00           O  
HETATM   11  C8  UNL     1      -1.360  -0.188  -0.564  1.00  0.00           C  
HETATM   12  C9  UNL     1      -2.597   0.112  -0.023  1.00  0.00           C  
HETATM   13  C10 UNL     1      -3.892  -0.148  -0.449  1.00  0.00           C  
HETATM   14  C11 UNL     1      -4.949   0.282   0.313  1.00  0.00           C  
HETATM   15  C12 UNL     1      -4.715   0.969   1.498  1.00  0.00           C  
HETATM   16  O4  UNL     1      -5.784   1.419   2.295  1.00  0.00           O  
HETATM   17  C13 UNL     1      -3.444   1.241   1.944  1.00  0.00           C  
HETATM   18  C14 UNL     1      -2.390   0.802   1.166  1.00  0.00           C  
HETATM   19  O5  UNL     1      -1.088   0.907   1.324  1.00  0.00           O  
HETATM   20  C15 UNL     1      -0.447   0.341   0.334  1.00  0.00           C  
HETATM   21  C16 UNL     1       2.563  -0.660  -1.453  1.00  0.00           C  
HETATM   22  O6  UNL     1       2.957  -1.321  -2.603  1.00  0.00           O  
HETATM   23  H1  UNL     1       5.861   1.274  -0.070  1.00  0.00           H  
HETATM   24  H2  UNL     1       6.872  -0.242  -0.365  1.00  0.00           H  
HETATM   25  H3  UNL     1       5.672  -0.211   0.954  1.00  0.00           H  
HETATM   26  H4  UNL     1       3.973   0.891   1.204  1.00  0.00           H  
HETATM   27  H5  UNL     1       1.584   1.189   1.762  1.00  0.00           H  
HETATM   28  H6  UNL     1      -4.001  -0.687  -1.380  1.00  0.00           H  
HETATM   29  H7  UNL     1      -5.951   0.075  -0.026  1.00  0.00           H  
HETATM   30  H8  UNL     1      -6.737   1.238   2.000  1.00  0.00           H  
HETATM   31  H9  UNL     1      -3.274   1.775   2.865  1.00  0.00           H  
HETATM   32  H10 UNL     1       2.237  -1.679  -3.209  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3
CONECT    3    4    4   21
CONECT    4    5   26
CONECT    5    6    6   27
CONECT    6    7   20
CONECT    7    8   21   21
CONECT    8    9
CONECT    9   10   10   11
CONECT   11   12   20   20
CONECT   12   13   13   18
CONECT   13   14   28
CONECT   14   15   15   29
CONECT   15   16   17
CONECT   16   30
CONECT   17   18   18   31
CONECT   18   19
CONECT   19   20
CONECT   21   22
CONECT   22   32
END

HMDB0033722
     RDKit          3D
Sativol
 32 35  0  0  0  0  0  0  0  0999 V2000
    5.8542    0.1594   -0.0965 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8609   -0.3525   -0.9633 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5345   -0.1653   -0.6153 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1765    0.5067    0.5531 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8529    0.6725    0.8640 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8814    0.1821    0.0340 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2343   -0.4876   -1.1304 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3061   -0.9617   -1.9331 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9735   -0.8466   -1.7107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8135   -1.3215   -2.5163 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3598   -0.1877   -0.5644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5973    0.1120   -0.0235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8925   -0.1481   -0.4494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9489    0.2816    0.3130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7150    0.9693    1.4977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7843    1.4188    2.2946 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4437    1.2409    1.9440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3903    0.8020    1.1658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0879    0.9072    1.3238 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4475    0.3414    0.3338 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5628   -0.6604   -1.4535 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9566   -1.3212   -2.6033 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8605    1.2740   -0.0695 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8715   -0.2424   -0.3650 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6715   -0.2113    0.9545 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9725    0.8913    1.2036 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5841    1.1888    1.7616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0012   -0.6872   -1.3795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9513    0.0751   -0.0258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7365    1.2383    1.9999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2743    1.7754    2.8650 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2373   -1.6792   -3.2090 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  2  0
  9 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
  7 21  2  0
 21 22  1  0
 21  3  1  0
 20  6  1  0
 20 11  2  0
 18 12  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
 13 28  1  0
 14 29  1  0
 16 30  1  0
 17 31  1  0
 22 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
6a-Hydroxymaackiain	Generator
6Α-hydroxymaackiain	Generator
3,6a-Dihydroxy-8,9-methylenedioxypterocarpan	HMDB
6a-Hydroxyinermin	HMDB
4,9-Dihydroxy-3-methoxycoumestan	HMDB
8,12-Dihydroxy-7-methoxycoumestan	HMDB

Chemical Formula

C₁₆H₁₀O₆

Average Molecular Weight

298.247

Monoisotopic Molecular Weight

298.047738052

IUPAC Name

6,14-dihydroxy-5-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-9-one

Traditional Name

6,14-dihydroxy-5-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-9-one

CAS Registry Number

7331-58-0

SMILES

COC1=C(O)C2=C(C=C1)C1=C(C3=C(O1)C=C(O)C=C3)C(=O)O2

InChI Identifier

InChI=1S/C16H10O6/c1-20-10-5-4-9-14-12(16(19)22-15(9)13(10)18)8-3-2-7(17)6-11(8)21-14/h2-6,17-18H,1H3

InChI Key

YLRNDYZYIUVEDH-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
Benzodioxole
Benzofuran
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Tertiary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Ether
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Pterocarpans (LMPK12070133 )
a small molecule (CPD-3942 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0033722)
Cytoplasm (HMDB: HMDB0033722)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033722)

Source

Exogenous

Food

Food (HMDB: HMDB0033722)

Herb and spice

Herb

Alfalfa (FooDB: FOOD00286)

Spice

Saffron (FooDB: FOOD00063)

Pulse

Pulses (FooDB: FOOD00867)

Endogenous

Plant

Plant (HMDB: HMDB0033722)
Fabaceae (HMDB: HMDB0033722)

Not Available

Nutrient (HMDB: HMDB0033722)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	303 °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	0.31 g/L	ALOGPS
logP	2.48	ALOGPS
logP	2.89	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	9.08	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	89.13 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	76.08 m³·mol⁻¹	ChemAxon
Polarizability	29.44 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]+	168.788	31661259
DarkChem	[M-H]-	168.973	31661259
DeepCCS	[M+H]+	176.331	30932474
DeepCCS	[M-H]-	173.973	30932474
DeepCCS	[M-2H]-	208.072	30932474
DeepCCS	[M+Na]+	183.299	30932474
AllCCS	[M+H]+	167.0	32859911
AllCCS	[M+H-H2O]+	163.3	32859911
AllCCS	[M+NH4]+	170.4	32859911
AllCCS	[M+Na]+	171.4	32859911
AllCCS	[M-H]-	168.7	32859911
AllCCS	[M+Na-2H]-	167.6	32859911
AllCCS	[M+HCOO]-	166.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Sativol	COC1=C(O)C2=C(C=C1)C1=C(C3=C(O1)C=C(O)C=C3)C(=O)O2	4309.7	Standard polar	33892256
Sativol	COC1=C(O)C2=C(C=C1)C1=C(C3=C(O1)C=C(O)C=C3)C(=O)O2	2882.2	Standard non polar	33892256
Sativol	COC1=C(O)C2=C(C=C1)C1=C(C3=C(O1)C=C(O)C=C3)C(=O)O2	3091.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Sativol,1TMS,isomer #1	COC1=CC=C2C(=C1O[Si](C)(C)C)OC(=O)C1=C2OC2=CC(O)=CC=C21	3083.6	Semi standard non polar	33892256
Sativol,1TMS,isomer #2	COC1=CC=C2C(=C1O)OC(=O)C1=C2OC2=CC(O[Si](C)(C)C)=CC=C21	3253.0	Semi standard non polar	33892256
Sativol,2TMS,isomer #1	COC1=CC=C2C(=C1O[Si](C)(C)C)OC(=O)C1=C2OC2=CC(O[Si](C)(C)C)=CC=C21	3209.8	Semi standard non polar	33892256
Sativol,1TBDMS,isomer #1	COC1=CC=C2C(=C1O[Si](C)(C)C(C)(C)C)OC(=O)C1=C2OC2=CC(O)=CC=C21	3295.1	Semi standard non polar	33892256
Sativol,1TBDMS,isomer #2	COC1=CC=C2C(=C1O)OC(=O)C1=C2OC2=CC(O[Si](C)(C)C(C)(C)C)=CC=C21	3463.1	Semi standard non polar	33892256
Sativol,2TBDMS,isomer #1	COC1=CC=C2C(=C1O[Si](C)(C)C(C)(C)C)OC(=O)C1=C2OC2=CC(O[Si](C)(C)C(C)(C)C)=CC=C21	3688.8	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 - Sativol GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-0790000000-8463a2699ea35ddc8f35	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sativol GC-MS (2 TMS) - 70eV, Positive	splash10-05i1-2019300000-e978a2229c6916f190d0	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sativol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sativol 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 - Sativol 10V, Positive-QTOF	splash10-0002-0090000000-1c2655c0874df2c777ab	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sativol 20V, Positive-QTOF	splash10-0002-0090000000-0c32dcdf67d63237b7db	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sativol 40V, Positive-QTOF	splash10-00pj-1090000000-c46fed3bc46b4bc5af33	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sativol 10V, Negative-QTOF	splash10-0002-0090000000-833559a945ff2bea2313	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sativol 20V, Negative-QTOF	splash10-0002-0090000000-c98d267548cdbf45b286	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sativol 40V, Negative-QTOF	splash10-003r-0090000000-74dca69cf78e048d00c1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sativol 10V, Negative-QTOF	splash10-0002-0090000000-96de5c56a94c496da9f8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sativol 20V, Negative-QTOF	splash10-0002-0090000000-76d3bcee39d7e768e000	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sativol 40V, Negative-QTOF	splash10-004i-0190000000-097d643257e5ee29d215	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sativol 10V, Positive-QTOF	splash10-0002-0090000000-0e40d1dc69d66b601127	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sativol 20V, Positive-QTOF	splash10-0002-0090000000-0e40d1dc69d66b601127	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sativol 40V, Positive-QTOF	splash10-054k-0190000000-ef86481e0614d93270c3	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB011839

KNApSAcK ID

C00009677

Chemspider ID

24785132

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44257487

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 Sativol (HMDB0033722)

MOL for HMDB0033722 (Sativol)

3D MOL for HMDB0033722 (Sativol)

3D SDF for HMDB0033722 (Sativol)

3D-SDF for HMDB0033722 (Sativol)

PDB for HMDB0033722 (Sativol)

3D PDB for HMDB0033722 (Sativol)

SMILES for HMDB0033722 (Sativol)

INCHI for HMDB0033722 (Sativol)

Structure for HMDB0033722 (Sativol)

3D Structure for HMDB0033722 (Sativol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra