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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:00:46 UTC

Update Date

2022-03-07 02:55:29 UTC

HMDB ID

HMDB0037754

Secondary Accession Numbers

HMDB37754

Metabolite Identification

Common Name

Wharangin

Description

Wharangin belongs to the class of organic compounds known as 3-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C3 atom of the flavonoid backbone. Thus, wharangin is considered to be a flavonoid. Wharangin has been detected, but not quantified in, green vegetables and spinaches (Spinacia oleracea). This could make wharangin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Wharangin.

Structure

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

HMDB0037754
     RDKit          3D
Wharangin
 37 40  0  0  0  0  0  0  0  0999 V2000
    1.1313   -3.2084    1.6024 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6540   -2.8636    0.3009 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1459   -1.7185    0.1322 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3944   -0.5014   -0.1854 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7963   -0.2075   -0.3994 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7408   -1.1706   -0.5398 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0998   -0.8554   -0.7010 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4951    0.4399   -0.7203 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8456    0.7403   -0.8807 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5402    1.4221   -0.5795 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9907    2.7385   -0.6058 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2050    1.1324   -0.4201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4430    0.5381   -0.3147 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7254    0.4059   -0.1489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5013    1.5508   -0.3073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8629    1.4847   -0.1472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4360    0.2808    0.1685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7026   -0.9049    0.3401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3497   -2.0627    0.6540 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3327   -0.8136    0.1738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5214   -1.9110    0.3195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9610   -3.0442    0.6060 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3954    2.7734   -0.3623 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3216    3.6896   -0.4008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1896    2.8646   -0.6179 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2707   -2.3337    2.2461 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4945   -3.9419    2.1056 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1180   -3.7030    1.4340 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5471   -2.2296   -0.5697 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8275   -1.6455   -0.8092 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1315    1.7194   -0.8937 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3671    3.5283   -0.5105 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4978    1.9356   -0.3141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5049    0.1980    0.3006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0848   -2.9753    0.8185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4375    4.3547   -1.2974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2317    4.2937    0.5234 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
  4 13  1  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
 18 20  2  0
 20 21  1  0
 21 22  2  0
 16 23  1  0
 23 24  1  0
 24 25  1  0
 21  3  1  0
 12  5  1  0
 20 14  1  0
 25 15  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  6 29  1  0
  7 30  1  0
  9 31  1  0
 11 32  1  0
 12 33  1  0
 17 34  1  0
 19 35  1  0
 24 36  1  0
 24 37  1  0
M  END


  Mrv0541 05061310002D          

 25 28  0  0  0  0            999 V2000
   -1.3693   -0.2372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9793   -0.9642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4140   -1.6655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2352   -1.7170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4083    1.7892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6601    0.0428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1547   -0.9900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0240   -2.3925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1994   -2.4182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5837    1.8150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7983    1.0622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1491    1.1137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3245    1.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2799   -0.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3637    0.3610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5391    0.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1101    0.4383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4586   -3.0937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1906   -3.1452    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1937    2.5420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0655    1.8665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9347    0.4640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5995    0.8656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8963   -0.2691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1045   -0.3145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  7  2  1  0  0  0  0
  7  4  2  0  0  0  0
  8  3  1  0  0  0  0
  9  4  1  0  0  0  0
  9  8  2  0  0  0  0
 10  5  2  0  0  0  0
 11  5  1  0  0  0  0
 12 10  1  0  0  0  0
 13 12  1  0  0  0  0
 14  7  1  0  0  0  0
 15 11  2  0  0  0  0
 16 12  2  0  0  0  0
 16 15  1  0  0  0  0
 17 13  1  0  0  0  0
 17 14  2  0  0  0  0
 18  8  1  0  0  0  0
 19  9  1  0  0  0  0
 20 10  1  0  0  0  0
 21 13  2  0  0  0  0
 22  1  1  0  0  0  0
 22 17  1  0  0  0  0
 23  6  1  0  0  0  0
 23 11  1  0  0  0  0
 24  6  1  0  0  0  0
 24 15  1  0  0  0  0
 25 14  1  0  0  0  0
 25 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0037754

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(OC2=C(C(O)=CC3=C2OCO3)C1=O)C1=CC(O)=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H12O8/c1-22-17-13(21)12-10(20)5-11-15(24-6-23-11)16(12)25-14(17)7-2-3-8(18)9(19)4-7/h2-5,18-20H,6H2,1H3

> <INCHI_KEY>
NOZQEJFGIXKUPM-UHFFFAOYSA-N

> <FORMULA>
C17H12O8

> <MOLECULAR_WEIGHT>
344.2724

> <EXACT_MASS>
344.05321736

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
32.78218788637191

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-2H,6H-[1,3]dioxolo[4,5-h]chromen-6-one

> <ALOGPS_LOGP>
2.63

> <JCHEM_LOGP>
2.1959256426666665

> <ALOGPS_LOGS>
-3.27

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.95572181097359

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.335135487256867

> <JCHEM_PKA_STRONGEST_BASIC>
-4.5380931597999155

> <JCHEM_POLAR_SURFACE_AREA>
114.68

> <JCHEM_REFRACTIVITY>
85.39940000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.84e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
wharangin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0037754
     RDKit          3D
Wharangin
 37 40  0  0  0  0  0  0  0  0999 V2000
    1.1313   -3.2084    1.6024 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6540   -2.8636    0.3009 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1459   -1.7185    0.1322 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3944   -0.5014   -0.1854 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7963   -0.2075   -0.3994 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7408   -1.1706   -0.5398 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0998   -0.8554   -0.7010 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4951    0.4399   -0.7203 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8456    0.7403   -0.8807 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5402    1.4221   -0.5795 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9907    2.7385   -0.6058 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2050    1.1324   -0.4201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4430    0.5381   -0.3147 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7254    0.4059   -0.1489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5013    1.5508   -0.3073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8629    1.4847   -0.1472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4360    0.2808    0.1685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7026   -0.9049    0.3401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3497   -2.0627    0.6540 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3327   -0.8136    0.1738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5214   -1.9110    0.3195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9610   -3.0442    0.6060 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3954    2.7734   -0.3623 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3216    3.6896   -0.4008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1896    2.8646   -0.6179 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2707   -2.3337    2.2461 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4945   -3.9419    2.1056 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1180   -3.7030    1.4340 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5471   -2.2296   -0.5697 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8275   -1.6455   -0.8092 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1315    1.7194   -0.8937 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3671    3.5283   -0.5105 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4978    1.9356   -0.3141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5049    0.1980    0.3006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0848   -2.9753    0.8185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4375    4.3547   -1.2974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2317    4.2937    0.5234 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
  4 13  1  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
 18 20  2  0
 20 21  1  0
 21 22  2  0
 16 23  1  0
 23 24  1  0
 24 25  1  0
 21  3  1  0
 12  5  1  0
 20 14  1  0
 25 15  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  6 29  1  0
  7 30  1  0
  9 31  1  0
 11 32  1  0
 12 33  1  0
 17 34  1  0
 19 35  1  0
 24 36  1  0
 24 37  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      -2.556  -0.443   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.828  -1.800   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.639  -3.109   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.439  -3.205   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.495   3.340   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.832   0.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.289  -1.848   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.911  -4.466   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.372  -4.514   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.956   3.388   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.223   1.983   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.145   2.079   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.606   2.127   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.522  -0.539   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.412   0.674   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.873   0.722   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.206   0.818   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -2.723  -5.775   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.356  -5.871   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       2.228   4.745   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -0.122   3.484   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -1.745   0.866   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       6.719   1.616   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       5.406  -0.502   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       2.062  -0.587   0.000  0.00  0.00           O+0
CONECT    1   22                                                            
CONECT    2    3    7                                                       
CONECT    3    2    8                                                       
CONECT    4    7    9                                                       
CONECT    5   10   11                                                       
CONECT    6   23   24                                                       
CONECT    7    2    4   14                                                  
CONECT    8    3    9   18                                                  
CONECT    9    4    8   19                                                  
CONECT   10    5   12   20                                                  
CONECT   11    5   15   23                                                  
CONECT   12   10   13   16                                                  
CONECT   13   12   17   21                                                  
CONECT   14    7   17   25                                                  
CONECT   15   11   16   24                                                  
CONECT   16   12   15   25                                                  
CONECT   17   13   14   22                                                  
CONECT   18    8                                                            
CONECT   19    9                                                            
CONECT   20   10                                                            
CONECT   21   13                                                            
CONECT   22    1   17                                                       
CONECT   23    6   11                                                       
CONECT   24    6   15                                                       
CONECT   25   14   16                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

COMPND    HMDB0037754
HETATM    1  C1  UNL     1       1.131  -3.208   1.602  1.00  0.00           C  
HETATM    2  O1  UNL     1       0.654  -2.864   0.301  1.00  0.00           O  
HETATM    3  C2  UNL     1      -0.146  -1.718   0.132  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.394  -0.501  -0.185  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.796  -0.207  -0.399  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.741  -1.171  -0.540  1.00  0.00           C  
HETATM    7  C6  UNL     1       4.100  -0.855  -0.701  1.00  0.00           C  
HETATM    8  C7  UNL     1       4.495   0.440  -0.720  1.00  0.00           C  
HETATM    9  O2  UNL     1       5.846   0.740  -0.881  1.00  0.00           O  
HETATM   10  C8  UNL     1       3.540   1.422  -0.579  1.00  0.00           C  
HETATM   11  O3  UNL     1       3.991   2.739  -0.606  1.00  0.00           O  
HETATM   12  C9  UNL     1       2.205   1.132  -0.420  1.00  0.00           C  
HETATM   13  O4  UNL     1      -0.443   0.538  -0.315  1.00  0.00           O  
HETATM   14  C10 UNL     1      -1.725   0.406  -0.149  1.00  0.00           C  
HETATM   15  C11 UNL     1      -2.501   1.551  -0.307  1.00  0.00           C  
HETATM   16  C12 UNL     1      -3.863   1.485  -0.147  1.00  0.00           C  
HETATM   17  C13 UNL     1      -4.436   0.281   0.168  1.00  0.00           C  
HETATM   18  C14 UNL     1      -3.703  -0.905   0.340  1.00  0.00           C  
HETATM   19  O5  UNL     1      -4.350  -2.063   0.654  1.00  0.00           O  
HETATM   20  C15 UNL     1      -2.333  -0.814   0.174  1.00  0.00           C  
HETATM   21  C16 UNL     1      -1.521  -1.911   0.319  1.00  0.00           C  
HETATM   22  O6  UNL     1      -1.961  -3.044   0.606  1.00  0.00           O  
HETATM   23  O7  UNL     1      -4.395   2.773  -0.362  1.00  0.00           O  
HETATM   24  C17 UNL     1      -3.322   3.690  -0.401  1.00  0.00           C  
HETATM   25  O8  UNL     1      -2.190   2.865  -0.618  1.00  0.00           O  
HETATM   26  H1  UNL     1       1.271  -2.334   2.246  1.00  0.00           H  
HETATM   27  H2  UNL     1       0.495  -3.942   2.106  1.00  0.00           H  
HETATM   28  H3  UNL     1       2.118  -3.703   1.434  1.00  0.00           H  
HETATM   29  H4  UNL     1       2.547  -2.230  -0.570  1.00  0.00           H  
HETATM   30  H5  UNL     1       4.827  -1.646  -0.809  1.00  0.00           H  
HETATM   31  H6  UNL     1       6.132   1.719  -0.894  1.00  0.00           H  
HETATM   32  H7  UNL     1       3.367   3.528  -0.510  1.00  0.00           H  
HETATM   33  H8  UNL     1       1.498   1.936  -0.314  1.00  0.00           H  
HETATM   34  H9  UNL     1      -5.505   0.198   0.301  1.00  0.00           H  
HETATM   35  H10 UNL     1      -4.085  -2.975   0.818  1.00  0.00           H  
HETATM   36  H11 UNL     1      -3.438   4.355  -1.297  1.00  0.00           H  
HETATM   37  H12 UNL     1      -3.232   4.294   0.523  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3
CONECT    3    4    4   21
CONECT    4    5   13
CONECT    5    6    6   12
CONECT    6    7   29
CONECT    7    8    8   30
CONECT    8    9   10
CONECT    9   31
CONECT   10   11   12   12
CONECT   11   32
CONECT   12   33
CONECT   13   14
CONECT   14   15   15   20
CONECT   15   16   25
CONECT   16   17   17   23
CONECT   17   18   34
CONECT   18   19   20   20
CONECT   19   35
CONECT   20   21
CONECT   21   22   22
CONECT   23   24
CONECT   24   25   36   37
END

HMDB0037754
     RDKit          3D
Wharangin
 37 40  0  0  0  0  0  0  0  0999 V2000
    1.1313   -3.2084    1.6024 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6540   -2.8636    0.3009 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1459   -1.7185    0.1322 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3944   -0.5014   -0.1854 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7963   -0.2075   -0.3994 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7408   -1.1706   -0.5398 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0998   -0.8554   -0.7010 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4951    0.4399   -0.7203 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8456    0.7403   -0.8807 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5402    1.4221   -0.5795 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9907    2.7385   -0.6058 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2050    1.1324   -0.4201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4430    0.5381   -0.3147 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7254    0.4059   -0.1489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5013    1.5508   -0.3073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8629    1.4847   -0.1472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4360    0.2808    0.1685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7026   -0.9049    0.3401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3497   -2.0627    0.6540 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3327   -0.8136    0.1738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5214   -1.9110    0.3195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9610   -3.0442    0.6060 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3954    2.7734   -0.3623 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3216    3.6896   -0.4008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1896    2.8646   -0.6179 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2707   -2.3337    2.2461 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4945   -3.9419    2.1056 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1180   -3.7030    1.4340 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5471   -2.2296   -0.5697 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8275   -1.6455   -0.8092 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1315    1.7194   -0.8937 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3671    3.5283   -0.5105 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4978    1.9356   -0.3141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5049    0.1980    0.3006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0848   -2.9753    0.8185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4375    4.3547   -1.2974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2317    4.2937    0.5234 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
  4 13  1  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
 18 20  2  0
 20 21  1  0
 21 22  2  0
 16 23  1  0
 23 24  1  0
 24 25  1  0
 21  3  1  0
 12  5  1  0
 20 14  1  0
 25 15  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  6 29  1  0
  7 30  1  0
  9 31  1  0
 11 32  1  0
 12 33  1  0
 17 34  1  0
 19 35  1  0
 24 36  1  0
 24 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3',4',5-Trihydroxy-3-methoxy-7,8-methylenedioxyflavone	HMDB

Chemical Formula

C₁₇H₁₂O₈

Average Molecular Weight

344.2724

Monoisotopic Molecular Weight

344.05321736

IUPAC Name

8-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-2H,6H-[1,3]dioxolo[4,5-h]chromen-6-one

Traditional Name

wharangin

CAS Registry Number

Not Available

SMILES

COC1=C(OC2=C(C(O)=CC3=C2OCO3)C1=O)C1=CC(O)=C(O)C=C1

InChI Identifier

InChI=1S/C17H12O8/c1-22-17-13(21)12-10(20)5-11-15(24-6-23-11)16(12)25-14(17)7-2-3-8(18)9(19)4-7/h2-5,18-20H,6H2,1H3

InChI Key

NOZQEJFGIXKUPM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C3 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

3-O-methylated flavonoids

Alternative Parents

Substituents

3-methoxyflavonoid-skeleton
Flavone
Hydroxyflavonoid
5-hydroxyflavonoid
4'-hydroxyflavonoid
3'-hydroxyflavonoid
3-methoxychromone
Chromone
1-benzopyran
Benzopyran
Benzodioxole
Catechol
Alkyl aryl ether
Pyranone
Phenol
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Pyran
Monocyclic benzene moiety
Heteroaromatic compound
Vinylogous acid
Oxacycle
Acetal
Organoheterocyclic compound
Ether
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavones and Flavonols (LMPK12113260 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0037754)
Cell membrane (HMDB: HMDB0037754)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037754)

Source

Exogenous

Exogenous (HMDB: HMDB0037754)

Food

Food (HMDB: HMDB0037754)

Vegetable

Leaf vegetable

Spinach (FooDB: FOOD00178)
Green vegetables (FooDB: FOOD00872)

Endogenous

Plant

Plant (HMDB: HMDB0037754)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0037754)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	277 - 278 °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	0.18 g/L	ALOGPS
logP	2.63	ALOGPS
logP	2.2	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	8.34	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	114.68 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	85.4 m³·mol⁻¹	ChemAxon
Polarizability	32.78 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]+	178.385	31661259
DarkChem	[M-H]-	180.698	31661259
DeepCCS	[M+H]+	182.948	30932474
DeepCCS	[M-H]-	180.59	30932474
DeepCCS	[M-2H]-	214.739	30932474
DeepCCS	[M+Na]+	189.966	30932474
AllCCS	[M+H]+	177.4	32859911
AllCCS	[M+H-H2O]+	174.0	32859911
AllCCS	[M+NH4]+	180.6	32859911
AllCCS	[M+Na]+	181.5	32859911
AllCCS	[M-H]-	177.6	32859911
AllCCS	[M+Na-2H]-	176.7	32859911
AllCCS	[M+HCOO]-	175.9	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.	6.14 minutes	32390414
Predicted by Siyang on May 30, 2022	13.018 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.76 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	24.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2483.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	275.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	145.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	168.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	266.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	623.1 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	633.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	143.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1005.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	464.2 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1605.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	357.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	434.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	469.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	223.9 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	184.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Wharangin	COC1=C(OC2=C(C(O)=CC3=C2OCO3)C1=O)C1=CC(O)=C(O)C=C1	4902.3	Standard polar	33892256
Wharangin	COC1=C(OC2=C(C(O)=CC3=C2OCO3)C1=O)C1=CC(O)=C(O)C=C1	3236.9	Standard non polar	33892256
Wharangin	COC1=C(OC2=C(C(O)=CC3=C2OCO3)C1=O)C1=CC(O)=C(O)C=C1	3259.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Wharangin,1TMS,isomer #1	COC1=C(C2=CC=C(O)C(O)=C2)OC2=C3OCOC3=CC(O[Si](C)(C)C)=C2C1=O	3245.3	Semi standard non polar	33892256
Wharangin,1TMS,isomer #2	COC1=C(C2=CC=C(O)C(O[Si](C)(C)C)=C2)OC2=C3OCOC3=CC(O)=C2C1=O	3283.6	Semi standard non polar	33892256
Wharangin,1TMS,isomer #3	COC1=C(C2=CC=C(O[Si](C)(C)C)C(O)=C2)OC2=C3OCOC3=CC(O)=C2C1=O	3320.4	Semi standard non polar	33892256
Wharangin,2TMS,isomer #1	COC1=C(C2=CC=C(O[Si](C)(C)C)C(O)=C2)OC2=C3OCOC3=CC(O[Si](C)(C)C)=C2C1=O	3321.0	Semi standard non polar	33892256
Wharangin,2TMS,isomer #2	COC1=C(C2=CC=C(O)C(O[Si](C)(C)C)=C2)OC2=C3OCOC3=CC(O[Si](C)(C)C)=C2C1=O	3296.1	Semi standard non polar	33892256
Wharangin,2TMS,isomer #3	COC1=C(C2=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C2)OC2=C3OCOC3=CC(O)=C2C1=O	3204.9	Semi standard non polar	33892256
Wharangin,3TMS,isomer #1	COC1=C(C2=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C2)OC2=C3OCOC3=CC(O[Si](C)(C)C)=C2C1=O	3248.2	Semi standard non polar	33892256
Wharangin,1TBDMS,isomer #1	COC1=C(C2=CC=C(O)C(O)=C2)OC2=C3OCOC3=CC(O[Si](C)(C)C(C)(C)C)=C2C1=O	3503.9	Semi standard non polar	33892256
Wharangin,1TBDMS,isomer #2	COC1=C(C2=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C2)OC2=C3OCOC3=CC(O)=C2C1=O	3530.3	Semi standard non polar	33892256
Wharangin,1TBDMS,isomer #3	COC1=C(C2=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C2)OC2=C3OCOC3=CC(O)=C2C1=O	3568.8	Semi standard non polar	33892256
Wharangin,2TBDMS,isomer #1	COC1=C(C2=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C2)OC2=C3OCOC3=CC(O[Si](C)(C)C(C)(C)C)=C2C1=O	3831.3	Semi standard non polar	33892256
Wharangin,2TBDMS,isomer #2	COC1=C(C2=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C2)OC2=C3OCOC3=CC(O[Si](C)(C)C(C)(C)C)=C2C1=O	3804.1	Semi standard non polar	33892256
Wharangin,2TBDMS,isomer #3	COC1=C(C2=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C2)OC2=C3OCOC3=CC(O)=C2C1=O	3690.5	Semi standard non polar	33892256
Wharangin,3TBDMS,isomer #1	COC1=C(C2=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C2)OC2=C3OCOC3=CC(O[Si](C)(C)C(C)(C)C)=C2C1=O	3971.3	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 - Wharangin GC-MS (Non-derivatized) - 70eV, Positive	splash10-02t9-1319000000-6fe234d64b0cd47e4b80	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Wharangin GC-MS (3 TMS) - 70eV, Positive	splash10-007a-2284890000-82546b8f4795f5c46801	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Wharangin 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 - Wharangin 10V, Positive-QTOF	splash10-0002-0009000000-99238d64e8cc4bbe8763	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Wharangin 20V, Positive-QTOF	splash10-0002-0119000000-dfe3f2d2016a3ba86ac2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Wharangin 40V, Positive-QTOF	splash10-0a59-2981000000-517a4628660069d3863d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Wharangin 10V, Negative-QTOF	splash10-0006-0009000000-ca5df1936db8bc8043c9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Wharangin 20V, Negative-QTOF	splash10-0006-0029000000-a8c65dbf1e1a8c29705f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Wharangin 40V, Negative-QTOF	splash10-03di-1900000000-cee762b52300c082c04c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Wharangin 10V, Negative-QTOF	splash10-0006-0009000000-830d07053efb41c3c321	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Wharangin 20V, Negative-QTOF	splash10-0006-0419000000-a36f87e7416a2c792508	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Wharangin 40V, Negative-QTOF	splash10-0693-1921000000-106555a57fb27e7a59bc	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Wharangin 10V, Positive-QTOF	splash10-0002-0009000000-3f68f407690ad3c91ed6	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Wharangin 20V, Positive-QTOF	splash10-0002-0009000000-8f95110c29a936beb027	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Wharangin 40V, Positive-QTOF	splash10-00ls-2914000000-7997437bd53f68400bf0	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB016893

KNApSAcK ID

C00005056

Chemspider ID

24845773

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12444939

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 Wharangin (HMDB0037754)

MOL for HMDB0037754 (Wharangin)

3D MOL for HMDB0037754 (Wharangin)

3D SDF for HMDB0037754 (Wharangin)

3D-SDF for HMDB0037754 (Wharangin)

PDB for HMDB0037754 (Wharangin)

3D PDB for HMDB0037754 (Wharangin)

SMILES for HMDB0037754 (Wharangin)

INCHI for HMDB0037754 (Wharangin)

Structure for HMDB0037754 (Wharangin)

3D Structure for HMDB0037754 (Wharangin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra