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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:59:30 UTC

Update Date

2022-03-07 02:55:51 UTC

HMDB ID

HMDB0038659

Secondary Accession Numbers

HMDB38659

Metabolite Identification

Common Name

Cicerin

Description

Cicerin belongs to the class of organic compounds known as 2'-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C2' atom of the isoflavonoid backbone. Isoflavonoids are natural products derived from 3-phenylchromen-4-one. Cicerin has been detected, but not quantified in, pulses. This could make cicerin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Cicerin.

Structure

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

HMDB0038659
     RDKit          3D
Cicerin
 38 41  0  0  0  0  0  0  0  0999 V2000
   -1.3635    2.1127    2.7715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9930    1.4372    1.6113 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7888    0.5545    0.9183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0675    0.2511    1.3262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8827   -0.6440    0.6277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3979   -1.2432   -0.5026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1151   -0.9588   -0.9390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3254   -0.0724   -0.2356 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0300    0.2435   -0.6769 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4349   -0.5022   -1.9351 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7898   -0.3958   -2.2157 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7751   -0.0645   -1.3200 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0938    0.1033   -1.7426 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0293    0.4329   -0.7948 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3609    0.6087   -1.1814 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7269    0.6024    0.5321 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4023    0.4366    0.9691 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0668    0.5994    2.2714 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4687    0.1052    0.0131 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0503   -0.0931    0.3815 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7487   -0.5142    1.5010 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4169   -2.0671   -0.9728 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5356   -2.0119   -0.1114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1749   -1.0765    0.8680 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4530    2.3974    2.7171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8113    3.0593    2.9340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2838    1.4066    3.6236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4800    0.7094    2.2176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8064   -1.4691   -1.8403 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1404    1.3290   -0.8742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1620   -0.1687   -2.8038 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1919   -1.5771   -1.7617 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3019   -0.0346   -2.7837 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0090   -0.1797   -1.1805 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4429    0.8608    1.2947 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1826    0.5276    2.6672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7198   -2.9828    0.3862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4683   -1.7218   -0.6382 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  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  1  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
  6 22  1  0
 22 23  1  0
 23 24  1  0
  8  3  1  0
 20  9  1  0
 24  5  1  0
 19 12  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  7 29  1  0
  9 30  1  0
 10 31  1  0
 10 32  1  0
 13 33  1  0
 15 34  1  0
 16 35  1  0
 18 36  1  0
 23 37  1  0
 23 38  1  0
M  END

  Mrv0541 05061310342D          

 24 27  0  0  0  0            999 V2000
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    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
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9933    4.6057    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    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    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
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1728    4.5195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3289    3.8520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8  2  2  0  0  0  0
  8  3  1  0  0  0  0
  9  4  2  0  0  0  0
 10  6  1  0  0  0  0
 10  9  1  0  0  0  0
 11  2  1  0  0  0  0
 12  5  2  0  0  0  0
 12  9  1  0  0  0  0
 13  4  1  0  0  0  0
 14  5  1  0  0  0  0
 14 13  2  0  0  0  0
 15  3  2  0  0  0  0
 16 11  2  0  0  0  0
 16 15  1  0  0  0  0
 17 10  1  0  0  0  0
 17 16  1  0  0  0  0
 18  8  1  0  0  0  0
 19 11  1  0  0  0  0
 20 17  2  0  0  0  0
 21  1  1  0  0  0  0
 21 12  1  0  0  0  0
 22  6  1  0  0  0  0
 22 15  1  0  0  0  0
 23  7  1  0  0  0  0
 23 13  1  0  0  0  0
 24  7  1  0  0  0  0
 24 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0038659

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=C(OCO2)C=C1C1COC2=CC(O)=CC(O)=C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C17H14O7/c1-21-12-5-14-13(23-7-24-14)4-9(12)10-6-22-15-3-8(18)2-11(19)16(15)17(10)20/h2-5,10,18-19H,6-7H2,1H3

> <INCHI_KEY>
MNXNLFUKHPLPES-UHFFFAOYSA-N

> <FORMULA>
C17H14O7

> <MOLECULAR_WEIGHT>
330.2889

> <EXACT_MASS>
330.073952802

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
31.712914891804566

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7-dihydroxy-3-(6-methoxy-2H-1,3-benzodioxol-5-yl)-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
2.26

> <JCHEM_LOGP>
2.496785637666666

> <ALOGPS_LOGS>
-3.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.628637331676707

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.905948483193821

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8648998793960905

> <JCHEM_POLAR_SURFACE_AREA>
94.45000000000002

> <JCHEM_REFRACTIVITY>
81.9257

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.78e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,7-dihydroxy-3-(6-methoxy-2H-1,3-benzodioxol-5-yl)-2,3-dihydro-1-benzopyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0038659
     RDKit          3D
Cicerin
 38 41  0  0  0  0  0  0  0  0999 V2000
   -1.3635    2.1127    2.7715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9930    1.4372    1.6113 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7888    0.5545    0.9183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0675    0.2511    1.3262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8827   -0.6440    0.6277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3979   -1.2432   -0.5026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1151   -0.9588   -0.9390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3254   -0.0724   -0.2356 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0300    0.2435   -0.6769 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4349   -0.5022   -1.9351 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7898   -0.3958   -2.2157 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7751   -0.0645   -1.3200 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0938    0.1033   -1.7426 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0293    0.4329   -0.7948 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3609    0.6087   -1.1814 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7269    0.6024    0.5321 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4023    0.4366    0.9691 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0668    0.5994    2.2714 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4687    0.1052    0.0131 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0503   -0.0931    0.3815 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7487   -0.5142    1.5010 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4169   -2.0671   -0.9728 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5356   -2.0119   -0.1114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1749   -1.0765    0.8680 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4530    2.3974    2.7171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8113    3.0593    2.9340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2838    1.4066    3.6236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4800    0.7094    2.2176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8064   -1.4691   -1.8403 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1404    1.3290   -0.8742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1620   -0.1687   -2.8038 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1919   -1.5771   -1.7617 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3019   -0.0346   -2.7837 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0090   -0.1797   -1.1805 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4429    0.8608    1.2947 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1826    0.5276    2.6672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7198   -2.9828    0.3862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4683   -1.7218   -0.6382 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  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  1  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
  6 22  1  0
 22 23  1  0
 23 24  1  0
  8  3  1  0
 20  9  1  0
 24  5  1  0
 19 12  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  7 29  1  0
  9 30  1  0
 10 31  1  0
 10 32  1  0
 13 33  1  0
 15 34  1  0
 16 35  1  0
 18 36  1  0
 23 37  1  0
 23 38  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       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.187   8.597   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.669   6.160   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       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       9.656   8.436   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      11.814   7.190   0.000  0.00  0.00           O+0
CONECT    1   21                                                            
CONECT    2    8   11                                                       
CONECT    3    8   15                                                       
CONECT    4    9   13                                                       
CONECT    5   12   14                                                       
CONECT    6   10   22                                                       
CONECT    7   23   24                                                       
CONECT    8    2    3   18                                                  
CONECT    9    4   10   12                                                  
CONECT   10    6    9   17                                                  
CONECT   11    2   16   19                                                  
CONECT   12    5    9   21                                                  
CONECT   13    4   14   23                                                  
CONECT   14    5   13   24                                                  
CONECT   15    3   16   22                                                  
CONECT   16   11   15   17                                                  
CONECT   17   10   16   20                                                  
CONECT   18    8                                                            
CONECT   19   11                                                            
CONECT   20   17                                                            
CONECT   21    1   12                                                       
CONECT   22    6   15                                                       
CONECT   23    7   13                                                       
CONECT   24    7   14                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

COMPND    HMDB0038659
HETATM    1  C1  UNL     1      -1.363   2.113   2.772  1.00  0.00           C  
HETATM    2  O1  UNL     1      -0.993   1.437   1.611  1.00  0.00           O  
HETATM    3  C2  UNL     1      -1.789   0.554   0.918  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.068   0.251   1.326  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.883  -0.644   0.628  1.00  0.00           C  
HETATM    6  C5  UNL     1      -3.398  -1.243  -0.503  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.115  -0.959  -0.939  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.325  -0.072  -0.236  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.030   0.243  -0.677  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.435  -0.502  -1.935  1.00  0.00           C  
HETATM   11  O2  UNL     1       1.790  -0.396  -2.216  1.00  0.00           O  
HETATM   12  C10 UNL     1       2.775  -0.064  -1.320  1.00  0.00           C  
HETATM   13  C11 UNL     1       4.094   0.103  -1.743  1.00  0.00           C  
HETATM   14  C12 UNL     1       5.029   0.433  -0.795  1.00  0.00           C  
HETATM   15  O3  UNL     1       6.361   0.609  -1.181  1.00  0.00           O  
HETATM   16  C13 UNL     1       4.727   0.602   0.532  1.00  0.00           C  
HETATM   17  C14 UNL     1       3.402   0.437   0.969  1.00  0.00           C  
HETATM   18  O4  UNL     1       3.067   0.599   2.271  1.00  0.00           O  
HETATM   19  C15 UNL     1       2.469   0.105   0.013  1.00  0.00           C  
HETATM   20  C16 UNL     1       1.050  -0.093   0.381  1.00  0.00           C  
HETATM   21  O5  UNL     1       0.749  -0.514   1.501  1.00  0.00           O  
HETATM   22  O6  UNL     1      -4.417  -2.067  -0.973  1.00  0.00           O  
HETATM   23  C17 UNL     1      -5.536  -2.012  -0.111  1.00  0.00           C  
HETATM   24  O7  UNL     1      -5.175  -1.076   0.868  1.00  0.00           O  
HETATM   25  H1  UNL     1      -2.453   2.397   2.717  1.00  0.00           H  
HETATM   26  H2  UNL     1      -0.811   3.059   2.934  1.00  0.00           H  
HETATM   27  H3  UNL     1      -1.284   1.407   3.624  1.00  0.00           H  
HETATM   28  H4  UNL     1      -3.480   0.709   2.218  1.00  0.00           H  
HETATM   29  H5  UNL     1      -1.806  -1.469  -1.840  1.00  0.00           H  
HETATM   30  H6  UNL     1       0.140   1.329  -0.874  1.00  0.00           H  
HETATM   31  H7  UNL     1      -0.162  -0.169  -2.804  1.00  0.00           H  
HETATM   32  H8  UNL     1       0.192  -1.577  -1.762  1.00  0.00           H  
HETATM   33  H9  UNL     1       4.302  -0.035  -2.784  1.00  0.00           H  
HETATM   34  H10 UNL     1       7.009  -0.180  -1.180  1.00  0.00           H  
HETATM   35  H11 UNL     1       5.443   0.861   1.295  1.00  0.00           H  
HETATM   36  H12 UNL     1       2.183   0.528   2.667  1.00  0.00           H  
HETATM   37  H13 UNL     1      -5.720  -2.983   0.386  1.00  0.00           H  
HETATM   38  H14 UNL     1      -6.468  -1.722  -0.638  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   28
CONECT    5    6    6   24
CONECT    6    7   22
CONECT    7    8    8   29
CONECT    8    9
CONECT    9   10   20   30
CONECT   10   11   31   32
CONECT   11   12
CONECT   12   13   13   19
CONECT   13   14   33
CONECT   14   15   16   16
CONECT   15   34
CONECT   16   17   35
CONECT   17   18   19   19
CONECT   18   36
CONECT   19   20
CONECT   20   21   21
CONECT   22   23
CONECT   23   24   37   38
END

HMDB0038659
     RDKit          3D
Cicerin
 38 41  0  0  0  0  0  0  0  0999 V2000
   -1.3635    2.1127    2.7715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9930    1.4372    1.6113 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7888    0.5545    0.9183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0675    0.2511    1.3262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8827   -0.6440    0.6277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3979   -1.2432   -0.5026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1151   -0.9588   -0.9390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3254   -0.0724   -0.2356 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0300    0.2435   -0.6769 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4349   -0.5022   -1.9351 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7898   -0.3958   -2.2157 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7751   -0.0645   -1.3200 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0938    0.1033   -1.7426 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0293    0.4329   -0.7948 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3609    0.6087   -1.1814 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7269    0.6024    0.5321 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4023    0.4366    0.9691 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0668    0.5994    2.2714 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4687    0.1052    0.0131 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0503   -0.0931    0.3815 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7487   -0.5142    1.5010 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4169   -2.0671   -0.9728 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5356   -2.0119   -0.1114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1749   -1.0765    0.8680 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4530    2.3974    2.7171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8113    3.0593    2.9340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2838    1.4066    3.6236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4800    0.7094    2.2176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8064   -1.4691   -1.8403 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1404    1.3290   -0.8742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1620   -0.1687   -2.8038 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1919   -1.5771   -1.7617 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3019   -0.0346   -2.7837 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0090   -0.1797   -1.1805 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4429    0.8608    1.2947 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1826    0.5276    2.6672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7198   -2.9828    0.3862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4683   -1.7218   -0.6382 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  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  1  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
  6 22  1  0
 22 23  1  0
 23 24  1  0
  8  3  1  0
 20  9  1  0
 24  5  1  0
 19 12  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  7 29  1  0
  9 30  1  0
 10 31  1  0
 10 32  1  0
 13 33  1  0
 15 34  1  0
 16 35  1  0
 18 36  1  0
 23 37  1  0
 23 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(3R3S)-Onogenin	ChEMBL, HMDB
2-chloro-1-Cyclopentanone	HMDB
2-chloro-Cyclopentanone	HMDB
2-Chlorocyclopentan-one	HMDB
2-Chlorocyclopentanone	HMDB
5,7-Dihydroxy-2'-methoxy-4',5'-methylenedioxyisoflavanone	HMDB
alpha-Chlorocyclopentanone	HMDB

Chemical Formula

C₁₇H₁₄O₇

Average Molecular Weight

330.2889

Monoisotopic Molecular Weight

330.073952802

IUPAC Name

5,7-dihydroxy-3-(6-methoxy-2H-1,3-benzodioxol-5-yl)-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

5,7-dihydroxy-3-(6-methoxy-2H-1,3-benzodioxol-5-yl)-2,3-dihydro-1-benzopyran-4-one

CAS Registry Number

12751-00-7

SMILES

COC1=CC2=C(OCO2)C=C1C1COC2=CC(O)=CC(O)=C2C1=O

InChI Identifier

InChI=1S/C17H14O7/c1-21-12-5-14-13(23-7-24-14)4-9(12)10-6-22-15-3-8(18)2-11(19)16(15)17(10)20/h2-5,10,18-19H,6-7H2,1H3

InChI Key

MNXNLFUKHPLPES-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2'-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C2' 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

2'-O-methylated isoflavonoids

Alternative Parents

Substituents

2p-methoxyisoflavonoid-skeleton
Isoflavanol
Isoflavanone
Hydroxyisoflavonoid
Isoflavan
Chromone
Chromane
Benzopyran
1-benzopyran
Benzodioxole
Anisole
Aryl alkyl ketone
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Vinylogous acid
Ketone
Acetal
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0038659)
Cytoplasm (HMDB: HMDB0038659)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0038659)

Source

Exogenous

Exogenous (HMDB: HMDB0038659)

Food

Food (HMDB: HMDB0038659)

Pulse

Pulses (FooDB: FOOD00867)

Endogenous

Plant

Plant (HMDB: HMDB0038659)
Fabaceae (HMDB: HMDB0038659)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0038659)

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	53.33 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	0.28 g/L	ALOGPS
logP	2.26	ALOGPS
logP	2.5	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	7.91	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	94.45 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	81.93 m³·mol⁻¹	ChemAxon
Polarizability	31.71 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]+	174.607	31661259
DarkChem	[M-H]-	176.447	31661259
DeepCCS	[M+H]+	171.742	30932474
DeepCCS	[M-H]-	169.384	30932474
DeepCCS	[M-2H]-	202.812	30932474
DeepCCS	[M+Na]+	178.038	30932474
AllCCS	[M+H]+	175.5	32859911
AllCCS	[M+H-H2O]+	172.1	32859911
AllCCS	[M+NH4]+	178.7	32859911
AllCCS	[M+Na]+	179.6	32859911
AllCCS	[M-H]-	177.8	32859911
AllCCS	[M+Na-2H]-	177.1	32859911
AllCCS	[M+HCOO]-	176.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cicerin	COC1=CC2=C(OCO2)C=C1C1COC2=CC(O)=CC(O)=C2C1=O	4326.8	Standard polar	33892256
Cicerin	COC1=CC2=C(OCO2)C=C1C1COC2=CC(O)=CC(O)=C2C1=O	2967.5	Standard non polar	33892256
Cicerin	COC1=CC2=C(OCO2)C=C1C1COC2=CC(O)=CC(O)=C2C1=O	3144.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cicerin,1TMS,isomer #1	COC1=CC2=C(C=C1C1COC3=CC(O[Si](C)(C)C)=CC(O)=C3C1=O)OCO2	3004.8	Semi standard non polar	33892256
Cicerin,1TMS,isomer #2	COC1=CC2=C(C=C1C1COC3=CC(O)=CC(O[Si](C)(C)C)=C3C1=O)OCO2	2976.6	Semi standard non polar	33892256
Cicerin,2TMS,isomer #1	COC1=CC2=C(C=C1C1COC3=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3C1=O)OCO2	3004.5	Semi standard non polar	33892256
Cicerin,1TBDMS,isomer #1	COC1=CC2=C(C=C1C1COC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C3C1=O)OCO2	3251.1	Semi standard non polar	33892256
Cicerin,1TBDMS,isomer #2	COC1=CC2=C(C=C1C1COC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C1=O)OCO2	3253.8	Semi standard non polar	33892256
Cicerin,2TBDMS,isomer #1	COC1=CC2=C(C=C1C1COC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C3C1=O)OCO2	3495.3	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 - Cicerin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0w29-0759000000-439af15876847a580b66	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cicerin GC-MS (2 TMS) - 70eV, Positive	splash10-0ikc-3930800000-f892e3baf03eaed3c0f4	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cicerin 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 - Cicerin 10V, Positive-QTOF	splash10-001i-0309000000-96e74d301b5afd132849	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cicerin 20V, Positive-QTOF	splash10-0ue9-0829000000-d90e607b2a3f3fd9b769	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cicerin 40V, Positive-QTOF	splash10-0uds-1910000000-7eaf378bedf6b1803cb8	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cicerin 10V, Negative-QTOF	splash10-004i-0009000000-18931895d5a1c04d46a4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cicerin 20V, Negative-QTOF	splash10-0fb9-0639000000-2ba8565a9878c1607e84	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cicerin 40V, Negative-QTOF	splash10-0udi-2910000000-351023edcb339c913f52	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cicerin 10V, Negative-QTOF	splash10-004i-0009000000-8e9d1a384717180cd0e2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cicerin 20V, Negative-QTOF	splash10-004i-0119000000-6496719f897a3468e4c1	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cicerin 40V, Negative-QTOF	splash10-0fb9-0494000000-f8fcbabb775b4c090865	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cicerin 10V, Positive-QTOF	splash10-001i-0009000000-931b28fcfeb1b8f804fe	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cicerin 20V, Positive-QTOF	splash10-0f89-0809000000-c5a95cdfa833cd0e6cd7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cicerin 40V, Positive-QTOF	splash10-0uy0-2944000000-899ba32072e1793bac8d	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB018057

KNApSAcK ID

C00054895

Chemspider ID

24665209

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

46881084

PDB ID

Not Available

ChEBI ID

174460

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1870271

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 Cicerin (HMDB0038659)

MOL for HMDB0038659 (Cicerin)

3D MOL for HMDB0038659 (Cicerin)

3D SDF for HMDB0038659 (Cicerin)

3D-SDF for HMDB0038659 (Cicerin)

PDB for HMDB0038659 (Cicerin)

3D PDB for HMDB0038659 (Cicerin)

SMILES for HMDB0038659 (Cicerin)

INCHI for HMDB0038659 (Cicerin)

Structure for HMDB0038659 (Cicerin)

3D Structure for HMDB0038659 (Cicerin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra