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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 14:26:02 UTC

Update Date

2021-09-26 23:09:24 UTC

HMDB ID

HMDB0254949

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Muraglitazar

Description

Muraglitazar, also known as pargluva, belongs to the class of organic compounds known as phenyl-1,3-oxazoles. These are aromatic heterocyclic compounds containing a 1,3-oxazole substituted at one or more positions by a phenyl group. However, the muraglitazar group had a higher all-cause mortality, greater incidence of edema and heart failure and more weight gain compared to the pioglitazone group. Muraglitazar is an extremely weak basic (essentially neutral) compound (based on its pKa). Data on muraglitazar is relatively sparse due to the recent introduction of this agent. A meta-analysis of the phase II and III clinical trials of muraglitazar revealed that it was associated with a greater incidence of myocardial infarction, stroke, transient ischemic attacks and congestive heart failure (CHF) when compared to placebo or pioglitazone. One double-blind randomized clinical trial comparing muraglitazar and pioglitazone found that the effects of the former were favourable in terms of HDL-C increase, decrease in total cholesterol, apolipoprotein B, triglycerides and a greater reduction in HbA1c (p <0.0001 for all comparisons). The drug had completed phase III clinical trials, however in May, 2006 Bristol-Myers Squibb announced that it had discontinued further development. Muraglitazar (proposed tradename Pargluva) is a dual peroxisome proliferator-activated receptor agonist with affinity to PPARα and PPARγ. This compound has been identified in human blood as reported by (PMID: 31557052 ). Muraglitazar is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Muraglitazar 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


  Mrv1572004221606572D          

 38 41  0  0  0  0            999 V2000
   -0.1876    1.5150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.1461    2.1150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.3256    2.0288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1762    3.4499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.1447   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  4  3  2  0  0  0  0
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 37 20  1  0  0  0  0
 37 28  1  0  0  0  0
 38 25  1  0  0  0  0
 38 29  1  0  0  0  0
M  END

HMDB0254949
     RDKit          3D
Muraglitazar
 66 69  0  0  0  0  0  0  0  0999 V2000
   -9.6259    2.3465   -2.7997 C   0  0  0  0  0  0  0  0  0  0  0  0
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 38 66  1  0
M  END


  Mrv1572004221606572D          

 38 41  0  0  0  0            999 V2000
   -0.1876    1.5150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 25 14  2  0  0  0  0
 25 15  1  0  0  0  0
 26 16  1  0  0  0  0
 26 20  2  0  0  0  0
 27 19  1  0  0  0  0
 28 22  1  0  0  0  0
 30 26  1  0  0  0  0
 30 28  2  0  0  0  0
 31 18  1  0  0  0  0
 31 19  1  0  0  0  0
 31 29  1  0  0  0  0
 32 27  2  0  0  0  0
 33 27  1  0  0  0  0
 34 29  2  0  0  0  0
 35  2  1  0  0  0  0
 35 23  1  0  0  0  0
 36 17  1  0  0  0  0
 36 24  1  0  0  0  0
 37 20  1  0  0  0  0
 37 28  1  0  0  0  0
 38 25  1  0  0  0  0
 38 29  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0254949

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC=C(OC(=O)N(CC(O)=O)CC2=CC=C(OCCC3=C(C)OC(=N3)C3=CC=CC=C3)C=C2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C29H28N2O7/c1-20-26(30-28(37-20)22-6-4-3-5-7-22)16-17-36-24-10-8-21(9-11-24)18-31(19-27(32)33)29(34)38-25-14-12-23(35-2)13-15-25/h3-15H,16-19H2,1-2H3,(H,32,33)

> <INCHI_KEY>
IRLWJILLXJGJTD-UHFFFAOYSA-N

> <FORMULA>
C29H28N2O7

> <MOLECULAR_WEIGHT>
516.55

> <EXACT_MASS>
516.18965125

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
54.85324869081978

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-{[(4-methoxyphenoxy)carbonyl]({4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl}methyl)amino}acetic acid

> <ALOGPS_LOGP>
5.04

> <JCHEM_LOGP>
4.790607983333334

> <ALOGPS_LOGS>
-4.60

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.185523196585518

> <JCHEM_PKA_STRONGEST_BASIC>
0.9306294815795827

> <JCHEM_POLAR_SURFACE_AREA>
111.33000000000001

> <JCHEM_REFRACTIVITY>
149.0346

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.29e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
muraglitazar

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0254949
     RDKit          3D
Muraglitazar
 66 69  0  0  0  0  0  0  0  0999 V2000
   -9.6259    2.3465   -2.7997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4785    1.5638   -3.0615 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4863    1.4103   -2.1075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5623    2.0078   -0.8586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5254    1.8090    0.0515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4436    1.0279   -0.2937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4077    0.8232    0.6022 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4709   -0.2537    1.4548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4814   -0.9991    1.3671 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4811   -0.5671    2.4107 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6724   -1.7254    3.2551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1490   -2.9674    2.6488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1285   -4.0380    3.2972 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6826   -2.9254    1.3471 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3045    0.2352    2.5816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2000   -0.3131    1.7648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2331   -1.1332    2.3521 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8111   -1.6530    1.6122 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9709   -1.4040    0.2679 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9731   -1.8764   -0.5306 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0460   -2.6618   -0.2569 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1217   -2.2001    0.6529 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8565   -0.9943    0.2266 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0745   -0.9558   -0.4019 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4286    0.3020   -0.6551 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6606    0.7835   -1.3161 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6210   -0.0676   -1.7654 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7676    0.4187   -2.3824 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9159    1.7867   -2.5322 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9623    2.6771   -2.0885 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8355    2.1369   -1.4788 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4634    1.0563   -0.2012 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4954    0.3156    0.3389 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2511    0.8837    0.9501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0058   -0.5773   -0.3201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0422   -0.0635    0.4213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3520    0.4265   -1.5309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3878    0.6292   -2.4308 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0605    2.0890   -1.8091 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4341    2.0861   -3.5417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3717    3.4159   -2.8820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4201    2.6183   -0.6051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5647    2.2703    1.0411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1351   -1.5295    4.2199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7695   -1.8307    3.4994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2994   -3.1859    0.5681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4819    1.3126    2.3807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9725    0.2127    3.6633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3429   -1.3422    3.4204 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5312   -2.2952    2.1060 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5081   -3.0513   -1.2149 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6642   -3.6395    0.2141 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8974   -3.0355    0.6632 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7782   -2.1406    1.6944 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4646   -1.1374   -1.6275 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5353   -0.2433   -2.7424 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7984    2.2184   -3.0100 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0862    3.7596   -2.2103 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0705    2.8259   -1.1216 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4779    1.0687    0.1931 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9450    0.2910    1.8119 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5123    1.9029    1.3589 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1006   -0.3661   -1.3872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7846    0.5757   -0.0519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5239   -0.1880   -1.8325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3431    0.1785   -3.3893 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 10 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 25 32  1  0
 32 33  1  0
 33 34  1  0
 19 35  1  0
 35 36  2  0
  6 37  1  0
 37 38  2  0
 38  3  1  0
 36 16  1  0
 33 23  2  0
 31 26  1  0
  1 39  1  0
  1 40  1  0
  1 41  1  0
  4 42  1  0
  5 43  1  0
 11 44  1  0
 11 45  1  0
 14 46  1  0
 15 47  1  0
 15 48  1  0
 17 49  1  0
 18 50  1  0
 21 51  1  0
 21 52  1  0
 22 53  1  0
 22 54  1  0
 27 55  1  0
 28 56  1  0
 29 57  1  0
 30 58  1  0
 31 59  1  0
 34 60  1  0
 34 61  1  0
 34 62  1  0
 35 63  1  0
 36 64  1  0
 37 65  1  0
 38 66  1  0
M  END

HEADER    PROTEIN                                 22-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-16         0                                  
HETATM    1  C   UNK     0      -0.350   2.828   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.670  -5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -8.366   5.355   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -7.739   3.948   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -7.461   6.601   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.208   3.787   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.929   6.440   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.337  -1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.003  -3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.000   6.160   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334   5.390   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.002   3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.668   0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.495   3.858   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -5.303   5.033   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      13.337  -3.080   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.001   5.390   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.669  -1.540   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.334   5.390   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -3.771   4.872   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.336   0.770   0.000  0.00  0.00           C+0
HETATM   30  N   UNK     0      -2.741   6.016   0.000  0.00  0.00           N+0
HETATM   31  N   UNK     0       8.002   1.540   0.000  0.00  0.00           N+0
HETATM   32  O   UNK     0       8.002  -1.540   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       5.335  -1.540   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      10.669   1.540   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      14.670  -3.850   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      -3.001   3.538   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
CONECT    1   20                                                            
CONECT    2   35                                                            
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4   22                                                       
CONECT    7    5   22                                                       
CONECT    8   10   21                                                       
CONECT    9   11   21                                                       
CONECT   10    8   24                                                       
CONECT   11    9   24                                                       
CONECT   12   14   23                                                       
CONECT   13   15   23                                                       
CONECT   14   12   25                                                       
CONECT   15   13   25                                                       
CONECT   16   17   26                                                       
CONECT   17   16   36                                                       
CONECT   18   21   31                                                       
CONECT   19   27   31                                                       
CONECT   20    1   26   37                                                  
CONECT   21    8    9   18                                                  
CONECT   22    6    7   28                                                  
CONECT   23   12   13   35                                                  
CONECT   24   10   11   36                                                  
CONECT   25   14   15   38                                                  
CONECT   26   16   20   30                                                  
CONECT   27   19   32   33                                                  
CONECT   28   22   30   37                                                  
CONECT   29   31   34   38                                                  
CONECT   30   26   28                                                       
CONECT   31   18   19   29                                                  
CONECT   32   27                                                            
CONECT   33   27                                                            
CONECT   34   29                                                            
CONECT   35    2   23                                                       
CONECT   36   17   24                                                       
CONECT   37   20   28                                                       
CONECT   38   25   29                                                       
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

COMPND    HMDB0254949
HETATM    1  C1  UNL     1      -9.626   2.347  -2.800  1.00  0.00           C  
HETATM    2  O1  UNL     1      -8.479   1.564  -3.062  1.00  0.00           O  
HETATM    3  C2  UNL     1      -7.486   1.410  -2.107  1.00  0.00           C  
HETATM    4  C3  UNL     1      -7.562   2.008  -0.859  1.00  0.00           C  
HETATM    5  C4  UNL     1      -6.525   1.809   0.051  1.00  0.00           C  
HETATM    6  C5  UNL     1      -5.444   1.028  -0.294  1.00  0.00           C  
HETATM    7  O2  UNL     1      -4.408   0.823   0.602  1.00  0.00           O  
HETATM    8  C6  UNL     1      -4.471  -0.254   1.455  1.00  0.00           C  
HETATM    9  O3  UNL     1      -5.481  -0.999   1.367  1.00  0.00           O  
HETATM   10  N1  UNL     1      -3.481  -0.567   2.411  1.00  0.00           N  
HETATM   11  C7  UNL     1      -3.672  -1.725   3.255  1.00  0.00           C  
HETATM   12  C8  UNL     1      -3.149  -2.967   2.649  1.00  0.00           C  
HETATM   13  O4  UNL     1      -3.129  -4.038   3.297  1.00  0.00           O  
HETATM   14  O5  UNL     1      -2.683  -2.925   1.347  1.00  0.00           O  
HETATM   15  C9  UNL     1      -2.304   0.235   2.582  1.00  0.00           C  
HETATM   16  C10 UNL     1      -1.200  -0.313   1.765  1.00  0.00           C  
HETATM   17  C11 UNL     1      -0.233  -1.133   2.352  1.00  0.00           C  
HETATM   18  C12 UNL     1       0.811  -1.653   1.612  1.00  0.00           C  
HETATM   19  C13 UNL     1       0.971  -1.404   0.268  1.00  0.00           C  
HETATM   20  O6  UNL     1       1.973  -1.876  -0.531  1.00  0.00           O  
HETATM   21  C14 UNL     1       3.046  -2.662  -0.257  1.00  0.00           C  
HETATM   22  C15 UNL     1       4.122  -2.200   0.653  1.00  0.00           C  
HETATM   23  C16 UNL     1       4.857  -0.994   0.227  1.00  0.00           C  
HETATM   24  N2  UNL     1       6.075  -0.956  -0.402  1.00  0.00           N  
HETATM   25  C17 UNL     1       6.429   0.302  -0.655  1.00  0.00           C  
HETATM   26  C18 UNL     1       7.661   0.784  -1.316  1.00  0.00           C  
HETATM   27  C19 UNL     1       8.621  -0.068  -1.765  1.00  0.00           C  
HETATM   28  C20 UNL     1       9.768   0.419  -2.382  1.00  0.00           C  
HETATM   29  C21 UNL     1       9.916   1.787  -2.532  1.00  0.00           C  
HETATM   30  C22 UNL     1       8.962   2.677  -2.088  1.00  0.00           C  
HETATM   31  C23 UNL     1       7.836   2.137  -1.479  1.00  0.00           C  
HETATM   32  O7  UNL     1       5.463   1.056  -0.201  1.00  0.00           O  
HETATM   33  C24 UNL     1       4.495   0.316   0.339  1.00  0.00           C  
HETATM   34  C25 UNL     1       3.251   0.884   0.950  1.00  0.00           C  
HETATM   35  C26 UNL     1      -0.006  -0.577  -0.320  1.00  0.00           C  
HETATM   36  C27 UNL     1      -1.042  -0.064   0.421  1.00  0.00           C  
HETATM   37  C28 UNL     1      -5.352   0.427  -1.531  1.00  0.00           C  
HETATM   38  C29 UNL     1      -6.388   0.629  -2.431  1.00  0.00           C  
HETATM   39  H1  UNL     1     -10.061   2.089  -1.809  1.00  0.00           H  
HETATM   40  H2  UNL     1     -10.434   2.086  -3.542  1.00  0.00           H  
HETATM   41  H3  UNL     1      -9.372   3.416  -2.882  1.00  0.00           H  
HETATM   42  H4  UNL     1      -8.420   2.618  -0.605  1.00  0.00           H  
HETATM   43  H5  UNL     1      -6.565   2.270   1.041  1.00  0.00           H  
HETATM   44  H6  UNL     1      -3.135  -1.530   4.220  1.00  0.00           H  
HETATM   45  H7  UNL     1      -4.770  -1.831   3.499  1.00  0.00           H  
HETATM   46  H8  UNL     1      -3.299  -3.186   0.568  1.00  0.00           H  
HETATM   47  H9  UNL     1      -2.482   1.313   2.381  1.00  0.00           H  
HETATM   48  H10 UNL     1      -1.973   0.213   3.663  1.00  0.00           H  
HETATM   49  H11 UNL     1      -0.343  -1.342   3.420  1.00  0.00           H  
HETATM   50  H12 UNL     1       1.531  -2.295   2.106  1.00  0.00           H  
HETATM   51  H13 UNL     1       3.508  -3.051  -1.215  1.00  0.00           H  
HETATM   52  H14 UNL     1       2.664  -3.639   0.214  1.00  0.00           H  
HETATM   53  H15 UNL     1       4.897  -3.036   0.663  1.00  0.00           H  
HETATM   54  H16 UNL     1       3.778  -2.141   1.694  1.00  0.00           H  
HETATM   55  H17 UNL     1       8.465  -1.137  -1.628  1.00  0.00           H  
HETATM   56  H18 UNL     1      10.535  -0.243  -2.742  1.00  0.00           H  
HETATM   57  H19 UNL     1      10.798   2.218  -3.010  1.00  0.00           H  
HETATM   58  H20 UNL     1       9.086   3.760  -2.210  1.00  0.00           H  
HETATM   59  H21 UNL     1       7.071   2.826  -1.122  1.00  0.00           H  
HETATM   60  H22 UNL     1       2.478   1.069   0.193  1.00  0.00           H  
HETATM   61  H23 UNL     1       2.945   0.291   1.812  1.00  0.00           H  
HETATM   62  H24 UNL     1       3.512   1.903   1.359  1.00  0.00           H  
HETATM   63  H25 UNL     1       0.101  -0.366  -1.387  1.00  0.00           H  
HETATM   64  H26 UNL     1      -1.785   0.576  -0.052  1.00  0.00           H  
HETATM   65  H27 UNL     1      -4.524  -0.188  -1.832  1.00  0.00           H  
HETATM   66  H28 UNL     1      -6.343   0.178  -3.389  1.00  0.00           H  
CONECT    1    2   39   40   41
CONECT    2    3
CONECT    3    4    4   38
CONECT    4    5   42
CONECT    5    6    6   43
CONECT    6    7   37
CONECT    7    8
CONECT    8    9    9   10
CONECT   10   11   15
CONECT   11   12   44   45
CONECT   12   13   13   14
CONECT   14   46
CONECT   15   16   47   48
CONECT   16   17   17   36
CONECT   17   18   49
CONECT   18   19   19   50
CONECT   19   20   35
CONECT   20   21
CONECT   21   22   51   52
CONECT   22   23   53   54
CONECT   23   24   33   33
CONECT   24   25   25
CONECT   25   26   32
CONECT   26   27   27   31
CONECT   27   28   55
CONECT   28   29   29   56
CONECT   29   30   57
CONECT   30   31   31   58
CONECT   31   59
CONECT   32   33
CONECT   33   34
CONECT   34   60   61   62
CONECT   35   36   36   63
CONECT   36   64
CONECT   37   38   38   65
CONECT   38   66
END

HMDB0254949
     RDKit          3D
Muraglitazar
 66 69  0  0  0  0  0  0  0  0999 V2000
   -9.6259    2.3465   -2.7997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4785    1.5638   -3.0615 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4863    1.4103   -2.1075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5623    2.0078   -0.8586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5254    1.8090    0.0515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4436    1.0279   -0.2937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4077    0.8232    0.6022 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4709   -0.2537    1.4548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4814   -0.9991    1.3671 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4811   -0.5671    2.4107 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6724   -1.7254    3.2551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1490   -2.9674    2.6488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1285   -4.0380    3.2972 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6826   -2.9254    1.3471 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3045    0.2352    2.5816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2000   -0.3131    1.7648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2331   -1.1332    2.3521 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8111   -1.6530    1.6122 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9709   -1.4040    0.2679 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9731   -1.8764   -0.5306 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0460   -2.6618   -0.2569 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1217   -2.2001    0.6529 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8565   -0.9943    0.2266 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0745   -0.9558   -0.4019 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4286    0.3020   -0.6551 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6606    0.7835   -1.3161 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6210   -0.0676   -1.7654 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7676    0.4187   -2.3824 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9159    1.7867   -2.5322 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9623    2.6771   -2.0885 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8355    2.1369   -1.4788 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4634    1.0563   -0.2012 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4954    0.3156    0.3389 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2511    0.8837    0.9501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0058   -0.5773   -0.3201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0422   -0.0635    0.4213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3520    0.4265   -1.5309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3878    0.6292   -2.4308 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0605    2.0890   -1.8091 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4341    2.0861   -3.5417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3717    3.4159   -2.8820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4201    2.6183   -0.6051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5647    2.2703    1.0411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1351   -1.5295    4.2199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7695   -1.8307    3.4994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2994   -3.1859    0.5681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4819    1.3126    2.3807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9725    0.2127    3.6633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3429   -1.3422    3.4204 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5312   -2.2952    2.1060 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5081   -3.0513   -1.2149 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6642   -3.6395    0.2141 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8974   -3.0355    0.6632 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7782   -2.1406    1.6944 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4646   -1.1374   -1.6275 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5353   -0.2433   -2.7424 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7984    2.2184   -3.0100 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0862    3.7596   -2.2103 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0705    2.8259   -1.1216 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4779    1.0687    0.1931 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9450    0.2910    1.8119 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5123    1.9029    1.3589 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1006   -0.3661   -1.3872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7846    0.5757   -0.0519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5239   -0.1880   -1.8325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3431    0.1785   -3.3893 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 10 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 25 32  1  0
 32 33  1  0
 33 34  1  0
 19 35  1  0
 35 36  2  0
  6 37  1  0
 37 38  2  0
 38  3  1  0
 36 16  1  0
 33 23  2  0
 31 26  1  0
  1 39  1  0
  1 40  1  0
  1 41  1  0
  4 42  1  0
  5 43  1  0
 11 44  1  0
 11 45  1  0
 14 46  1  0
 15 47  1  0
 15 48  1  0
 17 49  1  0
 18 50  1  0
 21 51  1  0
 21 52  1  0
 22 53  1  0
 22 54  1  0
 27 55  1  0
 28 56  1  0
 29 57  1  0
 30 58  1  0
 31 59  1  0
 34 60  1  0
 34 61  1  0
 34 62  1  0
 35 63  1  0
 36 64  1  0
 37 65  1  0
 38 66  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
N-((4-Methoxyphenoxy)carbonyl)-N-((4-(2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy)phenyl)methyl)glycine	MeSH
Pargluva	MeSH
BMS-298585Muraglitazar	ChEMBL
2-[(4-Methoxyphenoxy)carbonyl-[[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]methyl]amino]acetate	Generator
Muraglitazar	MeSH
2-{[(4-methoxyphenoxy)carbonyl]({4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl}methyl)amino}acetate	Generator

Chemical Formula

C₂₉H₂₈N₂O₇

Average Molecular Weight

516.55

Monoisotopic Molecular Weight

516.18965125

IUPAC Name

2-{[(4-methoxyphenoxy)carbonyl]({4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl}methyl)amino}acetic acid

Traditional Name

muraglitazar

CAS Registry Number

Not Available

SMILES

COC1=CC=C(OC(=O)N(CC(O)=O)CC2=CC=C(OCCC3=C(C)OC(=N3)C3=CC=CC=C3)C=C2)C=C1

InChI Identifier

InChI=1S/C29H28N2O7/c1-20-26(30-28(37-20)22-6-4-3-5-7-22)16-17-36-24-10-8-21(9-11-24)18-31(19-27(32)33)29(34)38-25-14-12-23(35-2)13-15-25/h3-15H,16-19H2,1-2H3,(H,32,33)

InChI Key

IRLWJILLXJGJTD-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenyl-1,3-oxazoles. These are aromatic heterocyclic compounds containing a 1,3-oxazole substituted at one or more positions by a phenyl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azoles

Sub Class

Oxazoles

Direct Parent

Phenyl-1,3-oxazoles

Alternative Parents

Substituents

Phenyl-1,3-oxazole
Alpha-amino acid or derivatives
2,4,5-trisubstituted 1,3-oxazole
Phenoxy compound
Anisole
Phenol ether
Methoxybenzene
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Heteroaromatic compound
Carbamic acid ester
Carbonic acid derivative
Carboxylic acid derivative
Carboxylic acid
Ether
Monocarboxylic acid or derivatives
Oxacycle
Azacycle
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Organopnictogen compound
Organic oxide
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (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	5.04	ALOGPS
logP	4.79	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	3.19	ChemAxon
pKa (Strongest Basic)	0.93	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	111.33 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	149.03 m³·mol⁻¹	ChemAxon
Polarizability	54.85 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	216.127	30932474
DeepCCS	[M-H]-	213.731	30932474
DeepCCS	[M-2H]-	246.614	30932474
DeepCCS	[M+Na]+	222.039	30932474
AllCCS	[M+H]+	224.5	32859911
AllCCS	[M+H-H2O]+	222.9	32859911
AllCCS	[M+NH4]+	226.0	32859911
AllCCS	[M+Na]+	226.4	32859911
AllCCS	[M-H]-	212.5	32859911
AllCCS	[M+Na-2H]-	213.1	32859911
AllCCS	[M+HCOO]-	213.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Muraglitazar	COC1=CC=C(OC(=O)N(CC(O)=O)CC2=CC=C(OCCC3=C(C)OC(=N3)C3=CC=CC=C3)C=C2)C=C1	5509.1	Standard polar	33892256
Muraglitazar	COC1=CC=C(OC(=O)N(CC(O)=O)CC2=CC=C(OCCC3=C(C)OC(=N3)C3=CC=CC=C3)C=C2)C=C1	4114.5	Standard non polar	33892256
Muraglitazar	COC1=CC=C(OC(=O)N(CC(O)=O)CC2=CC=C(OCCC3=C(C)OC(=N3)C3=CC=CC=C3)C=C2)C=C1	4324.8	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 - Muraglitazar GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Muraglitazar GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	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 - Muraglitazar 10V, Positive-QTOF	splash10-014l-0534490000-141f65c686f07d047493	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Muraglitazar 20V, Positive-QTOF	splash10-0553-0923210000-545424180b50b7436e58	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Muraglitazar 40V, Positive-QTOF	splash10-000l-3920000000-9456233bd3118b71ba8b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Muraglitazar 10V, Negative-QTOF	splash10-01b9-0237590000-29eb97b50659c5bb5fac	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Muraglitazar 20V, Negative-QTOF	splash10-00di-0977210000-2e1626b05dd67d4a17dc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Muraglitazar 40V, Negative-QTOF	splash10-05fr-2976000000-8b0e8cfe93b104340ad9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Muraglitazar 10V, Positive-QTOF	splash10-014i-0644290000-de40035c19627f60bc2d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Muraglitazar 20V, Positive-QTOF	splash10-0006-1598100000-6783ec2fc8447b6960ce	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Muraglitazar 40V, Positive-QTOF	splash10-000i-2910000000-88b2c70ebad9cbd4fc1f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Muraglitazar 10V, Negative-QTOF	splash10-05ai-0912310000-024f078ef40015e24f35	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Muraglitazar 20V, Negative-QTOF	splash10-052r-2905800000-27f84427711130daea72	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Muraglitazar 40V, Negative-QTOF	splash10-0059-4921000000-1a4b3b049cfd0c104de0	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

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

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB06510

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Muraglitazar

METLIN ID

Not Available

PubChem Compound

206044

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

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 Muraglitazar (HMDB0254949)

MOL for HMDB0254949 (Muraglitazar)

3D MOL for HMDB0254949 (Muraglitazar)

3D SDF for HMDB0254949 (Muraglitazar)

3D-SDF for HMDB0254949 (Muraglitazar)

PDB for HMDB0254949 (Muraglitazar)

3D PDB for HMDB0254949 (Muraglitazar)

SMILES for HMDB0254949 (Muraglitazar)

INCHI for HMDB0254949 (Muraglitazar)

Structure for HMDB0254949 (Muraglitazar)

3D Structure for HMDB0254949 (Muraglitazar)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra