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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 04:04:55 UTC

Update Date

2021-09-26 23:00:31 UTC

HMDB ID

HMDB0249566

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Calycosin

Description

Calycosin belongs to the class of organic compounds known as 3'-hydroxy,4'-methoxyisoflavonoids. These are isoflavonoids carrying a methoxy group attached to the C4' atom, as well as a hydroxyl group at the C3'-position of the isoflavonoid backbone. Thus, calycosin is considered to be a flavonoid. Calycosin is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Calycosin. This compound has been identified in human blood as reported by (PMID: 31557052 ). Calycosin is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Calycosin is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0249566
     RDKit          3D
Calycosin
 33 35  0  0  0  0  0  0  0  0999 V2000
    6.0160   -0.0661    0.0507 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9954   -0.6853    0.8041 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6488   -0.5906    0.4590 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2071    0.1149   -0.6448 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8663    0.2066   -0.9845 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9773   -0.4485   -0.1584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4399   -0.3652   -0.4974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8846   -0.5394   -1.7923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1764   -0.4459   -1.9970 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0304   -0.2011   -1.0458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3687   -0.1189   -1.3445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3068    0.1392   -0.3641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6792    0.2257   -0.6578 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9378    0.3259    0.9609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5936    0.2446    1.2681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6533   -0.0172    0.2672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3066   -0.1020    0.5557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9323    0.0582    1.7264 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3969   -1.1566    0.9459 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7346   -1.2395    1.2722 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1306   -1.9622    2.3943 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9106    0.1299    0.6967 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7080    0.9221   -0.3583 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2926   -0.7494   -0.7835 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9139    0.6214   -1.2806 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5302    0.7661   -1.8577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1743   -0.7432   -2.5843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7088   -0.2579   -2.3696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9935    1.1729   -0.8999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6977    0.5262    1.7028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2604    0.3834    2.2879 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7016   -1.6766    1.6032 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1142   -2.0170    2.6252 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
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
  6 19  1  0
 19 20  2  0
 20 21  1  0
 20  3  1  0
 17  7  1  0
 16 10  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
  8 27  1  0
 11 28  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  0
 19 32  1  0
 21 33  1  0
M  END

 
  Mrv0541 02271201332D          
 
 21 23  0  0  0  0            999 V2000
   24.3791  -16.4590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0804  -16.8715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6779  -16.8715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3791  -15.6340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8229  -16.4590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0804  -17.6965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9353  -16.4590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6779  -17.5728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.6779  -15.2215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.5242  -16.8715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8229  -18.1090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9353  -15.6340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1928  -16.8715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5242  -17.6965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1928  -15.2215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4916  -16.4590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2254  -18.1503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4916  -15.6340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9679  -17.7378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7903  -15.2215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.7915  -18.9239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  2  5  1  0  0  0  0
  2  6  2  0  0  0  0
  3  7  1  0  0  0  0
  3  8  2  0  0  0  0
  4  9  1  0  0  0  0
  5 10  2  0  0  0  0
  6 11  1  0  0  0  0
  7 12  2  0  0  0  0
  7 13  1  0  0  0  0
 10 14  1  0  0  0  0
 12 15  1  0  0  0  0
 13 16  2  0  0  0  0
 14 17  1  0  0  0  0
 15 18  2  0  0  0  0
 17 19  1  0  0  0  0
 18 20  1  0  0  0  0
  9 12  1  0  0  0  0
 11 14  2  0  0  0  0
 16 18  1  0  0  0  0
 11 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0249566

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C=C(C=C1)C1=COC2=C(C=CC(O)=C2)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H12O5/c1-20-14-5-2-9(6-13(14)18)12-8-21-15-7-10(17)3-4-11(15)16(12)19/h2-8,17-18H,1H3

> <INCHI_KEY>
ZZAJQOPSWWVMBI-UHFFFAOYSA-N

> <FORMULA>
C16H12O5

> <MOLECULAR_WEIGHT>
284.2635

> <EXACT_MASS>
284.068473494

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
28.815471381654383

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-hydroxy-3-(3-hydroxy-4-methoxyphenyl)-4H-chromen-4-one

> <ALOGPS_LOGP>
3.37

> <JCHEM_LOGP>
2.5727664456666663

> <ALOGPS_LOGS>
-3.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.20814141022319

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.477056369244067

> <JCHEM_PKA_STRONGEST_BASIC>
-4.763080974029341

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
76.1652

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.53e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
calycosin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0249566
     RDKit          3D
Calycosin
 33 35  0  0  0  0  0  0  0  0999 V2000
    6.0160   -0.0661    0.0507 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9954   -0.6853    0.8041 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6488   -0.5906    0.4590 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2071    0.1149   -0.6448 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8663    0.2066   -0.9845 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9773   -0.4485   -0.1584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4399   -0.3652   -0.4974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8846   -0.5394   -1.7923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1764   -0.4459   -1.9970 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0304   -0.2011   -1.0458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3687   -0.1189   -1.3445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3068    0.1392   -0.3641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6792    0.2257   -0.6578 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9378    0.3259    0.9609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5936    0.2446    1.2681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6533   -0.0172    0.2672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3066   -0.1020    0.5557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9323    0.0582    1.7264 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3969   -1.1566    0.9459 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7346   -1.2395    1.2722 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1306   -1.9622    2.3943 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9106    0.1299    0.6967 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7080    0.9221   -0.3583 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2926   -0.7494   -0.7835 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9139    0.6214   -1.2806 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5302    0.7661   -1.8577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1743   -0.7432   -2.5843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7088   -0.2579   -2.3696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9935    1.1729   -0.8999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6977    0.5262    1.7028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2604    0.3834    2.2879 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7016   -1.6766    1.6032 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1142   -2.0170    2.6252 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
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
  6 19  1  0
 19 20  2  0
 20 21  1  0
 20  3  1  0
 17  7  1  0
 16 10  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
  8 27  1  0
 11 28  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  0
 19 32  1  0
 21 33  1  0
M  END

HEADER    PROTEIN                                 27-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-FEB-12         0                                  
HETATM    1  C   UNK     0      45.508 -30.723   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      46.817 -31.493   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      44.199 -31.493   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      45.508 -29.183   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      48.203 -30.723   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      46.817 -33.033   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      42.813 -30.723   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      44.199 -32.803   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      44.199 -28.413   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      49.512 -31.493   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      48.203 -33.803   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      42.813 -29.183   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      41.427 -31.493   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      49.512 -33.033   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      41.427 -28.413   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      40.118 -30.723   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      50.821 -33.881   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      40.118 -29.183   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      52.207 -33.111   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      38.809 -28.413   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      48.144 -35.325   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7    8                                                  
CONECT    4    1    9                                                       
CONECT    5    2   10                                                       
CONECT    6    2   11                                                       
CONECT    7    3   12   13                                                  
CONECT    8    3                                                            
CONECT    9    4   12                                                       
CONECT   10    5   14                                                       
CONECT   11    6   14   21                                                  
CONECT   12    7   15    9                                                  
CONECT   13    7   16                                                       
CONECT   14   10   17   11                                                  
CONECT   15   12   18                                                       
CONECT   16   13   18                                                       
CONECT   17   14   19                                                       
CONECT   18   15   20   16                                                  
CONECT   19   17                                                            
CONECT   20   18                                                            
CONECT   21   11                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0249566
HETATM    1  C1  UNL     1       6.016  -0.066   0.051  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.995  -0.685   0.804  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.649  -0.591   0.459  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.207   0.115  -0.645  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.866   0.207  -0.985  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.977  -0.448  -0.158  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.440  -0.365  -0.497  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.885  -0.539  -1.792  1.00  0.00           C  
HETATM    9  O2  UNL     1      -2.176  -0.446  -1.997  1.00  0.00           O  
HETATM   10  C8  UNL     1      -3.030  -0.201  -1.046  1.00  0.00           C  
HETATM   11  C9  UNL     1      -4.369  -0.119  -1.344  1.00  0.00           C  
HETATM   12  C10 UNL     1      -5.307   0.139  -0.364  1.00  0.00           C  
HETATM   13  O3  UNL     1      -6.679   0.226  -0.658  1.00  0.00           O  
HETATM   14  C11 UNL     1      -4.938   0.326   0.961  1.00  0.00           C  
HETATM   15  C12 UNL     1      -3.594   0.245   1.268  1.00  0.00           C  
HETATM   16  C13 UNL     1      -2.653  -0.017   0.267  1.00  0.00           C  
HETATM   17  C14 UNL     1      -1.307  -0.102   0.556  1.00  0.00           C  
HETATM   18  O4  UNL     1      -0.932   0.058   1.726  1.00  0.00           O  
HETATM   19  C15 UNL     1       1.397  -1.157   0.946  1.00  0.00           C  
HETATM   20  C16 UNL     1       2.735  -1.239   1.272  1.00  0.00           C  
HETATM   21  O5  UNL     1       3.131  -1.962   2.394  1.00  0.00           O  
HETATM   22  H1  UNL     1       6.911   0.130   0.697  1.00  0.00           H  
HETATM   23  H2  UNL     1       5.708   0.922  -0.358  1.00  0.00           H  
HETATM   24  H3  UNL     1       6.293  -0.749  -0.784  1.00  0.00           H  
HETATM   25  H4  UNL     1       3.914   0.621  -1.281  1.00  0.00           H  
HETATM   26  H5  UNL     1       1.530   0.766  -1.858  1.00  0.00           H  
HETATM   27  H6  UNL     1      -0.174  -0.743  -2.584  1.00  0.00           H  
HETATM   28  H7  UNL     1      -4.709  -0.258  -2.370  1.00  0.00           H  
HETATM   29  H8  UNL     1      -6.994   1.173  -0.900  1.00  0.00           H  
HETATM   30  H9  UNL     1      -5.698   0.526   1.703  1.00  0.00           H  
HETATM   31  H10 UNL     1      -3.260   0.383   2.288  1.00  0.00           H  
HETATM   32  H11 UNL     1       0.702  -1.677   1.603  1.00  0.00           H  
HETATM   33  H12 UNL     1       4.114  -2.017   2.625  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3
CONECT    3    4    4   20
CONECT    4    5   25
CONECT    5    6    6   26
CONECT    6    7   19
CONECT    7    8    8   17
CONECT    8    9   27
CONECT    9   10
CONECT   10   11   11   16
CONECT   11   12   28
CONECT   12   13   14   14
CONECT   13   29
CONECT   14   15   30
CONECT   15   16   16   31
CONECT   16   17
CONECT   17   18   18
CONECT   19   20   20   32
CONECT   20   21
CONECT   21   33
END

HMDB0249566
     RDKit          3D
Calycosin
 33 35  0  0  0  0  0  0  0  0999 V2000
    6.0160   -0.0661    0.0507 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9954   -0.6853    0.8041 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6488   -0.5906    0.4590 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2071    0.1149   -0.6448 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8663    0.2066   -0.9845 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9773   -0.4485   -0.1584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4399   -0.3652   -0.4974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8846   -0.5394   -1.7923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1764   -0.4459   -1.9970 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0304   -0.2011   -1.0458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3687   -0.1189   -1.3445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3068    0.1392   -0.3641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6792    0.2257   -0.6578 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9378    0.3259    0.9609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5936    0.2446    1.2681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6533   -0.0172    0.2672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3066   -0.1020    0.5557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9323    0.0582    1.7264 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3969   -1.1566    0.9459 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7346   -1.2395    1.2722 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1306   -1.9622    2.3943 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9106    0.1299    0.6967 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7080    0.9221   -0.3583 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2926   -0.7494   -0.7835 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9139    0.6214   -1.2806 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5302    0.7661   -1.8577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1743   -0.7432   -2.5843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7088   -0.2579   -2.3696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9935    1.1729   -0.8999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6977    0.5262    1.7028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2604    0.3834    2.2879 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7016   -1.6766    1.6032 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1142   -2.0170    2.6252 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
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
  6 19  1  0
 19 20  2  0
 20 21  1  0
 20  3  1  0
 17  7  1  0
 16 10  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
  8 27  1  0
 11 28  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  0
 19 32  1  0
 21 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3'-Hydroxy-formononetin	ChEBI
7,3'-Dihydroxy-4'-methoxyisoflavone	ChEBI
7-Hydroxy-3-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one	ChEBI
7-Hydroxy-3-(3-hydroxy-4-methoxyphenyl)chromen-4-one	ChEBI
3'-Hydroxyformononetin	Kegg
Calycosin (old)	ChEBI

Chemical Formula

C₁₆H₁₂O₅

Average Molecular Weight

284.2635

Monoisotopic Molecular Weight

284.068473494

IUPAC Name

7-hydroxy-3-(3-hydroxy-4-methoxyphenyl)-4H-chromen-4-one

Traditional Name

calycosin

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=C(C=C1)C1=COC2=C(C=CC(O)=C2)C1=O

InChI Identifier

InChI=1S/C16H12O5/c1-20-14-5-2-9(6-13(14)18)12-8-21-15-7-10(17)3-4-11(15)16(12)19/h2-8,17-18H,1H3

InChI Key

ZZAJQOPSWWVMBI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3'-hydroxy,4'-methoxyisoflavonoids. These are isoflavonoids carrying a methoxy group attached to the C4' atom, as well as a hydroxyl group at the C3'-position of the isoflavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

O-methylated isoflavonoids

Direct Parent

3'-hydroxy,4'-methoxyisoflavonoids

Alternative Parents

Substituents

4p-o-methylisoflavone
3'-hydroxy,4'-methoxyisoflavonoid
Isoflavone
Hydroxyisoflavonoid
Chromone
Methoxyphenol
1-benzopyran
Benzopyran
Phenoxy compound
Phenol ether
Anisole
Methoxybenzene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Phenol
Pyran
Monocyclic benzene moiety
Benzenoid
Heteroaromatic compound
Ether
Organoheterocyclic compound
Oxacycle
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

methoxyisoflavone (CHEBI:17793 )
7-hydroxyisoflavones (CHEBI:17793 )
isoflavones (C01562 )
Isoflavonoids (C01562 )
Isoflavonoids (LMPK12050056 )
an isoflavone (CPD-9539 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (HMDB: HMDB0249566)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	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
logP	3.37	ALOGPS
logP	2.57	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	6.48	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	76.17 m³·mol⁻¹	ChemAxon
Polarizability	28.82 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
DeepCCS	[M+H]+	170.79	30932474
DeepCCS	[M-H]-	168.433	30932474
DeepCCS	[M-2H]-	201.319	30932474
DeepCCS	[M+Na]+	176.884	30932474
AllCCS	[M+H]+	165.1	32859911
AllCCS	[M+H-H2O]+	161.3	32859911
AllCCS	[M+NH4]+	168.6	32859911
AllCCS	[M+Na]+	169.6	32859911
AllCCS	[M-H]-	166.8	32859911
AllCCS	[M+Na-2H]-	166.1	32859911
AllCCS	[M+HCOO]-	165.5	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	11.1068 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.93 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1815.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	288.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	147.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	174.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	278.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	483.7 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	471.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	127.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	912.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	362.7 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	1235.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	328.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	352.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	394.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	298.5 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	82.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Calycosin	COC1=C(O)C=C(C=C1)C1=COC2=C(C=CC(O)=C2)C1=O	4104.6	Standard polar	33892256
Calycosin	COC1=C(O)C=C(C=C1)C1=COC2=C(C=CC(O)=C2)C1=O	2785.8	Standard non polar	33892256
Calycosin	COC1=C(O)C=C(C=C1)C1=COC2=C(C=CC(O)=C2)C1=O	3103.9	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 - Calycosin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a59-0490000000-1865706f4233b8371a6e	2017-07-27	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Calycosin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Calycosin GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Calycosin GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Calycosin GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Calycosin GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Calycosin GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Calycosin GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-03	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 - Calycosin 10V, Positive-QTOF	splash10-000i-0190000000-c48028ce0254f47fd02b	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calycosin 20V, Positive-QTOF	splash10-000i-0390000000-bf393135ef0ddbff2c4e	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calycosin 40V, Positive-QTOF	splash10-0fki-6930000000-b7225bf258eb7d0eb0ff	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calycosin 10V, Negative-QTOF	splash10-001i-0090000000-774b8cb4a4f1162dfb2d	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calycosin 20V, Negative-QTOF	splash10-001i-0390000000-101995a2ab9f72de62ab	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calycosin 40V, Negative-QTOF	splash10-02ti-2980000000-c30305547c36e7a4dcf1	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calycosin 10V, Positive-QTOF	splash10-000i-0090000000-edc9ea273e98ea6aa00a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calycosin 20V, Positive-QTOF	splash10-000i-0090000000-640c1e1fad2467a0c193	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calycosin 40V, Positive-QTOF	splash10-03di-1490000000-00d0f6eddddb6b72afdc	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calycosin 10V, Negative-QTOF	splash10-001i-0090000000-549f6b30f75977e8ff35	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calycosin 20V, Negative-QTOF	splash10-001i-0090000000-69fd4270dc11dde0a786	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calycosin 40V, Negative-QTOF	splash10-000i-0490000000-3b51419965bd7c30fffe	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Calycosin

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

17793

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Calycosin (HMDB0249566)

MOL for HMDB0249566 (Calycosin)

3D MOL for HMDB0249566 (Calycosin)

3D SDF for HMDB0249566 (Calycosin)

3D-SDF for HMDB0249566 (Calycosin)

PDB for HMDB0249566 (Calycosin)

3D PDB for HMDB0249566 (Calycosin)

SMILES for HMDB0249566 (Calycosin)

INCHI for HMDB0249566 (Calycosin)

Structure for HMDB0249566 (Calycosin)

3D Structure for HMDB0249566 (Calycosin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra