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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 21:48:36 UTC

Update Date

2022-11-23 22:29:21 UTC

HMDB ID

HMDB0259292

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Troglitazone

Description

Troglitazone, also known as rezulin, belongs to the class of organic compounds known as 1-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 1-position. Troglitazone is a drug which is used for the treatment of type ii diabetes mellitus. it is used alone or in combination with a sulfonylurea, metformin, or insulin as an adjunct to diet and exercise. Based on a literature review very few articles have been published on Troglitazone. This compound has been identified in human blood as reported by (PMID: 31557052 ). Troglitazone is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Troglitazone is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

197
  Mrv0541 02231214302D          

 31 34  0  0  1  0            999 V2000
   11.4977    0.4914    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.9739   -1.4254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9616   -0.2918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0929    0.2531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5379    1.3379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4273    1.6304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9595    1.7129    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7214   -1.0015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7214   -0.1421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9739    0.2817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2364   -0.1594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2364   -0.9844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5464   -1.0047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1312   -1.7176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5219    0.2531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5219   -1.3969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -0.9844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -0.1594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5219    1.0781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5219   -2.2219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0929   -1.3969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7866   -0.2950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4366   -0.3014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1964   -1.0110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2019    0.4179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2616   -0.3046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6769    0.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0214   -1.0143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0269    0.4146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3442    1.1632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6723    1.2977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 27  1  0  0  0  0
  1 31  1  0  0  0  0
  2  8  1  0  0  0  0
  2 12  1  0  0  0  0
  3 13  1  0  0  0  0
  3 22  1  0  0  0  0
  4 18  1  0  0  0  0
  5 30  2  0  0  0  0
  6 31  2  0  0  0  0
  7 30  1  0  0  0  0
  7 31  1  0  0  0  0
  8  9  1  0  0  0  0
  8 13  1  0  0  0  0
  8 14  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 15  1  0  0  0  0
 12 16  1  0  0  0  0
 15 18  2  0  0  0  0
 15 19  1  0  0  0  0
 16 17  2  0  0  0  0
 16 20  1  0  0  0  0
 17 18  1  0  0  0  0
 17 21  1  0  0  0  0
 22 24  2  0  0  0  0
 22 25  1  0  0  0  0
 23 26  1  0  0  0  0
 23 28  2  0  0  0  0
 23 29  1  0  0  0  0
 24 28  1  0  0  0  0
 25 29  2  0  0  0  0
 26 27  1  0  0  0  0
 27 30  1  0  0  0  0
M  END

HMDB0259292
     RDKit          3D
troglitazone
 58 61  0  0  0  0  0  0  0  0999 V2000
   -7.0533    1.3571   -1.3486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9107    0.5210   -0.8999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6345    1.0401   -0.9468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3960    2.4302   -1.4432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5377    0.3138   -0.5448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7563   -0.9712   -0.0856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0495   -1.4931   -0.0397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3146   -2.8794    0.4523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1379   -0.7598   -0.4433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4470   -1.2602   -0.4073 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6638   -1.8379    0.3688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3096   -1.2661    0.1110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2805    0.2550    0.2319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4781    0.6047    1.6920 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1312    0.6696   -0.1406 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9769    0.0029    0.7586 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3472    0.0934    0.7796 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0947    0.8473   -0.0729 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4708    0.8677    0.0346 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1540    0.1427    0.9895 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6254    0.1923    1.0705 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3014   -0.8498    0.2371 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1130   -0.6184    0.4762 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.3986    0.3538   -1.0140 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5069    0.8197   -1.3977 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1149    0.4575   -1.6194 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2259   -0.5559   -1.2171 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4270   -1.1755   -1.9945 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4023   -0.6240    1.8573 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0201   -0.6405    1.7445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2459    0.8565   -0.5988 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9929    1.5147   -2.4599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0144    0.8357   -1.1680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0864    2.3310   -0.8016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4658    2.4612   -2.0308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2372    2.6656   -2.1198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3446    3.1446   -0.5751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7746   -3.5028   -0.3628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0388   -2.8294    1.3054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3847   -3.3438    0.8454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6654   -2.1792   -0.0862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7332   -2.7975   -0.2202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8040   -2.1524    1.4345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8848   -1.5501   -0.8699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6255   -1.6435    0.9149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5486    0.6221    1.9714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9700    1.5706    1.9416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9302   -0.1704    2.2805 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3663    0.4220   -1.1985 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2367    1.7693   -0.0454 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5556    1.4218   -0.8293 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0631    1.4634   -0.6388 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0123    1.1838    0.7643 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9777    0.0470    2.1277 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0081   -1.8758    0.4633 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8314    1.2192   -2.3129 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9071   -1.2171    2.6333 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4480   -1.2585    2.4471 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
  6 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  1  0
 27 28  2  0
 20 29  1  0
 29 30  2  0
 13 31  1  0
  9  2  1  0
 30 17  1  0
 31  5  1  0
 27 22  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  4 35  1  0
  4 36  1  0
  4 37  1  0
  8 38  1  0
  8 39  1  0
  8 40  1  0
 10 41  1  0
 11 42  1  0
 11 43  1  0
 12 44  1  0
 12 45  1  0
 14 46  1  0
 14 47  1  0
 14 48  1  0
 15 49  1  0
 15 50  1  0
 18 51  1  0
 19 52  1  0
 21 53  1  0
 21 54  1  0
 22 55  1  0
 26 56  1  0
 29 57  1  0
 30 58  1  0
M  END

197
  Mrv0541 02231214302D          

 31 34  0  0  1  0            999 V2000
   11.4977    0.4914    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.9739   -1.4254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9616   -0.2918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0929    0.2531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5379    1.3379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4273    1.6304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9595    1.7129    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7214   -1.0015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7214   -0.1421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9739    0.2817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2364   -0.1594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2364   -0.9844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5464   -1.0047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1312   -1.7176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5219    0.2531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5219   -1.3969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -0.9844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -0.1594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5219    1.0781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5219   -2.2219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0929   -1.3969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7866   -0.2950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4366   -0.3014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1964   -1.0110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2019    0.4179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2616   -0.3046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6769    0.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0214   -1.0143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0269    0.4146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3442    1.1632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6723    1.2977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 27  1  0  0  0  0
  1 31  1  0  0  0  0
  2  8  1  0  0  0  0
  2 12  1  0  0  0  0
  3 13  1  0  0  0  0
  3 22  1  0  0  0  0
  4 18  1  0  0  0  0
  5 30  2  0  0  0  0
  6 31  2  0  0  0  0
  7 30  1  0  0  0  0
  7 31  1  0  0  0  0
  8  9  1  0  0  0  0
  8 13  1  0  0  0  0
  8 14  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 15  1  0  0  0  0
 12 16  1  0  0  0  0
 15 18  2  0  0  0  0
 15 19  1  0  0  0  0
 16 17  2  0  0  0  0
 16 20  1  0  0  0  0
 17 18  1  0  0  0  0
 17 21  1  0  0  0  0
 22 24  2  0  0  0  0
 22 25  1  0  0  0  0
 23 26  1  0  0  0  0
 23 28  2  0  0  0  0
 23 29  1  0  0  0  0
 24 28  1  0  0  0  0
 25 29  2  0  0  0  0
 26 27  1  0  0  0  0
 27 30  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0259292

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=C(C)C2=C(CCC(C)(COC3=CC=C(CC4SC(=O)NC4=O)C=C3)O2)C(C)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C24H27NO5S/c1-13-14(2)21-18(15(3)20(13)26)9-10-24(4,30-21)12-29-17-7-5-16(6-8-17)11-19-22(27)25-23(28)31-19/h5-8,19,26H,9-12H2,1-4H3,(H,25,27,28)

> <INCHI_KEY>
GXPHKUHSUJUWKP-UHFFFAOYSA-N

> <FORMULA>
C24H27NO5S

> <MOLECULAR_WEIGHT>
441.54

> <EXACT_MASS>
441.160993669

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
47.07923558471997

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-({4-[(6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-yl)methoxy]phenyl}methyl)-1,3-thiazolidine-2,4-dione

> <ALOGPS_LOGP>
4.16

> <JCHEM_LOGP>
5.495204457666666

> <ALOGPS_LOGS>
-5.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.79429140046759

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.61355777563998

> <JCHEM_PKA_STRONGEST_BASIC>
-4.558161720453246

> <JCHEM_POLAR_SURFACE_AREA>
84.86

> <JCHEM_REFRACTIVITY>
120.9914

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.21e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
troglitazone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0259292
     RDKit          3D
troglitazone
 58 61  0  0  0  0  0  0  0  0999 V2000
   -7.0533    1.3571   -1.3486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9107    0.5210   -0.8999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6345    1.0401   -0.9468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3960    2.4302   -1.4432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5377    0.3138   -0.5448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7563   -0.9712   -0.0856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0495   -1.4931   -0.0397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3146   -2.8794    0.4523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1379   -0.7598   -0.4433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4470   -1.2602   -0.4073 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6638   -1.8379    0.3688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3096   -1.2661    0.1110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2805    0.2550    0.2319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4781    0.6047    1.6920 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1312    0.6696   -0.1406 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9769    0.0029    0.7586 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3472    0.0934    0.7796 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0947    0.8473   -0.0729 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4708    0.8677    0.0346 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1540    0.1427    0.9895 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6254    0.1923    1.0705 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3014   -0.8498    0.2371 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1130   -0.6184    0.4762 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.3986    0.3538   -1.0140 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5069    0.8197   -1.3977 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1149    0.4575   -1.6194 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2259   -0.5559   -1.2171 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4270   -1.1755   -1.9945 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4023   -0.6240    1.8573 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0201   -0.6405    1.7445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2459    0.8565   -0.5988 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9929    1.5147   -2.4599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0144    0.8357   -1.1680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0864    2.3310   -0.8016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4658    2.4612   -2.0308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2372    2.6656   -2.1198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3446    3.1446   -0.5751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7746   -3.5028   -0.3628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0388   -2.8294    1.3054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3847   -3.3438    0.8454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6654   -2.1792   -0.0862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7332   -2.7975   -0.2202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8040   -2.1524    1.4345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8848   -1.5501   -0.8699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6255   -1.6435    0.9149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5486    0.6221    1.9714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9700    1.5706    1.9416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9302   -0.1704    2.2805 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3663    0.4220   -1.1985 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2367    1.7693   -0.0454 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5556    1.4218   -0.8293 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0631    1.4634   -0.6388 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0123    1.1838    0.7643 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9777    0.0470    2.1277 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0081   -1.8758    0.4633 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8314    1.2192   -2.3129 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9071   -1.2171    2.6333 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4480   -1.2585    2.4471 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
  6 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  1  0
 27 28  2  0
 20 29  1  0
 29 30  2  0
 13 31  1  0
  9  2  1  0
 30 17  1  0
 31  5  1  0
 27 22  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  4 35  1  0
  4 36  1  0
  4 37  1  0
  8 38  1  0
  8 39  1  0
  8 40  1  0
 10 41  1  0
 11 42  1  0
 11 43  1  0
 12 44  1  0
 12 45  1  0
 14 46  1  0
 14 47  1  0
 14 48  1  0
 15 49  1  0
 15 50  1  0
 18 51  1  0
 19 52  1  0
 21 53  1  0
 21 54  1  0
 22 55  1  0
 26 56  1  0
 29 57  1  0
 30 58  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 197                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0      21.462   0.917   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0       9.285  -2.661   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      12.995  -0.545   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       3.907   0.472   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      17.804   2.497   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      23.198   3.043   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0      20.458   3.197   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      10.680  -1.869   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.680  -0.265   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.285   0.526   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.908  -0.298   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.908  -1.838   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.220  -1.875   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.445  -3.206   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.574   0.472   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.574  -2.608   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.241  -1.838   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.241  -0.298   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.574   2.012   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.574  -4.148   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.907  -2.608   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      14.535  -0.551   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      17.615  -0.563   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      15.300  -1.887   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      15.310   0.780   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      19.155  -0.569   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      19.930   0.762   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      16.840  -1.893   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      16.850   0.774   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      19.309   2.171   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      21.788   2.422   0.000  0.00  0.00           C+0
CONECT    1   27   31                                                       
CONECT    2    8   12                                                       
CONECT    3   13   22                                                       
CONECT    4   18                                                            
CONECT    5   30                                                            
CONECT    6   31                                                            
CONECT    7   30   31                                                       
CONECT    8    2    9   13   14                                             
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   15                                                  
CONECT   12    2   11   16                                                  
CONECT   13    3    8                                                       
CONECT   14    8                                                            
CONECT   15   11   18   19                                                  
CONECT   16   12   17   20                                                  
CONECT   17   16   18   21                                                  
CONECT   18    4   15   17                                                  
CONECT   19   15                                                            
CONECT   20   16                                                            
CONECT   21   17                                                            
CONECT   22    3   24   25                                                  
CONECT   23   26   28   29                                                  
CONECT   24   22   28                                                       
CONECT   25   22   29                                                       
CONECT   26   23   27                                                       
CONECT   27    1   26   30                                                  
CONECT   28   23   24                                                       
CONECT   29   23   25                                                       
CONECT   30    5    7   27                                                  
CONECT   31    1    6    7                                                  
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

COMPND    HMDB0259292
HETATM    1  C1  UNL     1      -7.053   1.357  -1.349  1.00  0.00           C  
HETATM    2  C2  UNL     1      -5.911   0.521  -0.900  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.634   1.040  -0.947  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.396   2.430  -1.443  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.538   0.314  -0.545  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.756  -0.971  -0.086  1.00  0.00           C  
HETATM    7  C7  UNL     1      -5.049  -1.493  -0.040  1.00  0.00           C  
HETATM    8  C8  UNL     1      -5.315  -2.879   0.452  1.00  0.00           C  
HETATM    9  C9  UNL     1      -6.138  -0.760  -0.443  1.00  0.00           C  
HETATM   10  O1  UNL     1      -7.447  -1.260  -0.407  1.00  0.00           O  
HETATM   11  C10 UNL     1      -2.664  -1.838   0.369  1.00  0.00           C  
HETATM   12  C11 UNL     1      -1.310  -1.266   0.111  1.00  0.00           C  
HETATM   13  C12 UNL     1      -1.280   0.255   0.232  1.00  0.00           C  
HETATM   14  C13 UNL     1      -1.478   0.605   1.692  1.00  0.00           C  
HETATM   15  C14 UNL     1       0.131   0.670  -0.141  1.00  0.00           C  
HETATM   16  O2  UNL     1       0.977   0.003   0.759  1.00  0.00           O  
HETATM   17  C15 UNL     1       2.347   0.093   0.780  1.00  0.00           C  
HETATM   18  C16 UNL     1       3.095   0.847  -0.073  1.00  0.00           C  
HETATM   19  C17 UNL     1       4.471   0.868   0.035  1.00  0.00           C  
HETATM   20  C18 UNL     1       5.154   0.143   0.990  1.00  0.00           C  
HETATM   21  C19 UNL     1       6.625   0.192   1.071  1.00  0.00           C  
HETATM   22  C20 UNL     1       7.301  -0.850   0.237  1.00  0.00           C  
HETATM   23  S1  UNL     1       9.113  -0.618   0.476  1.00  0.00           S  
HETATM   24  C21 UNL     1       9.399   0.354  -1.014  1.00  0.00           C  
HETATM   25  O3  UNL     1      10.507   0.820  -1.398  1.00  0.00           O  
HETATM   26  N1  UNL     1       8.115   0.457  -1.619  1.00  0.00           N  
HETATM   27  C22 UNL     1       7.226  -0.556  -1.217  1.00  0.00           C  
HETATM   28  O4  UNL     1       6.427  -1.176  -1.995  1.00  0.00           O  
HETATM   29  C23 UNL     1       4.402  -0.624   1.857  1.00  0.00           C  
HETATM   30  C24 UNL     1       3.020  -0.641   1.744  1.00  0.00           C  
HETATM   31  O5  UNL     1      -2.246   0.857  -0.599  1.00  0.00           O  
HETATM   32  H1  UNL     1      -6.993   1.515  -2.460  1.00  0.00           H  
HETATM   33  H2  UNL     1      -8.014   0.836  -1.168  1.00  0.00           H  
HETATM   34  H3  UNL     1      -7.086   2.331  -0.802  1.00  0.00           H  
HETATM   35  H4  UNL     1      -3.466   2.461  -2.031  1.00  0.00           H  
HETATM   36  H5  UNL     1      -5.237   2.666  -2.120  1.00  0.00           H  
HETATM   37  H6  UNL     1      -4.345   3.145  -0.575  1.00  0.00           H  
HETATM   38  H7  UNL     1      -5.775  -3.503  -0.363  1.00  0.00           H  
HETATM   39  H8  UNL     1      -6.039  -2.829   1.305  1.00  0.00           H  
HETATM   40  H9  UNL     1      -4.385  -3.344   0.845  1.00  0.00           H  
HETATM   41  H10 UNL     1      -7.665  -2.179  -0.086  1.00  0.00           H  
HETATM   42  H11 UNL     1      -2.733  -2.798  -0.220  1.00  0.00           H  
HETATM   43  H12 UNL     1      -2.804  -2.152   1.435  1.00  0.00           H  
HETATM   44  H13 UNL     1      -0.885  -1.550  -0.870  1.00  0.00           H  
HETATM   45  H14 UNL     1      -0.626  -1.644   0.915  1.00  0.00           H  
HETATM   46  H15 UNL     1      -2.549   0.622   1.971  1.00  0.00           H  
HETATM   47  H16 UNL     1      -0.970   1.571   1.942  1.00  0.00           H  
HETATM   48  H17 UNL     1      -0.930  -0.170   2.280  1.00  0.00           H  
HETATM   49  H18 UNL     1       0.366   0.422  -1.198  1.00  0.00           H  
HETATM   50  H19 UNL     1       0.237   1.769  -0.045  1.00  0.00           H  
HETATM   51  H20 UNL     1       2.556   1.422  -0.829  1.00  0.00           H  
HETATM   52  H21 UNL     1       5.063   1.463  -0.639  1.00  0.00           H  
HETATM   53  H22 UNL     1       7.012   1.184   0.764  1.00  0.00           H  
HETATM   54  H23 UNL     1       6.978   0.047   2.128  1.00  0.00           H  
HETATM   55  H24 UNL     1       7.008  -1.876   0.463  1.00  0.00           H  
HETATM   56  H25 UNL     1       7.831   1.219  -2.313  1.00  0.00           H  
HETATM   57  H26 UNL     1       4.907  -1.217   2.633  1.00  0.00           H  
HETATM   58  H27 UNL     1       2.448  -1.258   2.447  1.00  0.00           H  
CONECT    1    2   32   33   34
CONECT    2    3    3    9
CONECT    3    4    5
CONECT    4   35   36   37
CONECT    5    6    6   31
CONECT    6    7   11
CONECT    7    8    9    9
CONECT    8   38   39   40
CONECT    9   10
CONECT   10   41
CONECT   11   12   42   43
CONECT   12   13   44   45
CONECT   13   14   15   31
CONECT   14   46   47   48
CONECT   15   16   49   50
CONECT   16   17
CONECT   17   18   18   30
CONECT   18   19   51
CONECT   19   20   20   52
CONECT   20   21   29
CONECT   21   22   53   54
CONECT   22   23   27   55
CONECT   23   24
CONECT   24   25   25   26
CONECT   26   27   56
CONECT   27   28   28
CONECT   29   30   30   57
CONECT   30   58
END

HMDB0259292
     RDKit          3D
troglitazone
 58 61  0  0  0  0  0  0  0  0999 V2000
   -7.0533    1.3571   -1.3486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9107    0.5210   -0.8999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6345    1.0401   -0.9468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3960    2.4302   -1.4432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5377    0.3138   -0.5448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7563   -0.9712   -0.0856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0495   -1.4931   -0.0397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3146   -2.8794    0.4523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1379   -0.7598   -0.4433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4470   -1.2602   -0.4073 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6638   -1.8379    0.3688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3096   -1.2661    0.1110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2805    0.2550    0.2319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4781    0.6047    1.6920 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1312    0.6696   -0.1406 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9769    0.0029    0.7586 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3472    0.0934    0.7796 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0947    0.8473   -0.0729 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4708    0.8677    0.0346 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1540    0.1427    0.9895 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6254    0.1923    1.0705 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3014   -0.8498    0.2371 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1130   -0.6184    0.4762 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.3986    0.3538   -1.0140 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5069    0.8197   -1.3977 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1149    0.4575   -1.6194 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2259   -0.5559   -1.2171 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4270   -1.1755   -1.9945 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4023   -0.6240    1.8573 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0201   -0.6405    1.7445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2459    0.8565   -0.5988 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9929    1.5147   -2.4599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0144    0.8357   -1.1680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0864    2.3310   -0.8016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4658    2.4612   -2.0308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2372    2.6656   -2.1198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3446    3.1446   -0.5751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7746   -3.5028   -0.3628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0388   -2.8294    1.3054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3847   -3.3438    0.8454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6654   -2.1792   -0.0862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7332   -2.7975   -0.2202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8040   -2.1524    1.4345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8848   -1.5501   -0.8699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6255   -1.6435    0.9149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5486    0.6221    1.9714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9700    1.5706    1.9416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9302   -0.1704    2.2805 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3663    0.4220   -1.1985 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2367    1.7693   -0.0454 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5556    1.4218   -0.8293 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0631    1.4634   -0.6388 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0123    1.1838    0.7643 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9777    0.0470    2.1277 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0081   -1.8758    0.4633 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8314    1.2192   -2.3129 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9071   -1.2171    2.6333 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4480   -1.2585    2.4471 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
  6 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  1  0
 27 28  2  0
 20 29  1  0
 29 30  2  0
 13 31  1  0
  9  2  1  0
 30 17  1  0
 31  5  1  0
 27 22  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  4 35  1  0
  4 36  1  0
  4 37  1  0
  8 38  1  0
  8 39  1  0
  8 40  1  0
 10 41  1  0
 11 42  1  0
 11 43  1  0
 12 44  1  0
 12 45  1  0
 14 46  1  0
 14 47  1  0
 14 48  1  0
 15 49  1  0
 15 50  1  0
 18 51  1  0
 19 52  1  0
 21 53  1  0
 21 54  1  0
 22 55  1  0
 26 56  1  0
 29 57  1  0
 30 58  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Rezulin	ChEBI
Romglizone	ChEBI
Troglitazona	ChEBI
Troglitazonum	ChEBI
Prelay	MeSH
Warner-lambert brand OF troglitazone	MeSH
Parke davis brand OF troglitazone	MeSH

Chemical Formula

C₂₄H₂₇NO₅S

Average Molecular Weight

441.54

Monoisotopic Molecular Weight

441.160993669

IUPAC Name

5-({4-[(6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-yl)methoxy]phenyl}methyl)-1,3-thiazolidine-2,4-dione

Traditional Name

troglitazone

CAS Registry Number

Not Available

SMILES

CC1=C(C)C2=C(CCC(C)(COC3=CC=C(CC4SC(=O)NC4=O)C=C3)O2)C(C)=C1O

InChI Identifier

InChI=1S/C24H27NO5S/c1-13-14(2)21-18(15(3)20(13)26)9-10-24(4,30-21)12-29-17-7-5-16(6-8-17)11-19-22(27)25-23(28)31-19/h5-8,19,26H,9-12H2,1-4H3,(H,25,27,28)

InChI Key

GXPHKUHSUJUWKP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 1-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

1-benzopyrans

Alternative Parents

Substituents

1-benzopyran
Phenoxy compound
Phenol ether
Alkyl aryl ether
Thiazolidinedione
Monocyclic benzene moiety
Benzenoid
Dicarboximide
Thiazolidine
Carbonic acid derivative
Thiocarbamic acid derivative
Carboxylic acid derivative
Ether
Oxacycle
Azacycle
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

thiazolidinone (CHEBI:9753 )
chromanes (CHEBI:9753 )
a small molecule (CPD-11439 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Cellular substructure

Membrane (HMDB: HMDB0259292)

Source

Exogenous

Exogenous (PMID: 31557052)

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
logP	4.16	ALOGPS
logP	5.5	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	6.61	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	84.86 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	120.99 m³·mol⁻¹	ChemAxon
Polarizability	47.08 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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
DeepCCS	[M+H]+	207.677	30932474
DeepCCS	[M-H]-	205.319	30932474
DeepCCS	[M-2H]-	239.159	30932474
DeepCCS	[M+Na]+	214.973	30932474
AllCCS	[M+H]+	208.0	32859911
AllCCS	[M+H-H2O]+	205.8	32859911
AllCCS	[M+NH4]+	210.1	32859911
AllCCS	[M+Na]+	210.6	32859911
AllCCS	[M-H]-	202.7	32859911
AllCCS	[M+Na-2H]-	202.9	32859911
AllCCS	[M+HCOO]-	203.2	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.	7.45 minutes	32390414
Predicted by Siyang on May 30, 2022	19.1486 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.08 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2703.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	427.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	243.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	215.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	227.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1015.5 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	1084.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	82.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1687.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	676.6 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	2027.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	577.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	506.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	297.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	257.0 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	8.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
troglitazone	CC1=C(C)C2=C(CCC(C)(COC3=CC=C(CC4SC(=O)NC4=O)C=C3)O2)C(C)=C1O	5283.1	Standard polar	33892256
troglitazone	CC1=C(C)C2=C(CCC(C)(COC3=CC=C(CC4SC(=O)NC4=O)C=C3)O2)C(C)=C1O	3857.0	Standard non polar	33892256
troglitazone	CC1=C(C)C2=C(CCC(C)(COC3=CC=C(CC4SC(=O)NC4=O)C=C3)O2)C(C)=C1O	3996.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
troglitazone,2TMS,isomer #1	CC1=C(C)C2=C(CCC(C)(COC3=CC=C(CC4SC(=O)N([Si](C)(C)C)C4=O)C=C3)O2)C(C)=C1O[Si](C)(C)C	3787.1	Semi standard non polar	33892256
troglitazone,2TMS,isomer #1	CC1=C(C)C2=C(CCC(C)(COC3=CC=C(CC4SC(=O)N([Si](C)(C)C)C4=O)C=C3)O2)C(C)=C1O[Si](C)(C)C	3580.1	Standard non polar	33892256
troglitazone,2TMS,isomer #1	CC1=C(C)C2=C(CCC(C)(COC3=CC=C(CC4SC(=O)N([Si](C)(C)C)C4=O)C=C3)O2)C(C)=C1O[Si](C)(C)C	4173.1	Standard polar	33892256
troglitazone,2TBDMS,isomer #1	CC1=C(C)C2=C(CCC(C)(COC3=CC=C(CC4SC(=O)N([Si](C)(C)C(C)(C)C)C4=O)C=C3)O2)C(C)=C1O[Si](C)(C)C(C)(C)C	4226.5	Semi standard non polar	33892256
troglitazone,2TBDMS,isomer #1	CC1=C(C)C2=C(CCC(C)(COC3=CC=C(CC4SC(=O)N([Si](C)(C)C(C)(C)C)C4=O)C=C3)O2)C(C)=C1O[Si](C)(C)C(C)(C)C	3959.0	Standard non polar	33892256
troglitazone,2TBDMS,isomer #1	CC1=C(C)C2=C(CCC(C)(COC3=CC=C(CC4SC(=O)N([Si](C)(C)C(C)(C)C)C4=O)C=C3)O2)C(C)=C1O[Si](C)(C)C(C)(C)C	4270.1	Standard polar	33892256

Spectra

Biological Properties

Cellular Locations

Not Available

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	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00197

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5389

KEGG Compound ID

Not Available

BioCyc ID

CPD-11439

BiGG ID

Not Available

Wikipedia Link

Troglitazone

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

9753

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Troglitazone (HMDB0259292)

MOL for HMDB0259292 (Troglitazone)

3D MOL for HMDB0259292 (Troglitazone)

3D SDF for HMDB0259292 (Troglitazone)

3D-SDF for HMDB0259292 (Troglitazone)

PDB for HMDB0259292 (Troglitazone)

3D PDB for HMDB0259292 (Troglitazone)

SMILES for HMDB0259292 (Troglitazone)

INCHI for HMDB0259292 (Troglitazone)

Structure for HMDB0259292 (Troglitazone)

3D Structure for HMDB0259292 (Troglitazone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized