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Showing metabocard for Methoxsalen (HMDB0014693)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (5) Show 5 proteinsXML
enzymes (5) Show 5 proteins
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2022-03-07 02:51:42 UTC
HMDB IDHMDB0014693
Secondary Accession Numbers
  • HMDB14693
Metabolite Identification
Common NameMethoxsalen
DescriptionMethoxsalen, also known as oxsoralen or 8-methoxypsoralen, belongs to the class of organic compounds known as 8-methoxypsoralens. These are psoralens containing a methoxy group attached at the C8 position of the psoralen group. An additional 32 species of the genus Heracleum were found to contain 5-methoxypsoralen (bergapten) or other furanocoumarins. Methoxsalen is a drug which is used for the treatment of psoriasis and vitiligo. Author John Howard Griffin (1920–1980) used the chemical to darken his skin in order to investigate racial segregation in the American South. Methoxsalen is an extremely weak basic (essentially neutral) compound (based on its pKa). Methoxsalen is a bitter tasting compound. Outside of the human body, Methoxsalen is found, on average, in the highest concentration within a few different foods, such as parsnips, parsley, and celery stalks and in a lower concentration in fennels, wild carrots, and lovages. Methoxsalen has also been detected, but not quantified in, several different foods, such as corns, dills, lambsquarters, green vegetables, and corianders. This could make methoxsalen a potential biomarker for the consumption of these foods. Methoxsalen is a potentially toxic compound. Phenylalanine is lysated into cinnamic acid, followed by hydroxylation by cinnamate 4-hydroxylase to yield 4-coumaric acid. The eyes must be protected from UVA radiation. The scale was developed after patients demonstrated symptoms of phototoxicity after oral ingestion of Methoxsalen followed by PUVA therapy.
Structure
Data?1582753209
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0014693 (Methoxsalen)

Xanthotoxin
  Mrv1652305271900202D          

 16 18  0  0  0  0            999 V2000
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 O   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
    4.0668   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -1.1104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102   -1.1104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -2.7604    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   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532   -1.2680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3683   -1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532   -2.6029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  3 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 12 16  1  0  0  0  0
M  END
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3D MOL for HMDB0014693 (Methoxsalen)

HMDB0014693
     RDKit          3D
Methoxsalen
 24 26  0  0  0  0  0  0  0  0999 V2000
   -1.0635    2.9003   -1.0544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7746    1.6032   -1.5157 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4997    0.5218   -0.7195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5155   -0.2889   -0.2872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8213   -0.2480   -0.4917 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4142   -1.2402    0.1251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4479   -1.9878    0.7801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2278   -1.3916    0.5258 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0785   -1.6371    0.8740 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1314   -0.8335    0.4517 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4376   -1.1136    0.8242 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4339   -0.2798    0.3730 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0530    0.7783   -0.4211 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9763    1.5533   -0.8410 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8080    1.0123   -0.7531 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7947    0.2514   -0.3554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6848    3.4840   -1.7317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0739    3.3886   -0.8420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5629    2.7692   -0.0504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4857   -1.4736    0.1446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5878   -2.8739    1.3833 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3087   -2.4878    1.5023 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6460   -1.9588    1.4457 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4915   -0.4478    0.6334 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
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16  3  1  0
  8  4  1  0
 16 10  2  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  6 20  1  0
  7 21  1  0
  9 22  1  0
 11 23  1  0
 12 24  1  0
M  END
Download

3D SDF for HMDB0014693 (Methoxsalen)

Xanthotoxin
  Mrv1652305271900202D          

 16 18  0  0  0  0            999 V2000
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 O   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
    4.0668   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -1.1104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102   -1.1104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -2.7604    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   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532   -1.2680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3683   -1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532   -2.6029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  3 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 12 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014693

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C2OC(=O)C=CC2=CC2=C1OC=C2

> <INCHI_IDENTIFIER>
InChI=1S/C12H8O4/c1-14-12-10-8(4-5-15-10)6-7-2-3-9(13)16-11(7)12/h2-6H,1H3

> <INCHI_KEY>
QXKHYNVANLEOEG-UHFFFAOYSA-N

> <FORMULA>
C12H8O4

> <MOLECULAR_WEIGHT>
216.192

> <EXACT_MASS>
216.042258738

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
20.978883414920794

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.10

> <JCHEM_LOGP>
1.7848117503333332

> <ALOGPS_LOGS>
-3.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9251351971985664

> <JCHEM_POLAR_SURFACE_AREA>
48.67

> <JCHEM_REFRACTIVITY>
56.852900000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.64e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methoxsalen

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0014693 (Methoxsalen)

HMDB0014693
     RDKit          3D
Methoxsalen
 24 26  0  0  0  0  0  0  0  0999 V2000
   -1.0635    2.9003   -1.0544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7746    1.6032   -1.5157 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4997    0.5218   -0.7195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5155   -0.2889   -0.2872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8213   -0.2480   -0.4917 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4142   -1.2402    0.1251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4479   -1.9878    0.7801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2278   -1.3916    0.5258 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0785   -1.6371    0.8740 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1314   -0.8335    0.4517 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4376   -1.1136    0.8242 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4339   -0.2798    0.3730 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0530    0.7783   -0.4211 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9763    1.5533   -0.8410 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8080    1.0123   -0.7531 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7947    0.2514   -0.3554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6848    3.4840   -1.7317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0739    3.3886   -0.8420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5629    2.7692   -0.0504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4857   -1.4736    0.1446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5878   -2.8739    1.3833 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3087   -2.4878    1.5023 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6460   -1.9588    1.4457 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4915   -0.4478    0.6334 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
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16  3  1  0
  8  4  1  0
 16 10  2  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  6 20  1  0
  7 21  1  0
  9 22  1  0
 11 23  1  0
 12 24  1  0
M  END
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PDB for HMDB0014693 (Methoxsalen)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Xanthotoxin                                       
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       6.258  -0.533   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.591  -2.843   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       8.925  -2.073   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      10.259  -2.843   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      11.592  -2.073   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      10.259  -4.383   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.925  -5.153   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.591  -4.383   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.258  -5.153   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.924  -4.383   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       3.459  -2.367   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.554  -3.613   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.459  -4.859   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   13                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    4   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   16                                                  
CONECT   13   12    3   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   12                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   36    0
END
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3D PDB for HMDB0014693 (Methoxsalen)

COMPND    HMDB0014693
HETATM    1  C1  UNL     1      -1.063   2.900  -1.054  1.00  0.00           C  
HETATM    2  O1  UNL     1      -0.775   1.603  -1.516  1.00  0.00           O  
HETATM    3  C2  UNL     1      -0.500   0.522  -0.720  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.516  -0.289  -0.287  1.00  0.00           C  
HETATM    5  O2  UNL     1      -2.821  -0.248  -0.492  1.00  0.00           O  
HETATM    6  C4  UNL     1      -3.414  -1.240   0.125  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.448  -1.988   0.780  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.228  -1.392   0.526  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.079  -1.637   0.874  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.131  -0.834   0.452  1.00  0.00           C  
HETATM   11  C9  UNL     1       2.438  -1.114   0.824  1.00  0.00           C  
HETATM   12  C10 UNL     1       3.434  -0.280   0.373  1.00  0.00           C  
HETATM   13  C11 UNL     1       3.053   0.778  -0.421  1.00  0.00           C  
HETATM   14  O3  UNL     1       3.976   1.553  -0.841  1.00  0.00           O  
HETATM   15  O4  UNL     1       1.808   1.012  -0.753  1.00  0.00           O  
HETATM   16  C12 UNL     1       0.795   0.251  -0.355  1.00  0.00           C  
HETATM   17  H1  UNL     1      -1.685   3.484  -1.732  1.00  0.00           H  
HETATM   18  H2  UNL     1      -0.074   3.389  -0.842  1.00  0.00           H  
HETATM   19  H3  UNL     1      -1.563   2.769  -0.050  1.00  0.00           H  
HETATM   20  H4  UNL     1      -4.486  -1.474   0.145  1.00  0.00           H  
HETATM   21  H5  UNL     1      -2.588  -2.874   1.383  1.00  0.00           H  
HETATM   22  H6  UNL     1       0.309  -2.488   1.502  1.00  0.00           H  
HETATM   23  H7  UNL     1       2.646  -1.959   1.446  1.00  0.00           H  
HETATM   24  H8  UNL     1       4.492  -0.448   0.633  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3
CONECT    3    4    4   16
CONECT    4    5    8
CONECT    5    6
CONECT    6    7    7   20
CONECT    7    8   21
CONECT    8    9    9
CONECT    9   10   22
CONECT   10   11   16   16
CONECT   11   12   12   23
CONECT   12   13   24
CONECT   13   14   14   15
CONECT   15   16
END
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SMILES for HMDB0014693 (Methoxsalen)

COC1=C2OC(=O)C=CC2=CC2=C1OC=C2
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INCHI for HMDB0014693 (Methoxsalen)

InChI=1S/C12H8O4/c1-14-12-10-8(4-5-15-10)6-7-2-3-9(13)16-11(7)12/h2-6H,1H3
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Synonyms
ValueSource
6-Hydroxy-7-methoxy-5-benzofuranacrylic acid delta-lactoneChEBI
8-Methoxy-2',3',6,7-furocoumarinChEBI
8-Methoxy-4',5':6,7-furocoumarinChEBI
8-Methoxy-[furano-3'.2':6.7-coumarin]ChEBI
8-MethoxyfuranocoumarinChEBI
8-MethoxypsoralenChEBI
8-MOPChEBI
8-MPChEBI
9-Methoxy-7H-furo[3,2-g][1]benzopyran-7-oneChEBI
MeladinineChEBI
MeloxineChEBI
O-MethylxanthotoxolChEBI
OxsoralenChEBI
Ultra mopChEBI
UvadexChEBI
XanthotoxinChEBI
6-Hydroxy-7-methoxy-5-benzofuranacrylate delta-lactoneGenerator
6-Hydroxy-7-methoxy-5-benzofuranacrylate δ-lactoneGenerator
6-Hydroxy-7-methoxy-5-benzofuranacrylic acid δ-lactoneGenerator
MethoxalenHMDB
XanthotoxineHMDB
XanthoxinHMDB
ZanthotoxinHMDB
8 MOPHMDB
Chinoin brand OF methoxsalenHMDB
DermoxHMDB
GeroxalenHMDB
ICN brand 2 OF methoxsalenHMDB
Methoxsalen mex-america brandHMDB
Oxsoralen ultraHMDB
Oxsoralen-ultraHMDB
8 MethoxypsoralenHMDB
AmmoidinHMDB
DB Brand OF methoxsalenHMDB
DeltasoralenHMDB
MeladininaHMDB
Methoxsalen Delta brandHMDB
Mex-america brand OF methoxsalenHMDB
MéladinineHMDB
Sanofi-synthelabo brand OF methoxsalenHMDB
8MOPHMDB
Boehringer ingelheim brand OF methoxsalenHMDB
Galderma brand OF methoxsalenHMDB
Methoxa-domeHMDB
Methoxsalen canderm brandHMDB
Methoxsalen chinoin brandHMDB
Methoxsalen dermatech brandHMDB
Methoxsalen sanofi-synthelabo brandHMDB
PuvalenHMDB
Sanofi synthelabo brand OF methoxsalenHMDB
UltramopHMDB
Canderm brand OF methoxsalenHMDB
Delta Brand OF methoxsalenHMDB
Dermatech brand OF methoxsalenHMDB
ICN brand 1 OF methoxsalenHMDB
ICN brand 3 OF methoxsalenHMDB
Methoxa domeHMDB
Mex america brand OF methoxsalenHMDB
Chemical FormulaC12H8O4
Average Molecular Weight216.192
Monoisotopic Molecular Weight216.042258738
IUPAC Name9-methoxy-7H-furo[3,2-g]chromen-7-one
Traditional Namemethoxsalen
CAS Registry Number298-81-7
SMILES
COC1=C2OC(=O)C=CC2=CC2=C1OC=C2
InChI Identifier
InChI=1S/C12H8O4/c1-14-12-10-8(4-5-15-10)6-7-2-3-9(13)16-11(7)12/h2-6H,1H3
InChI KeyQXKHYNVANLEOEG-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 8-methoxypsoralens. These are psoralens containing a methoxy group attached at the C8 position of the psoralen group.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassFuranocoumarins
Direct Parent8-methoxypsoralens
Alternative Parents
Substituents
  • 8-methoxypsoralen
  • Benzopyran
  • 1-benzopyran
  • Benzofuran
  • Anisole
  • Alkyl aryl ether
  • Pyranone
  • Pyran
  • Benzenoid
  • Furan
  • Heteroaromatic compound
  • Lactone
  • Oxacycle
  • Ether
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect
Health effectOrganoleptic effect
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Biological roleIndustrial applicationIndirect biological role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.16 g/LNot Available
LogP1.7Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available139.901http://allccs.zhulab.cn/database/detail?ID=AllCCS00001401
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.16 g/LALOGPS
logP2.1ALOGPS
logP1.78ChemAxon
logS-3.1ALOGPS
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area48.67 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity56.85 m³·mol⁻¹ChemAxon
Polarizability20.98 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+148.17731661259
DarkChem[M-H]-146.42731661259
DeepCCS[M+H]+145.2730932474
DeepCCS[M-H]-142.88530932474
DeepCCS[M-2H]-176.56630932474
DeepCCS[M+Na]+151.44630932474
AllCCS[M+H]+144.832859911
AllCCS[M+H-H2O]+140.432859911
AllCCS[M+NH4]+148.832859911
AllCCS[M+Na]+150.032859911
AllCCS[M-H]-146.432859911
AllCCS[M+Na-2H]-145.932859911
AllCCS[M+HCOO]-145.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
MethoxsalenCOC1=C2OC(=O)C=CC2=CC2=C1OC=C23032.0Standard polar33892256
MethoxsalenCOC1=C2OC(=O)C=CC2=CC2=C1OC=C21962.7Standard non polar33892256
MethoxsalenCOC1=C2OC(=O)C=CC2=CC2=C1OC=C22033.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Methoxsalen GC-EI-TOF (Non-derivatized)splash10-00ri-6940000000-921a3e8adbbde5f7a0c32017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methoxsalen GC-EI-TOF (Non-derivatized)splash10-003b-4950000000-4e2c001531825f6dddca2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methoxsalen GC-EI-TOF (Non-derivatized)splash10-00ri-6940000000-921a3e8adbbde5f7a0c32018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methoxsalen GC-EI-TOF (Non-derivatized)splash10-003b-4950000000-4e2c001531825f6dddca2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methoxsalen GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-1920000000-98f6cfda190045d0762a2017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methoxsalen GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-014i-9670000000-3e0fa2e9c81c3bc1d9362014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Methoxsalen LC-ESI-qTof , Positive-QTOFsplash10-014i-1590000000-f70cf2b0756e8c80c17b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methoxsalen LC-ESI-qTof , Positive-QTOFsplash10-014i-0890000000-f76d6fb28854a5d7b6cd2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methoxsalen LC-ESI-qTof , Positive-QTOFsplash10-0fk9-0920000000-c2bd0b76c5aed757e9042017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methoxsalen LC-ESI-QTOF , positive-QTOFsplash10-014i-0090000000-cecd035cc60695427f782017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methoxsalen LC-ESI-QTOF , positive-QTOFsplash10-0gb9-0290000000-2e17076c991ea61ced1a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methoxsalen LC-ESI-QTOF , positive-QTOFsplash10-0uk9-0970000000-59c3b8004baa44f8d3a52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methoxsalen LC-ESI-QTOF , positive-QTOFsplash10-014i-0190000000-cc04ec8c7265ba3a72972017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methoxsalen LC-ESI-QTOF , positive-QTOFsplash10-0udi-0970000000-82c4c7eefd54ad509f692017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methoxsalen LC-ESI-QTOF , positive-QTOFsplash10-00xs-0900000000-991b5b7dc028219e593b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methoxsalen Linear Ion Trap , positive-QTOFsplash10-0udi-0970000000-dc6cd01d5d2e5eeaae302017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methoxsalen Linear Ion Trap , positive-QTOFsplash10-0udi-0970000000-ee8aa480dca6e72a74fb2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methoxsalen , positive-QTOFsplash10-014i-0890000000-f76d6fb28854a5d7b6cd2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methoxsalen , positive-QTOFsplash10-014i-1590000000-f70cf2b0756e8c80c17b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methoxsalen , positive-QTOFsplash10-0fk9-0920000000-c2bd0b76c5aed757e9042017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methoxsalen , positive-QTOFsplash10-0gi0-1960000000-82bc07f73bc5b20446422017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methoxsalen , positive-QTOFsplash10-014i-0690000000-770dc5d0db7e86d8ba072017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methoxsalen 50V, Positive-QTOFsplash10-00dj-0900000000-b06196cd7070da3a2e982021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methoxsalen 15V, Positive-QTOFsplash10-014i-0090000000-ed4db851d39c50628cea2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methoxsalen 45V, Positive-QTOFsplash10-0uxr-0490000000-6e7169196da6a70b89d62021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methoxsalen 10V, Positive-QTOFsplash10-014i-0090000000-4767833559e7bd183ce02015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methoxsalen 20V, Positive-QTOFsplash10-014i-0090000000-c471bf567e8a63e00e512015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methoxsalen 40V, Positive-QTOFsplash10-01bi-0930000000-72a72a3eb013e045bdb02015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methoxsalen 10V, Negative-QTOFsplash10-014i-0290000000-c9557f276875a3bf1d2b2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methoxsalen 20V, Negative-QTOFsplash10-014i-0390000000-ff927b8db6ef70ef822d2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methoxsalen 40V, Negative-QTOFsplash10-00di-0910000000-d2e511be224be1b3530e2015-04-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00553 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00553 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00553
Phenol Explorer Compound ID719
FooDB IDFDB012474
KNApSAcK IDC00000576
Chemspider ID3971
KEGG Compound IDC01864
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMethoxsalen
METLIN IDNot Available
PubChem Compound4114
PDB ID8MO
ChEBI ID18358
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available

Enzymes

Enzyme Details
1. Cytochrome P450 3A4
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Enzyme Details
2. Cytochrome P450 1A1
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP1A1
Uniprot ID:
P04798
Molecular weight:
58164.815
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Enzyme Details
3. Cytochrome P450 2A13
General function:
Involved in monooxygenase activity
Specific function:
Exhibits a coumarin 7-hydroxylase activity. Active in the metabolic activation of hexamethylphosphoramide, N,N-dimethylaniline, 2'-methoxyacetophenone, N-nitrosomethylphenylamine, and the tobacco-specific carcinogen, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone. Possesses phenacetin O-deethylation activity.
Gene Name:
CYP2A13
Uniprot ID:
Q16696
Molecular weight:
56687.095
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Enzyme Details
4. Cytochrome P450 1A2
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular weight:
58406.915
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Enzyme Details
5. Cytochrome P450 2A6
General function:
Involved in monooxygenase activity
Specific function:
Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Constitutes the major nicotine C-oxidase. Acts as a 1,4-cineole 2-exo-monooxygenase. Possesses low phenacetin O-deethylation activity.
Gene Name:
CYP2A6
Uniprot ID:
P11509
Molecular weight:
56517.005
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]