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Showing metabocard for Psoralen (HMDB0034272)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 19:04:36 UTC
Update Date2023-02-21 17:24:08 UTC
HMDB IDHMDB0034272
Secondary Accession Numbers
  • HMDB34272
Metabolite Identification
Common NamePsoralen
DescriptionPsoralen, also known as psoralene, ficusin or manaderm, 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. Psoralen is the parent compound in a family of naturally occurring organic compounds known as the linear furanocoumarins. Psoralen is structurally related to coumarin by the addition of a fused furan ring and is considered as a derivative of umbelliferone. Biosynthetically, psoralen originates from coumarins in the shikimate pathway. Psoralen is produced exclusively by plants but can be found in animals that consume these plants. Psoralen can be found in several plant sources with Ficus carica (the common fig) being probably the most abundant source of psoralens. They are also found in small quantities in Ammi visnaga (bisnaga), Pastinaca sativa (parsnip), Petroselinum crispum (parsley), Levisticum officinale (lovage), Foeniculum vulgare (fruit, i.e., Fennel seeds), Daucus carota (carrot), Psoralea corylifolia (babchi), Apium graveolens (celery), and bergamot oil (bergapten, bergamottin). Psoralen is found in all citrus fruits. Psoralen is a well-known mutagen and is used for this purpose in molecular biology research. Psoralen intercalates into DNA and on exposure to ultraviolet (UVA) radiation can form monoadducts and covalent inter-strand cross-links (ICL) with thymines in the DNA molecule. Psoralen also functions as a drug. An important use of psoralen is in the treatment for skin problems such as psoriasis and, to a lesser extent, eczema and vitiligo. This treatment takes advantage of the high UV absorbance of psoralen. In treating these skin conditions psoralen is applied first to sensitise the skin, then UVA light is applied to clean up the skin problem. Psoralen has also been recommended for treating alopecia.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0034272 (Psoralen)

Psoralen
  Mrv1652305201902232D          

 14 16  0  0  0  0            999 V2000
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8419   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -0.1576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  6 10  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  2  0  0  0  0
  4 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  2 14  1  0  0  0  0
M  END
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3D MOL for HMDB0034272 (Psoralen)

HMDB0034272
     RDKit          3D
Psoralen
 20 22  0  0  0  0  0  0  0  0999 V2000
    4.1699   -0.3114   -1.6467 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1069   -0.2154   -0.9575 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1746   -0.1344    0.4152 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0081   -0.0299    1.1584 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7891   -0.0097    0.4882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3906    0.0929    1.1910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5700    0.1092    0.4901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9000    0.2018    0.9055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6469    0.1681   -0.2540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8386    0.0642   -1.2807 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5798    0.0258   -0.8743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3985   -0.0778   -1.5918 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7989   -0.0950   -0.8896 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9420   -0.1917   -1.5255 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1247   -0.1498    0.9425 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9855    0.0366    2.2210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4175    0.1596    2.2525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2183    0.2809    1.9309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7306    0.2206   -0.2876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4090   -0.1447   -2.6877 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14  2  1  0
 13  5  1  0
 11  7  2  0
  3 15  1  0
  4 16  1  0
  6 17  1  0
  8 18  1  0
  9 19  1  0
 12 20  1  0
M  END
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3D SDF for HMDB0034272 (Psoralen)

Psoralen
  Mrv1652305201902232D          

 14 16  0  0  0  0            999 V2000
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8419   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -0.1576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  6 10  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  2  0  0  0  0
  4 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  2 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034272

> <DATABASE_NAME>
hmdb

> <SMILES>
O=C1OC2=CC3=C(C=CO3)C=C2C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C11H6O3/c12-11-2-1-7-5-8-3-4-13-9(8)6-10(7)14-11/h1-6H

> <INCHI_KEY>
ZCCUUQDIBDJBTK-UHFFFAOYSA-N

> <FORMULA>
C11H6O3

> <MOLECULAR_WEIGHT>
186.166

> <EXACT_MASS>
186.031694053

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
18.095235182105146

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.15

> <JCHEM_LOGP>
1.9424830159999997

> <ALOGPS_LOGS>
-3.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8920811389599157

> <JCHEM_POLAR_SURFACE_AREA>
39.44

> <JCHEM_REFRACTIVITY>
50.389700000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.34e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
psoralen

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0034272 (Psoralen)

HMDB0034272
     RDKit          3D
Psoralen
 20 22  0  0  0  0  0  0  0  0999 V2000
    4.1699   -0.3114   -1.6467 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1069   -0.2154   -0.9575 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1746   -0.1344    0.4152 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0081   -0.0299    1.1584 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7891   -0.0097    0.4882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3906    0.0929    1.1910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5700    0.1092    0.4901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9000    0.2018    0.9055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6469    0.1681   -0.2540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8386    0.0642   -1.2807 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5798    0.0258   -0.8743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3985   -0.0778   -1.5918 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7989   -0.0950   -0.8896 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9420   -0.1917   -1.5255 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1247   -0.1498    0.9425 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9855    0.0366    2.2210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4175    0.1596    2.2525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2183    0.2809    1.9309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7306    0.2206   -0.2876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4090   -0.1447   -2.6877 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14  2  1  0
 13  5  1  0
 11  7  2  0
  3 15  1  0
  4 16  1  0
  6 17  1  0
  8 18  1  0
  9 19  1  0
 12 20  1  0
M  END
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PDB for HMDB0034272 (Psoralen)

HEADER    PROTEIN                                 20-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Psoralen                                          
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAY-19         0                                  
HETATM    1  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.133  -2.786   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.038  -1.540   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       8.133  -0.294   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   14                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   12                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   10                                                  
CONECT    7    6    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    6                                                       
CONECT   11    7   12                                                       
CONECT   12   11    4   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13    2                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   32    0
END
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3D PDB for HMDB0034272 (Psoralen)

COMPND    HMDB0034272
HETATM    1  O1  UNL     1       4.170  -0.311  -1.647  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.107  -0.215  -0.958  1.00  0.00           C  
HETATM    3  C2  UNL     1       3.175  -0.134   0.415  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.008  -0.030   1.158  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.789  -0.010   0.488  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.391   0.093   1.191  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.570   0.109   0.490  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.900   0.202   0.905  1.00  0.00           C  
HETATM    9  C8  UNL     1      -3.647   0.168  -0.254  1.00  0.00           C  
HETATM   10  O2  UNL     1      -2.839   0.064  -1.281  1.00  0.00           O  
HETATM   11  C9  UNL     1      -1.580   0.026  -0.874  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.399  -0.078  -1.592  1.00  0.00           C  
HETATM   13  C11 UNL     1       0.799  -0.095  -0.890  1.00  0.00           C  
HETATM   14  O3  UNL     1       1.942  -0.192  -1.525  1.00  0.00           O  
HETATM   15  H1  UNL     1       4.125  -0.150   0.943  1.00  0.00           H  
HETATM   16  H2  UNL     1       1.986   0.037   2.221  1.00  0.00           H  
HETATM   17  H3  UNL     1      -0.417   0.160   2.253  1.00  0.00           H  
HETATM   18  H4  UNL     1      -3.218   0.281   1.931  1.00  0.00           H  
HETATM   19  H5  UNL     1      -4.731   0.221  -0.288  1.00  0.00           H  
HETATM   20  H6  UNL     1      -0.409  -0.145  -2.688  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   14
CONECT    3    4    4   15
CONECT    4    5   16
CONECT    5    6    6   13
CONECT    6    7   17
CONECT    7    8   11   11
CONECT    8    9    9   18
CONECT    9   10   19
CONECT   10   11
CONECT   11   12
CONECT   12   13   13   20
CONECT   13   14
END
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SMILES for HMDB0034272 (Psoralen)

O=C1OC2=CC3=C(C=CO3)C=C2C=C1
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INCHI for HMDB0034272 (Psoralen)

InChI=1S/C11H6O3/c12-11-2-1-7-5-8-3-4-13-9(8)6-10(7)14-11/h1-6H
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View in JSmolView Stereo Labels
Synonyms
Chemical FormulaC11H6O3
Average Molecular Weight186.166
Monoisotopic Molecular Weight186.031694053
IUPAC Name7H-furo[3,2-g]chromen-7-one
Traditional Namepsoralen
CAS Registry Number66-97-7
SMILES
O=C1OC2=CC3=C(C=CO3)C=C2C=C1
InChI Identifier
InChI=1S/C11H6O3/c12-11-2-1-7-5-8-3-4-13-9(8)6-10(7)14-11/h1-6H
InChI KeyZCCUUQDIBDJBTK-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.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassFuranocoumarins
Direct ParentPsoralens
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 FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect
Health effect
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Industrial applicationBiological role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point171 °CNot Available
Boiling Point362.00 to 363.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility1925 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.67Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound ID718
FooDB IDFDB012605
KNApSAcK IDC00000297
Chemspider ID5964
KEGG Compound IDC09305
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPsoralen
METLIN IDNot Available
PubChem Compound6199
PDB IDNot Available
ChEBI ID27616
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1279301
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Rodighiero P, Guiotto A, Pastorini G, Manzini P, Bordin F, Baccichetti F, Carlassare F, Vedaldi D, Dall'Acqua F: Photochemical and photobiological properties of 4,5'-dimethylpsoralen, a bifunctional contaminant of synthetic 4,5'-dimethylangelicin. Farmaco Sci. 1981 Jul;36(7):648-62. [PubMed:7274446 ]
  2. Insawang M, Wongpraparut C: Recalcitrant solar urticaria induced by UVA and visible light: a case report. J Med Assoc Thai. 2010 Oct;93(10):1238-41. [PubMed:20973330 ]
  3. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .