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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:28:40 UTC

Update Date

2022-03-07 02:53:50 UTC

HMDB ID

HMDB0033720

Secondary Accession Numbers

HMDB33720

Metabolite Identification

Common Name

6alpha-Hydroxymaackiain

Description

6alpha-Hydroxymaackiain 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. 6alpha-Hydroxymaackiain has been detected, but not quantified in, several different foods, such as herbal tea, common peas (Pisum sativum), teas (Camellia sinensis), red tea, and herbs and spices. This could make 6alpha-hydroxymaackiain a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 6alpha-Hydroxymaackiain.

Structure

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

HMDB0033720
     RDKit          3D
6alpha-Hydroxymaackiain
 34 38  0  0  0  0  0  0  0  0999 V2000
    4.4189    2.8174   -0.4306 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5736    1.7622   -0.0751 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1030    1.6134    1.2291 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2689    0.5603    1.5500 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8972   -0.3407    0.6040 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3691   -0.1848   -0.6871 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1997    0.8506   -1.0403 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9862   -1.1036   -1.6386 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8815   -1.9474   -1.5592 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1743   -1.9298   -0.2394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2862   -3.2204    0.0408 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9809   -1.0149   -0.2028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9326   -0.6033   -1.1279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9233    0.2849   -0.7853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0194    0.8075    0.4874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0648    0.3913    1.4057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0602   -0.5056    1.0684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0083   -1.0508    1.8310 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0068   -1.4814    0.9043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1063    1.6668    0.5368 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8395    1.4508   -0.6545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9667    0.8223   -1.5550 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9635    3.6782   -0.7514 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4175    2.3458    1.9541 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9336    0.4918    2.5740 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5770    0.9838   -2.0511 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1682   -1.6307   -2.3733 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2290   -2.9825   -1.7587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6855   -3.3012    0.9337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8252   -1.0362   -2.1212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1425    0.8054    2.4107 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5483   -2.3004    1.4193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1452    2.4581   -1.0475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7296    0.8434   -0.4235 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 15 20  1  0
 20 21  1  0
 21 22  1  0
  7  2  1  0
 19 10  1  0
 19  5  1  0
 17 12  1  0
 22 14  1  0
  1 23  1  0
  3 24  1  0
  4 25  1  0
  7 26  1  0
  9 27  1  0
  9 28  1  0
 11 29  1  0
 13 30  1  0
 16 31  1  0
 19 32  1  0
 21 33  1  0
 21 34  1  0
M  END


  Mrv0541 05061307192D          

 22 26  0  0  0  0            999 V2000
    0.9678    2.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7908    2.3914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0671    0.9086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0288    0.8705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0867    2.5195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1743    0.3392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0405    1.6253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6059    1.5926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2519    1.7074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3292    1.3079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8901    0.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3582    2.1324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7573    1.2577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7863    2.0822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0749    1.7647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5361    1.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2171    1.5353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0663    0.4486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3513    0.2819    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5325    0.9754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5794    2.3094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5830    2.4147    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  8  1  1  0  0  0  0
  8  3  2  0  0  0  0
  9  2  1  0  0  0  0
 10  4  2  0  0  0  0
 11  3  1  0  0  0  0
 11  9  2  0  0  0  0
 12  5  2  0  0  0  0
 12 10  1  0  0  0  0
 13  4  1  0  0  0  0
 14  5  1  0  0  0  0
 14 13  2  0  0  0  0
 15  9  1  0  0  0  0
 16  6  1  0  0  0  0
 16 10  1  0  0  0  0
 16 15  1  0  0  0  0
 17  8  1  0  0  0  0
 18 16  1  0  0  0  0
 19  6  1  0  0  0  0
 19 11  1  0  0  0  0
 20  7  1  0  0  0  0
 20 13  1  0  0  0  0
 21  7  1  0  0  0  0
 21 14  1  0  0  0  0
 22 12  1  0  0  0  0
 22 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033720

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC2=C(C=C1)C1OC3=CC4=C(OCO4)C=C3C1(O)CO2

> <INCHI_IDENTIFIER>
InChI=1S/C16H12O6/c17-8-1-2-9-11(3-8)19-6-16(18)10-4-13-14(21-7-20-13)5-12(10)22-15(9)16/h1-5,15,17-18H,6-7H2

> <INCHI_KEY>
GLMPLZUBQDAZEN-UHFFFAOYSA-N

> <FORMULA>
C16H12O6

> <MOLECULAR_WEIGHT>
300.2629

> <EXACT_MASS>
300.063388116

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
29.440260064556306

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-2,4(8),9,13(18),14,16-hexaene-1,16-diol

> <ALOGPS_LOGP>
2.03

> <JCHEM_LOGP>
1.634947747666667

> <ALOGPS_LOGS>
-2.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.009343195182975

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.413307566628584

> <JCHEM_PKA_STRONGEST_BASIC>
-4.121505541933158

> <JCHEM_POLAR_SURFACE_AREA>
77.38000000000001

> <JCHEM_REFRACTIVITY>
73.45270000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.85e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6a-hydroxymaackiain

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033720
     RDKit          3D
6alpha-Hydroxymaackiain
 34 38  0  0  0  0  0  0  0  0999 V2000
    4.4189    2.8174   -0.4306 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5736    1.7622   -0.0751 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1030    1.6134    1.2291 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2689    0.5603    1.5500 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8972   -0.3407    0.6040 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3691   -0.1848   -0.6871 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1997    0.8506   -1.0403 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9862   -1.1036   -1.6386 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8815   -1.9474   -1.5592 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1743   -1.9298   -0.2394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2862   -3.2204    0.0408 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9809   -1.0149   -0.2028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9326   -0.6033   -1.1279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9233    0.2849   -0.7853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0194    0.8075    0.4874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0648    0.3913    1.4057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0602   -0.5056    1.0684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0083   -1.0508    1.8310 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0068   -1.4814    0.9043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1063    1.6668    0.5368 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8395    1.4508   -0.6545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9667    0.8223   -1.5550 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9635    3.6782   -0.7514 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4175    2.3458    1.9541 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9336    0.4918    2.5740 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5770    0.9838   -2.0511 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1682   -1.6307   -2.3733 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2290   -2.9825   -1.7587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6855   -3.3012    0.9337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8252   -1.0362   -2.1212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1425    0.8054    2.4107 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5483   -2.3004    1.4193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1452    2.4581   -1.0475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7296    0.8434   -0.4235 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 15 20  1  0
 20 21  1  0
 21 22  1  0
  7  2  1  0
 19 10  1  0
 19  5  1  0
 17 12  1  0
 22 14  1  0
  1 23  1  0
  3 24  1  0
  4 25  1  0
  7 26  1  0
  9 27  1  0
  9 28  1  0
 11 29  1  0
 13 30  1  0
 16 31  1  0
 19 32  1  0
 21 33  1  0
 21 34  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       1.807   4.357   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.343   4.464   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.992   1.696   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.387   1.625   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.495   4.703   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.925   0.633   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.142   3.034   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.131   2.973   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.204   3.187   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.081   2.441   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.528   1.803   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.135   3.980   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.747   2.348   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.801   3.887   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.740   3.294   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.601   2.017   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.405   2.866   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       7.590   0.837   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       4.389   0.526   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      12.194   1.821   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      12.282   4.311   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       6.688   4.507   0.000  0.00  0.00           O+0
CONECT    1    2    8                                                       
CONECT    2    1    9                                                       
CONECT    3    8   11                                                       
CONECT    4   10   13                                                       
CONECT    5   12   14                                                       
CONECT    6   16   19                                                       
CONECT    7   20   21                                                       
CONECT    8    1    3   17                                                  
CONECT    9    2   11   15                                                  
CONECT   10    4   12   16                                                  
CONECT   11    3    9   19                                                  
CONECT   12    5   10   22                                                  
CONECT   13    4   14   20                                                  
CONECT   14    5   13   21                                                  
CONECT   15    9   16   22                                                  
CONECT   16    6   10   15   18                                             
CONECT   17    8                                                            
CONECT   18   16                                                            
CONECT   19    6   11                                                       
CONECT   20    7   13                                                       
CONECT   21    7   14                                                       
CONECT   22   12   15                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   52    0
END

COMPND    HMDB0033720
HETATM    1  O1  UNL     1       4.419   2.817  -0.431  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.574   1.762  -0.075  1.00  0.00           C  
HETATM    3  C2  UNL     1       3.103   1.613   1.229  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.269   0.560   1.550  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.897  -0.341   0.604  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.369  -0.185  -0.687  1.00  0.00           C  
HETATM    7  C6  UNL     1       3.200   0.851  -1.040  1.00  0.00           C  
HETATM    8  O2  UNL     1       1.986  -1.104  -1.639  1.00  0.00           O  
HETATM    9  C7  UNL     1       0.881  -1.947  -1.559  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.174  -1.930  -0.239  1.00  0.00           C  
HETATM   11  O3  UNL     1      -0.286  -3.220   0.041  1.00  0.00           O  
HETATM   12  C9  UNL     1      -0.981  -1.015  -0.203  1.00  0.00           C  
HETATM   13  C10 UNL     1      -1.933  -0.603  -1.128  1.00  0.00           C  
HETATM   14  C11 UNL     1      -2.923   0.285  -0.785  1.00  0.00           C  
HETATM   15  C12 UNL     1      -3.019   0.807   0.487  1.00  0.00           C  
HETATM   16  C13 UNL     1      -2.065   0.391   1.406  1.00  0.00           C  
HETATM   17  C14 UNL     1      -1.060  -0.506   1.068  1.00  0.00           C  
HETATM   18  O4  UNL     1      -0.008  -1.051   1.831  1.00  0.00           O  
HETATM   19  C15 UNL     1       1.007  -1.481   0.904  1.00  0.00           C  
HETATM   20  O5  UNL     1      -4.106   1.667   0.537  1.00  0.00           O  
HETATM   21  C16 UNL     1      -4.839   1.451  -0.655  1.00  0.00           C  
HETATM   22  O6  UNL     1      -3.967   0.822  -1.555  1.00  0.00           O  
HETATM   23  H1  UNL     1       3.963   3.678  -0.751  1.00  0.00           H  
HETATM   24  H2  UNL     1       3.418   2.346   1.954  1.00  0.00           H  
HETATM   25  H3  UNL     1       1.934   0.492   2.574  1.00  0.00           H  
HETATM   26  H4  UNL     1       3.577   0.984  -2.051  1.00  0.00           H  
HETATM   27  H5  UNL     1       0.168  -1.631  -2.373  1.00  0.00           H  
HETATM   28  H6  UNL     1       1.229  -2.982  -1.759  1.00  0.00           H  
HETATM   29  H7  UNL     1      -0.685  -3.301   0.934  1.00  0.00           H  
HETATM   30  H8  UNL     1      -1.825  -1.036  -2.121  1.00  0.00           H  
HETATM   31  H9  UNL     1      -2.142   0.805   2.411  1.00  0.00           H  
HETATM   32  H10 UNL     1       1.548  -2.300   1.419  1.00  0.00           H  
HETATM   33  H11 UNL     1      -5.145   2.458  -1.048  1.00  0.00           H  
HETATM   34  H12 UNL     1      -5.730   0.843  -0.423  1.00  0.00           H  
CONECT    1    2   23
CONECT    2    3    3    7
CONECT    3    4   24
CONECT    4    5    5   25
CONECT    5    6   19
CONECT    6    7    7    8
CONECT    7   26
CONECT    8    9
CONECT    9   10   27   28
CONECT   10   11   12   19
CONECT   11   29
CONECT   12   13   13   17
CONECT   13   14   30
CONECT   14   15   15   22
CONECT   15   16   20
CONECT   16   17   17   31
CONECT   17   18
CONECT   18   19
CONECT   19   32
CONECT   20   21
CONECT   21   22   33   34
END

HMDB0033720
     RDKit          3D
6alpha-Hydroxymaackiain
 34 38  0  0  0  0  0  0  0  0999 V2000
    4.4189    2.8174   -0.4306 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5736    1.7622   -0.0751 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1030    1.6134    1.2291 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2689    0.5603    1.5500 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8972   -0.3407    0.6040 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3691   -0.1848   -0.6871 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1997    0.8506   -1.0403 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9862   -1.1036   -1.6386 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8815   -1.9474   -1.5592 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1743   -1.9298   -0.2394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2862   -3.2204    0.0408 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9809   -1.0149   -0.2028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9326   -0.6033   -1.1279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9233    0.2849   -0.7853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0194    0.8075    0.4874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0648    0.3913    1.4057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0602   -0.5056    1.0684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0083   -1.0508    1.8310 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0068   -1.4814    0.9043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1063    1.6668    0.5368 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8395    1.4508   -0.6545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9667    0.8223   -1.5550 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9635    3.6782   -0.7514 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4175    2.3458    1.9541 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9336    0.4918    2.5740 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5770    0.9838   -2.0511 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1682   -1.6307   -2.3733 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2290   -2.9825   -1.7587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6855   -3.3012    0.9337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8252   -1.0362   -2.1212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1425    0.8054    2.4107 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5483   -2.3004    1.4193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1452    2.4581   -1.0475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7296    0.8434   -0.4235 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 15 20  1  0
 20 21  1  0
 21 22  1  0
  7  2  1  0
 19 10  1  0
 19  5  1  0
 17 12  1  0
 22 14  1  0
  1 23  1  0
  3 24  1  0
  4 25  1  0
  7 26  1  0
  9 27  1  0
  9 28  1  0
 11 29  1  0
 13 30  1  0
 16 31  1  0
 19 32  1  0
 21 33  1  0
 21 34  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

Chemical Formula

C₁₆H₁₂O₆

Average Molecular Weight

300.2629

Monoisotopic Molecular Weight

300.063388116

IUPAC Name

5,7,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-2,4(8),9,13(18),14,16-hexaene-1,16-diol

Traditional Name

6a-hydroxymaackiain

CAS Registry Number

14602-93-8

SMILES

OC1=CC2=C(C=C1)C1OC3=CC4=C(OCO4)C=C3C1(O)CO2

InChI Identifier

InChI=1S/C16H12O6/c17-8-1-2-9-11(3-8)19-6-16(18)10-4-13-14(21-7-20-13)5-12(10)22-15(9)16/h1-5,15,17-18H,6-7H2

InChI Key

GLMPLZUBQDAZEN-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: HMDB0033720)
Cytoplasm (HMDB: HMDB0033720)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033720)

Source

Exogenous

Exogenous (HMDB: HMDB0033720)

Food

Food (HMDB: HMDB0033720)

Pulse

Pea

Common pea (FooDB: FOOD00141)

Pulses (FooDB: FOOD00867)

Tea

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0033720)
Fabaceae (HMDB: HMDB0033720)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033720)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	178 - 181 °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	1.85 g/L	ALOGPS
logP	2.03	ALOGPS
logP	1.63	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	9.41	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	77.38 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	73.45 m³·mol⁻¹	ChemAxon
Polarizability	29.44 Å³	ChemAxon
Number of Rings	5	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]+	168.787	31661259
DarkChem	[M-H]-	166.716	31661259
DeepCCS	[M+H]+	172.336	30932474
DeepCCS	[M-H]-	169.978	30932474
DeepCCS	[M-2H]-	203.302	30932474
DeepCCS	[M+Na]+	178.529	30932474
AllCCS	[M+H]+	169.3	32859911
AllCCS	[M+H-H2O]+	165.7	32859911
AllCCS	[M+NH4]+	172.7	32859911
AllCCS	[M+Na]+	173.6	32859911
AllCCS	[M-H]-	172.4	32859911
AllCCS	[M+Na-2H]-	171.5	32859911
AllCCS	[M+HCOO]-	170.5	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.	5.35 minutes	32390414
Predicted by Siyang on May 30, 2022	11.4741 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.19 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	29.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1883.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	264.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	141.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	176.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	113.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	476.3 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	531.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	123.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	915.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	404.0 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	1393.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	343.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	314.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	399.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	239.2 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	113.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
6alpha-Hydroxymaackiain	OC1=CC2=C(C=C1)C1OC3=CC4=C(OCO4)C=C3C1(O)CO2	4096.8	Standard polar	33892256
6alpha-Hydroxymaackiain	OC1=CC2=C(C=C1)C1OC3=CC4=C(OCO4)C=C3C1(O)CO2	2630.1	Standard non polar	33892256
6alpha-Hydroxymaackiain	OC1=CC2=C(C=C1)C1OC3=CC4=C(OCO4)C=C3C1(O)CO2	2883.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
6alpha-Hydroxymaackiain,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C2C(=C1)OCC1(O)C3=CC4=C(C=C3OC21)OCO4	2743.9	Semi standard non polar	33892256
6alpha-Hydroxymaackiain,1TMS,isomer #2	C[Si](C)(C)OC12COC3=CC(O)=CC=C3C1OC1=CC3=C(C=C12)OCO3	2734.3	Semi standard non polar	33892256
6alpha-Hydroxymaackiain,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C2C(=C1)OCC1(O[Si](C)(C)C)C3=CC4=C(C=C3OC21)OCO4	2771.3	Semi standard non polar	33892256
6alpha-Hydroxymaackiain,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)OCC1(O)C3=CC4=C(C=C3OC21)OCO4	3033.5	Semi standard non polar	33892256
6alpha-Hydroxymaackiain,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC12COC3=CC(O)=CC=C3C1OC1=CC3=C(C=C12)OCO3	3027.6	Semi standard non polar	33892256
6alpha-Hydroxymaackiain,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)OCC1(O[Si](C)(C)C(C)(C)C)C3=CC4=C(C=C3OC21)OCO4	3323.3	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 - 6alpha-Hydroxymaackiain GC-MS (Non-derivatized) - 70eV, Positive	splash10-00e9-2491000000-26f6a52bb1441a699a1c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6alpha-Hydroxymaackiain GC-MS (2 TMS) - 70eV, Positive	splash10-00di-9306600000-9d9cfc38667e60ad550d	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6alpha-Hydroxymaackiain GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6alpha-Hydroxymaackiain 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 - 6alpha-Hydroxymaackiain 10V, Positive-QTOF	splash10-0udi-0119000000-88a12010467f51a16e7e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6alpha-Hydroxymaackiain 20V, Positive-QTOF	splash10-0udi-0159000000-97ea99b0a2cc0e95db0f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6alpha-Hydroxymaackiain 40V, Positive-QTOF	splash10-059i-4920000000-65e43ccd24522d03a1cd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6alpha-Hydroxymaackiain 10V, Negative-QTOF	splash10-0002-0090000000-77092a5451958d1ef64d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6alpha-Hydroxymaackiain 20V, Negative-QTOF	splash10-0002-0090000000-30dabe2d04d67da1bc9e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6alpha-Hydroxymaackiain 40V, Negative-QTOF	splash10-01bi-2390000000-21099091b447e32b1fd2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6alpha-Hydroxymaackiain 10V, Positive-QTOF	splash10-0udi-0009000000-545fc7c692e0abcd7966	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6alpha-Hydroxymaackiain 20V, Positive-QTOF	splash10-0udi-0019000000-62fb017d6994744e8a87	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6alpha-Hydroxymaackiain 40V, Positive-QTOF	splash10-03dr-1932000000-709479526669a409c2c8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6alpha-Hydroxymaackiain 10V, Negative-QTOF	splash10-0002-0090000000-fb4a565723d52a1e4624	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6alpha-Hydroxymaackiain 20V, Negative-QTOF	splash10-0002-0090000000-57430cab9f56e0ef7f5b	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6alpha-Hydroxymaackiain 40V, Negative-QTOF	splash10-0002-0490000000-b932f2770060ce88c6b0	2021-09-25	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 6alpha-Hydroxymaackiain (HMDB0033720)

MOL for HMDB0033720 (6alpha-Hydroxymaackiain)

3D MOL for HMDB0033720 (6alpha-Hydroxymaackiain)

3D SDF for HMDB0033720 (6alpha-Hydroxymaackiain)

3D-SDF for HMDB0033720 (6alpha-Hydroxymaackiain)

PDB for HMDB0033720 (6alpha-Hydroxymaackiain)

3D PDB for HMDB0033720 (6alpha-Hydroxymaackiain)

SMILES for HMDB0033720 (6alpha-Hydroxymaackiain)

INCHI for HMDB0033720 (6alpha-Hydroxymaackiain)

Structure for HMDB0033720 (6alpha-Hydroxymaackiain)

3D Structure for HMDB0033720 (6alpha-Hydroxymaackiain)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra