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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:34:50 UTC

Update Date

2022-03-07 02:52:26 UTC

HMDB ID

HMDB0030110

Secondary Accession Numbers

HMDB30110

Metabolite Identification

Common Name

Celerin

Description

Celerin belongs to the class of organic compounds known as hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to the coumarin skeleton. Celerin has been detected, but not quantified in, green vegetables and wild celeries (Apium graveolens). This could make celerin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Celerin.

Structure

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

HMDB0030110
     RDKit          3D
Celerin
 35 36  0  0  0  0  0  0  0  0999 V2000
   -3.5963    0.0882    1.0538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2776    0.0646    1.0865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5265   -0.4090   -0.1253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6952   -1.9149   -0.1673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1565    0.1319   -1.3914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0831   -0.1080   -0.0489 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8841   -1.1056   -0.0670 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2235   -0.8621    0.0131 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1637   -1.8842   -0.0078 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6956   -3.2148   -0.1164 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6849    0.4232    0.1185 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0409    0.7270    0.2036 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7609    1.4602    0.1410 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2022    2.7111    0.2423 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3851    3.7334    0.2677 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8642    4.9090    0.3662 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0181    3.5696    0.1906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4548    2.2558    0.0839 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4054    1.1963    0.0587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1862   -0.2159    0.1978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1298    0.4297    1.9284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7694    0.3863    1.9836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2598   -2.2891   -1.1166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2841   -2.4145    0.7376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7909   -2.1848   -0.2443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4527   -0.6710   -2.0990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3525    0.7076   -1.9339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0561    0.7362   -1.2078 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5237   -2.1398   -0.1515 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9614   -3.3795    0.7180 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5632   -3.8844   -0.0330 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1696   -3.3148   -1.0952 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6937   -0.0487    0.1850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6645    4.4161    0.2112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5043    2.0950    0.0181 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  3  5  1  0
  3  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19  6  1  0
 19 13  2  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  4 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  5 28  1  0
  7 29  1  0
 10 30  1  0
 10 31  1  0
 10 32  1  0
 12 33  1  0
 17 34  1  0
 18 35  1  0
M  END


  Mrv0541 05061305002D          

 19 20  0  0  0  0            999 V2000
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7474    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3974    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.8875    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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    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
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  2  0  0  0  0
  7  6  2  0  0  0  0
  9  6  1  0  0  0  0
 10  8  2  0  0  0  0
 10  9  1  0  0  0  0
 11  8  1  0  0  0  0
 12  7  1  0  0  0  0
 13 11  2  0  0  0  0
 14  9  2  0  0  0  0
 14 13  1  0  0  0  0
 15  2  1  0  0  0  0
 15  3  1  0  0  0  0
 15  5  1  0  0  0  0
 15 10  1  0  0  0  0
 16 12  2  0  0  0  0
 17 13  1  0  0  0  0
 18  4  1  0  0  0  0
 18 11  1  0  0  0  0
 19 12  1  0  0  0  0
 19 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030110

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C2=C(C=CC(=O)O2)C(=C1)C(C)(C)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C15H16O4/c1-5-15(2,3)10-8-11(18-4)13(17)14-9(10)6-7-12(16)19-14/h5-8,17H,1H2,2-4H3

> <INCHI_KEY>
KATNIMBVOAPAGX-UHFFFAOYSA-N

> <FORMULA>
C15H16O4

> <MOLECULAR_WEIGHT>
260.2851

> <EXACT_MASS>
260.104859

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
27.278819853355632

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-hydroxy-7-methoxy-5-(2-methylbut-3-en-2-yl)-2H-chromen-2-one

> <ALOGPS_LOGP>
3.70

> <JCHEM_LOGP>
3.6577599773333325

> <ALOGPS_LOGS>
-3.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.690811794353959

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4929138704568645

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
73.30370000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.44e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-hydroxy-7-methoxy-5-(2-methylbut-3-en-2-yl)chromen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030110
     RDKit          3D
Celerin
 35 36  0  0  0  0  0  0  0  0999 V2000
   -3.5963    0.0882    1.0538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2776    0.0646    1.0865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5265   -0.4090   -0.1253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6952   -1.9149   -0.1673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1565    0.1319   -1.3914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0831   -0.1080   -0.0489 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8841   -1.1056   -0.0670 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2235   -0.8621    0.0131 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1637   -1.8842   -0.0078 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6956   -3.2148   -0.1164 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6849    0.4232    0.1185 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0409    0.7270    0.2036 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7609    1.4602    0.1410 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2022    2.7111    0.2423 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3851    3.7334    0.2677 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8642    4.9090    0.3662 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0181    3.5696    0.1906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4548    2.2558    0.0839 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4054    1.1963    0.0587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1862   -0.2159    0.1978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1298    0.4297    1.9284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7694    0.3863    1.9836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2598   -2.2891   -1.1166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2841   -2.4145    0.7376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7909   -2.1848   -0.2443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4527   -0.6710   -2.0990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3525    0.7076   -1.9339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0561    0.7362   -1.2078 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5237   -2.1398   -0.1515 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9614   -3.3795    0.7180 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5632   -3.8844   -0.0330 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1696   -3.3148   -1.0952 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6937   -0.0487    0.1850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6645    4.4161    0.2112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5043    2.0950    0.0181 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  3  5  1  0
  3  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19  6  1  0
 19 13  2  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  4 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  5 28  1  0
  7 29  1  0
 10 30  1  0
 10 31  1  0
 10 32  1  0
 12 33  1  0
 17 34  1  0
 18 35  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   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.128   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.208   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668   5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
CONECT    1    5                                                            
CONECT    2   15                                                            
CONECT    3   15                                                            
CONECT    4   18                                                            
CONECT    5    1   15                                                       
CONECT    6    7    9                                                       
CONECT    7    6   12                                                       
CONECT    8   10   11                                                       
CONECT    9    6   10   14                                                  
CONECT   10    8    9   15                                                  
CONECT   11    8   13   18                                                  
CONECT   12    7   16   19                                                  
CONECT   13   11   14   17                                                  
CONECT   14    9   13   19                                                  
CONECT   15    2    3    5   10                                             
CONECT   16   12                                                            
CONECT   17   13                                                            
CONECT   18    4   11                                                       
CONECT   19   12   14                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0030110
HETATM    1  C1  UNL     1      -3.596   0.088   1.054  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.278   0.065   1.087  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.526  -0.409  -0.125  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.695  -1.915  -0.167  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.156   0.132  -1.391  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.083  -0.108  -0.049  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.884  -1.106  -0.067  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.223  -0.862   0.013  1.00  0.00           C  
HETATM    9  O1  UNL     1       3.164  -1.884  -0.008  1.00  0.00           O  
HETATM   10  C9  UNL     1       2.696  -3.215  -0.116  1.00  0.00           C  
HETATM   11  C10 UNL     1       2.685   0.423   0.119  1.00  0.00           C  
HETATM   12  O2  UNL     1       4.041   0.727   0.204  1.00  0.00           O  
HETATM   13  C11 UNL     1       1.761   1.460   0.141  1.00  0.00           C  
HETATM   14  O3  UNL     1       2.202   2.711   0.242  1.00  0.00           O  
HETATM   15  C12 UNL     1       1.385   3.733   0.268  1.00  0.00           C  
HETATM   16  O4  UNL     1       1.864   4.909   0.366  1.00  0.00           O  
HETATM   17  C13 UNL     1       0.018   3.570   0.191  1.00  0.00           C  
HETATM   18  C14 UNL     1      -0.455   2.256   0.084  1.00  0.00           C  
HETATM   19  C15 UNL     1       0.405   1.196   0.059  1.00  0.00           C  
HETATM   20  H1  UNL     1      -4.186  -0.216   0.198  1.00  0.00           H  
HETATM   21  H2  UNL     1      -4.130   0.430   1.928  1.00  0.00           H  
HETATM   22  H3  UNL     1      -1.769   0.386   1.984  1.00  0.00           H  
HETATM   23  H4  UNL     1      -1.260  -2.289  -1.117  1.00  0.00           H  
HETATM   24  H5  UNL     1      -1.284  -2.415   0.738  1.00  0.00           H  
HETATM   25  H6  UNL     1      -2.791  -2.185  -0.244  1.00  0.00           H  
HETATM   26  H7  UNL     1      -2.453  -0.671  -2.099  1.00  0.00           H  
HETATM   27  H8  UNL     1      -1.352   0.708  -1.934  1.00  0.00           H  
HETATM   28  H9  UNL     1      -3.056   0.736  -1.208  1.00  0.00           H  
HETATM   29  H10 UNL     1       0.524  -2.140  -0.151  1.00  0.00           H  
HETATM   30  H11 UNL     1       1.961  -3.380   0.718  1.00  0.00           H  
HETATM   31  H12 UNL     1       3.563  -3.884  -0.033  1.00  0.00           H  
HETATM   32  H13 UNL     1       2.170  -3.315  -1.095  1.00  0.00           H  
HETATM   33  H14 UNL     1       4.694  -0.049   0.185  1.00  0.00           H  
HETATM   34  H15 UNL     1      -0.665   4.416   0.211  1.00  0.00           H  
HETATM   35  H16 UNL     1      -1.504   2.095   0.018  1.00  0.00           H  
CONECT    1    2    2   20   21
CONECT    2    3   22
CONECT    3    4    5    6
CONECT    4   23   24   25
CONECT    5   26   27   28
CONECT    6    7    7   19
CONECT    7    8   29
CONECT    8    9   11   11
CONECT    9   10
CONECT   10   30   31   32
CONECT   11   12   13
CONECT   12   33
CONECT   13   14   19   19
CONECT   14   15
CONECT   15   16   16   17
CONECT   17   18   18   34
CONECT   18   19   35
END

HMDB0030110
     RDKit          3D
Celerin
 35 36  0  0  0  0  0  0  0  0999 V2000
   -3.5963    0.0882    1.0538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2776    0.0646    1.0865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5265   -0.4090   -0.1253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6952   -1.9149   -0.1673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1565    0.1319   -1.3914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0831   -0.1080   -0.0489 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8841   -1.1056   -0.0670 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2235   -0.8621    0.0131 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1637   -1.8842   -0.0078 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6956   -3.2148   -0.1164 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6849    0.4232    0.1185 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0409    0.7270    0.2036 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7609    1.4602    0.1410 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2022    2.7111    0.2423 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3851    3.7334    0.2677 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8642    4.9090    0.3662 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0181    3.5696    0.1906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4548    2.2558    0.0839 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4054    1.1963    0.0587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1862   -0.2159    0.1978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1298    0.4297    1.9284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7694    0.3863    1.9836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2598   -2.2891   -1.1166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2841   -2.4145    0.7376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7909   -2.1848   -0.2443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4527   -0.6710   -2.0990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3525    0.7076   -1.9339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0561    0.7362   -1.2078 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5237   -2.1398   -0.1515 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9614   -3.3795    0.7180 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5632   -3.8844   -0.0330 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1696   -3.3148   -1.0952 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6937   -0.0487    0.1850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6645    4.4161    0.2112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5043    2.0950    0.0181 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  3  5  1  0
  3  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19  6  1  0
 19 13  2  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  4 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  5 28  1  0
  7 29  1  0
 10 30  1  0
 10 31  1  0
 10 32  1  0
 12 33  1  0
 17 34  1  0
 18 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-(1,1-Dimethyl-2-propenyl)-8-hydroxy-7-methoxy-2H-1-benzopyran-2-one	HMDB

Chemical Formula

C₁₅H₁₆O₄

Average Molecular Weight

260.2851

Monoisotopic Molecular Weight

260.104859

IUPAC Name

8-hydroxy-7-methoxy-5-(2-methylbut-3-en-2-yl)-2H-chromen-2-one

Traditional Name

8-hydroxy-7-methoxy-5-(2-methylbut-3-en-2-yl)chromen-2-one

CAS Registry Number

73815-20-0

SMILES

COC1=C(O)C2=C(C=CC(=O)O2)C(=C1)C(C)(C)C=C

InChI Identifier

InChI=1S/C15H16O4/c1-5-15(2,3)10-8-11(18-4)13(17)14-9(10)6-7-12(16)19-14/h5-8,17H,1H2,2-4H3

InChI Key

KATNIMBVOAPAGX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to the coumarin skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Hydroxycoumarins

Direct Parent

Hydroxycoumarins

Alternative Parents

Substituents

Hydroxycoumarin
Benzopyran
1-benzopyran
Anisole
Alkyl aryl ether
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Lactone
Ether
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0030110)
Cell membrane (HMDB: HMDB0030110)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030110)

Source

Endogenous

Endogenous (HMDB: HMDB0030110)

Plant

Plant (HMDB: HMDB0030110)

Exogenous

Food

Food (HMDB: HMDB0030110)

Herb and spice

Spice

Wild celery (FooDB: FOOD00015)

Vegetable

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Exogenous (HMDB: HMDB0030110)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	158 - 159.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	44.73 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	0.074 g/L	ALOGPS
logP	3.7	ALOGPS
logP	3.66	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	10.69	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	73.3 m³·mol⁻¹	ChemAxon
Polarizability	27.28 Å³	ChemAxon
Number of Rings	2	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]+	159.966	31661259
DarkChem	[M-H]-	160.416	31661259
DeepCCS	[M+H]+	165.223	30932474
DeepCCS	[M-H]-	162.865	30932474
DeepCCS	[M-2H]-	195.76	30932474
DeepCCS	[M+Na]+	171.316	30932474
AllCCS	[M+H]+	156.9	32859911
AllCCS	[M+H-H2O]+	153.1	32859911
AllCCS	[M+NH4]+	160.4	32859911
AllCCS	[M+Na]+	161.4	32859911
AllCCS	[M-H]-	162.1	32859911
AllCCS	[M+Na-2H]-	161.8	32859911
AllCCS	[M+HCOO]-	161.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.9 minutes	32390414
Predicted by Siyang on May 30, 2022	13.4152 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.02 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2141.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	343.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	172.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	197.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	114.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	584.5 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	695.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	76.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1114.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	435.0 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	1377.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	340.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	369.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	331.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	338.8 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	8.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Celerin	COC1=C(O)C2=C(C=CC(=O)O2)C(=C1)C(C)(C)C=C	2888.8	Standard polar	33892256
Celerin	COC1=C(O)C2=C(C=CC(=O)O2)C(=C1)C(C)(C)C=C	2196.9	Standard non polar	33892256
Celerin	COC1=C(O)C2=C(C=CC(=O)O2)C(=C1)C(C)(C)C=C	2245.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Celerin,1TMS,isomer #1	C=CC(C)(C)C1=CC(OC)=C(O[Si](C)(C)C)C2=C1C=CC(=O)O2	2300.5	Semi standard non polar	33892256
Celerin,1TBDMS,isomer #1	C=CC(C)(C)C1=CC(OC)=C(O[Si](C)(C)C(C)(C)C)C2=C1C=CC(=O)O2	2526.8	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 - Celerin GC-MS (Non-derivatized) - 70eV, Positive	splash10-00l2-1190000000-2e9c3f7107f3b3b5afb9	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Celerin GC-MS (1 TMS) - 70eV, Positive	splash10-0609-5096000000-65e1b9aabfd195b0d681	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Celerin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Celerin 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 - Celerin 10V, Positive-QTOF	splash10-03di-0090000000-31d6fcd8accd497f8122	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Celerin 20V, Positive-QTOF	splash10-03di-1090000000-326e6df4234bf47b578c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Celerin 40V, Positive-QTOF	splash10-0i00-3590000000-1f447fb4ea39688a3367	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Celerin 10V, Negative-QTOF	splash10-0a4i-0090000000-b356f884751fb099cd4c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Celerin 20V, Negative-QTOF	splash10-0a4i-0090000000-7a5c6fed30fe6e424aff	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Celerin 40V, Negative-QTOF	splash10-000m-1930000000-ac59ec50a820ec7429b0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Celerin 10V, Negative-QTOF	splash10-0a4i-0090000000-07597ad49430bb51c246	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Celerin 20V, Negative-QTOF	splash10-0a6r-0290000000-a016184895e85b1d094e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Celerin 40V, Negative-QTOF	splash10-004i-0910000000-80db532eab3d414803db	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Celerin 10V, Positive-QTOF	splash10-03di-0090000000-7c144831ce29a88ab6f9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Celerin 20V, Positive-QTOF	splash10-03dr-0090000000-0f8f85350df0e55f11a0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Celerin 40V, Positive-QTOF	splash10-0ftb-8980000000-0ddf989829c993c35274	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB001910

KNApSAcK ID

C00054485

Chemspider ID

137753

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

156431

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1817121

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 Celerin (HMDB0030110)

MOL for HMDB0030110 (Celerin)

3D MOL for HMDB0030110 (Celerin)

3D SDF for HMDB0030110 (Celerin)

3D-SDF for HMDB0030110 (Celerin)

PDB for HMDB0030110 (Celerin)

3D PDB for HMDB0030110 (Celerin)

SMILES for HMDB0030110 (Celerin)

INCHI for HMDB0030110 (Celerin)

Structure for HMDB0030110 (Celerin)

3D Structure for HMDB0030110 (Celerin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra