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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:00:17 UTC

Update Date

2021-09-14 15:48:20 UTC

HMDB ID

HMDB0013871

Secondary Accession Numbers

HMDB13871

Metabolite Identification

Common Name

5-Hydroxythalidomide

Description

5-hydroxythalidomide 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. Based on a literature review very few articles have been published on 5-hydroxythalidomide.

Structure

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

HMDB0013871
     RDKit          3D
5-Hydroxythalidomide
 30 32  0  0  0  0  0  0  0  0999 V2000
    4.7468    0.0080    2.0123 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9528   -0.2842    1.0891 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9502    0.5440   -0.1407 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5351    0.8328   -0.5588 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7119   -0.3933   -0.7665 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2919   -0.1496   -0.5998 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7662   -0.2776   -1.5104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6491   -0.6507   -2.7040 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0426    0.0789   -0.9015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3524    0.1287   -1.3328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3912    0.5163   -0.5113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0920    0.8695    0.8057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1016    1.2677    1.6758 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7784    0.8159    1.2260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7366    0.4290    0.4082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2879    0.2957    0.6237 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2587    0.5472    1.7138 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1259   -1.5297    0.0837 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6313   -2.6717   -0.1699 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0463   -1.3761    1.1569 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4594   -0.0605   -0.9483 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4719    1.4893    0.0354 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0989    1.4898    0.2502 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5634    1.4737   -1.4697 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8694   -0.7335   -1.8319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5771   -0.1482   -2.3605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4186    0.5572   -0.8434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0381    1.2973    1.3473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5396    1.0912    2.2549 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0576   -2.0403    1.9664 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  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
  5 18  1  0
 18 19  2  0
 18 20  1  0
 20  2  1  0
 16  6  1  0
 15  9  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
 10 26  1  0
 11 27  1  0
 13 28  1  0
 14 29  1  0
 20 30  1  0
M  END

  Mrv0541 06191310242D          

 20 22  0  0  0  0            999 V2000
    9.5953   -5.2514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5450   -5.2706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5450   -2.3744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0702   -3.8225    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7703   -3.8225    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8328   -4.5370    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5953   -3.8225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0078   -3.1080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8328   -3.1080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0078   -4.5370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2889   -4.4864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2889   -3.1586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5083   -4.2350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5083   -3.4100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2453   -3.8225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7937   -4.6475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7937   -2.9975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0792   -4.2350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0792   -3.4100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3648   -4.6475    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
 18 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0013871

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC=C2C(=O)N(C3CCC(=O)NC3=O)C(=O)C2=C1

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

> <INCHI_KEY>
LJBQRRQTZUJWRC-UHFFFAOYSA-N

> <FORMULA>
C13H10N2O5

> <MOLECULAR_WEIGHT>
274.2289

> <EXACT_MASS>
274.05897144

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
25.352265899739894

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
0.34

> <JCHEM_LOGP>
-0.2878579656666665

> <ALOGPS_LOGS>
-1.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.59334265215638

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.75946994703461

> <JCHEM_PKA_STRONGEST_BASIC>
-6.428597276970739

> <JCHEM_POLAR_SURFACE_AREA>
103.78

> <JCHEM_REFRACTIVITY>
66.3057

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.99e+00 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0013871
     RDKit          3D
5-Hydroxythalidomide
 30 32  0  0  0  0  0  0  0  0999 V2000
    4.7468    0.0080    2.0123 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9528   -0.2842    1.0891 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9502    0.5440   -0.1407 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5351    0.8328   -0.5588 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7119   -0.3933   -0.7665 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2919   -0.1496   -0.5998 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7662   -0.2776   -1.5104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6491   -0.6507   -2.7040 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0426    0.0789   -0.9015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3524    0.1287   -1.3328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3912    0.5163   -0.5113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0920    0.8695    0.8057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1016    1.2677    1.6758 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7784    0.8159    1.2260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7366    0.4290    0.4082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2879    0.2957    0.6237 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2587    0.5472    1.7138 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1259   -1.5297    0.0837 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6313   -2.6717   -0.1699 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0463   -1.3761    1.1569 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4594   -0.0605   -0.9483 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4719    1.4893    0.0354 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0989    1.4898    0.2502 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5634    1.4737   -1.4697 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8694   -0.7335   -1.8319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5771   -0.1482   -2.3605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4186    0.5572   -0.8434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0381    1.2973    1.3473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5396    1.0912    2.2549 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0576   -2.0403    1.9664 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  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
  5 18  1  0
 18 19  2  0
 18 20  1  0
 20  2  1  0
 16  6  1  0
 15  9  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
 10 26  1  0
 11 27  1  0
 13 28  1  0
 14 29  1  0
 20 30  1  0
M  END

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      17.911  -9.803   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      15.951  -9.839   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      15.951  -4.432   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      22.531  -7.135   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0      16.371  -7.135   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0      20.221  -8.469   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      17.911  -7.135   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      18.681  -5.802   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      20.221  -5.802   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      18.681  -8.469   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      15.473  -8.375   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      15.473  -5.896   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.015  -7.905   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.015  -6.365   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      20.991  -7.135   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.682  -8.675   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.682  -5.595   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.348  -7.905   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.348  -6.365   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      10.014  -8.675   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                                                       
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   20                                                  
CONECT   19   17   18                                                       
CONECT   20   18                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0013871
HETATM    1  O1  UNL     1       4.747   0.008   2.012  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.953  -0.284   1.089  1.00  0.00           C  
HETATM    3  C2  UNL     1       3.950   0.544  -0.141  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.535   0.833  -0.559  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.712  -0.393  -0.767  1.00  0.00           C  
HETATM    6  N1  UNL     1       0.292  -0.150  -0.600  1.00  0.00           N  
HETATM    7  C5  UNL     1      -0.766  -0.278  -1.510  1.00  0.00           C  
HETATM    8  O2  UNL     1      -0.649  -0.651  -2.704  1.00  0.00           O  
HETATM    9  C6  UNL     1      -2.043   0.079  -0.901  1.00  0.00           C  
HETATM   10  C7  UNL     1      -3.352   0.129  -1.333  1.00  0.00           C  
HETATM   11  C8  UNL     1      -4.391   0.516  -0.511  1.00  0.00           C  
HETATM   12  C9  UNL     1      -4.092   0.870   0.806  1.00  0.00           C  
HETATM   13  O3  UNL     1      -5.102   1.268   1.676  1.00  0.00           O  
HETATM   14  C10 UNL     1      -2.778   0.816   1.226  1.00  0.00           C  
HETATM   15  C11 UNL     1      -1.737   0.429   0.408  1.00  0.00           C  
HETATM   16  C12 UNL     1      -0.288   0.296   0.624  1.00  0.00           C  
HETATM   17  O4  UNL     1       0.259   0.547   1.714  1.00  0.00           O  
HETATM   18  C13 UNL     1       2.126  -1.530   0.084  1.00  0.00           C  
HETATM   19  O5  UNL     1       1.631  -2.672  -0.170  1.00  0.00           O  
HETATM   20  N2  UNL     1       3.046  -1.376   1.157  1.00  0.00           N  
HETATM   21  H1  UNL     1       4.459  -0.060  -0.948  1.00  0.00           H  
HETATM   22  H2  UNL     1       4.472   1.489   0.035  1.00  0.00           H  
HETATM   23  H3  UNL     1       2.099   1.490   0.250  1.00  0.00           H  
HETATM   24  H4  UNL     1       2.563   1.474  -1.470  1.00  0.00           H  
HETATM   25  H5  UNL     1       1.869  -0.734  -1.832  1.00  0.00           H  
HETATM   26  H6  UNL     1      -3.577  -0.148  -2.361  1.00  0.00           H  
HETATM   27  H7  UNL     1      -5.419   0.557  -0.843  1.00  0.00           H  
HETATM   28  H8  UNL     1      -6.038   1.297   1.347  1.00  0.00           H  
HETATM   29  H9  UNL     1      -2.540   1.091   2.255  1.00  0.00           H  
HETATM   30  H10 UNL     1       3.058  -2.040   1.966  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   20
CONECT    3    4   21   22
CONECT    4    5   23   24
CONECT    5    6   18   25
CONECT    6    7   16
CONECT    7    8    8    9
CONECT    9   10   10   15
CONECT   10   11   26
CONECT   11   12   12   27
CONECT   12   13   14
CONECT   13   28
CONECT   14   15   15   29
CONECT   15   16
CONECT   16   17   17
CONECT   18   19   19   20
CONECT   20   30
END

HMDB0013871
     RDKit          3D
5-Hydroxythalidomide
 30 32  0  0  0  0  0  0  0  0999 V2000
    4.7468    0.0080    2.0123 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9528   -0.2842    1.0891 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9502    0.5440   -0.1407 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5351    0.8328   -0.5588 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7119   -0.3933   -0.7665 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2919   -0.1496   -0.5998 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7662   -0.2776   -1.5104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6491   -0.6507   -2.7040 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0426    0.0789   -0.9015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3524    0.1287   -1.3328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3912    0.5163   -0.5113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0920    0.8695    0.8057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1016    1.2677    1.6758 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7784    0.8159    1.2260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7366    0.4290    0.4082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2879    0.2957    0.6237 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2587    0.5472    1.7138 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1259   -1.5297    0.0837 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6313   -2.6717   -0.1699 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0463   -1.3761    1.1569 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4594   -0.0605   -0.9483 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4719    1.4893    0.0354 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0989    1.4898    0.2502 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5634    1.4737   -1.4697 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8694   -0.7335   -1.8319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5771   -0.1482   -2.3605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4186    0.5572   -0.8434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0381    1.2973    1.3473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5396    1.0912    2.2549 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0576   -2.0403    1.9664 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  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
  5 18  1  0
 18 19  2  0
 18 20  1  0
 20  2  1  0
 16  6  1  0
 15  9  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
 10 26  1  0
 11 27  1  0
 13 28  1  0
 14 29  1  0
 20 30  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(+/-)-hydroxythalidomide	ChEMBL, HMDB
5-Hydroxythalidomide	MeSH

Chemical Formula

C₁₃H₁₀N₂O₅

Average Molecular Weight

274.2289

Monoisotopic Molecular Weight

274.05897144

IUPAC Name

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

Traditional Name

2-(2,6-dioxopiperidin-3-yl)-5-hydroxyisoindole-1,3-dione

CAS Registry Number

Not Available

SMILES

OC1=CC=C2C(=O)N(C3CCC(=O)NC3=O)C(=O)C2=C1

InChI Identifier

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

InChI Key

LJBQRRQTZUJWRC-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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isoindoles and derivatives

Sub Class

Isoindolines

Direct Parent

Phthalimides

Alternative Parents

Substituents

Phthalimide
Alpha-amino acid or derivatives
Isoindole
Piperidinedione
1-hydroxy-2-unsubstituted benzenoid
Delta-lactam
Piperidinone
Benzenoid
Piperidine
Carboxylic acid imide, n-substituted
Carboxylic acid imide
Dicarboximide
Carboxylic acid imide, n-unsubstituted
Lactam
Carboxylic acid derivative
Azacycle
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Organ

Liver (HMDB: HMDB0013871)
Kidney (HMDB: HMDB0013871)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Extracellular (HMDB: HMDB0013871)

Source

Endogenous

Endogenous (HMDB: HMDB0013871)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.99 g/L	ALOGPS
logP	0.34	ALOGPS
logP	-0.29	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	7.76	ChemAxon
pKa (Strongest Basic)	-6.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	103.78 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	66.31 m³·mol⁻¹	ChemAxon
Polarizability	25.35 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	164.322	31661259
DarkChem	[M-H]-	161.456	31661259
DeepCCS	[M+H]+	161.429	30932474
DeepCCS	[M-H]-	159.071	30932474
DeepCCS	[M-2H]-	191.96	30932474
DeepCCS	[M+Na]+	167.522	30932474
AllCCS	[M+H]+	160.9	32859911
AllCCS	[M+H-H2O]+	157.4	32859911
AllCCS	[M+NH4]+	164.1	32859911
AllCCS	[M+Na]+	165.1	32859911
AllCCS	[M-H]-	161.4	32859911
AllCCS	[M+Na-2H]-	160.8	32859911
AllCCS	[M+HCOO]-	160.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5-Hydroxythalidomide	OC1=CC=C2C(=O)N(C3CCC(=O)NC3=O)C(=O)C2=C1	4236.4	Standard polar	33892256
5-Hydroxythalidomide	OC1=CC=C2C(=O)N(C3CCC(=O)NC3=O)C(=O)C2=C1	2730.0	Standard non polar	33892256
5-Hydroxythalidomide	OC1=CC=C2C(=O)N(C3CCC(=O)NC3=O)C(=O)C2=C1	2764.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5-Hydroxythalidomide,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C2C(=O)N(C3CCC(=O)NC3=O)C(=O)C2=C1	2740.5	Semi standard non polar	33892256
5-Hydroxythalidomide,1TMS,isomer #2	C[Si](C)(C)N1C(=O)CCC(N2C(=O)C3=CC=C(O)C=C3C2=O)C1=O	2529.4	Semi standard non polar	33892256
5-Hydroxythalidomide,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C2C(=O)N(C3CCC(=O)N([Si](C)(C)C)C3=O)C(=O)C2=C1	2622.0	Semi standard non polar	33892256
5-Hydroxythalidomide,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C2C(=O)N(C3CCC(=O)N([Si](C)(C)C)C3=O)C(=O)C2=C1	2784.1	Standard non polar	33892256
5-Hydroxythalidomide,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C2C(=O)N(C3CCC(=O)N([Si](C)(C)C)C3=O)C(=O)C2=C1	3544.9	Standard polar	33892256
5-Hydroxythalidomide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2C(=O)N(C3CCC(=O)NC3=O)C(=O)C2=C1	2999.7	Semi standard non polar	33892256
5-Hydroxythalidomide,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C(=O)CCC(N2C(=O)C3=CC=C(O)C=C3C2=O)C1=O	2826.6	Semi standard non polar	33892256
5-Hydroxythalidomide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2C(=O)N(C3CCC(=O)N([Si](C)(C)C(C)(C)C)C3=O)C(=O)C2=C1	3110.1	Semi standard non polar	33892256
5-Hydroxythalidomide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2C(=O)N(C3CCC(=O)N([Si](C)(C)C(C)(C)C)C3=O)C(=O)C2=C1	3199.6	Standard non polar	33892256
5-Hydroxythalidomide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2C(=O)N(C3CCC(=O)N([Si](C)(C)C(C)(C)C)C3=O)C(=O)C2=C1	3565.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Hydroxythalidomide GC-MS (Non-derivatized) - 70eV, Positive	splash10-009b-3690000000-8679b84cbd1f0bfac25c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Hydroxythalidomide GC-MS (1 TMS) - 70eV, Positive	splash10-0uk9-6596000000-437d240fb35612bd8447	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Hydroxythalidomide 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 - 5-Hydroxythalidomide 10V, Positive-QTOF	splash10-004i-0090000000-ffe708fcb4d4bd9f78d4	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxythalidomide 20V, Positive-QTOF	splash10-0kdi-0190000000-a9980b10cc2c23d7360d	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxythalidomide 40V, Positive-QTOF	splash10-0f6x-9750000000-e51ca57f9da2b89f9678	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxythalidomide 10V, Negative-QTOF	splash10-00di-0190000000-67f60994b310f52481ac	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxythalidomide 20V, Negative-QTOF	splash10-0229-1390000000-935397246221e1a7e29e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxythalidomide 40V, Negative-QTOF	splash10-03dl-9610000000-b9bf4ee195a1c4857bf9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxythalidomide 10V, Negative-QTOF	splash10-0229-0590000000-701e2335afdc23da1222	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxythalidomide 20V, Negative-QTOF	splash10-0229-0590000000-d8224820a02cabea7145	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxythalidomide 40V, Negative-QTOF	splash10-03dl-4910000000-a570ad90f88dece8da63	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxythalidomide 10V, Positive-QTOF	splash10-03fr-0960000000-aaba1dc1ec7c840fd39b	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxythalidomide 20V, Positive-QTOF	splash10-01t9-0690000000-39f23796b8f97f1b6611	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxythalidomide 40V, Positive-QTOF	splash10-00dj-3930000000-54b1ffe9695df26fa66a	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

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	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4675403

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5743568

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for 5-Hydroxythalidomide (HMDB0013871)

MOL for HMDB0013871 (5-Hydroxythalidomide)

3D MOL for HMDB0013871 (5-Hydroxythalidomide)

3D SDF for HMDB0013871 (5-Hydroxythalidomide)

3D-SDF for HMDB0013871 (5-Hydroxythalidomide)

PDB for HMDB0013871 (5-Hydroxythalidomide)

3D PDB for HMDB0013871 (5-Hydroxythalidomide)

SMILES for HMDB0013871 (5-Hydroxythalidomide)

INCHI for HMDB0013871 (5-Hydroxythalidomide)

Structure for HMDB0013871 (5-Hydroxythalidomide)

3D Structure for HMDB0013871 (5-Hydroxythalidomide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra