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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:46:08 UTC

Update Date

2022-03-07 02:53:56 UTC

HMDB ID

HMDB0033993

Secondary Accession Numbers

HMDB33993

Metabolite Identification

Common Name

Wairol

Description

Wairol belongs to the class of organic compounds known as coumestans. These are polycyclic aromatic compounds containing a coumestan moiety, which consists of a benzoxole fused to a chromen-2-one to form 1-Benzoxolo[3,2-c]chromen-6-one. They are oxidation products of pterocarpan. Thus, wairol is considered to be a flavonoid. Wairol has been detected, but not quantified in, alfalfas (Medicago sativa) and pulses. This could make wairol a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Wairol.

Structure

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

HMDB0033993
     RDKit          3D
Wairol
 35 38  0  0  0  0  0  0  0  0999 V2000
    4.9781   -2.2177   -0.0337 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6724   -0.8494   -0.0607 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3656   -0.3905   -0.0663 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1357    0.9679   -0.0933 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8323    1.4549   -0.0995 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5649    2.8086   -0.1263 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5224    3.8240   -0.1497 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8039    0.5664   -0.0785 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0619   -0.8032   -0.0514 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3430   -1.3149   -0.0446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0917   -1.4229   -0.0355 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0764   -0.5586   -0.0503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4632   -0.6994   -0.0435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0425   -1.9588   -0.0162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4080   -2.0944   -0.0096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2666   -1.0147   -0.0291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6559   -1.1579   -0.0223 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6865    0.2353   -0.0562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2972    0.3940   -0.0634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7638    1.5922   -0.0893 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4514    1.7780   -0.0968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9921    2.9427   -0.1218 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5691    0.7226   -0.0778 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0893   -2.3268    0.0776 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4897   -2.6985    0.8258 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7400   -2.7266   -1.0064 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9483    1.6768   -0.1100 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4565    3.5812   -0.6514 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7733    4.1827    0.8873 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0941    4.7143   -0.6969 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5787   -2.3681   -0.0238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3896   -2.8342   -0.0002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8679   -3.0742    0.0117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1236   -2.0310   -0.0032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3044    1.0998   -0.0721 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  1  0
  6  7  1  0
  5  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 10  3  1  0
 23 12  2  0
 23  8  1  0
 19 13  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  7 28  1  0
  7 29  1  0
  7 30  1  0
 10 31  1  0
 14 32  1  0
 15 33  1  0
 17 34  1  0
 18 35  1  0
M  END

  Mrv0541 05061307292D          

 23 26  0  0  0  0            999 V2000
   -1.9532    2.4880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0191    4.8244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2891    2.1084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4655    2.0613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2075    3.5350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4867    3.2441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1682    1.9741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6601    2.8453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5259    2.4201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0128    2.7510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3838    3.4879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2466    3.6222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9014    2.3522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9407    3.1762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7365    3.3936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1892    2.7039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1075    4.1305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4838    2.8924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6548    4.8202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2591    2.0420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2858    4.4463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6731    2.0602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9312    4.1776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  8  3  1  0  0  0  0
  8  5  2  0  0  0  0
  9  6  2  0  0  0  0
  9  7  1  0  0  0  0
 10  4  1  0  0  0  0
 11  5  1  0  0  0  0
 11 10  2  0  0  0  0
 12  6  1  0  0  0  0
 13  7  2  0  0  0  0
 14 12  2  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 10  1  0  0  0  0
 16 15  2  0  0  0  0
 17 15  1  0  0  0  0
 18  8  1  0  0  0  0
 19 17  2  0  0  0  0
 20  1  1  0  0  0  0
 20  9  1  0  0  0  0
 21  2  1  0  0  0  0
 21 12  1  0  0  0  0
 22 13  1  0  0  0  0
 22 16  1  0  0  0  0
 23 11  1  0  0  0  0
 23 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033993

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(OC)=C2C(OC3=C2C(=O)OC2=C3C=CC(O)=C2)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H12O6/c1-20-9-6-12(21-2)14-13(7-9)22-16-10-4-3-8(18)5-11(10)23-17(19)15(14)16/h3-7,18H,1-2H3

> <INCHI_KEY>
GYNHMEBOILXPQT-UHFFFAOYSA-N

> <FORMULA>
C17H12O6

> <MOLECULAR_WEIGHT>
312.2736

> <EXACT_MASS>
312.063388116

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
31.346714831997502

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-hydroxy-12,14-dimethoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11,13,15-heptaen-9-one

> <ALOGPS_LOGP>
2.48

> <JCHEM_LOGP>
2.385544112666666

> <ALOGPS_LOGS>
-3.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.1565543727419385

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8612841439459626

> <JCHEM_POLAR_SURFACE_AREA>
78.13000000000001

> <JCHEM_REFRACTIVITY>
80.56500000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.27e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
wairol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033993
     RDKit          3D
Wairol
 35 38  0  0  0  0  0  0  0  0999 V2000
    4.9781   -2.2177   -0.0337 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6724   -0.8494   -0.0607 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3656   -0.3905   -0.0663 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1357    0.9679   -0.0933 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8323    1.4549   -0.0995 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5649    2.8086   -0.1263 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5224    3.8240   -0.1497 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8039    0.5664   -0.0785 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0619   -0.8032   -0.0514 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3430   -1.3149   -0.0446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0917   -1.4229   -0.0355 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0764   -0.5586   -0.0503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4632   -0.6994   -0.0435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0425   -1.9588   -0.0162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4080   -2.0944   -0.0096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2666   -1.0147   -0.0291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6559   -1.1579   -0.0223 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6865    0.2353   -0.0562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2972    0.3940   -0.0634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7638    1.5922   -0.0893 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4514    1.7780   -0.0968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9921    2.9427   -0.1218 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5691    0.7226   -0.0778 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0893   -2.3268    0.0776 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4897   -2.6985    0.8258 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7400   -2.7266   -1.0064 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9483    1.6768   -0.1100 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4565    3.5812   -0.6514 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7733    4.1827    0.8873 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0941    4.7143   -0.6969 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5787   -2.3681   -0.0238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3896   -2.8342   -0.0002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8679   -3.0742    0.0117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1236   -2.0310   -0.0032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3044    1.0998   -0.0721 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  1  0
  6  7  1  0
  5  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 10  3  1  0
 23 12  2  0
 23  8  1  0
 19 13  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  7 28  1  0
  7 29  1  0
  7 30  1  0
 10 31  1  0
 14 32  1  0
 15 33  1  0
 17 34  1  0
 18 35  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      -3.646   4.644   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.902   9.006   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.006   3.936   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.469   3.848   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.854   6.599   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.909   6.056   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.314   3.685   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.699   5.311   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.982   4.518   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.624   5.135   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.316   6.511   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.460   6.761   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.683   4.391   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.756   5.929   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.241   6.335   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.087   5.047   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.934   7.710   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      10.236   5.399   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       3.089   8.998   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -2.350   3.812   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       0.533   8.300   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       3.123   3.846   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       5.472   7.798   0.000  0.00  0.00           O+0
CONECT    1   20                                                            
CONECT    2   21                                                            
CONECT    3    4    8                                                       
CONECT    4    3   10                                                       
CONECT    5    8   11                                                       
CONECT    6    9   12                                                       
CONECT    7    9   13                                                       
CONECT    8    3    5   18                                                  
CONECT    9    6    7   20                                                  
CONECT   10    4   11   16                                                  
CONECT   11    5   10   23                                                  
CONECT   12    6   14   21                                                  
CONECT   13    7   14   22                                                  
CONECT   14   12   13   15                                                  
CONECT   15   14   16   17                                                  
CONECT   16   10   15   22                                                  
CONECT   17   15   19   23                                                  
CONECT   18    8                                                            
CONECT   19   17                                                            
CONECT   20    1    9                                                       
CONECT   21    2   12                                                       
CONECT   22   13   16                                                       
CONECT   23   11   17                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

COMPND    HMDB0033993
HETATM    1  C1  UNL     1       4.978  -2.218  -0.034  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.672  -0.849  -0.061  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.366  -0.391  -0.066  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.136   0.968  -0.093  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.832   1.455  -0.100  1.00  0.00           C  
HETATM    6  O2  UNL     1       1.565   2.809  -0.126  1.00  0.00           O  
HETATM    7  C5  UNL     1       2.522   3.824  -0.150  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.804   0.566  -0.079  1.00  0.00           C  
HETATM    9  C7  UNL     1       1.062  -0.803  -0.051  1.00  0.00           C  
HETATM   10  C8  UNL     1       2.343  -1.315  -0.045  1.00  0.00           C  
HETATM   11  O3  UNL     1      -0.092  -1.423  -0.035  1.00  0.00           O  
HETATM   12  C9  UNL     1      -1.076  -0.559  -0.050  1.00  0.00           C  
HETATM   13  C10 UNL     1      -2.463  -0.699  -0.043  1.00  0.00           C  
HETATM   14  C11 UNL     1      -3.043  -1.959  -0.016  1.00  0.00           C  
HETATM   15  C12 UNL     1      -4.408  -2.094  -0.010  1.00  0.00           C  
HETATM   16  C13 UNL     1      -5.267  -1.015  -0.029  1.00  0.00           C  
HETATM   17  O4  UNL     1      -6.656  -1.158  -0.022  1.00  0.00           O  
HETATM   18  C14 UNL     1      -4.687   0.235  -0.056  1.00  0.00           C  
HETATM   19  C15 UNL     1      -3.297   0.394  -0.063  1.00  0.00           C  
HETATM   20  O5  UNL     1      -2.764   1.592  -0.089  1.00  0.00           O  
HETATM   21  C16 UNL     1      -1.451   1.778  -0.097  1.00  0.00           C  
HETATM   22  O6  UNL     1      -0.992   2.943  -0.122  1.00  0.00           O  
HETATM   23  C17 UNL     1      -0.569   0.723  -0.078  1.00  0.00           C  
HETATM   24  H1  UNL     1       6.089  -2.327   0.078  1.00  0.00           H  
HETATM   25  H2  UNL     1       4.490  -2.698   0.826  1.00  0.00           H  
HETATM   26  H3  UNL     1       4.740  -2.727  -1.006  1.00  0.00           H  
HETATM   27  H4  UNL     1       3.948   1.677  -0.110  1.00  0.00           H  
HETATM   28  H5  UNL     1       3.456   3.581  -0.651  1.00  0.00           H  
HETATM   29  H6  UNL     1       2.773   4.183   0.887  1.00  0.00           H  
HETATM   30  H7  UNL     1       2.094   4.714  -0.697  1.00  0.00           H  
HETATM   31  H8  UNL     1       2.579  -2.368  -0.024  1.00  0.00           H  
HETATM   32  H9  UNL     1      -2.390  -2.834  -0.000  1.00  0.00           H  
HETATM   33  H10 UNL     1      -4.868  -3.074   0.012  1.00  0.00           H  
HETATM   34  H11 UNL     1      -7.124  -2.031  -0.003  1.00  0.00           H  
HETATM   35  H12 UNL     1      -5.304   1.100  -0.072  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3
CONECT    3    4    4   10
CONECT    4    5   27
CONECT    5    6    8    8
CONECT    6    7
CONECT    7   28   29   30
CONECT    8    9   23
CONECT    9   10   10   11
CONECT   10   31
CONECT   11   12
CONECT   12   13   23   23
CONECT   13   14   14   19
CONECT   14   15   32
CONECT   15   16   16   33
CONECT   16   17   18
CONECT   17   34
CONECT   18   19   19   35
CONECT   19   20
CONECT   20   21
CONECT   21   22   22   23
END

HMDB0033993
     RDKit          3D
Wairol
 35 38  0  0  0  0  0  0  0  0999 V2000
    4.9781   -2.2177   -0.0337 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6724   -0.8494   -0.0607 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3656   -0.3905   -0.0663 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1357    0.9679   -0.0933 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8323    1.4549   -0.0995 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5649    2.8086   -0.1263 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5224    3.8240   -0.1497 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8039    0.5664   -0.0785 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0619   -0.8032   -0.0514 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3430   -1.3149   -0.0446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0917   -1.4229   -0.0355 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0764   -0.5586   -0.0503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4632   -0.6994   -0.0435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0425   -1.9588   -0.0162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4080   -2.0944   -0.0096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2666   -1.0147   -0.0291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6559   -1.1579   -0.0223 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6865    0.2353   -0.0562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2972    0.3940   -0.0634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7638    1.5922   -0.0893 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4514    1.7780   -0.0968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9921    2.9427   -0.1218 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5691    0.7226   -0.0778 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0893   -2.3268    0.0776 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4897   -2.6985    0.8258 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7400   -2.7266   -1.0064 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9483    1.6768   -0.1100 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4565    3.5812   -0.6514 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7733    4.1827    0.8873 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0941    4.7143   -0.6969 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5787   -2.3681   -0.0238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3896   -2.8342   -0.0002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8679   -3.0742    0.0117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1236   -2.0310   -0.0032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3044    1.0998   -0.0721 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  1  0
  6  7  1  0
  5  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 10  3  1  0
 23 12  2  0
 23  8  1  0
 19 13  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  7 28  1  0
  7 29  1  0
  7 30  1  0
 10 31  1  0
 14 32  1  0
 15 33  1  0
 17 34  1  0
 18 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-Hydroxy-7,9-dimethoxycoumestan	HMDB
7-Hydroxy-10,12-dimethoxycoumestan	HMDB

Chemical Formula

C₁₇H₁₂O₆

Average Molecular Weight

312.2736

Monoisotopic Molecular Weight

312.063388116

IUPAC Name

5-hydroxy-12,14-dimethoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11,13,15-heptaen-9-one

Traditional Name

wairol

CAS Registry Number

77331-73-8

SMILES

COC1=CC(OC)=C2C(OC3=C2C(=O)OC2=C3C=CC(O)=C2)=C1

InChI Identifier

InChI=1S/C17H12O6/c1-20-9-6-12(21-2)14-13(7-9)22-16-10-4-3-8(18)5-11(10)23-17(19)15(14)16/h3-7,18H,1-2H3

InChI Key

GYNHMEBOILXPQT-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumestans. These are polycyclic aromatic compounds containing a coumestan moiety, which consists of a benzoxole fused to a chromen-2-one to form 1-Benzoxolo[3,2-c]chromen-6-one. They are oxidation products of pterocarpan.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Coumestans

Direct Parent

Coumestans

Alternative Parents

Substituents

Coumestan
Angular furanocoumarin
Furanocoumarin
Coumarin
Benzopyran
1-benzopyran
Benzofuran
Furopyran
Anisole
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Furan
Lactone
Organoheterocyclic compound
Oxacycle
Ether
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Coumestan flavonoids (LMPK12090031 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0033993)
Cytoplasm (HMDB: HMDB0033993)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033993)

Source

Exogenous

Exogenous (HMDB: HMDB0033993)

Food

Food (HMDB: HMDB0033993)

Herb and spice

Herb

Alfalfa (FooDB: FOOD00286)

Pulse

Pulses (FooDB: FOOD00867)

Endogenous

Plant

Plant (HMDB: HMDB0033993)
Fabaceae (HMDB: HMDB0033993)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033993)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	292 - 294 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	39.44 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.13 g/L	ALOGPS
logP	2.48	ALOGPS
logP	2.39	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	7.16	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	78.13 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	80.56 m³·mol⁻¹	ChemAxon
Polarizability	31.35 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]+	170.382	31661259
DarkChem	[M-H]-	171.993	31661259
DeepCCS	[M+H]+	177.227	30932474
DeepCCS	[M-H]-	174.87	30932474
DeepCCS	[M-2H]-	208.759	30932474
DeepCCS	[M+Na]+	183.987	30932474
AllCCS	[M+H]+	170.6	32859911
AllCCS	[M+H-H2O]+	167.0	32859911
AllCCS	[M+NH4]+	173.9	32859911
AllCCS	[M+Na]+	174.9	32859911
AllCCS	[M-H]-	173.2	32859911
AllCCS	[M+Na-2H]-	172.2	32859911
AllCCS	[M+HCOO]-	171.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Wairol	COC1=CC(OC)=C2C(OC3=C2C(=O)OC2=C3C=CC(O)=C2)=C1	4405.8	Standard polar	33892256
Wairol	COC1=CC(OC)=C2C(OC3=C2C(=O)OC2=C3C=CC(O)=C2)=C1	3037.5	Standard non polar	33892256
Wairol	COC1=CC(OC)=C2C(OC3=C2C(=O)OC2=C3C=CC(O)=C2)=C1	3145.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Wairol,1TMS,isomer #1	COC1=CC(OC)=C2C(=C1)OC1=C2C(=O)OC2=CC(O[Si](C)(C)C)=CC=C21	3186.6	Semi standard non polar	33892256
Wairol,1TBDMS,isomer #1	COC1=CC(OC)=C2C(=C1)OC1=C2C(=O)OC2=CC(O[Si](C)(C)C(C)(C)C)=CC=C21	3398.8	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 - Wairol GC-MS (Non-derivatized) - 70eV, Positive	splash10-00ls-0091000000-5d85530019f4920b724e	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Wairol GC-MS (1 TMS) - 70eV, Positive	splash10-01b9-2429000000-6d3570acd18747099377	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Wairol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Wairol 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 - Wairol 10V, Positive-QTOF	splash10-03di-0009000000-54baec802857fee21878	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Wairol 20V, Positive-QTOF	splash10-03di-0009000000-318256c07afe65ae6be3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Wairol 40V, Positive-QTOF	splash10-014j-0090000000-2458e9700a1169091116	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Wairol 10V, Negative-QTOF	splash10-03di-0009000000-d8d58a8a68eaaaee361c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Wairol 20V, Negative-QTOF	splash10-03di-0049000000-0add473485d461dd0cda	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Wairol 40V, Negative-QTOF	splash10-014j-0090000000-c7d6b21ced36c6f74cc9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Wairol 10V, Positive-QTOF	splash10-03di-0009000000-fbd933023572de11abf0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Wairol 20V, Positive-QTOF	splash10-03di-0009000000-fbd933023572de11abf0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Wairol 40V, Positive-QTOF	splash10-02ti-0191000000-cb34067a635732e93321	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Wairol 10V, Negative-QTOF	splash10-03di-0009000000-b504eaff11e6208b17b1	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Wairol 20V, Negative-QTOF	splash10-03di-0009000000-b504eaff11e6208b17b1	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Wairol 40V, Negative-QTOF	splash10-0gb9-0090000000-14a33ca28fa0e0bf9e47	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

FDB012227

KNApSAcK ID

C00009767

Chemspider ID

4589918

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5488650

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1839681

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 Wairol (HMDB0033993)

MOL for HMDB0033993 (Wairol)

3D MOL for HMDB0033993 (Wairol)

3D SDF for HMDB0033993 (Wairol)

3D-SDF for HMDB0033993 (Wairol)

PDB for HMDB0033993 (Wairol)

3D PDB for HMDB0033993 (Wairol)

SMILES for HMDB0033993 (Wairol)

INCHI for HMDB0033993 (Wairol)

Structure for HMDB0033993 (Wairol)

3D Structure for HMDB0033993 (Wairol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra