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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:39:35 UTC

Update Date

2022-03-07 02:52:44 UTC

HMDB ID

HMDB0030882

Secondary Accession Numbers

HMDB30882

Metabolite Identification

Common Name

(S)-Rutaretin

Description

(S)-Rutaretin 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 (S)-Rutaretin has been detected, but not quantified in, wild celeries (Apium graveolens). This could make (S)-rutaretin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (S)-Rutaretin.

Structure

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

HMDB0030882
     RDKit          3D
(S)-Rutaretin
 33 35  0  0  0  0  0  0  0  0999 V2000
   -3.8133    1.2716    0.5231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1788    0.2372   -0.3823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4704   -1.1182    0.1664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7755    0.3403   -1.6353 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7163    0.5519   -0.5037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9521   -0.4052   -1.3519 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4306   -0.2914   -0.7993 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6881   -0.5919   -1.2725 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8436   -0.3916   -0.5548 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0715   -0.7157   -1.0911 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1814   -0.4844   -0.3077 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9993    0.0488    0.9453 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0118    0.2537    1.6453 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8058    0.3352    1.3973 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6975    0.1464    0.7171 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4612    0.4636    1.2350 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3873    0.9963    2.5086 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3173    0.2414    0.4668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0401    0.4668    0.7377 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2089    2.1454   -0.0406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6479    0.8311    1.1341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0247    1.6844    1.1994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5524   -1.1441    0.4416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9228   -1.3005    1.1246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3228   -1.9396   -0.5604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7329    0.1717   -1.6388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6234    1.5623   -0.9375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9765   -0.1790   -2.4349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2747   -1.4515   -1.1409 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7604   -1.0086   -2.2659 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1968   -1.1326   -2.0743 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1418   -0.7320   -0.7128 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2391    1.1384    3.0243 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19  5  1  0
 18  7  1  0
 15  9  2  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  8 30  1  0
 10 31  1  0
 11 32  1  0
 17 33  1  0
M  END


  Mrv0541 05061305342D          

 19 21  0  0  0  0            999 V2000
   -2.2784    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534    0.6979    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
    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
   -1.4534    1.5229    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
   -1.4534    2.3479    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  3  1  0  0  0  0
  7  5  2  0  0  0  0
  8  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  6  1  0  0  0  0
 10  4  1  0  0  0  0
 12  7  1  0  0  0  0
 12 11  2  0  0  0  0
 13  8  2  0  0  0  0
 13 11  1  0  0  0  0
 14  1  1  0  0  0  0
 14  2  1  0  0  0  0
 14  9  1  0  0  0  0
 15 10  2  0  0  0  0
 16 11  1  0  0  0  0
 17 14  1  0  0  0  0
 18  9  1  0  0  0  0
 18 13  1  0  0  0  0
 19 10  1  0  0  0  0
 19 12  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030882

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C14H14O5/c1-14(2,17)9-6-8-5-7-3-4-10(15)19-12(7)11(16)13(8)18-9/h3-5,9,16-17H,6H2,1-2H3

> <INCHI_KEY>
FVFQELHSZVFPDZ-UHFFFAOYSA-N

> <FORMULA>
C14H14O5

> <MOLECULAR_WEIGHT>
262.258

> <EXACT_MASS>
262.084123558

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
26.5358211256679

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.82

> <JCHEM_LOGP>
2.078828285333333

> <ALOGPS_LOGS>
-2.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.296996011757301

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.739061745297457

> <JCHEM_PKA_STRONGEST_BASIC>
-3.106456812414117

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
68.32180000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.42e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030882
     RDKit          3D
(S)-Rutaretin
 33 35  0  0  0  0  0  0  0  0999 V2000
   -3.8133    1.2716    0.5231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1788    0.2372   -0.3823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4704   -1.1182    0.1664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7755    0.3403   -1.6353 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7163    0.5519   -0.5037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9521   -0.4052   -1.3519 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4306   -0.2914   -0.7993 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6881   -0.5919   -1.2725 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8436   -0.3916   -0.5548 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0715   -0.7157   -1.0911 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1814   -0.4844   -0.3077 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9993    0.0488    0.9453 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0118    0.2537    1.6453 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8058    0.3352    1.3973 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6975    0.1464    0.7171 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4612    0.4636    1.2350 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3873    0.9963    2.5086 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3173    0.2414    0.4668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0401    0.4668    0.7377 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2089    2.1454   -0.0406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6479    0.8311    1.1341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0247    1.6844    1.1994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5524   -1.1441    0.4416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9228   -1.3005    1.1246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3228   -1.9396   -0.5604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7329    0.1717   -1.6388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6234    1.5623   -0.9375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9765   -0.1790   -2.4349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2747   -1.4515   -1.1409 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7604   -1.0086   -2.2659 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1968   -1.1326   -2.0743 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1418   -0.7320   -0.7128 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2391    1.1384    3.0243 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19  5  1  0
 18  7  1  0
 15  9  2  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  8 30  1  0
 10 31  1  0
 11 32  1  0
 17 33  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      -4.253   2.843   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.713   1.303   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       3.864   2.073   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.197   2.073   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.173   2.843   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.531   3.613   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.530   4.383   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.864   3.613   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.197   3.613   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.713   2.843   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      -2.713   4.383   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -0.268   4.089   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.198   4.383   0.000  0.00  0.00           O+0
CONECT    1   14                                                            
CONECT    2   14                                                            
CONECT    3    4    7                                                       
CONECT    4    3   10                                                       
CONECT    5    7    8                                                       
CONECT    6    8    9                                                       
CONECT    7    3    5   12                                                  
CONECT    8    5    6   13                                                  
CONECT    9    6   14   18                                                  
CONECT   10    4   15   19                                                  
CONECT   11   12   13   16                                                  
CONECT   12    7   11   19                                                  
CONECT   13    8   11   18                                                  
CONECT   14    1    2    9   17                                             
CONECT   15   10                                                            
CONECT   16   11                                                            
CONECT   17   14                                                            
CONECT   18    9   13                                                       
CONECT   19   10   12                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0030882
HETATM    1  C1  UNL     1      -3.813   1.272   0.523  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.179   0.237  -0.382  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.470  -1.118   0.166  1.00  0.00           C  
HETATM    4  O1  UNL     1      -3.776   0.340  -1.635  1.00  0.00           O  
HETATM    5  C4  UNL     1      -1.716   0.552  -0.504  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.952  -0.405  -1.352  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.431  -0.291  -0.799  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.688  -0.592  -1.273  1.00  0.00           C  
HETATM    9  C8  UNL     1       2.844  -0.392  -0.555  1.00  0.00           C  
HETATM   10  C9  UNL     1       4.071  -0.716  -1.091  1.00  0.00           C  
HETATM   11  C10 UNL     1       5.181  -0.484  -0.308  1.00  0.00           C  
HETATM   12  C11 UNL     1       4.999   0.049   0.945  1.00  0.00           C  
HETATM   13  O2  UNL     1       6.012   0.254   1.645  1.00  0.00           O  
HETATM   14  O3  UNL     1       3.806   0.335   1.397  1.00  0.00           O  
HETATM   15  C12 UNL     1       2.698   0.146   0.717  1.00  0.00           C  
HETATM   16  C13 UNL     1       1.461   0.464   1.235  1.00  0.00           C  
HETATM   17  O4  UNL     1       1.387   0.996   2.509  1.00  0.00           O  
HETATM   18  C14 UNL     1       0.317   0.241   0.467  1.00  0.00           C  
HETATM   19  O5  UNL     1      -1.040   0.467   0.738  1.00  0.00           O  
HETATM   20  H1  UNL     1      -4.209   2.145  -0.041  1.00  0.00           H  
HETATM   21  H2  UNL     1      -4.648   0.831   1.134  1.00  0.00           H  
HETATM   22  H3  UNL     1      -3.025   1.684   1.199  1.00  0.00           H  
HETATM   23  H4  UNL     1      -4.552  -1.144   0.442  1.00  0.00           H  
HETATM   24  H5  UNL     1      -2.923  -1.300   1.125  1.00  0.00           H  
HETATM   25  H6  UNL     1      -3.323  -1.940  -0.560  1.00  0.00           H  
HETATM   26  H7  UNL     1      -4.733   0.172  -1.639  1.00  0.00           H  
HETATM   27  H8  UNL     1      -1.623   1.562  -0.937  1.00  0.00           H  
HETATM   28  H9  UNL     1      -0.976  -0.179  -2.435  1.00  0.00           H  
HETATM   29  H10 UNL     1      -1.275  -1.452  -1.141  1.00  0.00           H  
HETATM   30  H11 UNL     1       1.760  -1.009  -2.266  1.00  0.00           H  
HETATM   31  H12 UNL     1       4.197  -1.133  -2.074  1.00  0.00           H  
HETATM   32  H13 UNL     1       6.142  -0.732  -0.713  1.00  0.00           H  
HETATM   33  H14 UNL     1       2.239   1.138   3.024  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3    4    5
CONECT    3   23   24   25
CONECT    4   26
CONECT    5    6   19   27
CONECT    6    7   28   29
CONECT    7    8    8   18
CONECT    8    9   30
CONECT    9   10   15   15
CONECT   10   11   11   31
CONECT   11   12   32
CONECT   12   13   13   14
CONECT   14   15
CONECT   15   16
CONECT   16   17   18   18
CONECT   17   33
CONECT   18   19
END

HMDB0030882
     RDKit          3D
(S)-Rutaretin
 33 35  0  0  0  0  0  0  0  0999 V2000
   -3.8133    1.2716    0.5231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1788    0.2372   -0.3823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4704   -1.1182    0.1664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7755    0.3403   -1.6353 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7163    0.5519   -0.5037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9521   -0.4052   -1.3519 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4306   -0.2914   -0.7993 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6881   -0.5919   -1.2725 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8436   -0.3916   -0.5548 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0715   -0.7157   -1.0911 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1814   -0.4844   -0.3077 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9993    0.0488    0.9453 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0118    0.2537    1.6453 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8058    0.3352    1.3973 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6975    0.1464    0.7171 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4612    0.4636    1.2350 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3873    0.9963    2.5086 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3173    0.2414    0.4668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0401    0.4668    0.7377 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2089    2.1454   -0.0406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6479    0.8311    1.1341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0247    1.6844    1.1994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5524   -1.1441    0.4416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9228   -1.3005    1.1246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3228   -1.9396   -0.5604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7329    0.1717   -1.6388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6234    1.5623   -0.9375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9765   -0.1790   -2.4349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2747   -1.4515   -1.1409 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7604   -1.0086   -2.2659 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1968   -1.1326   -2.0743 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1418   -0.7320   -0.7128 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2391    1.1384    3.0243 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19  5  1  0
 18  7  1  0
 15  9  2  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  8 30  1  0
 10 31  1  0
 11 32  1  0
 17 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₄H₁₄O₅

Average Molecular Weight

262.258

Monoisotopic Molecular Weight

262.084123558

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C14H14O5/c1-14(2,17)9-6-8-5-7-3-4-10(15)19-12(7)11(16)13(8)18-9/h3-5,9,16-17H,6H2,1-2H3

InChI Key

FVFQELHSZVFPDZ-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
Tertiary alcohol
Lactone
Oxacycle
Ether
Organoheterocyclic compound
Alcohol
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0030882)
Extracellular (HMDB: HMDB0030882)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030882)

Source

Endogenous

Endogenous (HMDB: HMDB0030882)

Plant

Plant (HMDB: HMDB0030882)

Exogenous

Food

Food (HMDB: HMDB0030882)

Herb and spice

Spice

Wild celery (FooDB: FOOD00015)

Process

Not Available

Role

Not Available

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	0.84 g/L	ALOGPS
logP	1.82	ALOGPS
logP	2.08	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	10.74	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	68.32 m³·mol⁻¹	ChemAxon
Polarizability	26.54 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]+	159.288	31661259
DarkChem	[M-H]-	158.102	31661259
DeepCCS	[M+H]+	161.329	30932474
DeepCCS	[M-H]-	158.971	30932474
DeepCCS	[M-2H]-	191.857	30932474
DeepCCS	[M+Na]+	167.422	30932474
AllCCS	[M+H]+	158.8	32859911
AllCCS	[M+H-H2O]+	155.0	32859911
AllCCS	[M+NH4]+	162.3	32859911
AllCCS	[M+Na]+	163.4	32859911
AllCCS	[M-H]-	162.9	32859911
AllCCS	[M+Na-2H]-	162.5	32859911
AllCCS	[M+HCOO]-	162.2	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.	4.19 minutes	32390414
Predicted by Siyang on May 30, 2022	10.6142 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.87 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	39.0 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1522.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	289.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	137.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	172.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	60.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	471.7 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	382.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	116.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	726.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	313.6 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	1050.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	248.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	287.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	332.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	329.3 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	61.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(S)-Rutaretin	CC(C)(O)C1CC2=C(O1)C(O)=C1OC(=O)C=CC1=C2	3445.9	Standard polar	33892256
(S)-Rutaretin	CC(C)(O)C1CC2=C(O1)C(O)=C1OC(=O)C=CC1=C2	2339.5	Standard non polar	33892256
(S)-Rutaretin	CC(C)(O)C1CC2=C(O1)C(O)=C1OC(=O)C=CC1=C2	2384.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(S)-Rutaretin,1TMS,isomer #1	CC(C)(O[Si](C)(C)C)C1CC2=CC3=C(OC(=O)C=C3)C(O)=C2O1	2520.2	Semi standard non polar	33892256
(S)-Rutaretin,1TMS,isomer #2	CC(C)(O)C1CC2=CC3=C(OC(=O)C=C3)C(O[Si](C)(C)C)=C2O1	2446.0	Semi standard non polar	33892256
(S)-Rutaretin,2TMS,isomer #1	CC(C)(O[Si](C)(C)C)C1CC2=CC3=C(OC(=O)C=C3)C(O[Si](C)(C)C)=C2O1	2538.4	Semi standard non polar	33892256
(S)-Rutaretin,1TBDMS,isomer #1	CC(C)(O[Si](C)(C)C(C)(C)C)C1CC2=CC3=C(OC(=O)C=C3)C(O)=C2O1	2752.4	Semi standard non polar	33892256
(S)-Rutaretin,1TBDMS,isomer #2	CC(C)(O)C1CC2=CC3=C(OC(=O)C=C3)C(O[Si](C)(C)C(C)(C)C)=C2O1	2684.2	Semi standard non polar	33892256
(S)-Rutaretin,2TBDMS,isomer #1	CC(C)(O[Si](C)(C)C(C)(C)C)C1CC2=CC3=C(OC(=O)C=C3)C(O[Si](C)(C)C(C)(C)C)=C2O1	2977.3	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 - (S)-Rutaretin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4l-8290000000-38de7d1f94973817e284	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (S)-Rutaretin GC-MS (2 TMS) - 70eV, Positive	splash10-00al-9316000000-2fbbfc1729ced72ba498	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (S)-Rutaretin 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 - (S)-Rutaretin 10V, Positive-QTOF	splash10-03dj-0090000000-1d5beb3d34465de789d6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Rutaretin 20V, Positive-QTOF	splash10-03dj-0190000000-faeced033e232a9b26ee	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Rutaretin 40V, Positive-QTOF	splash10-0fvi-5490000000-ff86400a73119da8d078	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Rutaretin 10V, Negative-QTOF	splash10-03di-0090000000-00c3cb5112421dece865	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Rutaretin 20V, Negative-QTOF	splash10-03dl-0190000000-aa9e3091b3cfffc7efa5	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Rutaretin 40V, Negative-QTOF	splash10-0ldl-2930000000-0fd02ff0bc7fa12f1cbf	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Rutaretin 10V, Positive-QTOF	splash10-03di-0090000000-8ac9d9fe7456d72f2493	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Rutaretin 20V, Positive-QTOF	splash10-03dj-0190000000-c9b20ec1aacd210cf2ed	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Rutaretin 40V, Positive-QTOF	splash10-05r0-2920000000-aa4974e1e8ca8d03a4cd	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Rutaretin 10V, Negative-QTOF	splash10-03di-0090000000-93bfdf863c3cb5cacdff	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Rutaretin 20V, Negative-QTOF	splash10-03di-0290000000-7314e939edf66b1b6851	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Rutaretin 40V, Negative-QTOF	splash10-004j-0910000000-fb2ad7f575d00093b6bf	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

FDB002844

KNApSAcK ID

Not Available

Chemspider ID

9283262

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11108126

PDB ID

Not Available

ChEBI ID

174445

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.. .

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

(S)-Rutaretin → 3,4,5-trihydroxy-6-{[2-(2-hydroxypropan-2-yl)-7-oxo-2H,3H,7H-furo[3,2-g]chromen-9-yl]oxy}oxane-2-carboxylic acid	details

Showing metabocard for (S)-Rutaretin (HMDB0030882)

MOL for HMDB0030882 ((S)-Rutaretin)

3D MOL for HMDB0030882 ((S)-Rutaretin)

3D SDF for HMDB0030882 ((S)-Rutaretin)

3D-SDF for HMDB0030882 ((S)-Rutaretin)

PDB for HMDB0030882 ((S)-Rutaretin)

3D PDB for HMDB0030882 ((S)-Rutaretin)

SMILES for HMDB0030882 ((S)-Rutaretin)

INCHI for HMDB0030882 ((S)-Rutaretin)

Structure for HMDB0030882 ((S)-Rutaretin)

3D Structure for HMDB0030882 ((S)-Rutaretin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions