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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:52:02 UTC

HMDB ID

HMDB0015575

Secondary Accession Numbers

HMDB15575

Metabolite Identification

Common Name

Trioxsalen

Description

Trioxsalen, also known as trimethylpsoralen, trioxysalen or trisoralen, belongs to the group of drugs called psoralens. It is also known as a furanocoumarin (PMID: 3196695 ). Trioxsalen is a pigmenting photosensitizing agent used to treat vitiligo, a condition characterized by loss of skin color (PMID: 4828534 , 4441118 ). It is administered in conjunction with ultraviolet light A (UVA) to increase the skin's sensitivity to sunlight. Trioxsalen functions through inducing interstrand crosslinks in DNA. It has been reported that use of trioxsalen increases the chance of skin cancer and cataracts. Trioxsalen is only found in individuals that have used or taken this drug.

Structure

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

HMDB0015575
     RDKit          3D
Trioxsalen
 29 31  0  0  0  0  0  0  0  0999 V2000
    4.6360   -0.7653   -0.7007 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1992   -0.4628   -0.4666 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1964   -1.4110   -0.5843 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9884   -0.8032   -0.3018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3322   -1.1925   -0.2484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3120   -0.2969    0.0784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6353   -0.7025    0.1281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0450   -2.0856   -0.1614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5784    0.2417    0.4625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1496    1.5233    0.7253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9630    2.4416    1.0389 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8863    1.8693    0.6678 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9614    1.0095    0.3559 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3552    1.4422    0.3135 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7234    2.8435    0.6120 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3248    0.5188   -0.0189 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6330    0.6610   -0.1308 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0408   -1.4745    0.0235 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -1.1984   -1.7103 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1789    0.2040   -0.5923 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2983   -2.4603   -0.8501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5754   -2.2060   -0.4669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3741   -2.8541    0.2446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2573   -2.2286   -1.2582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0421   -2.2627    0.3323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6294   -0.0145    0.5180 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7876    2.9947    0.4055 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1417    3.5196   -0.0651 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4564    3.1498    1.6494 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17  2  1  0
 16  4  1  0
 13  6  2  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  5 22  1  0
  8 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  0
 15 27  1  0
 15 28  1  0
 15 29  1  0
M  END


  Mrv0541 02241214202D          

 17 19  0  0  0  0            999 V2000
    4.0668   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  2  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 10 14  1  0  0  0  0
 14 15  2  0  0  0  0
  7 15  1  0  0  0  0
 15 16  1  0  0  0  0
 12 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015575

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC2=CC3=C(OC(=O)C=C3C)C(C)=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C14H12O3/c1-7-4-12(15)17-14-9(3)13-10(6-11(7)14)5-8(2)16-13/h4-6H,1-3H3

> <INCHI_KEY>
FMHHVULEAZTJMA-UHFFFAOYSA-N

> <FORMULA>
C14H12O3

> <MOLECULAR_WEIGHT>
228.2433

> <EXACT_MASS>
228.07864425

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
24.77029403260193

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,5,9-trimethyl-7H-furo[3,2-g]chromen-7-one

> <ALOGPS_LOGP>
3.26

> <JCHEM_LOGP>
2.9548603333333343

> <ALOGPS_LOGS>
-3.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.6890069728978894

> <JCHEM_POLAR_SURFACE_AREA>
39.44

> <JCHEM_REFRACTIVITY>
64.8626

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.27e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
trioxsalen

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0015575
     RDKit          3D
Trioxsalen
 29 31  0  0  0  0  0  0  0  0999 V2000
    4.6360   -0.7653   -0.7007 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1992   -0.4628   -0.4666 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1964   -1.4110   -0.5843 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9884   -0.8032   -0.3018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3322   -1.1925   -0.2484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3120   -0.2969    0.0784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6353   -0.7025    0.1281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0450   -2.0856   -0.1614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5784    0.2417    0.4625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1496    1.5233    0.7253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9630    2.4416    1.0389 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8863    1.8693    0.6678 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9614    1.0095    0.3559 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3552    1.4422    0.3135 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7234    2.8435    0.6120 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3248    0.5188   -0.0189 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6330    0.6610   -0.1308 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0408   -1.4745    0.0235 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -1.1984   -1.7103 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1789    0.2040   -0.5923 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2983   -2.4603   -0.8501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5754   -2.2060   -0.4669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3741   -2.8541    0.2446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2573   -2.2286   -1.2582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0421   -2.2627    0.3323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6294   -0.0145    0.5180 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7876    2.9947    0.4055 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1417    3.5196   -0.0651 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4564    3.1498    1.6494 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17  2  1  0
 16  4  1  0
 13  6  2  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  5 22  1  0
  8 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  0
 15 27  1  0
 15 28  1  0
 15 29  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       7.591  -0.237   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.591   1.303   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.925   2.073   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.925   3.613   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      10.259   4.383   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       7.591   4.383   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.126   4.089   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.924   5.923   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.320   2.843   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   15                                                  
CONECT    8    7    2    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   14                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   10   15                                                  
CONECT   15   14    7   16                                                  
CONECT   16   15                                                            
CONECT   17   12                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

COMPND    HMDB0015575
HETATM    1  C1  UNL     1       4.636  -0.765  -0.701  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.199  -0.463  -0.467  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.196  -1.411  -0.584  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.988  -0.803  -0.302  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.332  -1.192  -0.248  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.312  -0.297   0.078  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.635  -0.703   0.128  1.00  0.00           C  
HETATM    8  C8  UNL     1      -3.045  -2.086  -0.161  1.00  0.00           C  
HETATM    9  C9  UNL     1      -3.578   0.242   0.463  1.00  0.00           C  
HETATM   10  C10 UNL     1      -3.150   1.523   0.725  1.00  0.00           C  
HETATM   11  O1  UNL     1      -3.963   2.442   1.039  1.00  0.00           O  
HETATM   12  O2  UNL     1      -1.886   1.869   0.668  1.00  0.00           O  
HETATM   13  C11 UNL     1      -0.961   1.010   0.356  1.00  0.00           C  
HETATM   14  C12 UNL     1       0.355   1.442   0.313  1.00  0.00           C  
HETATM   15  C13 UNL     1       0.723   2.843   0.612  1.00  0.00           C  
HETATM   16  C14 UNL     1       1.325   0.519  -0.019  1.00  0.00           C  
HETATM   17  O3  UNL     1       2.633   0.661  -0.131  1.00  0.00           O  
HETATM   18  H1  UNL     1       5.041  -1.474   0.023  1.00  0.00           H  
HETATM   19  H2  UNL     1       4.781  -1.198  -1.710  1.00  0.00           H  
HETATM   20  H3  UNL     1       5.179   0.204  -0.592  1.00  0.00           H  
HETATM   21  H4  UNL     1       2.298  -2.460  -0.850  1.00  0.00           H  
HETATM   22  H5  UNL     1      -0.575  -2.206  -0.467  1.00  0.00           H  
HETATM   23  H6  UNL     1      -2.374  -2.854   0.245  1.00  0.00           H  
HETATM   24  H7  UNL     1      -3.257  -2.229  -1.258  1.00  0.00           H  
HETATM   25  H8  UNL     1      -4.042  -2.263   0.332  1.00  0.00           H  
HETATM   26  H9  UNL     1      -4.629  -0.015   0.518  1.00  0.00           H  
HETATM   27  H10 UNL     1       1.788   2.995   0.405  1.00  0.00           H  
HETATM   28  H11 UNL     1       0.142   3.520  -0.065  1.00  0.00           H  
HETATM   29  H12 UNL     1       0.456   3.150   1.649  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3    3   17
CONECT    3    4   21
CONECT    4    5    5   16
CONECT    5    6   22
CONECT    6    7   13   13
CONECT    7    8    9    9
CONECT    8   23   24   25
CONECT    9   10   26
CONECT   10   11   11   12
CONECT   12   13
CONECT   13   14
CONECT   14   15   16   16
CONECT   15   27   28   29
CONECT   16   17
END

HMDB0015575
     RDKit          3D
Trioxsalen
 29 31  0  0  0  0  0  0  0  0999 V2000
    4.6360   -0.7653   -0.7007 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1992   -0.4628   -0.4666 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1964   -1.4110   -0.5843 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9884   -0.8032   -0.3018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3322   -1.1925   -0.2484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3120   -0.2969    0.0784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6353   -0.7025    0.1281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0450   -2.0856   -0.1614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5784    0.2417    0.4625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1496    1.5233    0.7253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9630    2.4416    1.0389 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8863    1.8693    0.6678 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9614    1.0095    0.3559 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3552    1.4422    0.3135 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7234    2.8435    0.6120 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3248    0.5188   -0.0189 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6330    0.6610   -0.1308 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0408   -1.4745    0.0235 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -1.1984   -1.7103 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1789    0.2040   -0.5923 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2983   -2.4603   -0.8501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5754   -2.2060   -0.4669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3741   -2.8541    0.2446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2573   -2.2286   -1.2582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0421   -2.2627    0.3323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6294   -0.0145    0.5180 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7876    2.9947    0.4055 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1417    3.5196   -0.0651 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4564    3.1498    1.6494 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17  2  1  0
 16  4  1  0
 13  6  2  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  5 22  1  0
  8 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  0
 15 27  1  0
 15 28  1  0
 15 29  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2',4,8-Trimethylpsoralen	ChEBI
4,5',8-Trimethylpsoralen	ChEBI
4,8,5'-Trimethylpsoralen	ChEBI
6-Hydroxy-beta,2,7-trimethyl-5-benzofuranacrylic acid, delta-lactone	ChEBI
Trimethylpsoralen	ChEBI
Trioxisaleno	ChEBI
Trioxysalen	ChEBI
Trioxysalene	ChEBI
Trioxysalenum	ChEBI
Trisoralen	Kegg
6-Hydroxy-b,2,7-trimethyl-5-benzofuranacrylate, delta-lactone	Generator
6-Hydroxy-b,2,7-trimethyl-5-benzofuranacrylic acid, delta-lactone	Generator
6-Hydroxy-beta,2,7-trimethyl-5-benzofuranacrylate, delta-lactone	Generator
6-Hydroxy-β,2,7-trimethyl-5-benzofuranacrylate, δ-lactone	Generator
6-Hydroxy-β,2,7-trimethyl-5-benzofuranacrylic acid, δ-lactone	Generator
6-Hydroxy-b,2,7-trimethyl-5-benzofuranacrylate, δ-lactone	Generator, HMDB
6-Hydroxy-b,2,7-trimethyl-5-benzofuranacrylic acid, δ-lactone	Generator, HMDB
Trioxisalenum	MeSH, HMDB
2,5,9-Trimethyl-7H-furo(3,2-g)benzopyran-7-one	MeSH, HMDB
ICN brand OF trioxsalen	MeSH, HMDB

Chemical Formula

C₁₄H₁₂O₃

Average Molecular Weight

228.2433

Monoisotopic Molecular Weight

228.07864425

IUPAC Name

2,5,9-trimethyl-7H-furo[3,2-g]chromen-7-one

Traditional Name

trioxsalen

CAS Registry Number

3902-71-4

SMILES

CC1=CC2=CC3=C(OC(=O)C=C3C)C(C)=C2O1

InChI Identifier

InChI=1S/C14H12O3/c1-7-4-12(15)17-14-9(3)13-10(6-11(7)14)5-8(2)16-13/h4-6H,1-3H3

InChI Key

FMHHVULEAZTJMA-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
Benzofuran
Pyranone
Benzenoid
Pyran
Furan
Heteroaromatic compound
Lactone
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

psoralens (CHEBI:28329 )
Furanocoumarins (C09314 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0015575)

Source

Exogenous

Exogenous (HMDB: HMDB0015575)

Food

Herb and spice

Spice

Wild celery (FooDB: FOOD00015)

Endogenous

Plant

Plant (HMDB: HMDB0015575)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0015575)

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

Photosensitizing agent (HMDB: HMDB0015575)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	21.51 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	147.445	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001388

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.063 g/L	ALOGPS
logP	3.26	ALOGPS
logP	2.95	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	39.44 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	64.86 m³·mol⁻¹	ChemAxon
Polarizability	24.77 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	152.498	31661259
DarkChem	[M-H]-	153.727	31661259
DeepCCS	[M+H]+	155.822	30932474
DeepCCS	[M-H]-	153.464	30932474
DeepCCS	[M-2H]-	186.702	30932474
DeepCCS	[M+Na]+	161.916	30932474
AllCCS	[M+H]+	147.7	32859911
AllCCS	[M+H-H2O]+	143.5	32859911
AllCCS	[M+NH4]+	151.6	32859911
AllCCS	[M+Na]+	152.7	32859911
AllCCS	[M-H]-	153.3	32859911
AllCCS	[M+Na-2H]-	152.7	32859911
AllCCS	[M+HCOO]-	152.1	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.	7.26 minutes	32390414
Predicted by Siyang on May 30, 2022	17.3596 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.8 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1832.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	625.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	237.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	387.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	235.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	565.6 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	733.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	125.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1438.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	513.6 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	1693.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	481.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	378.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	428.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	414.0 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	8.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Trioxsalen	CC1=CC2=CC3=C(OC(=O)C=C3C)C(C)=C2O1	2948.4	Standard polar	33892256
Trioxsalen	CC1=CC2=CC3=C(OC(=O)C=C3C)C(C)=C2O1	2166.5	Standard non polar	33892256
Trioxsalen	CC1=CC2=CC3=C(OC(=O)C=C3C)C(C)=C2O1	2157.5	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 - Trioxsalen GC-MS (Non-derivatized) - 70eV, Positive	splash10-0h10-0960000000-966d52d94de4b47d3acd	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Trioxsalen 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 - Trioxsalen 10V, Positive-QTOF	splash10-004i-0090000000-dcfc8fb3d1851500be83	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trioxsalen 20V, Positive-QTOF	splash10-0fb9-0090000000-9cf76c0cd3483f70877e	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trioxsalen 40V, Positive-QTOF	splash10-0ik9-1930000000-364eb5a4711246301410	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trioxsalen 10V, Negative-QTOF	splash10-004i-0090000000-c823a179ff02e7127dc9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trioxsalen 20V, Negative-QTOF	splash10-004i-0090000000-e4873a737dacdeebcb1a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trioxsalen 40V, Negative-QTOF	splash10-003f-2920000000-c752e5912988325469f0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trioxsalen 10V, Positive-QTOF	splash10-004i-0090000000-c89325e1a7192ec227f4	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trioxsalen 20V, Positive-QTOF	splash10-004i-0090000000-971e5b85c60e64223aa5	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trioxsalen 40V, Positive-QTOF	splash10-0gvk-1930000000-c960ea7d61bacac4f3df	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trioxsalen 10V, Negative-QTOF	splash10-004i-0090000000-f0e0fc28215258fdeb31	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trioxsalen 20V, Negative-QTOF	splash10-004i-0190000000-11b09e07d8088345c5cb	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trioxsalen 40V, Negative-QTOF	splash10-004i-0690000000-74d27c4f6ef3bff95576	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB04571	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB04571	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB04571

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Trioxsalen

METLIN ID

Not Available

PubChem Compound

5585

PDB ID

Not Available

ChEBI ID

28329

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1195461

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

van Coevorden AM, Kamphof WG, van Sonderen E, Bruynzeel DP, Coenraads PJ: Comparison of oral psoralen-UV-A with a portable tanning unit at home vs hospital-administered bath psoralen-UV-A in patients with chronic hand eczema: an open-label randomized controlled trial of efficacy. Arch Dermatol. 2004 Dec;140(12):1463-6. [PubMed:15611423 ]
Higuchi M, Yamayoshi A, Kobori A, Yamaoka T, Murakami A: Synthesis and properties of photo-reactive antisense oligonucleotides containing 2'-O-psoralen-conjugated adenosine. Nucleic Acids Symp Ser (Oxf). 2005;(49):331-2. [PubMed:17150768 ]
Thazhathveetil AK, Liu ST, Indig FE, Seidman MM: Psoralen conjugates for visualization of genomic interstrand cross-links localized by laser photoactivation. Bioconjug Chem. 2007 Mar-Apr;18(2):431-7. [PubMed:17373769 ]
Goldenberg M, Welsh J, Haas R, Rideout DC, Cantor CR: Synthesis and properties of novel psoralen derivatives. Biochemistry. 1988 Sep 6;27(18):6971-6. doi: 10.1021/bi00418a045. [PubMed:3196695 ]
Kaidbey KH, Kligman AM: Photopigmentation with trioxsalen. Arch Dermatol. 1974 May;109(5):674-7. [PubMed:4828534 ]
Sehgal VN: Editorial: Effectiveness of trioxsalen therapy for vitiligo. Arch Dermatol. 1974 Dec;110(6):957-8. doi: 10.1001/archderm.1974.01630120089029. [PubMed:4441118 ]

Showing metabocard for Trioxsalen (HMDB0015575)

MOL for HMDB0015575 (Trioxsalen)

3D MOL for HMDB0015575 (Trioxsalen)

3D SDF for HMDB0015575 (Trioxsalen)

3D-SDF for HMDB0015575 (Trioxsalen)

PDB for HMDB0015575 (Trioxsalen)

3D PDB for HMDB0015575 (Trioxsalen)

SMILES for HMDB0015575 (Trioxsalen)

INCHI for HMDB0015575 (Trioxsalen)

Structure for HMDB0015575 (Trioxsalen)

3D Structure for HMDB0015575 (Trioxsalen)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra