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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:33:13 UTC

Update Date

2022-03-07 02:55:16 UTC

HMDB ID

HMDB0037315

Secondary Accession Numbers

HMDB37315

Metabolite Identification

Common Name

Cerasinone

Description

Cerasinone belongs to the class of organic compounds known as 5-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C5 atom of the flavonoid backbone. Thus, cerasinone is considered to be a flavonoid. Cerasinone has been detected, but not quantified in, fruits and sour cherries (Prunus cerasus). This could make cerasinone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Cerasinone.

Structure

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

HMDB0037315
     RDKit          3D
Cerasinone
 42 44  0  0  0  0  0  0  0  0999 V2000
   -6.4218    0.5592   -0.7473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4991    1.5279   -1.1920 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1567    1.3652   -0.8922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1983    2.2890   -1.3045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8609    2.0911   -0.9843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4502    0.9803   -0.2535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0377    0.7839    0.0772 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8221    1.8895   -0.4592 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2484    1.5583   -0.2477 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0799    2.4830   -0.1194 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6782    0.1911   -0.1895 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0031   -0.1899   -0.0290 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9337    0.8486    0.0773 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2848    0.5357    0.2406 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3855   -1.5137    0.0233 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4647   -2.5360   -0.0819 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8396   -3.8712   -0.0305 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1458   -2.1605   -0.2417 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7494   -0.8427   -0.2956 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4245   -0.4498   -0.4561 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3984    0.0716    0.1513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0380   -1.0296    0.8688 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8783   -2.0295    1.3447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7213    0.2763   -0.1709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4496    0.7648   -1.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0844   -0.4627   -1.0775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4370    0.5086    0.3728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5116    3.1407   -1.8647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1698    2.8455   -1.3348 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0640    0.7993    1.1922 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6829    1.9959   -1.5680 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6176    2.8509    0.0706 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8773    1.4723    0.1791 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4208    0.0699    1.2436 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6049   -0.2282   -0.5002 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4281   -1.7742    0.1494 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8879   -4.3982    0.8324 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4070   -2.9340   -0.3263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2645   -1.7965    2.3786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7416   -2.2655    0.7277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2742   -2.9733    1.4398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4567   -0.4429    0.1517 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  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
  6 21  1  0
 21 22  1  0
 22 23  1  0
 21 24  2  0
 24  3  1  0
 20  7  1  0
 19 11  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  5 29  1  0
  7 30  1  0
  8 31  1  0
  8 32  1  0
 14 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 17 37  1  0
 18 38  1  0
 23 39  1  0
 23 40  1  0
 23 41  1  0
 24 42  1  0
M  END


  Mrv1652304201815042D          

 24 26  0  0  0  0            999 V2000
    7.1447    2.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    0.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    1.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0012    0.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0012    1.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.2750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.2000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    1.5125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    1.5125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.2000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.2750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
 10  6  2  0  0  0  0
 10  7  1  0  0  0  0
 11  4  1  0  0  0  0
 11  8  2  0  0  0  0
 12  5  1  0  0  0  0
 13  9  1  0  0  0  0
 14  8  1  0  0  0  0
 14 12  2  0  0  0  0
 15  9  1  0  0  0  0
 15 12  1  0  0  0  0
 16  6  1  0  0  0  0
 17  7  2  0  0  0  0
 18 13  1  0  0  0  0
 18 16  2  0  0  0  0
 18 17  1  0  0  0  0
 19 10  1  0  0  0  0
 20 13  2  0  0  0  0
 21  1  1  0  0  0  0
 21 11  1  0  0  0  0
 22  2  1  0  0  0  0
 22 14  1  0  0  0  0
 23  3  1  0  0  0  0
 23 16  1  0  0  0  0
 24 15  1  0  0  0  0
 24 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0037315

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(OC)=C(C=C1)C1CC(=O)C2=C(OC)C=C(O)C=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C18H18O6/c1-21-11-4-5-12(14(8-11)22-2)15-9-13(20)18-16(23-3)6-10(19)7-17(18)24-15/h4-8,15,19H,9H2,1-3H3

> <INCHI_KEY>
JVUGHKAZGNYYCA-UHFFFAOYSA-N

> <FORMULA>
C18H18O6

> <MOLECULAR_WEIGHT>
330.3319

> <EXACT_MASS>
330.110338308

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
34.33813646575076

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(2,4-dimethoxyphenyl)-7-hydroxy-5-methoxy-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
1.60

> <JCHEM_LOGP>
2.319224896666666

> <ALOGPS_LOGS>
-3.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.317886285715513

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.857101412333729

> <JCHEM_PKA_STRONGEST_BASIC>
-4.280543350878845

> <JCHEM_POLAR_SURFACE_AREA>
74.22000000000001

> <JCHEM_REFRACTIVITY>
86.71759999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.78e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cerasinone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0037315
     RDKit          3D
Cerasinone
 42 44  0  0  0  0  0  0  0  0999 V2000
   -6.4218    0.5592   -0.7473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4991    1.5279   -1.1920 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1567    1.3652   -0.8922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1983    2.2890   -1.3045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8609    2.0911   -0.9843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4502    0.9803   -0.2535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0377    0.7839    0.0772 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8221    1.8895   -0.4592 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2484    1.5583   -0.2477 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0799    2.4830   -0.1194 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6782    0.1911   -0.1895 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0031   -0.1899   -0.0290 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9337    0.8486    0.0773 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2848    0.5357    0.2406 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3855   -1.5137    0.0233 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4647   -2.5360   -0.0819 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8396   -3.8712   -0.0305 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1458   -2.1605   -0.2417 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7494   -0.8427   -0.2956 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4245   -0.4498   -0.4561 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3984    0.0716    0.1513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0380   -1.0296    0.8688 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8783   -2.0295    1.3447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7213    0.2763   -0.1709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4496    0.7648   -1.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0844   -0.4627   -1.0775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4370    0.5086    0.3728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5116    3.1407   -1.8647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1698    2.8455   -1.3348 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0640    0.7993    1.1922 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6829    1.9959   -1.5680 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6176    2.8509    0.0706 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8773    1.4723    0.1791 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4208    0.0699    1.2436 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6049   -0.2282   -0.5002 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4281   -1.7742    0.1494 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8879   -4.3982    0.8324 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4070   -2.9340   -0.3263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2645   -1.7965    2.3786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7416   -2.2655    0.7277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2742   -2.9733    1.4398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4567   -0.4429    0.1517 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  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
  6 21  1  0
 21 22  1  0
 22 23  1  0
 21 24  2  0
 24  3  1  0
 20  7  1  0
 19 11  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  5 29  1  0
  7 30  1  0
  8 31  1  0
  8 32  1  0
 14 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 17 37  1  0
 18 38  1  0
 23 39  1  0
 23 40  1  0
 23 41  1  0
 24 42  1  0
M  END

HEADER    PROTEIN                                 20-APR-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-18         0                                  
HETATM    1  C   UNK     0      13.337   4.363   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668   2.053   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -4.877   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.003   0.513   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.669  -0.257   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -1.797   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001   0.513   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.669   2.823   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002  -1.797   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -0.257   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.003   2.053   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.336   0.513   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -2.567   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.336   2.053   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002  -0.257   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001  -2.567   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335  -0.257   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335  -1.797   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.334   0.513   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       6.668  -4.107   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      13.337   2.823   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       8.002   2.823   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       4.001  -4.107   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       6.668   0.513   0.000  0.00  0.00           O+0
CONECT    1   21                                                            
CONECT    2   22                                                            
CONECT    3   23                                                            
CONECT    4    5   11                                                       
CONECT    5    4   12                                                       
CONECT    6   10   16                                                       
CONECT    7   10   17                                                       
CONECT    8   11   14                                                       
CONECT    9   13   15                                                       
CONECT   10    6    7   19                                                  
CONECT   11    4    8   21                                                  
CONECT   12    5   14   15                                                  
CONECT   13    9   18   20                                                  
CONECT   14    8   12   22                                                  
CONECT   15    9   12   24                                                  
CONECT   16    6   18   23                                                  
CONECT   17    7   18   24                                                  
CONECT   18   13   16   17                                                  
CONECT   19   10                                                            
CONECT   20   13                                                            
CONECT   21    1   11                                                       
CONECT   22    2   14                                                       
CONECT   23    3   16                                                       
CONECT   24   15   17                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0037315
HETATM    1  C1  UNL     1      -6.422   0.559  -0.747  1.00  0.00           C  
HETATM    2  O1  UNL     1      -5.499   1.528  -1.192  1.00  0.00           O  
HETATM    3  C2  UNL     1      -4.157   1.365  -0.892  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.198   2.289  -1.305  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.861   2.091  -0.984  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.450   0.980  -0.253  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.038   0.784   0.077  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.822   1.890  -0.459  1.00  0.00           C  
HETATM    9  C8  UNL     1       2.248   1.558  -0.248  1.00  0.00           C  
HETATM   10  O2  UNL     1       3.080   2.483  -0.119  1.00  0.00           O  
HETATM   11  C9  UNL     1       2.678   0.191  -0.189  1.00  0.00           C  
HETATM   12  C10 UNL     1       4.003  -0.190  -0.029  1.00  0.00           C  
HETATM   13  O3  UNL     1       4.934   0.849   0.077  1.00  0.00           O  
HETATM   14  C11 UNL     1       6.285   0.536   0.241  1.00  0.00           C  
HETATM   15  C12 UNL     1       4.386  -1.514   0.023  1.00  0.00           C  
HETATM   16  C13 UNL     1       3.465  -2.536  -0.082  1.00  0.00           C  
HETATM   17  O4  UNL     1       3.840  -3.871  -0.030  1.00  0.00           O  
HETATM   18  C14 UNL     1       2.146  -2.161  -0.242  1.00  0.00           C  
HETATM   19  C15 UNL     1       1.749  -0.843  -0.296  1.00  0.00           C  
HETATM   20  O5  UNL     1       0.425  -0.450  -0.456  1.00  0.00           O  
HETATM   21  C16 UNL     1      -2.398   0.072   0.151  1.00  0.00           C  
HETATM   22  O6  UNL     1      -2.038  -1.030   0.869  1.00  0.00           O  
HETATM   23  C17 UNL     1      -2.878  -2.029   1.345  1.00  0.00           C  
HETATM   24  C18 UNL     1      -3.721   0.276  -0.171  1.00  0.00           C  
HETATM   25  H1  UNL     1      -7.450   0.765  -1.091  1.00  0.00           H  
HETATM   26  H2  UNL     1      -6.084  -0.463  -1.077  1.00  0.00           H  
HETATM   27  H3  UNL     1      -6.437   0.509   0.373  1.00  0.00           H  
HETATM   28  H4  UNL     1      -3.512   3.141  -1.865  1.00  0.00           H  
HETATM   29  H5  UNL     1      -1.170   2.845  -1.335  1.00  0.00           H  
HETATM   30  H6  UNL     1       0.064   0.799   1.192  1.00  0.00           H  
HETATM   31  H7  UNL     1       0.683   1.996  -1.568  1.00  0.00           H  
HETATM   32  H8  UNL     1       0.618   2.851   0.071  1.00  0.00           H  
HETATM   33  H9  UNL     1       6.877   1.472   0.179  1.00  0.00           H  
HETATM   34  H10 UNL     1       6.421   0.070   1.244  1.00  0.00           H  
HETATM   35  H11 UNL     1       6.605  -0.228  -0.500  1.00  0.00           H  
HETATM   36  H12 UNL     1       5.428  -1.774   0.149  1.00  0.00           H  
HETATM   37  H13 UNL     1       3.888  -4.398   0.832  1.00  0.00           H  
HETATM   38  H14 UNL     1       1.407  -2.934  -0.326  1.00  0.00           H  
HETATM   39  H15 UNL     1      -3.265  -1.796   2.379  1.00  0.00           H  
HETATM   40  H16 UNL     1      -3.742  -2.266   0.728  1.00  0.00           H  
HETATM   41  H17 UNL     1      -2.274  -2.973   1.440  1.00  0.00           H  
HETATM   42  H18 UNL     1      -4.457  -0.443   0.152  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3
CONECT    3    4    4   24
CONECT    4    5   28
CONECT    5    6    6   29
CONECT    6    7   21
CONECT    7    8   20   30
CONECT    8    9   31   32
CONECT    9   10   10   11
CONECT   11   12   12   19
CONECT   12   13   15
CONECT   13   14
CONECT   14   33   34   35
CONECT   15   16   16   36
CONECT   16   17   18
CONECT   17   37
CONECT   18   19   19   38
CONECT   19   20
CONECT   21   22   24   24
CONECT   22   23
CONECT   23   39   40   41
CONECT   24   42
END

HMDB0037315
     RDKit          3D
Cerasinone
 42 44  0  0  0  0  0  0  0  0999 V2000
   -6.4218    0.5592   -0.7473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4991    1.5279   -1.1920 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1567    1.3652   -0.8922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1983    2.2890   -1.3045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8609    2.0911   -0.9843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4502    0.9803   -0.2535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0377    0.7839    0.0772 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8221    1.8895   -0.4592 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2484    1.5583   -0.2477 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0799    2.4830   -0.1194 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6782    0.1911   -0.1895 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0031   -0.1899   -0.0290 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9337    0.8486    0.0773 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2848    0.5357    0.2406 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3855   -1.5137    0.0233 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4647   -2.5360   -0.0819 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8396   -3.8712   -0.0305 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1458   -2.1605   -0.2417 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7494   -0.8427   -0.2956 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4245   -0.4498   -0.4561 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3984    0.0716    0.1513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0380   -1.0296    0.8688 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8783   -2.0295    1.3447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7213    0.2763   -0.1709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4496    0.7648   -1.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0844   -0.4627   -1.0775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4370    0.5086    0.3728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5116    3.1407   -1.8647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1698    2.8455   -1.3348 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0640    0.7993    1.1922 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6829    1.9959   -1.5680 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6176    2.8509    0.0706 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8773    1.4723    0.1791 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4208    0.0699    1.2436 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6049   -0.2282   -0.5002 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4281   -1.7742    0.1494 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8879   -4.3982    0.8324 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4070   -2.9340   -0.3263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2645   -1.7965    2.3786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7416   -2.2655    0.7277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2742   -2.9733    1.4398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4567   -0.4429    0.1517 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  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
  6 21  1  0
 21 22  1  0
 22 23  1  0
 21 24  2  0
 24  3  1  0
 20  7  1  0
 19 11  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  5 29  1  0
  7 30  1  0
  8 31  1  0
  8 32  1  0
 14 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 17 37  1  0
 18 38  1  0
 23 39  1  0
 23 40  1  0
 23 41  1  0
 24 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
7-Hydroxy-2',4',5-trimethoxyflavanone	HMDB

Chemical Formula

C₁₈H₁₈O₆

Average Molecular Weight

330.3319

Monoisotopic Molecular Weight

330.110338308

IUPAC Name

2-(2,4-dimethoxyphenyl)-7-hydroxy-5-methoxy-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

cerasinone

CAS Registry Number

64166-14-9

SMILES

COC1=CC(OC)=C(C=C1)C1CC(=O)C2=C(OC)C=C(O)C=C2O1

InChI Identifier

InChI=1S/C18H18O6/c1-21-11-4-5-12(14(8-11)22-2)15-9-13(20)18-16(23-3)6-10(19)7-17(18)24-15/h4-8,15,19H,9H2,1-3H3

InChI Key

JVUGHKAZGNYYCA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 5-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C5 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

5-O-methylated flavonoids

Alternative Parents

Substituents

2p-methoxyflavonoid-skeleton
4p-methoxyflavonoid-skeleton
5-methoxyflavonoid-skeleton
7-hydroxyflavonoid
Flavanone
Hydroxyflavonoid
Flavan
Chromone
Chromane
Benzopyran
M-dimethoxybenzene
1-benzopyran
Dimethoxybenzene
Aryl alkyl ketone
Phenol ether
Aryl ketone
Anisole
Phenoxy compound
Methoxybenzene
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Ketone
Organoheterocyclic compound
Ether
Oxacycle
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavanones (LMPK12140530 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0037315)
Cytoplasm (HMDB: HMDB0037315)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037315)

Source

Exogenous

Food

Food (HMDB: HMDB0037315)

Fruit

Drupe

Sour cherry (FooDB: FOOD00146)

Fruits (FooDB: FOOD00871)

Endogenous

Plant

Plant (HMDB: HMDB0037315)

Not Available

Nutrient (HMDB: HMDB0037315)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	200 - 201 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	78.5 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	0.048 g/L	ALOGPS
logP	1.6	ALOGPS
logP	2.32	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	7.86	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	74.22 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	86.72 m³·mol⁻¹	ChemAxon
Polarizability	34.34 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]+	178.734	31661259
DarkChem	[M-H]-	179.37	31661259
DeepCCS	[M+H]+	177.854	30932474
DeepCCS	[M-H]-	175.496	30932474
DeepCCS	[M-2H]-	209.045	30932474
DeepCCS	[M+Na]+	184.272	30932474
AllCCS	[M+H]+	178.6	32859911
AllCCS	[M+H-H2O]+	175.3	32859911
AllCCS	[M+NH4]+	181.8	32859911
AllCCS	[M+Na]+	182.7	32859911
AllCCS	[M-H]-	181.0	32859911
AllCCS	[M+Na-2H]-	180.7	32859911
AllCCS	[M+HCOO]-	180.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cerasinone	COC1=CC(OC)=C(C=C1)C1CC(=O)C2=C(OC)C=C(O)C=C2O1	4313.7	Standard polar	33892256
Cerasinone	COC1=CC(OC)=C(C=C1)C1CC(=O)C2=C(OC)C=C(O)C=C2O1	2926.8	Standard non polar	33892256
Cerasinone	COC1=CC(OC)=C(C=C1)C1CC(=O)C2=C(OC)C=C(O)C=C2O1	3052.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cerasinone,1TMS,isomer #1	COC1=CC=C(C2CC(=O)C3=C(OC)C=C(O[Si](C)(C)C)C=C3O2)C(OC)=C1	2857.4	Semi standard non polar	33892256
Cerasinone,1TBDMS,isomer #1	COC1=CC=C(C2CC(=O)C3=C(OC)C=C(O[Si](C)(C)C(C)(C)C)C=C3O2)C(OC)=C1	3088.0	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 - Cerasinone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-0649000000-9ef46f2318f2855eab74	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cerasinone GC-MS (1 TMS) - 70eV, Positive	splash10-0079-2319000000-4c8ce066c36550546cef	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cerasinone 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 - Cerasinone 10V, Positive-QTOF	splash10-001i-0219000000-06570873b3aa80e6a62e	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cerasinone 20V, Positive-QTOF	splash10-0i0r-0936000000-ae7181c06a26a50ad35e	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cerasinone 40V, Positive-QTOF	splash10-0159-1910000000-7ac67f85284cce1494c5	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cerasinone 10V, Negative-QTOF	splash10-004i-0009000000-65d43016bb14bc1abec9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cerasinone 20V, Negative-QTOF	splash10-0200-0369000000-710eef61ab0b88fab49b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cerasinone 40V, Negative-QTOF	splash10-053r-5791000000-f9ce49340b34aad579b2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cerasinone 10V, Positive-QTOF	splash10-001i-0509000000-b32d86729342c43b4690	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cerasinone 20V, Positive-QTOF	splash10-00lu-0906000000-b4f7ec2263789b2cacae	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cerasinone 40V, Positive-QTOF	splash10-014i-0900000000-97286f22eb316576247c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cerasinone 10V, Negative-QTOF	splash10-004i-0009000000-7272262cb3813925b77d	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cerasinone 20V, Negative-QTOF	splash10-004i-0309000000-8cef8939dacad00fd328	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cerasinone 40V, Negative-QTOF	splash10-00or-3900000000-05facf4e24165d856e87	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB016334

KNApSAcK ID

C00008355

Chemspider ID

24846540

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

42608054

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1859761

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 Cerasinone (HMDB0037315)

MOL for HMDB0037315 (Cerasinone)

3D MOL for HMDB0037315 (Cerasinone)

3D SDF for HMDB0037315 (Cerasinone)

3D-SDF for HMDB0037315 (Cerasinone)

PDB for HMDB0037315 (Cerasinone)

3D PDB for HMDB0037315 (Cerasinone)

SMILES for HMDB0037315 (Cerasinone)

INCHI for HMDB0037315 (Cerasinone)

Structure for HMDB0037315 (Cerasinone)

3D Structure for HMDB0037315 (Cerasinone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra