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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:24:43 UTC

Update Date

2022-03-07 02:55:38 UTC

HMDB ID

HMDB0038128

Secondary Accession Numbers

HMDB38128

Metabolite Identification

Common Name

(±)-Sphaerosin

Description

(±)-Sphaerosin belongs to the class of organic compounds known as 3'-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C3' atom of the isoflavonoid backbone. Isoflavonoids are natural products derived from 3-phenylchromen-4-one. Thus, (±)-sphaerosin is considered to be a flavonoid (±)-Sphaerosin has been detected, but not quantified in, several different foods, such as common beans (Phaseolus vulgaris), green beans (Phaseolus vulgaris), hyacinth beans (Lablab purpureus), pulses, and yellow wax beans (Phaseolus vulgaris). This could make (±)-sphaerosin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (±)-Sphaerosin.

Structure

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

HMDB0038128
     RDKit          3D
(±)-Sphaerosin
 40 42  0  0  0  0  0  0  0  0999 V2000
   -4.7656    1.4974    0.1901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3732    0.2659   -0.3302 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2767   -0.4705    0.0225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3444   -1.3902    1.0294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5579   -1.5881    1.7206 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2252   -2.1065    1.3498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0292   -1.8996    0.6545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9390   -0.9736   -0.3682 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3669   -0.7488   -1.0999 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2340   -1.9776   -0.8708 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0658   -1.8337    0.2637 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9330   -0.7372    0.2736 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2370   -0.7997    0.7358 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0566    0.3043    0.7228 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3442    0.1824    1.1930 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5268    1.4838    0.2305 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2373    1.5676   -0.2315 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4234    0.4385   -0.2106 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0237    0.5086   -0.6740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0774   -0.2640   -0.6726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0457    0.6761   -1.6930 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7589    2.0322   -1.4521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9867    1.8163    0.9261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7894    2.2882   -0.5982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7797    1.4058    0.6603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5719   -2.2741    2.4596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2928   -2.8453    2.1658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1809   -2.4673    0.9380 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1681   -0.7021   -2.1913 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6352   -2.8881   -0.7960 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8753   -2.1501   -1.7933 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5910   -1.7565    1.1139 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0188    0.9255    1.2242 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1609    2.3886    0.2033 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7893    2.4914   -0.6307 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9892    1.3029   -1.4892 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4665    1.0144    0.1737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4462    2.2597   -0.4162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7001    2.5942   -1.7123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0019    2.4295   -2.1681 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
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
  8 20  2  0
 20 21  1  0
 21 22  1  0
 20  3  1  0
 19  9  1  0
 18 12  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  0
  6 27  1  0
  7 28  1  0
  9 29  1  0
 10 30  1  0
 10 31  1  0
 13 32  1  0
 15 33  1  0
 16 34  1  0
 17 35  1  0
 19 36  1  0
 19 37  1  0
 22 38  1  0
 22 39  1  0
 22 40  1  0
M  END


  Mrv0541 05061310142D          

 22 24  0  0  0  0            999 V2000
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  6  5  2  0  0  0  0
 10  3  1  0  0  0  0
 10  7  1  0  0  0  0
 11  7  1  0  0  0  0
 11  9  1  0  0  0  0
 12  4  1  0  0  0  0
 12  8  2  0  0  0  0
 13  5  1  0  0  0  0
 13 11  1  0  0  0  0
 14  6  1  0  0  0  0
 15  8  1  0  0  0  0
 15 10  2  0  0  0  0
 16 13  2  0  0  0  0
 17 14  2  0  0  0  0
 17 16  1  0  0  0  0
 18 12  1  0  0  0  0
 19 14  1  0  0  0  0
 20  1  1  0  0  0  0
 20 16  1  0  0  0  0
 21  2  1  0  0  0  0
 21 17  1  0  0  0  0
 22  9  1  0  0  0  0
 22 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0038128

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C=CC(C2COC3=C(C2)C=CC(O)=C3)=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C17H18O5/c1-20-16-13(5-6-14(19)17(16)21-2)11-7-10-3-4-12(18)8-15(10)22-9-11/h3-6,8,11,18-19H,7,9H2,1-2H3

> <INCHI_KEY>
HHNUTZFOMIAQMX-UHFFFAOYSA-N

> <FORMULA>
C17H18O5

> <MOLECULAR_WEIGHT>
302.3218

> <EXACT_MASS>
302.115423686

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
32.005051086629095

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.83

> <JCHEM_LOGP>
2.8763353459999994

> <ALOGPS_LOGS>
-3.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.376626338188515

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.654108980790125

> <JCHEM_PKA_STRONGEST_BASIC>
-4.428364034807329

> <JCHEM_POLAR_SURFACE_AREA>
68.15

> <JCHEM_REFRACTIVITY>
81.8866

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.82e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sphaerosin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0038128
     RDKit          3D
(±)-Sphaerosin
 40 42  0  0  0  0  0  0  0  0999 V2000
   -4.7656    1.4974    0.1901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3732    0.2659   -0.3302 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2767   -0.4705    0.0225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3444   -1.3902    1.0294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5579   -1.5881    1.7206 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2252   -2.1065    1.3498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0292   -1.8996    0.6545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9390   -0.9736   -0.3682 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3669   -0.7488   -1.0999 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2340   -1.9776   -0.8708 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0658   -1.8337    0.2637 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9330   -0.7372    0.2736 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2370   -0.7997    0.7358 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0566    0.3043    0.7228 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3442    0.1824    1.1930 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5268    1.4838    0.2305 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2373    1.5676   -0.2315 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4234    0.4385   -0.2106 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0237    0.5086   -0.6740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0774   -0.2640   -0.6726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0457    0.6761   -1.6930 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7589    2.0322   -1.4521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9867    1.8163    0.9261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7894    2.2882   -0.5982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7797    1.4058    0.6603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5719   -2.2741    2.4596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2928   -2.8453    2.1658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1809   -2.4673    0.9380 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1681   -0.7021   -2.1913 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6352   -2.8881   -0.7960 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8753   -2.1501   -1.7933 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5910   -1.7565    1.1139 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0188    0.9255    1.2242 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1609    2.3886    0.2033 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7893    2.4914   -0.6307 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9892    1.3029   -1.4892 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4665    1.0144    0.1737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4462    2.2597   -0.4162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7001    2.5942   -1.7123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0019    2.4295   -2.1681 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
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
  8 20  2  0
 20 21  1  0
 21 22  1  0
 20  3  1  0
 19  9  1  0
 18 12  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  0
  6 27  1  0
  7 28  1  0
  9 29  1  0
 10 30  1  0
 10 31  1  0
 13 32  1  0
 15 33  1  0
 16 34  1  0
 17 35  1  0
 19 36  1  0
 19 37  1  0
 22 38  1  0
 22 39  1  0
 22 40  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       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      12.003   2.310   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       6.668   2.310   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       9.336   3.850   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
CONECT    1   20                                                            
CONECT    2   21                                                            
CONECT    3    4   10                                                       
CONECT    4    3   12                                                       
CONECT    5    6   13                                                       
CONECT    6    5   14                                                       
CONECT    7   10   11                                                       
CONECT    8   12   15                                                       
CONECT    9   11   22                                                       
CONECT   10    3    7   15                                                  
CONECT   11    7    9   13                                                  
CONECT   12    4    8   18                                                  
CONECT   13    5   11   16                                                  
CONECT   14    6   17   19                                                  
CONECT   15    8   10   22                                                  
CONECT   16   13   17   20                                                  
CONECT   17   14   16   21                                                  
CONECT   18   12                                                            
CONECT   19   14                                                            
CONECT   20    1   16                                                       
CONECT   21    2   17                                                       
CONECT   22    9   15                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0038128
HETATM    1  C1  UNL     1      -4.766   1.497   0.190  1.00  0.00           C  
HETATM    2  O1  UNL     1      -4.373   0.266  -0.330  1.00  0.00           O  
HETATM    3  C2  UNL     1      -3.277  -0.470   0.022  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.344  -1.390   1.029  1.00  0.00           C  
HETATM    5  O2  UNL     1      -4.558  -1.588   1.721  1.00  0.00           O  
HETATM    6  C4  UNL     1      -2.225  -2.107   1.350  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.029  -1.900   0.655  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.939  -0.974  -0.368  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.367  -0.749  -1.100  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.234  -1.978  -0.871  1.00  0.00           C  
HETATM   11  O3  UNL     1       2.066  -1.834   0.264  1.00  0.00           O  
HETATM   12  C9  UNL     1       2.933  -0.737   0.274  1.00  0.00           C  
HETATM   13  C10 UNL     1       4.237  -0.800   0.736  1.00  0.00           C  
HETATM   14  C11 UNL     1       5.057   0.304   0.723  1.00  0.00           C  
HETATM   15  O4  UNL     1       6.344   0.182   1.193  1.00  0.00           O  
HETATM   16  C12 UNL     1       4.527   1.484   0.230  1.00  0.00           C  
HETATM   17  C13 UNL     1       3.237   1.568  -0.231  1.00  0.00           C  
HETATM   18  C14 UNL     1       2.423   0.438  -0.211  1.00  0.00           C  
HETATM   19  C15 UNL     1       1.024   0.509  -0.674  1.00  0.00           C  
HETATM   20  C16 UNL     1      -2.077  -0.264  -0.673  1.00  0.00           C  
HETATM   21  O5  UNL     1      -2.046   0.676  -1.693  1.00  0.00           O  
HETATM   22  C17 UNL     1      -1.759   2.032  -1.452  1.00  0.00           C  
HETATM   23  H1  UNL     1      -3.987   1.816   0.926  1.00  0.00           H  
HETATM   24  H2  UNL     1      -4.789   2.288  -0.598  1.00  0.00           H  
HETATM   25  H3  UNL     1      -5.780   1.406   0.660  1.00  0.00           H  
HETATM   26  H4  UNL     1      -4.572  -2.274   2.460  1.00  0.00           H  
HETATM   27  H5  UNL     1      -2.293  -2.845   2.166  1.00  0.00           H  
HETATM   28  H6  UNL     1      -0.181  -2.467   0.938  1.00  0.00           H  
HETATM   29  H7  UNL     1       0.168  -0.702  -2.191  1.00  0.00           H  
HETATM   30  H8  UNL     1       0.635  -2.888  -0.796  1.00  0.00           H  
HETATM   31  H9  UNL     1       1.875  -2.150  -1.793  1.00  0.00           H  
HETATM   32  H10 UNL     1       4.591  -1.757   1.114  1.00  0.00           H  
HETATM   33  H11 UNL     1       7.019   0.925   1.224  1.00  0.00           H  
HETATM   34  H12 UNL     1       5.161   2.389   0.203  1.00  0.00           H  
HETATM   35  H13 UNL     1       2.789   2.491  -0.631  1.00  0.00           H  
HETATM   36  H14 UNL     1       0.989   1.303  -1.489  1.00  0.00           H  
HETATM   37  H15 UNL     1       0.467   1.014   0.174  1.00  0.00           H  
HETATM   38  H16 UNL     1      -1.446   2.260  -0.416  1.00  0.00           H  
HETATM   39  H17 UNL     1      -2.700   2.594  -1.712  1.00  0.00           H  
HETATM   40  H18 UNL     1      -1.002   2.430  -2.168  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3
CONECT    3    4    4   20
CONECT    4    5    6
CONECT    5   26
CONECT    6    7    7   27
CONECT    7    8   28
CONECT    8    9   20   20
CONECT    9   10   19   29
CONECT   10   11   30   31
CONECT   11   12
CONECT   12   13   13   18
CONECT   13   14   32
CONECT   14   15   16   16
CONECT   15   33
CONECT   16   17   34
CONECT   17   18   18   35
CONECT   18   19
CONECT   19   36   37
CONECT   20   21
CONECT   21   22
CONECT   22   38   39   40
END

HMDB0038128
     RDKit          3D
(±)-Sphaerosin
 40 42  0  0  0  0  0  0  0  0999 V2000
   -4.7656    1.4974    0.1901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3732    0.2659   -0.3302 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2767   -0.4705    0.0225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3444   -1.3902    1.0294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5579   -1.5881    1.7206 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2252   -2.1065    1.3498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0292   -1.8996    0.6545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9390   -0.9736   -0.3682 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3669   -0.7488   -1.0999 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2340   -1.9776   -0.8708 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0658   -1.8337    0.2637 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9330   -0.7372    0.2736 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2370   -0.7997    0.7358 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0566    0.3043    0.7228 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3442    0.1824    1.1930 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5268    1.4838    0.2305 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2373    1.5676   -0.2315 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4234    0.4385   -0.2106 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0237    0.5086   -0.6740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0774   -0.2640   -0.6726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0457    0.6761   -1.6930 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7589    2.0322   -1.4521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9867    1.8163    0.9261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7894    2.2882   -0.5982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7797    1.4058    0.6603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5719   -2.2741    2.4596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2928   -2.8453    2.1658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1809   -2.4673    0.9380 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1681   -0.7021   -2.1913 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6352   -2.8881   -0.7960 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8753   -2.1501   -1.7933 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5910   -1.7565    1.1139 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0188    0.9255    1.2242 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1609    2.3886    0.2033 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7893    2.4914   -0.6307 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9892    1.3029   -1.4892 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4665    1.0144    0.1737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4462    2.2597   -0.4162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7001    2.5942   -1.7123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0019    2.4295   -2.1681 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
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
  8 20  2  0
 20 21  1  0
 21 22  1  0
 20  3  1  0
 19  9  1  0
 18 12  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  0
  6 27  1  0
  7 28  1  0
  9 29  1  0
 10 30  1  0
 10 31  1  0
 13 32  1  0
 15 33  1  0
 16 34  1  0
 17 35  1  0
 19 36  1  0
 19 37  1  0
 22 38  1  0
 22 39  1  0
 22 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+/-)-sphaerosin	HMDB
7,4'-Dihydroxy-2',3'-dimethoxyisoflavan	HMDB
Laxifloran	HMDB

Chemical Formula

C₁₇H₁₈O₅

Average Molecular Weight

302.3218

Monoisotopic Molecular Weight

302.115423686

IUPAC Name

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

Traditional Name

sphaerosin

CAS Registry Number

52305-06-3

SMILES

COC1=C(O)C=CC(C2COC3=C(C2)C=CC(O)=C3)=C1OC

InChI Identifier

InChI=1S/C17H18O5/c1-20-16-13(5-6-14(19)17(16)21-2)11-7-10-3-4-12(18)8-15(10)22-9-11/h3-6,8,11,18-19H,7,9H2,1-2H3

InChI Key

HHNUTZFOMIAQMX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3'-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C3' atom of the isoflavonoid backbone. Isoflavonoids are natural products derived from 3-phenylchromen-4-one.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

O-methylated isoflavonoids

Direct Parent

3'-O-methylated isoflavonoids

Alternative Parents

Substituents

2p-methoxyisoflavonoid-skeleton
3p-methoxyisoflavonoid-skeleton
Isoflavanol
Hydroxyisoflavonoid
Isoflavan
Chromane
Benzopyran
Methoxyphenol
1-benzopyran
Dimethoxybenzene
O-dimethoxybenzene
Anisole
Phenol ether
Phenoxy compound
Methoxybenzene
Phenol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Ether
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Isoflavans (LMPK12080034 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0038128)

Cellular substructure

Membrane (HMDB: HMDB0038128)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0038128)

Source

Exogenous

Food

Food (HMDB: HMDB0038128)

Pulse

Bean

Pulses (FooDB: FOOD00867)

Endogenous

Plant

Plant (HMDB: HMDB0038128)
Fabaceae (HMDB: HMDB0038128)

Not Available

Nutrient (HMDB: HMDB0038128)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	170 - 171 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	109.6 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	0.058 g/L	ALOGPS
logP	2.83	ALOGPS
logP	2.88	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	9.65	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	68.15 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	81.89 m³·mol⁻¹	ChemAxon
Polarizability	32.01 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	170.169	31661259
DarkChem	[M-H]-	170.302	31661259
DeepCCS	[M+H]+	173.21	30932474
DeepCCS	[M-H]-	170.852	30932474
DeepCCS	[M-2H]-	204.148	30932474
DeepCCS	[M+Na]+	179.374	30932474
AllCCS	[M+H]+	170.9	32859911
AllCCS	[M+H-H2O]+	167.3	32859911
AllCCS	[M+NH4]+	174.2	32859911
AllCCS	[M+Na]+	175.1	32859911
AllCCS	[M-H]-	174.9	32859911
AllCCS	[M+Na-2H]-	174.5	32859911
AllCCS	[M+HCOO]-	174.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(??)-Sphaerosin	COC1=C(O)C=CC(C2COC3=C(C2)C=CC(O)=C3)=C1OC	3749.1	Standard polar	33892256
(??)-Sphaerosin	COC1=C(O)C=CC(C2COC3=C(C2)C=CC(O)=C3)=C1OC	2648.8	Standard non polar	33892256
(??)-Sphaerosin	COC1=C(O)C=CC(C2COC3=C(C2)C=CC(O)=C3)=C1OC	2837.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(??)-Sphaerosin,1TMS,isomer #1	COC1=C(O[Si](C)(C)C)C=CC(C2COC3=CC(O)=CC=C3C2)=C1OC	2739.2	Semi standard non polar	33892256
(??)-Sphaerosin,1TMS,isomer #2	COC1=C(O)C=CC(C2COC3=CC(O[Si](C)(C)C)=CC=C3C2)=C1OC	2617.5	Semi standard non polar	33892256
(??)-Sphaerosin,2TMS,isomer #1	COC1=C(O[Si](C)(C)C)C=CC(C2COC3=CC(O[Si](C)(C)C)=CC=C3C2)=C1OC	2622.9	Semi standard non polar	33892256
(??)-Sphaerosin,1TBDMS,isomer #1	COC1=C(O[Si](C)(C)C(C)(C)C)C=CC(C2COC3=CC(O)=CC=C3C2)=C1OC	2989.8	Semi standard non polar	33892256
(??)-Sphaerosin,1TBDMS,isomer #2	COC1=C(O)C=CC(C2COC3=CC(O[Si](C)(C)C(C)(C)C)=CC=C3C2)=C1OC	2861.7	Semi standard non polar	33892256
(??)-Sphaerosin,2TBDMS,isomer #1	COC1=C(O[Si](C)(C)C(C)(C)C)C=CC(C2COC3=CC(O[Si](C)(C)C(C)(C)C)=CC=C3C2)=C1OC	3054.9	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 - (±)-Sphaerosin GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dr-0691000000-addfc61017b8e4cc49cb	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (±)-Sphaerosin GC-MS (2 TMS) - 70eV, Positive	splash10-00e9-2123900000-f06f1cc1a404585ca098	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (±)-Sphaerosin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (±)-Sphaerosin 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 - (±)-Sphaerosin 10V, Positive-QTOF	splash10-0uk9-0918000000-31b4fc6f362560229ac2	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Sphaerosin 20V, Positive-QTOF	splash10-00di-0941000000-d7d8eaeb1453d0ffdda5	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Sphaerosin 40V, Positive-QTOF	splash10-05fr-4900000000-c0fee25bcc919ba9be32	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Sphaerosin 10V, Negative-QTOF	splash10-0udi-0319000000-c305dd626dae3cc018e6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Sphaerosin 20V, Negative-QTOF	splash10-0udi-0964000000-f7b1b7f58d2911710785	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Sphaerosin 40V, Negative-QTOF	splash10-00di-2940000000-586c4d9999236b0c383d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Sphaerosin 10V, Positive-QTOF	splash10-0udi-0809000000-ca46340f673cd477dd19	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Sphaerosin 20V, Positive-QTOF	splash10-0udj-0904000000-2348a04dac2eb134a1cc	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Sphaerosin 40V, Positive-QTOF	splash10-05gj-0910000000-6a1b4dab8415324b6a79	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Sphaerosin 10V, Negative-QTOF	splash10-0udi-0009000000-65359146e4ae89379a4a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Sphaerosin 20V, Negative-QTOF	splash10-0udi-0689000000-18775aae706dce95e95b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Sphaerosin 40V, Negative-QTOF	splash10-052r-2930000000-816622cd98b89a175a40	2021-09-24	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

FDB017355

KNApSAcK ID

C00009717

Chemspider ID

153700

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

176471

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1865971

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 (±)-Sphaerosin (HMDB0038128)

MOL for HMDB0038128 ((±)-Sphaerosin)

3D MOL for HMDB0038128 ((±)-Sphaerosin)

3D SDF for HMDB0038128 ((±)-Sphaerosin)

3D-SDF for HMDB0038128 ((±)-Sphaerosin)

PDB for HMDB0038128 ((±)-Sphaerosin)

3D PDB for HMDB0038128 ((±)-Sphaerosin)

SMILES for HMDB0038128 ((±)-Sphaerosin)

INCHI for HMDB0038128 ((±)-Sphaerosin)

Structure for HMDB0038128 ((±)-Sphaerosin)

3D Structure for HMDB0038128 ((±)-Sphaerosin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra