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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 15:13:05 UTC

Update Date

2021-09-26 23:10:28 UTC

HMDB ID

HMDB0255551

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Netoglitazone

Description

Netoglitazone belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings. Netoglitazone is an extremely weak basic (essentially neutral) compound (based on its pKa). Netoglitazone (also called MCC-555) is a hypoglycemic agent belonging to the thiazolidinedione group. This compound has been identified in human blood as reported by (PMID: 31557052 ). Netoglitazone is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Netoglitazone 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


  Mrv1572010161518162D          

 27 30  0  0  0  0            999 V2000
   -1.4083    1.0297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4083    0.2047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6938   -0.2077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0206    0.2047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0206    1.0297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6938    1.4422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7351   -0.2077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4495    0.2047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4495    1.0297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7351    1.4422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1552    1.4372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8555    1.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8425    0.2047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6244   -0.0632    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1208    0.5976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6458    1.2739    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.9435    0.6257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1661   -0.2705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1227   -0.2077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8272    0.1990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5269   -0.2048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2289    0.2005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9434   -0.2118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9435   -1.0368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2415   -1.4422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5270   -1.0298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2289    1.0296    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  5 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 12 16  1  0  0  0  0
 15 17  2  0  0  0  0
 13 18  2  0  0  0  0
  2 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 21 26  1  0  0  0  0
 22 27  1  0  0  0  0
M  END

HMDB0255551
     RDKit          3D
Netoglitazone
 43 46  0  0  0  0  0  0  0  0999 V2000
    7.2244   -0.0347    2.5733 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8018    0.1692    1.4319 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4130   -0.1724    0.2098 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9297    0.5380   -0.8953 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6066    0.9638   -1.8953 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4627    0.7915   -0.8380 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7254   -0.4539   -1.2573 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2699   -0.3005   -1.2325 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6265    0.1505   -2.3881 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2771    0.2997   -2.3865 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5487    0.0115   -1.2627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8163    0.1641   -1.2663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6239   -0.1025   -0.1819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9907    0.0646   -0.2290 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7742   -0.2237    0.9135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2051    0.0082    0.6907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6346    0.4589   -0.5372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9560    0.6800   -0.7643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8636    0.4518    0.2373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4654    0.0032    1.4690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1227   -0.2187    1.6916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6776   -0.6599    2.8851 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0085   -0.5469    0.9634 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3698   -0.7173    1.0166 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1511   -0.4408   -0.0892 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5169   -0.5857   -0.1097 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2717    0.9672    0.9877 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.1785   -0.9059    0.1179 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1515    1.6879   -1.3644 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0750   -0.7629   -2.2824 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9922   -1.2879   -0.5780 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2331    0.3689   -3.2580 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7741    0.6454   -3.2689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2982    0.5146   -2.1707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6488   -1.3059    1.1706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4421    0.4266    1.7657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9116    0.6442   -1.3455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3091    1.0373   -1.7334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9353    0.6165    0.0975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1936   -0.1800    2.2730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6216   -0.7649    1.8340 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8666   -1.0662    1.9110 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0327   -0.9329    0.7732 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 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  2  0
 21 22  1  0
 13 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
  6 27  1  0
 27  2  1  0
 26  8  1  0
 25 11  1  0
 21 16  1  0
  3 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  9 32  1  0
 10 33  1  0
 12 34  1  0
 15 35  1  0
 15 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
 20 40  1  0
 23 41  1  0
 24 42  1  0
 26 43  1  0
M  END


  Mrv1572010161518162D          

 27 30  0  0  0  0            999 V2000
   -1.4083    1.0297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4083    0.2047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6938   -0.2077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0206    0.2047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0206    1.0297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6938    1.4422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7351   -0.2077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4495    0.2047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4495    1.0297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7351    1.4422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1552    1.4372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8555    1.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8425    0.2047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6244   -0.0632    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1208    0.5976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6458    1.2739    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.9435    0.6257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1661   -0.2705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1227   -0.2077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8272    0.1990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5269   -0.2048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2289    0.2005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9434   -0.2118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9435   -1.0368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2415   -1.4422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5270   -1.0298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2289    1.0296    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  5 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 12 16  1  0  0  0  0
 15 17  2  0  0  0  0
 13 18  2  0  0  0  0
  2 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 21 26  1  0  0  0  0
 22 27  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0255551

> <DATABASE_NAME>
hmdb

> <SMILES>
FC1=C(COC2=CC=C3C=C(CC4SC(=O)NC4=O)C=CC3=C2)C=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C21H16FNO3S/c22-18-4-2-1-3-16(18)12-26-17-8-7-14-9-13(5-6-15(14)11-17)10-19-20(24)23-21(25)27-19/h1-9,11,19H,10,12H2,(H,23,24,25)

> <INCHI_KEY>
PKWDZWYVIHVNKS-UHFFFAOYSA-N

> <FORMULA>
C21H16FNO3S

> <MOLECULAR_WEIGHT>
381.42

> <EXACT_MASS>
381.083492716

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
38.92619438299258

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-({6-[(2-fluorophenyl)methoxy]naphthalen-2-yl}methyl)-1,3-thiazolidine-2,4-dione

> <ALOGPS_LOGP>
4.17

> <JCHEM_LOGP>
4.646306905

> <ALOGPS_LOGS>
-5.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
16.572426280527928

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.613586391133686

> <JCHEM_PKA_STRONGEST_BASIC>
-4.8669463286778285

> <JCHEM_POLAR_SURFACE_AREA>
55.400000000000006

> <JCHEM_REFRACTIVITY>
102.39489999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.24e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
netoglitazone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0255551
     RDKit          3D
Netoglitazone
 43 46  0  0  0  0  0  0  0  0999 V2000
    7.2244   -0.0347    2.5733 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8018    0.1692    1.4319 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4130   -0.1724    0.2098 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9297    0.5380   -0.8953 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6066    0.9638   -1.8953 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4627    0.7915   -0.8380 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7254   -0.4539   -1.2573 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2699   -0.3005   -1.2325 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6265    0.1505   -2.3881 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2771    0.2997   -2.3865 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5487    0.0115   -1.2627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8163    0.1641   -1.2663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6239   -0.1025   -0.1819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9907    0.0646   -0.2290 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7742   -0.2237    0.9135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2051    0.0082    0.6907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6346    0.4589   -0.5372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9560    0.6800   -0.7643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8636    0.4518    0.2373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4654    0.0032    1.4690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1227   -0.2187    1.6916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6776   -0.6599    2.8851 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0085   -0.5469    0.9634 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3698   -0.7173    1.0166 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1511   -0.4408   -0.0892 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5169   -0.5857   -0.1097 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2717    0.9672    0.9877 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.1785   -0.9059    0.1179 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1515    1.6879   -1.3644 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0750   -0.7629   -2.2824 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9922   -1.2879   -0.5780 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2331    0.3689   -3.2580 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7741    0.6454   -3.2689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2982    0.5146   -2.1707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6488   -1.3059    1.1706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4421    0.4266    1.7657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9116    0.6442   -1.3455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3091    1.0373   -1.7334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9353    0.6165    0.0975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1936   -0.1800    2.2730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6216   -0.7649    1.8340 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8666   -1.0662    1.9110 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0327   -0.9329    0.7732 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 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  2  0
 21 22  1  0
 13 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
  6 27  1  0
 27  2  1  0
 26  8  1  0
 25 11  1  0
 21 16  1  0
  3 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  9 32  1  0
 10 33  1  0
 12 34  1  0
 15 35  1  0
 15 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
 20 40  1  0
 23 41  1  0
 24 42  1  0
 26 43  1  0
M  END

HEADER    PROTEIN                                 16-OCT-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-OCT-15         0                                  
HETATM    1  C   UNK     0      -2.629   1.922   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.629   0.382   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.295  -0.388   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.038   0.382   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.038   1.922   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.295   2.692   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.372  -0.388   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.706   0.382   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.706   1.922   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.372   2.692   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.023   2.683   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.330   1.928   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.306   0.382   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       6.766  -0.118   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       7.692   1.116   0.000  0.00  0.00           C+0
HETATM   16  S   UNK     0       6.805   2.378   0.000  0.00  0.00           S+0
HETATM   17  O   UNK     0       9.228   1.168   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       4.043  -0.505   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -3.962  -0.388   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -5.277   0.371   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -6.584  -0.382   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -7.894   0.374   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -9.228  -0.395   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -9.228  -1.935   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -7.917  -2.692   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -6.584  -1.922   0.000  0.00  0.00           C+0
HETATM   27  F   UNK     0      -7.894   1.922   0.000  0.00  0.00           F+0
CONECT    1    2    6                                                       
CONECT    2    1    3   19                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9    5                                                       
CONECT   11    9   12                                                       
CONECT   12   11   13   16                                                  
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15   12                                                       
CONECT   17   15                                                            
CONECT   18   13                                                            
CONECT   19    2   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   21                                                       
CONECT   27   22                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

COMPND    HMDB0255551
HETATM    1  O1  UNL     1       7.224  -0.035   2.573  1.00  0.00           O  
HETATM    2  C1  UNL     1       6.802   0.169   1.432  1.00  0.00           C  
HETATM    3  N1  UNL     1       7.413  -0.172   0.210  1.00  0.00           N  
HETATM    4  C2  UNL     1       6.930   0.538  -0.895  1.00  0.00           C  
HETATM    5  O2  UNL     1       7.607   0.964  -1.895  1.00  0.00           O  
HETATM    6  C3  UNL     1       5.463   0.791  -0.838  1.00  0.00           C  
HETATM    7  C4  UNL     1       4.725  -0.454  -1.257  1.00  0.00           C  
HETATM    8  C5  UNL     1       3.270  -0.300  -1.232  1.00  0.00           C  
HETATM    9  C6  UNL     1       2.627   0.150  -2.388  1.00  0.00           C  
HETATM   10  C7  UNL     1       1.277   0.300  -2.387  1.00  0.00           C  
HETATM   11  C8  UNL     1       0.549   0.011  -1.263  1.00  0.00           C  
HETATM   12  C9  UNL     1      -0.816   0.164  -1.266  1.00  0.00           C  
HETATM   13  C10 UNL     1      -1.624  -0.102  -0.182  1.00  0.00           C  
HETATM   14  O3  UNL     1      -2.991   0.065  -0.229  1.00  0.00           O  
HETATM   15  C11 UNL     1      -3.774  -0.224   0.913  1.00  0.00           C  
HETATM   16  C12 UNL     1      -5.205   0.008   0.691  1.00  0.00           C  
HETATM   17  C13 UNL     1      -5.635   0.459  -0.537  1.00  0.00           C  
HETATM   18  C14 UNL     1      -6.956   0.680  -0.764  1.00  0.00           C  
HETATM   19  C15 UNL     1      -7.864   0.452   0.237  1.00  0.00           C  
HETATM   20  C16 UNL     1      -7.465   0.003   1.469  1.00  0.00           C  
HETATM   21  C17 UNL     1      -6.123  -0.219   1.692  1.00  0.00           C  
HETATM   22  F1  UNL     1      -5.678  -0.660   2.885  1.00  0.00           F  
HETATM   23  C18 UNL     1      -1.009  -0.547   0.963  1.00  0.00           C  
HETATM   24  C19 UNL     1       0.370  -0.717   1.017  1.00  0.00           C  
HETATM   25  C20 UNL     1       1.151  -0.441  -0.089  1.00  0.00           C  
HETATM   26  C21 UNL     1       2.517  -0.586  -0.110  1.00  0.00           C  
HETATM   27  S1  UNL     1       5.272   0.967   0.988  1.00  0.00           S  
HETATM   28  H1  UNL     1       8.179  -0.906   0.118  1.00  0.00           H  
HETATM   29  H2  UNL     1       5.152   1.688  -1.364  1.00  0.00           H  
HETATM   30  H3  UNL     1       5.075  -0.763  -2.282  1.00  0.00           H  
HETATM   31  H4  UNL     1       4.992  -1.288  -0.578  1.00  0.00           H  
HETATM   32  H5  UNL     1       3.233   0.369  -3.258  1.00  0.00           H  
HETATM   33  H6  UNL     1       0.774   0.645  -3.269  1.00  0.00           H  
HETATM   34  H7  UNL     1      -1.298   0.515  -2.171  1.00  0.00           H  
HETATM   35  H8  UNL     1      -3.649  -1.306   1.171  1.00  0.00           H  
HETATM   36  H9  UNL     1      -3.442   0.427   1.766  1.00  0.00           H  
HETATM   37  H10 UNL     1      -4.912   0.644  -1.345  1.00  0.00           H  
HETATM   38  H11 UNL     1      -7.309   1.037  -1.733  1.00  0.00           H  
HETATM   39  H12 UNL     1      -8.935   0.616   0.098  1.00  0.00           H  
HETATM   40  H13 UNL     1      -8.194  -0.180   2.273  1.00  0.00           H  
HETATM   41  H14 UNL     1      -1.622  -0.765   1.834  1.00  0.00           H  
HETATM   42  H15 UNL     1       0.867  -1.066   1.911  1.00  0.00           H  
HETATM   43  H16 UNL     1       3.033  -0.933   0.773  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   27
CONECT    3    4   28
CONECT    4    5    5    6
CONECT    6    7   27   29
CONECT    7    8   30   31
CONECT    8    9    9   26
CONECT    9   10   32
CONECT   10   11   11   33
CONECT   11   12   25
CONECT   12   13   13   34
CONECT   13   14   23
CONECT   14   15
CONECT   15   16   35   36
CONECT   16   17   17   21
CONECT   17   18   37
CONECT   18   19   19   38
CONECT   19   20   39
CONECT   20   21   21   40
CONECT   21   22
CONECT   23   24   24   41
CONECT   24   25   42
CONECT   25   26   26
CONECT   26   43
END

HMDB0255551
     RDKit          3D
Netoglitazone
 43 46  0  0  0  0  0  0  0  0999 V2000
    7.2244   -0.0347    2.5733 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8018    0.1692    1.4319 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4130   -0.1724    0.2098 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9297    0.5380   -0.8953 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6066    0.9638   -1.8953 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4627    0.7915   -0.8380 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7254   -0.4539   -1.2573 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2699   -0.3005   -1.2325 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6265    0.1505   -2.3881 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2771    0.2997   -2.3865 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5487    0.0115   -1.2627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8163    0.1641   -1.2663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6239   -0.1025   -0.1819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9907    0.0646   -0.2290 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7742   -0.2237    0.9135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2051    0.0082    0.6907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6346    0.4589   -0.5372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9560    0.6800   -0.7643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8636    0.4518    0.2373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4654    0.0032    1.4690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1227   -0.2187    1.6916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6776   -0.6599    2.8851 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0085   -0.5469    0.9634 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3698   -0.7173    1.0166 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1511   -0.4408   -0.0892 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5169   -0.5857   -0.1097 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2717    0.9672    0.9877 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.1785   -0.9059    0.1179 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1515    1.6879   -1.3644 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0750   -0.7629   -2.2824 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9922   -1.2879   -0.5780 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2331    0.3689   -3.2580 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7741    0.6454   -3.2689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2982    0.5146   -2.1707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6488   -1.3059    1.1706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4421    0.4266    1.7657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9116    0.6442   -1.3455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3091    1.0373   -1.7334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9353    0.6165    0.0975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1936   -0.1800    2.2730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6216   -0.7649    1.8340 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8666   -1.0662    1.9110 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0327   -0.9329    0.7732 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 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  2  0
 21 22  1  0
 13 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
  6 27  1  0
 27  2  1  0
 26  8  1  0
 25 11  1  0
 21 16  1  0
  3 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  9 32  1  0
 10 33  1  0
 12 34  1  0
 15 35  1  0
 15 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
 20 40  1  0
 23 41  1  0
 24 42  1  0
 26 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
RWJ-241947MCC-555Netoglitazone	ChEMBL
MCC-555	MeSH
5-((6-((2-Fluorophenyl)methoxy)-2-naphthalenyl)methyl)-2,4-thiazolidinedione	MeSH
MCC 555	MeSH

Chemical Formula

C₂₁H₁₆FNO₃S

Average Molecular Weight

381.42

Monoisotopic Molecular Weight

381.083492716

IUPAC Name

5-({6-[(2-fluorophenyl)methoxy]naphthalen-2-yl}methyl)-1,3-thiazolidine-2,4-dione

Traditional Name

netoglitazone

CAS Registry Number

Not Available

SMILES

FC1=C(COC2=CC=C3C=C(CC4SC(=O)NC4=O)C=CC3=C2)C=CC=C1

InChI Identifier

InChI=1S/C21H16FNO3S/c22-18-4-2-1-3-16(18)12-26-17-8-7-14-9-13(5-6-15(14)11-17)10-19-20(24)23-21(25)27-19/h1-9,11,19H,10,12H2,(H,23,24,25)

InChI Key

PKWDZWYVIHVNKS-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Naphthalenes

Sub Class

Not Available

Direct Parent

Naphthalenes

Alternative Parents

Substituents

Naphthalene
Alkyl aryl ether
Fluorobenzene
Halobenzene
Thiazolidinedione
Aryl fluoride
Aryl halide
Monocyclic benzene moiety
Dicarboximide
Thiazolidine
Thiocarbamic acid derivative
Carbonic acid derivative
Carboxylic acid derivative
Ether
Azacycle
Organoheterocyclic compound
Organopnictogen compound
Organic oxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Carbonyl group
Organic oxide
Organooxygen compound
Organonitrogen compound
Organohalogen compound
Organofluoride
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 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	4.17	ALOGPS
logP	4.65	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	6.61	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.4 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	102.39 m³·mol⁻¹	ChemAxon
Polarizability	38.93 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	196.81	30932474
DeepCCS	[M-H]-	194.194	30932474
DeepCCS	[M-2H]-	228.869	30932474
DeepCCS	[M+Na]+	204.993	30932474
AllCCS	[M+H]+	189.6	32859911
AllCCS	[M+H-H2O]+	186.8	32859911
AllCCS	[M+NH4]+	192.2	32859911
AllCCS	[M+Na]+	192.9	32859911
AllCCS	[M-H]-	184.6	32859911
AllCCS	[M+Na-2H]-	183.7	32859911
AllCCS	[M+HCOO]-	182.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Netoglitazone	FC1=C(COC2=CC=C3C=C(CC4SC(=O)NC4=O)C=CC3=C2)C=CC=C1	4991.8	Standard polar	33892256
Netoglitazone	FC1=C(COC2=CC=C3C=C(CC4SC(=O)NC4=O)C=CC3=C2)C=CC=C1	3406.0	Standard non polar	33892256
Netoglitazone	FC1=C(COC2=CC=C3C=C(CC4SC(=O)NC4=O)C=CC3=C2)C=CC=C1	3435.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Netoglitazone,1TMS,isomer #1	C[Si](C)(C)N1C(=O)SC(CC2=CC=C3C=C(OCC4=CC=CC=C4F)C=CC3=C2)C1=O	3440.2	Semi standard non polar	33892256
Netoglitazone,1TMS,isomer #1	C[Si](C)(C)N1C(=O)SC(CC2=CC=C3C=C(OCC4=CC=CC=C4F)C=CC3=C2)C1=O	3295.0	Standard non polar	33892256
Netoglitazone,1TMS,isomer #1	C[Si](C)(C)N1C(=O)SC(CC2=CC=C3C=C(OCC4=CC=CC=C4F)C=CC3=C2)C1=O	4338.0	Standard polar	33892256
Netoglitazone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)SC(CC2=CC=C3C=C(OCC4=CC=CC=C4F)C=CC3=C2)C1=O	3682.7	Semi standard non polar	33892256
Netoglitazone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)SC(CC2=CC=C3C=C(OCC4=CC=CC=C4F)C=CC3=C2)C1=O	3512.1	Standard non polar	33892256
Netoglitazone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)SC(CC2=CC=C3C=C(OCC4=CC=CC=C4F)C=CC3=C2)C1=O	4270.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Netoglitazone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0bt9-8968000000-bfabee922581a02e9b21	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Netoglitazone 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 - Netoglitazone 10V, Positive-QTOF	splash10-001i-0019000000-79e904adaa257aa7ab7b	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Netoglitazone 20V, Positive-QTOF	splash10-03di-0129000000-3c66082aba065c3e79ac	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Netoglitazone 40V, Positive-QTOF	splash10-06ri-1981000000-5bb19de00fa895597b2b	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Netoglitazone 10V, Negative-QTOF	splash10-001i-0009000000-0f5d36756c7f21826272	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Netoglitazone 20V, Negative-QTOF	splash10-0a4i-2019000000-0e706788d6d33f0dbf6d	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Netoglitazone 40V, Negative-QTOF	splash10-0006-9301000000-7e5e37e1099146cc9024	2017-07-26	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

DB09199

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

Netoglitazone

METLIN ID

Not Available

PubChem Compound

204109

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 Netoglitazone (HMDB0255551)

MOL for HMDB0255551 (Netoglitazone)

3D MOL for HMDB0255551 (Netoglitazone)

3D SDF for HMDB0255551 (Netoglitazone)

3D-SDF for HMDB0255551 (Netoglitazone)

PDB for HMDB0255551 (Netoglitazone)

3D PDB for HMDB0255551 (Netoglitazone)

SMILES for HMDB0255551 (Netoglitazone)

INCHI for HMDB0255551 (Netoglitazone)

Structure for HMDB0255551 (Netoglitazone)

3D Structure for HMDB0255551 (Netoglitazone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra