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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:37:44 UTC

Update Date

2022-03-07 02:52:36 UTC

HMDB ID

HMDB0030578

Secondary Accession Numbers

HMDB30578

Metabolite Identification

Common Name

Apigravin

Description

Apigravin belongs to the class of organic compounds known as 7-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to the C7 position the coumarin skeleton. Apigravin has been detected, but not quantified in, green vegetables and wild celeries (Apium graveolens). This could make apigravin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Apigravin.

Structure

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

HMDB0030578
     RDKit          3D
Apigravin
 35 36  0  0  0  0  0  0  0  0999 V2000
   -4.1207   -1.9061    0.4922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2313   -1.0060    1.1325 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1275   -0.4735    0.4343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8968   -1.1088    0.4343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7311   -2.2768    1.1219 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.5697   -0.2528 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5095   -1.1622   -0.3177 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3161   -0.9604    0.8901 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4596   -0.3421    0.8257 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9424    0.1583   -0.4811 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3352   -0.0987    2.0194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0527    0.6075   -0.9318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2817    1.2530   -0.9382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5015    2.4382   -1.6177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7381    3.0656   -1.6101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7402    2.4400   -0.8849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8903    2.9460   -0.8289 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5121    1.3145   -0.2460 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3469    0.7113   -0.2454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5864   -2.8162    0.1704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5889   -1.4585   -0.4079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8919   -2.1781    1.2387 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1428   -2.7586    1.1394 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0304   -0.8378   -1.2563 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3560   -2.2744   -0.4242 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9606   -1.3248    1.8332 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2026    0.8749   -0.8859 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9614    0.5966   -0.4134 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0553   -0.7293   -1.1695 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2940   -0.6542    1.9111 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5435    0.9981    2.1316 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8351   -0.4345    2.9413 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7501    1.0929   -1.5038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6858    2.8852   -2.1678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9262    3.9884   -2.1329 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  3
  9 10  1  0
  9 11  1  0
  6 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19  3  1  0
 19 13  2  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  5 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  0
 10 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 14 34  1  0
 15 35  1  0
M  END

  Mrv0541 05061305212D          

 19 20  0  0  0  0            999 V2000
    5.0013    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
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    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
    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
    2.1434    1.2375    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
   -0.7145    2.0625    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
    0.7145    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
   -1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    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
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  7  6  2  0  0  0  0
  9  1  1  0  0  0  0
  9  2  1  0  0  0  0
  9  4  2  0  0  0  0
 10  5  1  0  0  0  0
 10  8  2  0  0  0  0
 11  6  1  0  0  0  0
 11  8  1  0  0  0  0
 12  7  1  0  0  0  0
 13 10  1  0  0  0  0
 14 11  2  0  0  0  0
 15 13  2  0  0  0  0
 15 14  1  0  0  0  0
 16 12  2  0  0  0  0
 17 13  1  0  0  0  0
 18  3  1  0  0  0  0
 18 15  1  0  0  0  0
 19 12  1  0  0  0  0
 19 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030578

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C(CC=C(C)C)=CC2=C1OC(=O)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C15H16O4/c1-9(2)4-5-10-8-11-6-7-12(16)19-14(11)15(18-3)13(10)17/h4,6-8,17H,5H2,1-3H3

> <INCHI_KEY>
NYTURSQQJRVHPG-UHFFFAOYSA-N

> <FORMULA>
C15H16O4

> <MOLECULAR_WEIGHT>
260.2851

> <EXACT_MASS>
260.104859

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
27.791064538135743

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-hydroxy-8-methoxy-6-(3-methylbut-2-en-1-yl)-2H-chromen-2-one

> <ALOGPS_LOGP>
2.91

> <JCHEM_LOGP>
3.0506900273333324

> <ALOGPS_LOGS>
-3.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.204995823634663

> <JCHEM_PKA_STRONGEST_BASIC>
-4.96832550957644

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
74.23550000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.92e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-hydroxy-8-methoxy-6-(3-methylbut-2-en-1-yl)chromen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030578
     RDKit          3D
Apigravin
 35 36  0  0  0  0  0  0  0  0999 V2000
   -4.1207   -1.9061    0.4922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2313   -1.0060    1.1325 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1275   -0.4735    0.4343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8968   -1.1088    0.4343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7311   -2.2768    1.1219 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.5697   -0.2528 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5095   -1.1622   -0.3177 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3161   -0.9604    0.8901 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4596   -0.3421    0.8257 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9424    0.1583   -0.4811 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3352   -0.0987    2.0194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0527    0.6075   -0.9318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2817    1.2530   -0.9382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5015    2.4382   -1.6177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7381    3.0656   -1.6101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7402    2.4400   -0.8849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8903    2.9460   -0.8289 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5121    1.3145   -0.2460 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3469    0.7113   -0.2454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5864   -2.8162    0.1704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5889   -1.4585   -0.4079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8919   -2.1781    1.2387 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1428   -2.7586    1.1394 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0304   -0.8378   -1.2563 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3560   -2.2744   -0.4242 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9606   -1.3248    1.8332 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2026    0.8749   -0.8859 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9614    0.5966   -0.4134 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0553   -0.7293   -1.1695 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2940   -0.6542    1.9111 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5435    0.9981    2.1316 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8351   -0.4345    2.9413 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7501    1.0929   -1.5038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6858    2.8852   -2.1678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9262    3.9884   -2.1329 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  3
  9 10  1  0
  9 11  1  0
  6 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19  3  1  0
 19 13  2  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  5 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  0
 10 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 14 34  1  0
 15 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       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.667   4.620   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       5.335   4.620   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2    9                                                            
CONECT    3   18                                                            
CONECT    4    5    9                                                       
CONECT    5    4   10                                                       
CONECT    6    7   11                                                       
CONECT    7    6   12                                                       
CONECT    8   10   11                                                       
CONECT    9    1    2    4                                                  
CONECT   10    5    8   13                                                  
CONECT   11    6    8   14                                                  
CONECT   12    7   16   19                                                  
CONECT   13   10   15   17                                                  
CONECT   14   11   15   19                                                  
CONECT   15   13   14   18                                                  
CONECT   16   12                                                            
CONECT   17   13                                                            
CONECT   18    3   15                                                       
CONECT   19   12   14                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0030578
HETATM    1  C1  UNL     1      -4.121  -1.906   0.492  1.00  0.00           C  
HETATM    2  O1  UNL     1      -3.231  -1.006   1.133  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.127  -0.473   0.434  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.897  -1.109   0.434  1.00  0.00           C  
HETATM    5  O2  UNL     1      -0.731  -2.277   1.122  1.00  0.00           O  
HETATM    6  C4  UNL     1       0.155  -0.570  -0.253  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.510  -1.162  -0.318  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.316  -0.960   0.890  1.00  0.00           C  
HETATM    9  C7  UNL     1       3.460  -0.342   0.826  1.00  0.00           C  
HETATM   10  C8  UNL     1       3.942   0.158  -0.481  1.00  0.00           C  
HETATM   11  C9  UNL     1       4.335  -0.099   2.019  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.053   0.608  -0.932  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.282   1.253  -0.938  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.501   2.438  -1.618  1.00  0.00           C  
HETATM   15  C13 UNL     1      -2.738   3.066  -1.610  1.00  0.00           C  
HETATM   16  C14 UNL     1      -3.740   2.440  -0.885  1.00  0.00           C  
HETATM   17  O3  UNL     1      -4.890   2.946  -0.829  1.00  0.00           O  
HETATM   18  O4  UNL     1      -3.512   1.315  -0.246  1.00  0.00           O  
HETATM   19  C15 UNL     1      -2.347   0.711  -0.245  1.00  0.00           C  
HETATM   20  H1  UNL     1      -3.586  -2.816   0.170  1.00  0.00           H  
HETATM   21  H2  UNL     1      -4.589  -1.458  -0.408  1.00  0.00           H  
HETATM   22  H3  UNL     1      -4.892  -2.178   1.239  1.00  0.00           H  
HETATM   23  H4  UNL     1       0.143  -2.759   1.139  1.00  0.00           H  
HETATM   24  H5  UNL     1       2.030  -0.838  -1.256  1.00  0.00           H  
HETATM   25  H6  UNL     1       1.356  -2.274  -0.424  1.00  0.00           H  
HETATM   26  H7  UNL     1       1.961  -1.325   1.833  1.00  0.00           H  
HETATM   27  H8  UNL     1       3.203   0.875  -0.886  1.00  0.00           H  
HETATM   28  H9  UNL     1       4.961   0.597  -0.413  1.00  0.00           H  
HETATM   29  H10 UNL     1       4.055  -0.729  -1.170  1.00  0.00           H  
HETATM   30  H11 UNL     1       5.294  -0.654   1.911  1.00  0.00           H  
HETATM   31  H12 UNL     1       4.544   0.998   2.132  1.00  0.00           H  
HETATM   32  H13 UNL     1       3.835  -0.434   2.941  1.00  0.00           H  
HETATM   33  H14 UNL     1       0.750   1.093  -1.504  1.00  0.00           H  
HETATM   34  H15 UNL     1      -0.686   2.885  -2.168  1.00  0.00           H  
HETATM   35  H16 UNL     1      -2.926   3.988  -2.133  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3
CONECT    3    4    4   19
CONECT    4    5    6
CONECT    5   23
CONECT    6    7   12   12
CONECT    7    8   24   25
CONECT    8    9    9   26
CONECT    9   10   11
CONECT   10   27   28   29
CONECT   11   30   31   32
CONECT   12   13   33
CONECT   13   14   19   19
CONECT   14   15   15   34
CONECT   15   16   35
CONECT   16   17   17   18
CONECT   18   19
END

HMDB0030578
     RDKit          3D
Apigravin
 35 36  0  0  0  0  0  0  0  0999 V2000
   -4.1207   -1.9061    0.4922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2313   -1.0060    1.1325 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1275   -0.4735    0.4343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8968   -1.1088    0.4343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7311   -2.2768    1.1219 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.5697   -0.2528 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5095   -1.1622   -0.3177 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3161   -0.9604    0.8901 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4596   -0.3421    0.8257 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9424    0.1583   -0.4811 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3352   -0.0987    2.0194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0527    0.6075   -0.9318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2817    1.2530   -0.9382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5015    2.4382   -1.6177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7381    3.0656   -1.6101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7402    2.4400   -0.8849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8903    2.9460   -0.8289 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5121    1.3145   -0.2460 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3469    0.7113   -0.2454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5864   -2.8162    0.1704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5889   -1.4585   -0.4079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8919   -2.1781    1.2387 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1428   -2.7586    1.1394 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0304   -0.8378   -1.2563 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3560   -2.2744   -0.4242 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9606   -1.3248    1.8332 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2026    0.8749   -0.8859 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9614    0.5966   -0.4134 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0553   -0.7293   -1.1695 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2940   -0.6542    1.9111 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5435    0.9981    2.1316 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8351   -0.4345    2.9413 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7501    1.0929   -1.5038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6858    2.8852   -2.1678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9262    3.9884   -2.1329 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  3
  9 10  1  0
  9 11  1  0
  6 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19  3  1  0
 19 13  2  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  5 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  0
 10 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 14 34  1  0
 15 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
7-Hydroxy-8-methoxy-6-(3-methyl-2-butenyl)-2H-1-benzopyran-2-one	HMDB
7-Hydroxy-8-methoxy-6-prenylcoumarin	HMDB

Chemical Formula

C₁₅H₁₆O₄

Average Molecular Weight

260.2851

Monoisotopic Molecular Weight

260.104859

IUPAC Name

7-hydroxy-8-methoxy-6-(3-methylbut-2-en-1-yl)-2H-chromen-2-one

Traditional Name

7-hydroxy-8-methoxy-6-(3-methylbut-2-en-1-yl)chromen-2-one

CAS Registry Number

72963-64-5

SMILES

COC1=C(O)C(CC=C(C)C)=CC2=C1OC(=O)C=C2

InChI Identifier

InChI=1S/C15H16O4/c1-9(2)4-5-10-8-11-6-7-12(16)19-14(11)15(18-3)13(10)17/h4,6-8,17H,5H2,1-3H3

InChI Key

NYTURSQQJRVHPG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 7-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to the C7 position the coumarin skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Hydroxycoumarins

Direct Parent

7-hydroxycoumarins

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0030578)
Cell membrane (HMDB: HMDB0030578)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030578)

Source

Endogenous

Endogenous (HMDB: HMDB0030578)

Plant

Plant (HMDB: HMDB0030578)

Exogenous

Food

Food (HMDB: HMDB0030578)

Herb and spice

Spice

Wild celery (FooDB: FOOD00015)

Vegetable

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Exogenous (HMDB: HMDB0030578)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	167 - 169 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	37.57 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	0.039 g/L	ALOGPS
logP	2.91	ALOGPS
logP	3.05	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	8.2	ChemAxon
pKa (Strongest Basic)	-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	74.24 m³·mol⁻¹	ChemAxon
Polarizability	27.79 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]+	161.396	31661259
DarkChem	[M-H]-	162.435	31661259
DeepCCS	[M+H]+	164.045	30932474
DeepCCS	[M-H]-	161.687	30932474
DeepCCS	[M-2H]-	194.573	30932474
DeepCCS	[M+Na]+	170.139	30932474
AllCCS	[M+H]+	158.4	32859911
AllCCS	[M+H-H2O]+	154.6	32859911
AllCCS	[M+NH4]+	162.0	32859911
AllCCS	[M+Na]+	163.0	32859911
AllCCS	[M-H]-	162.2	32859911
AllCCS	[M+Na-2H]-	161.9	32859911
AllCCS	[M+HCOO]-	161.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Apigravin	COC1=C(O)C(CC=C(C)C)=CC2=C1OC(=O)C=C2	3438.1	Standard polar	33892256
Apigravin	COC1=C(O)C(CC=C(C)C)=CC2=C1OC(=O)C=C2	2233.7	Standard non polar	33892256
Apigravin	COC1=C(O)C(CC=C(C)C)=CC2=C1OC(=O)C=C2	2269.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Apigravin,1TMS,isomer #1	COC1=C(O[Si](C)(C)C)C(CC=C(C)C)=CC2=C1OC(=O)C=C2	2309.7	Semi standard non polar	33892256
Apigravin,1TBDMS,isomer #1	COC1=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=CC2=C1OC(=O)C=C2	2555.1	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 - Apigravin GC-MS (Non-derivatized) - 70eV, Positive	splash10-00lu-1190000000-377c7a571e0b59dc9ede	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Apigravin GC-MS (1 TMS) - 70eV, Positive	splash10-01bi-4097000000-cba173d2ca89e0c2c58f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Apigravin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Apigravin 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 - Apigravin 10V, Negative-QTOF	splash10-0a4i-0090000000-14816d746de9a02d6649	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apigravin 20V, Negative-QTOF	splash10-0a4i-0190000000-7872070c0464a4a269e0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apigravin 40V, Negative-QTOF	splash10-0005-1920000000-99fd85bdef1f58f3d689	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apigravin 10V, Negative-QTOF	splash10-0a4i-0090000000-07597ad49430bb51c246	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apigravin 20V, Negative-QTOF	splash10-0a4i-0290000000-2410cf60e295d798e394	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apigravin 40V, Negative-QTOF	splash10-02vr-0920000000-6c753cc050056bd17fe1	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apigravin 10V, Positive-QTOF	splash10-03di-0090000000-069baa528db0b6b9bf1c	2016-06-20	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apigravin 20V, Positive-QTOF	splash10-0900-1090000000-105c5209ba5bf2ee1036	2016-06-20	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apigravin 40V, Positive-QTOF	splash10-066u-7950000000-8cef089e41b0d95dfa8d	2016-06-20	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apigravin 10V, Positive-QTOF	splash10-03di-0090000000-e179edd6ab45804dd28a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apigravin 20V, Positive-QTOF	splash10-0229-0190000000-6624840c8cfa2df49665	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apigravin 40V, Positive-QTOF	splash10-0fi3-1910000000-c7ecb7ff077faadf9518	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB002469

KNApSAcK ID

C00054508

Chemspider ID

30776837

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

85982833

PDB ID

Not Available

ChEBI ID

174409

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1637281

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.. .

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

Apigravin → 3,4,5-trihydroxy-6-{[8-methoxy-6-(3-methylbut-2-en-1-yl)-2-oxo-2H-chromen-7-yl]oxy}oxane-2-carboxylic acid	details

Showing metabocard for Apigravin (HMDB0030578)

MOL for HMDB0030578 (Apigravin)

3D MOL for HMDB0030578 (Apigravin)

3D SDF for HMDB0030578 (Apigravin)

3D-SDF for HMDB0030578 (Apigravin)

PDB for HMDB0030578 (Apigravin)

3D PDB for HMDB0030578 (Apigravin)

SMILES for HMDB0030578 (Apigravin)

INCHI for HMDB0030578 (Apigravin)

Structure for HMDB0030578 (Apigravin)

3D Structure for HMDB0030578 (Apigravin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions