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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:56 UTC

HMDB ID

HMDB0015318

Secondary Accession Numbers

HMDB15318

Metabolite Identification

Common Name

Iophendylate

Description

Iophendylate is a mixture of isomers used as contrast medium, mainly for brain and spinal cord visualization. Iophendylate is a myelographic oil-ester (U.S. Patent 2,348,231). Iophendylate, which was never shown to be safe, was initially introduced for use in small amounts (1-2cc) for locating spinal tumors. It next appeared on the world scene for high volume (12-15cc), routine use, in diagnosing disc herniations. A number of clinicians have published on the dangers of oil myelography. In 1942 Van Wagenen (a neurosurgical colleague of Warrens, at the University of Rochester) identified Iophendylate as causing chemical meningitis in 30 patients where 'space-displacing masses within the spinal canal were suspected'.

Structure

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

HMDB0015318
     RDKit          3D
Iophendylate
 51 51  0  0  0  0  0  0  0  0999 V2000
    7.1061    1.6075   -0.2902 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6092    1.6013   -0.4315 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0994    0.3699   -0.8616 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2220   -0.8439   -0.2188 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8369   -0.9363    0.8455 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5916   -2.0365   -0.8357 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2237   -2.1656   -0.1004 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5565   -0.8421   -0.3302 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1562   -0.7665    0.3154 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6708    0.6346    0.0491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5821    1.1031    0.5463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9013    0.5967    0.1008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2103   -0.8024    0.3032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6404   -1.2238    0.0009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8310   -1.0162   -1.5269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5978   -0.1595    0.5373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7147    1.0696   -0.0707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6375    2.0061    0.4224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4473    1.7123    1.5228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2982    0.4673    2.0936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3780   -0.4735    1.6080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2284   -2.3613    2.5780 I   0  0  0  0  0  0  0  0  0  0  0  0
    7.5306    0.6149   -0.5350 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3982    1.7946    0.7889 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5555    2.3694   -0.9736 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1186    1.8582    0.5450 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2859    2.3738   -1.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3085   -1.8246   -1.8752 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1631   -2.9577   -0.7639 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5013   -2.2651    0.9627 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6738   -3.0216   -0.5150 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4335   -0.5992   -1.4191 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1431    0.0003    0.1109 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2356   -0.9871    1.3976 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5208   -1.5103   -0.1512 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7858    0.7998   -1.0911 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4943    1.3613    0.4148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6652    2.2534    0.4308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5648    0.9873    1.7103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0495    0.9374   -0.9650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6868    1.2210    0.6875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6212   -1.3919   -0.5072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8154   -1.2570    1.2401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9154   -2.2024    0.3173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6255   -2.0141   -2.0211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0216   -0.3712   -1.8698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8298   -0.6307   -1.7377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1729    1.3435   -0.9666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7409    2.9801   -0.0471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1637    2.4294    1.9029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8812    0.1677    2.9758 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21 16  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  0
 12 41  1  0
 13 42  1  0
 13 43  1  0
 14 44  1  0
 15 45  1  0
 15 46  1  0
 15 47  1  0
 17 48  1  0
 18 49  1  0
 19 50  1  0
 20 51  1  0
M  END

1187
  Mrv0541 02231215182D          

 22 22  0  0  1  0            999 V2000
    1.6500   -3.3001    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    3.7126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    2.4751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -3.3001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    2.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -3.7126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -3.7126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -4.5376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -4.5376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    2.8876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -4.9501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    4.1251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    4.9501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 15  1  0  0  0  0
  2 19  1  0  0  0  0
  2 21  1  0  0  0  0
  3 19  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7 11  1  0  0  0  0
  7 13  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 12  1  0  0  0  0
 11 15  1  0  0  0  0
 11 16  2  0  0  0  0
 12 14  1  0  0  0  0
 14 19  1  0  0  0  0
 15 17  2  0  0  0  0
 16 18  1  0  0  0  0
 17 20  1  0  0  0  0
 18 20  2  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015318

> <DATABASE_NAME>
hmdb

> <SMILES>
CCOC(=O)CCCCCCCCC(C)C1=CC=CC=C1I

> <INCHI_IDENTIFIER>
InChI=1S/C19H29IO2/c1-3-22-19(21)15-9-7-5-4-6-8-12-16(2)17-13-10-11-14-18(17)20/h10-11,13-14,16H,3-9,12,15H2,1-2H3

> <INCHI_KEY>
IWRUDYQZPTVTPA-UHFFFAOYSA-N

> <FORMULA>
C19H29IO2

> <MOLECULAR_WEIGHT>
416.3368

> <EXACT_MASS>
416.121223592

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
41.29389553153006

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
ethyl 10-(2-iodophenyl)undecanoate

> <ALOGPS_LOGP>
6.79

> <JCHEM_LOGP>
6.886209010666667

> <ALOGPS_LOGS>
-7.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.032123337017739

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
101.60239999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.52e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
iophendylate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015318
     RDKit          3D
Iophendylate
 51 51  0  0  0  0  0  0  0  0999 V2000
    7.1061    1.6075   -0.2902 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6092    1.6013   -0.4315 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0994    0.3699   -0.8616 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2220   -0.8439   -0.2188 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8369   -0.9363    0.8455 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5916   -2.0365   -0.8357 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2237   -2.1656   -0.1004 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5565   -0.8421   -0.3302 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1562   -0.7665    0.3154 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6708    0.6346    0.0491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5821    1.1031    0.5463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9013    0.5967    0.1008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2103   -0.8024    0.3032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6404   -1.2238    0.0009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8310   -1.0162   -1.5269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5978   -0.1595    0.5373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7147    1.0696   -0.0707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6375    2.0061    0.4224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4473    1.7123    1.5228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2982    0.4673    2.0936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3780   -0.4735    1.6080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2284   -2.3613    2.5780 I   0  0  0  0  0  0  0  0  0  0  0  0
    7.5306    0.6149   -0.5350 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3982    1.7946    0.7889 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5555    2.3694   -0.9736 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1186    1.8582    0.5450 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2859    2.3738   -1.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3085   -1.8246   -1.8752 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1631   -2.9577   -0.7639 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5013   -2.2651    0.9627 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6738   -3.0216   -0.5150 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4335   -0.5992   -1.4191 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1431    0.0003    0.1109 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2356   -0.9871    1.3976 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5208   -1.5103   -0.1512 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7858    0.7998   -1.0911 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4943    1.3613    0.4148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6652    2.2534    0.4308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5648    0.9873    1.7103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0495    0.9374   -0.9650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6868    1.2210    0.6875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6212   -1.3919   -0.5072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8154   -1.2570    1.2401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9154   -2.2024    0.3173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6255   -2.0141   -2.0211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0216   -0.3712   -1.8698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8298   -0.6307   -1.7377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1729    1.3435   -0.9666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7409    2.9801   -0.0471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1637    2.4294    1.9029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8812    0.1677    2.9758 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21 16  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  0
 12 41  1  0
 13 42  1  0
 13 43  1  0
 14 44  1  0
 15 45  1  0
 15 46  1  0
 15 47  1  0
 17 48  1  0
 18 49  1  0
 19 50  1  0
 20 51  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1187                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  I   UNK     0       3.080  -6.160   0.000  0.00  0.00           I+0
HETATM    2  O   UNK     0      12.416   6.930   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      13.750   4.620   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       7.081  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.081  -3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.415  -1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.748  -4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.415   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.748   0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.748   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.748  -6.160   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.082   3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.414  -3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.082   4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.414  -6.930   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.081  -6.930   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.414  -8.470   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.081  -8.470   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.416   5.390   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.748  -9.240   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.750   7.700   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.750   9.240   0.000  0.00  0.00           C+0
CONECT    1   15                                                            
CONECT    2   19   21                                                       
CONECT    3   19                                                            
CONECT    4    5    6                                                       
CONECT    5    4    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5   11   13                                                  
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   12                                                       
CONECT   11    7   15   16                                                  
CONECT   12   10   14                                                       
CONECT   13    7                                                            
CONECT   14   12   19                                                       
CONECT   15    1   11   17                                                  
CONECT   16   11   18                                                       
CONECT   17   15   20                                                       
CONECT   18   16   20                                                       
CONECT   19    2    3   14                                                  
CONECT   20   17   18                                                       
CONECT   21    2   22                                                       
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   44    0
END

COMPND    HMDB0015318
HETATM    1  C1  UNL     1       7.106   1.607  -0.290  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.609   1.601  -0.432  1.00  0.00           C  
HETATM    3  O1  UNL     1       5.099   0.370  -0.862  1.00  0.00           O  
HETATM    4  C3  UNL     1       5.222  -0.844  -0.219  1.00  0.00           C  
HETATM    5  O2  UNL     1       5.837  -0.936   0.845  1.00  0.00           O  
HETATM    6  C4  UNL     1       4.592  -2.037  -0.836  1.00  0.00           C  
HETATM    7  C5  UNL     1       3.224  -2.166  -0.100  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.557  -0.842  -0.330  1.00  0.00           C  
HETATM    9  C7  UNL     1       1.156  -0.766   0.315  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.671   0.635   0.049  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.582   1.103   0.546  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.901   0.597   0.101  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.210  -0.802   0.303  1.00  0.00           C  
HETATM   14  C12 UNL     1      -3.640  -1.224   0.001  1.00  0.00           C  
HETATM   15  C13 UNL     1      -3.831  -1.016  -1.527  1.00  0.00           C  
HETATM   16  C14 UNL     1      -4.598  -0.159   0.537  1.00  0.00           C  
HETATM   17  C15 UNL     1      -4.715   1.070  -0.071  1.00  0.00           C  
HETATM   18  C16 UNL     1      -5.638   2.006   0.422  1.00  0.00           C  
HETATM   19  C17 UNL     1      -6.447   1.712   1.523  1.00  0.00           C  
HETATM   20  C18 UNL     1      -6.298   0.467   2.094  1.00  0.00           C  
HETATM   21  C19 UNL     1      -5.378  -0.473   1.608  1.00  0.00           C  
HETATM   22  I1  UNL     1      -5.228  -2.361   2.578  1.00  0.00           I  
HETATM   23  H1  UNL     1       7.531   0.615  -0.535  1.00  0.00           H  
HETATM   24  H2  UNL     1       7.398   1.795   0.789  1.00  0.00           H  
HETATM   25  H3  UNL     1       7.556   2.369  -0.974  1.00  0.00           H  
HETATM   26  H4  UNL     1       5.119   1.858   0.545  1.00  0.00           H  
HETATM   27  H5  UNL     1       5.286   2.374  -1.177  1.00  0.00           H  
HETATM   28  H6  UNL     1       4.308  -1.825  -1.875  1.00  0.00           H  
HETATM   29  H7  UNL     1       5.163  -2.958  -0.764  1.00  0.00           H  
HETATM   30  H8  UNL     1       3.501  -2.265   0.963  1.00  0.00           H  
HETATM   31  H9  UNL     1       2.674  -3.022  -0.515  1.00  0.00           H  
HETATM   32  H10 UNL     1       2.434  -0.599  -1.419  1.00  0.00           H  
HETATM   33  H11 UNL     1       3.143   0.000   0.111  1.00  0.00           H  
HETATM   34  H12 UNL     1       1.236  -0.987   1.398  1.00  0.00           H  
HETATM   35  H13 UNL     1       0.521  -1.510  -0.151  1.00  0.00           H  
HETATM   36  H14 UNL     1       0.786   0.800  -1.091  1.00  0.00           H  
HETATM   37  H15 UNL     1       1.494   1.361   0.415  1.00  0.00           H  
HETATM   38  H16 UNL     1      -0.665   2.253   0.431  1.00  0.00           H  
HETATM   39  H17 UNL     1      -0.565   0.987   1.710  1.00  0.00           H  
HETATM   40  H18 UNL     1      -2.049   0.937  -0.965  1.00  0.00           H  
HETATM   41  H19 UNL     1      -2.687   1.221   0.687  1.00  0.00           H  
HETATM   42  H20 UNL     1      -1.621  -1.392  -0.507  1.00  0.00           H  
HETATM   43  H21 UNL     1      -1.815  -1.257   1.240  1.00  0.00           H  
HETATM   44  H22 UNL     1      -3.915  -2.202   0.317  1.00  0.00           H  
HETATM   45  H23 UNL     1      -3.625  -2.014  -2.021  1.00  0.00           H  
HETATM   46  H24 UNL     1      -3.022  -0.371  -1.870  1.00  0.00           H  
HETATM   47  H25 UNL     1      -4.830  -0.631  -1.738  1.00  0.00           H  
HETATM   48  H26 UNL     1      -4.173   1.343  -0.967  1.00  0.00           H  
HETATM   49  H27 UNL     1      -5.741   2.980  -0.047  1.00  0.00           H  
HETATM   50  H28 UNL     1      -7.164   2.429   1.903  1.00  0.00           H  
HETATM   51  H29 UNL     1      -6.881   0.168   2.976  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3   26   27
CONECT    3    4
CONECT    4    5    5    6
CONECT    6    7   28   29
CONECT    7    8   30   31
CONECT    8    9   32   33
CONECT    9   10   34   35
CONECT   10   11   36   37
CONECT   11   12   38   39
CONECT   12   13   40   41
CONECT   13   14   42   43
CONECT   14   15   16   44
CONECT   15   45   46   47
CONECT   16   17   17   21
CONECT   17   18   48
CONECT   18   19   19   49
CONECT   19   20   50
CONECT   20   21   21   51
CONECT   21   22
END

HMDB0015318
     RDKit          3D
Iophendylate
 51 51  0  0  0  0  0  0  0  0999 V2000
    7.1061    1.6075   -0.2902 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6092    1.6013   -0.4315 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0994    0.3699   -0.8616 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2220   -0.8439   -0.2188 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8369   -0.9363    0.8455 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5916   -2.0365   -0.8357 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2237   -2.1656   -0.1004 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5565   -0.8421   -0.3302 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1562   -0.7665    0.3154 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6708    0.6346    0.0491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5821    1.1031    0.5463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9013    0.5967    0.1008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2103   -0.8024    0.3032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6404   -1.2238    0.0009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8310   -1.0162   -1.5269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5978   -0.1595    0.5373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7147    1.0696   -0.0707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6375    2.0061    0.4224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4473    1.7123    1.5228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2982    0.4673    2.0936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3780   -0.4735    1.6080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2284   -2.3613    2.5780 I   0  0  0  0  0  0  0  0  0  0  0  0
    7.5306    0.6149   -0.5350 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3982    1.7946    0.7889 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5555    2.3694   -0.9736 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1186    1.8582    0.5450 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2859    2.3738   -1.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3085   -1.8246   -1.8752 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1631   -2.9577   -0.7639 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5013   -2.2651    0.9627 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6738   -3.0216   -0.5150 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4335   -0.5992   -1.4191 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1431    0.0003    0.1109 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2356   -0.9871    1.3976 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5208   -1.5103   -0.1512 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7858    0.7998   -1.0911 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4943    1.3613    0.4148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6652    2.2534    0.4308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5648    0.9873    1.7103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0495    0.9374   -0.9650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6868    1.2210    0.6875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6212   -1.3919   -0.5072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8154   -1.2570    1.2401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9154   -2.2024    0.3173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6255   -2.0141   -2.0211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0216   -0.3712   -1.8698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8298   -0.6307   -1.7377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1729    1.3435   -0.9666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7409    2.9801   -0.0471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1637    2.4294    1.9029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8812    0.1677    2.9758 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21 16  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  0
 12 41  1  0
 13 42  1  0
 13 43  1  0
 14 44  1  0
 15 45  1  0
 15 46  1  0
 15 47  1  0
 17 48  1  0
 18 49  1  0
 19 50  1  0
 20 51  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Iophendylic acid	Generator
Isophendylate	HMDB
Maiodil	HMDB
Myodil	HMDB
Ethiodan	HMDB
Iofendylate	HMDB
Ioglunide	HMDB
Panthopaque	HMDB
Iodophendylate	HMDB
Ethyl 10-(2-iodophenyl)undecanoic acid	HMDB

Chemical Formula

C₁₉H₂₉IO₂

Average Molecular Weight

416.3368

Monoisotopic Molecular Weight

416.121223592

IUPAC Name

ethyl 10-(2-iodophenyl)undecanoate

Traditional Name

iophendylate

CAS Registry Number

99-79-6

SMILES

CCOC(=O)CCCCCCCCC(C)C1=CC=CC=C1I

InChI Identifier

InChI=1S/C19H29IO2/c1-3-22-19(21)15-9-7-5-4-6-8-12-16(2)17-13-10-11-14-18(17)20/h10-11,13-14,16H,3-9,12,15H2,1-2H3

InChI Key

IWRUDYQZPTVTPA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as iodobenzenes. These are aromatic compounds containing one or more iodine atoms attached to a benzene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Halobenzenes

Direct Parent

Iodobenzenes

Alternative Parents

Substituents

Fatty acid ester
Iodobenzene
Aryl halide
Aryl iodide
Fatty acyl
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organoiodide
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organic oxygen compound
Organohalogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015318)

Source

Exogenous

Exogenous (HMDB: HMDB0015318)

Process

Not Available

Role

Not Available

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	2.5e-05 g/L	Not Available
LogP	7.7	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.5e-05 g/L	ALOGPS
logP	6.79	ALOGPS
logP	6.89	ChemAxon
logS	-7.2	ALOGPS
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	101.6 m³·mol⁻¹	ChemAxon
Polarizability	41.29 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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
DeepCCS	[M+H]+	184.96	30932474
DeepCCS	[M-H]-	182.602	30932474
DeepCCS	[M-2H]-	215.488	30932474
DeepCCS	[M+Na]+	191.129	30932474
AllCCS	[M+H]+	195.2	32859911
AllCCS	[M+H-H2O]+	192.7	32859911
AllCCS	[M+NH4]+	197.5	32859911
AllCCS	[M+Na]+	198.1	32859911
AllCCS	[M-H]-	195.5	32859911
AllCCS	[M+Na-2H]-	197.5	32859911
AllCCS	[M+HCOO]-	199.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	8.21 minutes	32390414
Predicted by Siyang on May 30, 2022	23.4921 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.82 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2967.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	746.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	288.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	401.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	556.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1083.2 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	936.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	102.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	2151.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	695.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	2007.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	756.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	523.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	582.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	666.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Iophendylate	CCOC(=O)CCCCCCCCC(C)C1=CC=CC=C1I	2924.4	Standard polar	33892256
Iophendylate	CCOC(=O)CCCCCCCCC(C)C1=CC=CC=C1I	2399.4	Standard non polar	33892256
Iophendylate	CCOC(=O)CCCCCCCCC(C)C1=CC=CC=C1I	2512.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Iophendylate GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-2393000000-c63b6b1c060a30fc786c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Iophendylate 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 - Iophendylate 10V, Positive-QTOF	splash10-014i-1136900000-908d7aa49bdf879b6a36	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iophendylate 20V, Positive-QTOF	splash10-00te-4049100000-d9249f50b00af7fb7890	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iophendylate 40V, Positive-QTOF	splash10-000x-9331000000-b93ea3bf748f61553f13	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iophendylate 10V, Negative-QTOF	splash10-014i-2007900000-e9d1ba3553953e569a0e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iophendylate 20V, Negative-QTOF	splash10-014i-5009300000-db5e210428edec304101	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iophendylate 40V, Negative-QTOF	splash10-052g-9014000000-3af47d70f97da690a9a4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iophendylate 10V, Positive-QTOF	splash10-014i-2639800000-14b868e357d7d314e64e	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iophendylate 20V, Positive-QTOF	splash10-008a-4963000000-11c2c8aa5ad03bd9d921	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iophendylate 40V, Positive-QTOF	splash10-001i-4390000000-107b7e745bba4809ff52	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iophendylate 10V, Negative-QTOF	splash10-014i-0002900000-65bad5756c6ad5ec21f2	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iophendylate 20V, Negative-QTOF	splash10-014l-1109000000-00e606d74bce9c6c4a79	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iophendylate 40V, Negative-QTOF	splash10-056u-1974000000-bc21acfcd9f5ef6bc1c4	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01187	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01187	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01187

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2301035

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Iofendylate

METLIN ID

Not Available

PubChem Compound

3037234

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 Iophendylate (HMDB0015318)

MOL for HMDB0015318 (Iophendylate)

3D MOL for HMDB0015318 (Iophendylate)

3D SDF for HMDB0015318 (Iophendylate)

3D-SDF for HMDB0015318 (Iophendylate)

PDB for HMDB0015318 (Iophendylate)

3D PDB for HMDB0015318 (Iophendylate)

SMILES for HMDB0015318 (Iophendylate)

INCHI for HMDB0015318 (Iophendylate)

Structure for HMDB0015318 (Iophendylate)

3D Structure for HMDB0015318 (Iophendylate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra