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Showing metabocard for cis,trans-5'-Hydroxythalidomide (HMDB0013870)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:00:17 UTC
Update Date2021-09-14 15:38:57 UTC
HMDB IDHMDB0013870
Secondary Accession Numbers
  • HMDB13870
Metabolite Identification
Common Namecis,trans-5'-Hydroxythalidomide
Descriptioncis,trans-5'-Hydroxythalidomide, also known as 5'-OH-thalidomide, belongs to the class of organic compounds known as phthalimides. These are aromatic heterocyclic compounds containing a 1,3-dioxoisoindoline moiety. They are imide derivatives of phthalic anhydrides. cis,trans-5'-Hydroxythalidomide is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0013870 (cis,trans-5'-Hydroxythalidomide)

  Mrv0541 06191311472D          

 20 22  0  0  0  0            999 V2000
    9.2381   -5.2514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1878   -5.2706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1878   -2.3744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7130   -3.8225    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4131   -3.8225    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4755   -4.5370    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2381   -3.8225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6506   -3.1080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4755   -3.1080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6506   -4.5370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9316   -4.4864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9316   -3.1586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1511   -4.2350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1511   -3.4100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8880   -3.8225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4365   -4.6475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4365   -2.9975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7220   -4.2350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7220   -3.4100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8880   -2.3936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 10  2  0  0  0  0
  2 11  2  0  0  0  0
  3 12  2  0  0  0  0
  4 15  2  0  0  0  0
  5  7  1  0  0  0  0
  5 11  1  0  0  0  0
  5 12  1  0  0  0  0
  6 10  1  0  0  0  0
  6 15  1  0  0  0  0
  7  8  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  1  0  0  0  0
  9 15  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  1  0  0  0  0
 13 14  1  0  0  0  0
 13 16  2  0  0  0  0
 14 17  2  0  0  0  0
 16 18  1  0  0  0  0
 17 19  1  0  0  0  0
 18 19  2  0  0  0  0
  9 20  1  0  0  0  0
M  END
Download

3D MOL for HMDB0013870 (cis,trans-5'-Hydroxythalidomide)

HMDB0013870
     RDKit          3D
cis,trans-5'-Hydroxythalidomide
 30 32  0  0  0  0  0  0  0  0999 V2000
   -4.5099   -1.9445   -0.7296 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6771   -1.0127   -0.5907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7662   -0.6890   -1.6357 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7904    0.3027   -1.3539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2797    0.9772   -2.2762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3436    0.5736    0.0342 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0748    0.4208    0.1098 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9797    1.4733    0.3986 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6987    2.6979    0.6335 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3490    0.9630    0.3956 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5913    1.5514    0.6128 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7619    0.8363    0.5519 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6962   -0.5115    0.2650 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4790   -1.1263    0.0441 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3045   -0.3853    0.1101 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8891   -0.7324   -0.0698 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4173   -1.8598   -0.3414 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0888   -0.2597    1.0450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5680   -0.1859    0.6403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3957   -0.6355    1.6556 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8237   -1.1687   -2.5697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6202    1.6289    0.2341 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5723    2.6242    0.8358 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7050    1.3561    0.7321 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6242   -1.0968    0.2128 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4019   -2.1750   -0.1812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0319    0.1878    2.0469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8184   -1.3132    1.0508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8581    0.8455    0.3628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9735   -1.3424    1.2771 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
  6 18  1  0
 18 19  1  0
 19 20  1  0
 19  2  1  0
 16  7  1  0
 15 10  1  0
  3 21  1  0
  6 22  1  0
 11 23  1  0
 12 24  1  0
 13 25  1  0
 14 26  1  0
 18 27  1  0
 18 28  1  0
 19 29  1  0
 20 30  1  0
M  END
Download

3D SDF for HMDB0013870 (cis,trans-5'-Hydroxythalidomide)

  Mrv0541 06191311472D          

 20 22  0  0  0  0            999 V2000
    9.2381   -5.2514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1878   -5.2706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1878   -2.3744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7130   -3.8225    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4131   -3.8225    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4755   -4.5370    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2381   -3.8225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6506   -3.1080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4755   -3.1080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6506   -4.5370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9316   -4.4864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9316   -3.1586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1511   -4.2350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1511   -3.4100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8880   -3.8225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4365   -4.6475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4365   -2.9975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7220   -4.2350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7220   -3.4100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8880   -2.3936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 10  2  0  0  0  0
  2 11  2  0  0  0  0
  3 12  2  0  0  0  0
  4 15  2  0  0  0  0
  5  7  1  0  0  0  0
  5 11  1  0  0  0  0
  5 12  1  0  0  0  0
  6 10  1  0  0  0  0
  6 15  1  0  0  0  0
  7  8  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  1  0  0  0  0
  9 15  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  1  0  0  0  0
 13 14  1  0  0  0  0
 13 16  2  0  0  0  0
 14 17  2  0  0  0  0
 16 18  1  0  0  0  0
 17 19  1  0  0  0  0
 18 19  2  0  0  0  0
  9 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0013870

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1CC(N2C(=O)C3=CC=CC=C3C2=O)C(=O)NC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C13H10N2O5/c16-9-5-8(10(17)14-11(9)18)15-12(19)6-3-1-2-4-7(6)13(15)20/h1-4,8-9,16H,5H2,(H,14,17,18)

> <INCHI_KEY>
HHTOWVWIVBSOKC-UHFFFAOYSA-N

> <FORMULA>
C13H10N2O5

> <MOLECULAR_WEIGHT>
274.2289

> <EXACT_MASS>
274.05897144

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
25.193599445012104

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(5-hydroxy-2,6-dioxopiperidin-3-yl)-2,3-dihydro-1H-isoindole-1,3-dione

> <ALOGPS_LOGP>
-0.18

> <JCHEM_LOGP>
-0.9281525706666667

> <ALOGPS_LOGS>
-1.62

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.388887505916735

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.212959648754811

> <JCHEM_PKA_STRONGEST_BASIC>
-3.648991385556452

> <JCHEM_POLAR_SURFACE_AREA>
103.78

> <JCHEM_REFRACTIVITY>
65.77340000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.51e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(5-hydroxy-2,6-dioxopiperidin-3-yl)isoindole-1,3-dione

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0013870 (cis,trans-5'-Hydroxythalidomide)

HMDB0013870
     RDKit          3D
cis,trans-5'-Hydroxythalidomide
 30 32  0  0  0  0  0  0  0  0999 V2000
   -4.5099   -1.9445   -0.7296 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6771   -1.0127   -0.5907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7662   -0.6890   -1.6357 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7904    0.3027   -1.3539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2797    0.9772   -2.2762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3436    0.5736    0.0342 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0748    0.4208    0.1098 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9797    1.4733    0.3986 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6987    2.6979    0.6335 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3490    0.9630    0.3956 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5913    1.5514    0.6128 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7619    0.8363    0.5519 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6962   -0.5115    0.2650 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4790   -1.1263    0.0441 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3045   -0.3853    0.1101 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8891   -0.7324   -0.0698 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4173   -1.8598   -0.3414 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0888   -0.2597    1.0450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5680   -0.1859    0.6403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3957   -0.6355    1.6556 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8237   -1.1687   -2.5697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6202    1.6289    0.2341 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5723    2.6242    0.8358 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7050    1.3561    0.7321 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6242   -1.0968    0.2128 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4019   -2.1750   -0.1812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0319    0.1878    2.0469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8184   -1.3132    1.0508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8581    0.8455    0.3628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9735   -1.3424    1.2771 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
  6 18  1  0
 18 19  1  0
 19 20  1  0
 19  2  1  0
 16  7  1  0
 15 10  1  0
  3 21  1  0
  6 22  1  0
 11 23  1  0
 12 24  1  0
 13 25  1  0
 14 26  1  0
 18 27  1  0
 18 28  1  0
 19 29  1  0
 20 30  1  0
M  END
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PDB for HMDB0013870 (cis,trans-5'-Hydroxythalidomide)

HEADER    PROTEIN                                 19-JUN-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-13         0                                  
HETATM    1  O   UNK     0      17.244  -9.803   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      15.284  -9.839   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      15.284  -4.432   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      21.864  -7.135   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0      15.704  -7.135   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0      19.554  -8.469   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      17.244  -7.135   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      18.014  -5.802   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      19.554  -5.802   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      18.014  -8.469   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.806  -8.375   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.806  -5.896   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.349  -7.905   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.349  -6.365   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      20.324  -7.135   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.015  -8.675   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.015  -5.595   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.681  -7.905   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.681  -6.365   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      20.324  -4.468   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2   11                                                            
CONECT    3   12                                                            
CONECT    4   15                                                            
CONECT    5    7   11   12                                                  
CONECT    6   10   15                                                       
CONECT    7    5    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8   15   20                                                  
CONECT   10    1    6    7                                                  
CONECT   11    2    5   13                                                  
CONECT   12    3    5   14                                                  
CONECT   13   11   14   16                                                  
CONECT   14   12   13   17                                                  
CONECT   15    4    6    9                                                  
CONECT   16   13   18                                                       
CONECT   17   14   19                                                       
CONECT   18   16   19                                                       
CONECT   19   17   18                                                       
CONECT   20    9                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END
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3D PDB for HMDB0013870 (cis,trans-5'-Hydroxythalidomide)

COMPND    HMDB0013870
HETATM    1  O1  UNL     1      -4.510  -1.945  -0.730  1.00  0.00           O  
HETATM    2  C1  UNL     1      -3.677  -1.013  -0.591  1.00  0.00           C  
HETATM    3  N1  UNL     1      -2.766  -0.689  -1.636  1.00  0.00           N  
HETATM    4  C2  UNL     1      -1.790   0.303  -1.354  1.00  0.00           C  
HETATM    5  O2  UNL     1      -1.280   0.977  -2.276  1.00  0.00           O  
HETATM    6  C3  UNL     1      -1.344   0.574   0.034  1.00  0.00           C  
HETATM    7  N2  UNL     1       0.075   0.421   0.110  1.00  0.00           N  
HETATM    8  C4  UNL     1       0.980   1.473   0.399  1.00  0.00           C  
HETATM    9  O3  UNL     1       0.699   2.698   0.633  1.00  0.00           O  
HETATM   10  C5  UNL     1       2.349   0.963   0.396  1.00  0.00           C  
HETATM   11  C6  UNL     1       3.591   1.551   0.613  1.00  0.00           C  
HETATM   12  C7  UNL     1       4.762   0.836   0.552  1.00  0.00           C  
HETATM   13  C8  UNL     1       4.696  -0.512   0.265  1.00  0.00           C  
HETATM   14  C9  UNL     1       3.479  -1.126   0.044  1.00  0.00           C  
HETATM   15  C10 UNL     1       2.305  -0.385   0.110  1.00  0.00           C  
HETATM   16  C11 UNL     1       0.889  -0.732  -0.070  1.00  0.00           C  
HETATM   17  O4  UNL     1       0.417  -1.860  -0.341  1.00  0.00           O  
HETATM   18  C12 UNL     1      -2.089  -0.260   1.045  1.00  0.00           C  
HETATM   19  C13 UNL     1      -3.568  -0.186   0.640  1.00  0.00           C  
HETATM   20  O5  UNL     1      -4.396  -0.635   1.656  1.00  0.00           O  
HETATM   21  H1  UNL     1      -2.824  -1.169  -2.570  1.00  0.00           H  
HETATM   22  H2  UNL     1      -1.620   1.629   0.234  1.00  0.00           H  
HETATM   23  H3  UNL     1       3.572   2.624   0.836  1.00  0.00           H  
HETATM   24  H4  UNL     1       5.705   1.356   0.732  1.00  0.00           H  
HETATM   25  H5  UNL     1       5.624  -1.097   0.213  1.00  0.00           H  
HETATM   26  H6  UNL     1       3.402  -2.175  -0.181  1.00  0.00           H  
HETATM   27  H7  UNL     1      -2.032   0.188   2.047  1.00  0.00           H  
HETATM   28  H8  UNL     1      -1.818  -1.313   1.051  1.00  0.00           H  
HETATM   29  H9  UNL     1      -3.858   0.846   0.363  1.00  0.00           H  
HETATM   30  H10 UNL     1      -4.973  -1.342   1.277  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   19
CONECT    3    4   21
CONECT    4    5    5    6
CONECT    6    7   18   22
CONECT    7    8   16
CONECT    8    9    9   10
CONECT   10   11   11   15
CONECT   11   12   23
CONECT   12   13   13   24
CONECT   13   14   25
CONECT   14   15   15   26
CONECT   15   16
CONECT   16   17   17
CONECT   18   19   27   28
CONECT   19   20   29
CONECT   20   30
END
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SMILES for HMDB0013870 (cis,trans-5'-Hydroxythalidomide)

OC1CC(N2C(=O)C3=CC=CC=C3C2=O)C(=O)NC1=O
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INCHI for HMDB0013870 (cis,trans-5'-Hydroxythalidomide)

InChI=1S/C13H10N2O5/c16-9-5-8(10(17)14-11(9)18)15-12(19)6-3-1-2-4-7(6)13(15)20/h1-4,8-9,16H,5H2,(H,14,17,18)
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Synonyms
ValueSource
5'-OH-ThalidomideHMDB
5'-HydroxythalidomideMeSH
Chemical FormulaC13H10N2O5
Average Molecular Weight274.2289
Monoisotopic Molecular Weight274.05897144
IUPAC Name2-(5-hydroxy-2,6-dioxopiperidin-3-yl)-2,3-dihydro-1H-isoindole-1,3-dione
Traditional Name2-(5-hydroxy-2,6-dioxopiperidin-3-yl)isoindole-1,3-dione
CAS Registry NumberNot Available
SMILES
OC1CC(N2C(=O)C3=CC=CC=C3C2=O)C(=O)NC1=O
InChI Identifier
InChI=1S/C13H10N2O5/c16-9-5-8(10(17)14-11(9)18)15-12(19)6-3-1-2-4-7(6)13(15)20/h1-4,8-9,16H,5H2,(H,14,17,18)
InChI KeyHHTOWVWIVBSOKC-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phthalimides. These are aromatic heterocyclic compounds containing a 1,3-dioxoisoindoline moiety. They are imide derivatives of phthalic anhydrides.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIsoindoles and derivatives
Sub ClassIsoindolines
Direct ParentPhthalimides
Alternative Parents
Substituents
  • Phthalimide
  • Alpha-amino acid or derivatives
  • Isoindole
  • Piperidinedione
  • Delta-lactam
  • Piperidinone
  • Benzenoid
  • Piperidine
  • Carboxylic acid imide, n-substituted
  • Carboxylic acid imide
  • Dicarboximide
  • Carboxylic acid imide, n-unsubstituted
  • Lactam
  • Secondary alcohol
  • Carboxylic acid derivative
  • Azacycle
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID8054323
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9878646
PDB IDNot Available
ChEBI ID212535
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Only showing the first 10 proteins. There are 11 proteins in total.

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Enzymes

Enzyme Details
1. Prostaglandin G/H synthase 2
General function:
Involved in peroxidase activity
Specific function:
Mediates the formation of prostaglandins from arachidonate. May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity.
Gene Name:
PTGS2
Uniprot ID:
P35354
Molecular weight:
68995.625
References
  1. Horrobin DF: A low toxicity maintenance regime, using eicosapentaenoic acid and readily available drugs, for mantle cell lymphoma and other malignancies with excess cyclin D1 levels. Med Hypotheses. 2003 May;60(5):615-23. [PubMed:12710892 ]
  2. Hada M, Mizutari K: [A case report of metastatic pancreatic cancer that responded remarkably to the combination of thalidomide, celecoxib and irinotecan]. Gan To Kagaku Ryoho. 2004 Sep;31(9):1407-10. [PubMed:15446566 ]
  3. Payvandi F, Wu L, Haley M, Schafer PH, Zhang LH, Chen RS, Muller GW, Stirling DI: Immunomodulatory drugs inhibit expression of cyclooxygenase-2 from TNF-alpha, IL-1beta, and LPS-stimulated human PBMC in a partially IL-10-dependent manner. Cell Immunol. 2004 Aug;230(2):81-8. [PubMed:15598423 ]
  4. Wiedmann MW, Caca K: Molecularly targeted therapy for gastrointestinal cancer. Curr Cancer Drug Targets. 2005 May;5(3):171-93. [PubMed:15892618 ]
  5. Du GJ, Lin HH, Xu QT, Wang MW: Thalidomide inhibits growth of tumors through COX-2 degradation independent of antiangiogenesis. Vascul Pharmacol. 2005 Aug;43(2):112-9. [PubMed:15982930 ]
  6. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
Enzyme Details
2. Prostaglandin G/H synthase 1
General function:
Involved in peroxidase activity
Specific function:
May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells.
Gene Name:
PTGS1
Uniprot ID:
P23219
Molecular weight:
68685.82
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
Enzyme Details
3. Cytochrome P450 2C9
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. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular weight:
55627.365
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
Enzyme Details
4. Cytochrome P450 2C19
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular weight:
55944.565
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  2. 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. Fibroblast growth factor receptor 2
General function:
Involved in protein kinase activity
Specific function:
Receptor for acidic and basic fibroblast growth factors
Gene Name:
FGFR2
Uniprot ID:
P21802
Molecular weight:
92024.3
References
  1. Eichholz A, Merchant S, Gaya AM: Anti-angiogenesis therapies: their potential in cancer management. Onco Targets Ther. 2010 Jun 24;3:69-82. [PubMed:20616958 ]
Enzyme Details
6. Cytochrome P450 2E1
General function:
Involved in monooxygenase activity
Specific function:
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:
CYP2E1
Uniprot ID:
P05181
Molecular weight:
56848.42
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
Enzyme Details
7. Cytochrome P450 3A5
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:
CYP3A5
Uniprot ID:
P20815
Molecular weight:
57108.065
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
Enzyme Details
8. 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. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
Enzyme Details
9. 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. Wang B, Zhou SF: Synthetic and natural compounds that interact with human cytochrome P450 1A2 and implications in drug development. Curr Med Chem. 2009;16(31):4066-218. [PubMed:19754423 ]
  2. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
Enzyme Details
10. Tumor necrosis factor
General function:
Involved in tumor necrosis factor receptor binding
Specific function:
Cytokine that binds to TNFRSF1A/TNFR1 and TNFRSF1B/TNFBR. It is mainly secreted by macrophages and can induce cell death of certain tumor cell lines. It is potent pyrogen causing fever by direct action or by stimulation of interleukin-1 secretion and is implicated in the induction of cachexia, Under certain conditions it can stimulate cell proliferation and induce cell differentiation
Gene Name:
TNF
Uniprot ID:
P01375
Molecular weight:
25644.1
References
  1. Richardson P, Hideshima T, Anderson K: Thalidomide in multiple myeloma. Biomed Pharmacother. 2002 May;56(3):115-28. [PubMed:12046682 ]
  2. Fu LM, Fu-Liu CS: Thalidomide and tuberculosis. Int J Tuberc Lung Dis. 2002 Jul;6(7):569-72. [PubMed:12102294 ]
  3. Enomoto N, Takei Y, Hirose M, Ikejima K, Miwa H, Kitamura T, Sato N: Thalidomide prevents alcoholic liver injury in rats through suppression of Kupffer cell sensitization and TNF-alpha production. Gastroenterology. 2002 Jul;123(1):291-300. [PubMed:12105857 ]
  4. Rajkumar SV: Thalidomide in the treatment of multiple myeloma. Expert Rev Anticancer Ther. 2001 Jun;1(1):20-8. [PubMed:12113124 ]
  5. Vescovo G, Ravara B, Angelini A, Sandri M, Carraro U, Ceconi C, Dalla Libera L: Effect of thalidomide on the skeletal muscle in experimental heart failure. Eur J Heart Fail. 2002 Aug;4(4):455-60. [PubMed:12167383 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Only showing the first 10 proteins. There are 11 proteins in total.

Show all enzymes and transporters