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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 02:29:08 UTC

Update Date

2022-03-07 02:56:46 UTC

HMDB ID

HMDB0040876

Secondary Accession Numbers

HMDB40876

Metabolite Identification

Common Name

(R)-Apiumetin

Description

(R)-Apiumetin belongs to the class of organic compounds known as psoralens. These are organic compounds containing a psoralen moiety, which consists of a furan fused to a chromenone to for 7H-furo[3,2-g]chromen-7-one (R)-Apiumetin has been detected, but not quantified in, green vegetables. This could make (R)-apiumetin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (R)-Apiumetin.

Structure

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

HMDB0040876
     RDKit          3D
(R)-Apiumetin
 30 32  0  0  0  0  0  0  0  0999 V2000
   -4.5316   -0.0800    0.7566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4487   -0.1709   -0.0116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6194   -0.5296   -1.4387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1464    0.0947    0.6200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3854    1.2268    0.0262 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0251    0.7305    0.0527 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2209    1.4390   -0.1076 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3995    0.7310   -0.0382 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6271    1.3694   -0.1884 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7583    0.5950   -0.1065 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6163   -0.7499    0.1165 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6537   -1.4789    0.1947 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4719   -1.3627    0.2594 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3718   -0.6334    0.1835 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1883   -1.3210    0.3400 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1012   -2.6858    0.5640 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0183   -0.6200    0.2728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3399   -1.0731    0.3967 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5417   -0.2659    0.3497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5028    0.1752    1.8052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1611    0.2475   -2.0092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6670   -0.8408   -1.9150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2813   -1.4418   -1.4884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2251    0.2180    1.7060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6217    1.4301   -1.0341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4918    2.1881    0.5731 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2084    2.5014   -0.2789 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6231    2.4307   -0.3599 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7296    1.0649   -0.2196 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9872   -3.1884    0.6114 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18  4  1  0
 17  6  1  0
 14  8  2  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  7 27  1  0
  9 28  1  0
 10 29  1  0
 16 30  1  0
M  END


  Mrv0541 05061312122D          

 18 20  0  0  0  0            999 V2000
   -1.8659    0.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8659    2.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  7  1  2  0  0  0  0
  7  2  1  0  0  0  0
  8  3  1  0  0  0  0
  8  5  2  0  0  0  0
  9  5  1  0  0  0  0
  9  6  1  0  0  0  0
 10  6  1  0  0  0  0
 10  7  1  0  0  0  0
 11  4  1  0  0  0  0
 13  8  1  0  0  0  0
 13 12  2  0  0  0  0
 14  9  2  0  0  0  0
 14 12  1  0  0  0  0
 15 11  2  0  0  0  0
 16 12  1  0  0  0  0
 17 10  1  0  0  0  0
 17 14  1  0  0  0  0
 18 11  1  0  0  0  0
 18 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0040876

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=C)C1CC2=C(O1)C(O)=C1OC(=O)C=CC1=C2

> <INCHI_IDENTIFIER>
InChI=1S/C14H12O4/c1-7(2)10-6-9-5-8-3-4-11(15)18-13(8)12(16)14(9)17-10/h3-5,10,16H,1,6H2,2H3

> <INCHI_KEY>
VIUKEEZPYOJNOJ-UHFFFAOYSA-N

> <FORMULA>
C14H12O4

> <MOLECULAR_WEIGHT>
244.2427

> <EXACT_MASS>
244.073558872

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
24.995103135187925

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
9-hydroxy-2-(prop-1-en-2-yl)-2H,3H,7H-furo[3,2-g]chromen-7-one

> <ALOGPS_LOGP>
2.26

> <JCHEM_LOGP>
3.046389699333333

> <ALOGPS_LOGS>
-2.50

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.730122583496085

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5000248590384375

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
66.41720000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.76e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9-hydroxy-2-(prop-1-en-2-yl)-2H,3H-furo[3,2-g]chromen-7-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0040876
     RDKit          3D
(R)-Apiumetin
 30 32  0  0  0  0  0  0  0  0999 V2000
   -4.5316   -0.0800    0.7566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4487   -0.1709   -0.0116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6194   -0.5296   -1.4387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1464    0.0947    0.6200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3854    1.2268    0.0262 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0251    0.7305    0.0527 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2209    1.4390   -0.1076 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3995    0.7310   -0.0382 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6271    1.3694   -0.1884 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7583    0.5950   -0.1065 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6163   -0.7499    0.1165 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6537   -1.4789    0.1947 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4719   -1.3627    0.2594 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3718   -0.6334    0.1835 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1883   -1.3210    0.3400 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1012   -2.6858    0.5640 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0183   -0.6200    0.2728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3399   -1.0731    0.3967 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5417   -0.2659    0.3497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5028    0.1752    1.8052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1611    0.2475   -2.0092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6670   -0.8408   -1.9150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2813   -1.4418   -1.4884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2251    0.2180    1.7060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6217    1.4301   -1.0341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4918    2.1881    0.5731 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2084    2.5014   -0.2789 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6231    2.4307   -0.3599 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7296    1.0649   -0.2196 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9872   -3.1884    0.6114 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18  4  1  0
 17  6  1  0
 14  8  2  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  7 27  1  0
  9 28  1  0
 10 29  1  0
 16 30  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      -3.483   1.509   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.483   4.176   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.198   1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.531   2.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.530   1.303   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.268   1.597   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.713   2.843   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.864   2.073   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.197   2.073   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.173   2.843   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.531   3.613   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.530   4.383   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.864   3.613   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.197   3.613   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       7.865   4.383   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       2.530   5.923   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -0.268   4.089   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       5.198   4.383   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2    7                                                            
CONECT    3    4    8                                                       
CONECT    4    3   11                                                       
CONECT    5    8    9                                                       
CONECT    6    9   10                                                       
CONECT    7    1    2   10                                                  
CONECT    8    3    5   13                                                  
CONECT    9    5    6   14                                                  
CONECT   10    6    7   17                                                  
CONECT   11    4   15   18                                                  
CONECT   12   13   14   16                                                  
CONECT   13    8   12   18                                                  
CONECT   14    9   12   17                                                  
CONECT   15   11                                                            
CONECT   16   12                                                            
CONECT   17   10   14                                                       
CONECT   18   11   13                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

COMPND    HMDB0040876
HETATM    1  C1  UNL     1      -4.532  -0.080   0.757  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.449  -0.171  -0.012  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.619  -0.530  -1.439  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.146   0.095   0.620  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.385   1.227   0.026  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.025   0.730   0.053  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.221   1.439  -0.108  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.399   0.731  -0.038  1.00  0.00           C  
HETATM    9  C9  UNL     1       3.627   1.369  -0.188  1.00  0.00           C  
HETATM   10  C10 UNL     1       4.758   0.595  -0.106  1.00  0.00           C  
HETATM   11  C11 UNL     1       4.616  -0.750   0.116  1.00  0.00           C  
HETATM   12  O1  UNL     1       5.654  -1.479   0.195  1.00  0.00           O  
HETATM   13  O2  UNL     1       3.472  -1.363   0.259  1.00  0.00           O  
HETATM   14  C12 UNL     1       2.372  -0.633   0.184  1.00  0.00           C  
HETATM   15  C13 UNL     1       1.188  -1.321   0.340  1.00  0.00           C  
HETATM   16  O3  UNL     1       1.101  -2.686   0.564  1.00  0.00           O  
HETATM   17  C14 UNL     1      -0.018  -0.620   0.273  1.00  0.00           C  
HETATM   18  O4  UNL     1      -1.340  -1.073   0.397  1.00  0.00           O  
HETATM   19  H1  UNL     1      -5.542  -0.266   0.350  1.00  0.00           H  
HETATM   20  H2  UNL     1      -4.503   0.175   1.805  1.00  0.00           H  
HETATM   21  H3  UNL     1      -4.161   0.248  -2.009  1.00  0.00           H  
HETATM   22  H4  UNL     1      -2.667  -0.841  -1.915  1.00  0.00           H  
HETATM   23  H5  UNL     1      -4.281  -1.442  -1.488  1.00  0.00           H  
HETATM   24  H6  UNL     1      -2.225   0.218   1.706  1.00  0.00           H  
HETATM   25  H7  UNL     1      -1.622   1.430  -1.034  1.00  0.00           H  
HETATM   26  H8  UNL     1      -1.492   2.188   0.573  1.00  0.00           H  
HETATM   27  H9  UNL     1       1.208   2.501  -0.279  1.00  0.00           H  
HETATM   28  H10 UNL     1       3.623   2.431  -0.360  1.00  0.00           H  
HETATM   29  H11 UNL     1       5.730   1.065  -0.220  1.00  0.00           H  
HETATM   30  H12 UNL     1       1.987  -3.188   0.611  1.00  0.00           H  
CONECT    1    2    2   19   20
CONECT    2    3    4
CONECT    3   21   22   23
CONECT    4    5   18   24
CONECT    5    6   25   26
CONECT    6    7    7   17
CONECT    7    8   27
CONECT    8    9   14   14
CONECT    9   10   10   28
CONECT   10   11   29
CONECT   11   12   12   13
CONECT   13   14
CONECT   14   15
CONECT   15   16   17   17
CONECT   16   30
CONECT   17   18
END

HMDB0040876
     RDKit          3D
(R)-Apiumetin
 30 32  0  0  0  0  0  0  0  0999 V2000
   -4.5316   -0.0800    0.7566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4487   -0.1709   -0.0116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6194   -0.5296   -1.4387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1464    0.0947    0.6200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3854    1.2268    0.0262 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0251    0.7305    0.0527 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2209    1.4390   -0.1076 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3995    0.7310   -0.0382 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6271    1.3694   -0.1884 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7583    0.5950   -0.1065 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6163   -0.7499    0.1165 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6537   -1.4789    0.1947 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4719   -1.3627    0.2594 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3718   -0.6334    0.1835 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1883   -1.3210    0.3400 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1012   -2.6858    0.5640 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0183   -0.6200    0.2728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3399   -1.0731    0.3967 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5417   -0.2659    0.3497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5028    0.1752    1.8052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1611    0.2475   -2.0092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6670   -0.8408   -1.9150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2813   -1.4418   -1.4884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2251    0.2180    1.7060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6217    1.4301   -1.0341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4918    2.1881    0.5731 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2084    2.5014   -0.2789 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6231    2.4307   -0.3599 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7296    1.0649   -0.2196 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9872   -3.1884    0.6114 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18  4  1  0
 17  6  1  0
 14  8  2  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  7 27  1  0
  9 28  1  0
 10 29  1  0
 16 30  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₄H₁₂O₄

Average Molecular Weight

244.2427

Monoisotopic Molecular Weight

244.073558872

IUPAC Name

9-hydroxy-2-(prop-1-en-2-yl)-2H,3H,7H-furo[3,2-g]chromen-7-one

Traditional Name

9-hydroxy-2-(prop-1-en-2-yl)-2H,3H-furo[3,2-g]chromen-7-one

CAS Registry Number

Not Available

SMILES

CC(=C)C1CC2=C(O1)C(O)=C1OC(=O)C=CC1=C2

InChI Identifier

InChI=1S/C14H12O4/c1-7(2)10-6-9-5-8-3-4-11(15)18-13(8)12(16)14(9)17-10/h3-5,10,16H,1,6H2,2H3

InChI Key

VIUKEEZPYOJNOJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as psoralens. These are organic compounds containing a psoralen moiety, which consists of a furan fused to a chromenone to for 7H-furo[3,2-g]chromen-7-one.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Furanocoumarins

Direct Parent

Psoralens

Alternative Parents

Substituents

Psoralen
Benzopyran
1-benzopyran
Coumaran
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Lactone
Oxacycle
Ether
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0040876)
Extracellular (HMDB: HMDB0040876)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040876)

Source

Exogenous

Exogenous (HMDB: HMDB0040876)

Food

Food (HMDB: HMDB0040876)

Herb and spice

Spice

Wild celery (FooDB: FOOD00015)

Endogenous

Plant

Plant (HMDB: HMDB0040876)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0040876)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	198 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.78 g/L	ALOGPS
logP	2.26	ALOGPS
logP	3.05	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	10.73	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	1	ChemAxon
Refractivity	66.42 m³·mol⁻¹	ChemAxon
Polarizability	25 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]+	158.753	31661259
DarkChem	[M-H]-	154.954	31661259
DeepCCS	[M+H]+	157.758	30932474
DeepCCS	[M-H]-	155.4	30932474
DeepCCS	[M-2H]-	188.367	30932474
DeepCCS	[M+Na]+	163.851	30932474
AllCCS	[M+H]+	154.3	32859911
AllCCS	[M+H-H2O]+	150.3	32859911
AllCCS	[M+NH4]+	158.1	32859911
AllCCS	[M+Na]+	159.1	32859911
AllCCS	[M-H]-	157.0	32859911
AllCCS	[M+Na-2H]-	156.4	32859911
AllCCS	[M+HCOO]-	155.8	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.	5.52 minutes	32390414
Predicted by Siyang on May 30, 2022	12.5685 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.41 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	26.9 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1783.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	380.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	169.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	206.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	97.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	555.8 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	534.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	90.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1017.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	412.7 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1328.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	315.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	365.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	368.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	329.2 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	17.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(R)-Apiumetin	CC(=C)C1CC2=C(O1)C(O)=C1OC(=O)C=CC1=C2	3244.7	Standard polar	33892256
(R)-Apiumetin	CC(=C)C1CC2=C(O1)C(O)=C1OC(=O)C=CC1=C2	2220.3	Standard non polar	33892256
(R)-Apiumetin	CC(=C)C1CC2=C(O1)C(O)=C1OC(=O)C=CC1=C2	2304.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(R)-Apiumetin,1TMS,isomer #1	C=C(C)C1CC2=CC3=C(OC(=O)C=C3)C(O[Si](C)(C)C)=C2O1	2291.2	Semi standard non polar	33892256
(R)-Apiumetin,1TBDMS,isomer #1	C=C(C)C1CC2=CC3=C(OC(=O)C=C3)C(O[Si](C)(C)C(C)(C)C)=C2O1	2505.3	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 - (R)-Apiumetin GC-MS (Non-derivatized) - 70eV, Positive	splash10-00kf-4390000000-7a586710aa44881be4ae	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-Apiumetin GC-MS (1 TMS) - 70eV, Positive	splash10-00dl-5192000000-8524562b7fd748e20a04	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-Apiumetin 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 - (R)-Apiumetin 10V, Positive-QTOF	splash10-0002-0090000000-66d4c3b1e40aaddb47fb	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Apiumetin 20V, Positive-QTOF	splash10-0002-0390000000-2a535e197aed68a0ae2a	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Apiumetin 40V, Positive-QTOF	splash10-0uxs-7950000000-e744b9847990696b0358	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Apiumetin 10V, Negative-QTOF	splash10-0006-0290000000-588dbf616f5df75b5777	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Apiumetin 20V, Negative-QTOF	splash10-0006-0490000000-8e2609c91deebb308cee	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Apiumetin 40V, Negative-QTOF	splash10-0595-3910000000-11983c2169398d0b78f8	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Apiumetin 10V, Negative-QTOF	splash10-0006-0090000000-c3ceff739ebba19f299c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Apiumetin 20V, Negative-QTOF	splash10-0006-0190000000-bb2f2400c76aeb6164ed	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Apiumetin 40V, Negative-QTOF	splash10-004j-0910000000-0f246f0ffc2700845f64	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Apiumetin 10V, Positive-QTOF	splash10-0002-0090000000-cdc531ec256a40729fd7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Apiumetin 20V, Positive-QTOF	splash10-0002-0190000000-a991a19b9d845ea44b41	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Apiumetin 40V, Positive-QTOF	splash10-004i-0910000000-cab0d21915e75b8fe053	2021-09-22	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

FDB020707

KNApSAcK ID

Not Available

Chemspider ID

35015037

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131752966

PDB ID

Not Available

ChEBI ID

174260

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for (R)-Apiumetin (HMDB0040876)

MOL for HMDB0040876 ((R)-Apiumetin)

3D MOL for HMDB0040876 ((R)-Apiumetin)

3D SDF for HMDB0040876 ((R)-Apiumetin)

3D-SDF for HMDB0040876 ((R)-Apiumetin)

PDB for HMDB0040876 ((R)-Apiumetin)

3D PDB for HMDB0040876 ((R)-Apiumetin)

SMILES for HMDB0040876 ((R)-Apiumetin)

INCHI for HMDB0040876 ((R)-Apiumetin)

Structure for HMDB0040876 ((R)-Apiumetin)

3D Structure for HMDB0040876 ((R)-Apiumetin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra