Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (4)transporters (7) Show 11 proteins XML

enzymes (4)transporters (7) Show 11 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:55 UTC

HMDB ID

HMDB0015269

Secondary Accession Numbers

HMDB15269

Metabolite Identification

Common Name

Sulfinpyrazone

Description

Sulfinpyrazone is only found in individuals that have used or taken this drug. It is a uricosuric drug that is used to reduce the serum urate levels in gout therapy. It lacks anti-inflammatory, analgesic, and diuretic properties. [PubChem]Sulfinpyrazone is an oral uricosuric agent (pyrazolone derivative) used to treat chronic or intermittent gouty arthritis. Sulfinpyrazone competitively inhibits the reabsorption of uric acid at the proximal convoluted tubule, thereby facilitating urinary excretion of uric acid and decreasing plasma urate concentrations. This is likely done through inhibition of the urate anion transporter (hURAT1) as well as the human organic anion transporter 4 (hOAT4). Sulfinpyrazone is not intended for the treatment of acute attacks because it lacks therapeutically useful analgesic and anti-inflammatory effects. Sulfinpyrazone and its sulfide metabolite possess COX inhibitory effects. Sulfinpyrazone has also been shown to be a UDP-glucuronsyltransferase inhibitor and a very potent CYP2C9 inhibitor. Sulfinpyrazone is also known to be a cystic fibrosis transmembrane conductance regulator (CFTR) inhibitor as well as an inhibitor of several multridrug resistance proteins (MRPs).

Structure

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

1138
  Mrv0541 02231215162D          

 29 32  0  0  1  0            999 V2000
    2.4705    1.7861    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.4148    0.3649    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0653   -1.3421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.6999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1848   -1.0871    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5174   -1.5721    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1049   -0.3025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6199    0.3649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9299   -0.3025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8499   -1.0871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9555    1.1186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9694   -1.3421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5174   -2.3971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5826   -0.7900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2318   -2.8096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1409   -2.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8028   -2.8096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8061    2.5397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3672   -1.0450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2318   -3.6346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9256   -2.4040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8028   -3.6346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5387   -1.8520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5174   -4.0471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6266    2.6260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3212    3.2073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9621    3.3797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6567    3.9609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4772    4.0471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  2  0  0  0  0
  1 11  1  0  0  0  0
  1 18  1  0  0  0  0
  2  9  2  0  0  0  0
  3 10  2  0  0  0  0
  5  6  1  0  0  0  0
  5  9  1  0  0  0  0
  5 12  1  0  0  0  0
  6 10  1  0  0  0  0
  6 13  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  1  0  0  0  0
  8 11  1  0  0  0  0
 12 14  2  0  0  0  0
 12 16  1  0  0  0  0
 13 15  2  0  0  0  0
 13 17  1  0  0  0  0
 14 19  1  0  0  0  0
 15 20  1  0  0  0  0
 16 21  2  0  0  0  0
 17 22  2  0  0  0  0
 18 25  2  0  0  0  0
 18 26  1  0  0  0  0
 19 23  2  0  0  0  0
 20 24  2  0  0  0  0
 21 23  1  0  0  0  0
 22 24  1  0  0  0  0
 25 27  1  0  0  0  0
 26 28  2  0  0  0  0
 27 29  2  0  0  0  0
 28 29  1  0  0  0  0
M  END

HMDB0015269
     RDKit          3D
Sulfinpyrazone
 49 52  0  0  0  0  0  0  0  0999 V2000
    0.4231    1.4235    0.8146 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2087    0.3484    0.7854 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3228   -1.0021    0.9954 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5034   -1.3395    0.1256 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6712   -0.4270    0.3463 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0000   -0.9647   -0.7754 S   0  0  0  0  0  4  0  0  0  0  0  0
    4.4138   -2.3976   -0.4790 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4220    0.0723   -0.5642 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5341    1.2380   -1.2809 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6499    2.0403   -1.1006 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6578    1.7102   -0.2245 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5269    0.5265    0.4918 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4057   -0.2840    0.3140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8111   -1.8494    0.5555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6986   -3.0981    0.3652 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9808   -1.0512    0.3943 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2677   -1.6096    0.1513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6993   -2.6769    0.9166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9480   -3.2665    0.7303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7908   -2.7837   -0.2414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3575   -1.7103   -1.0119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1133   -1.1371   -0.8126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6119    0.2677    0.5311 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5295    1.3546    0.4164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3793    2.1977   -0.6622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2083    3.2844   -0.8698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2310    3.5333    0.0458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3946    2.7031    1.1255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5464    1.6273    1.2993 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5464   -1.1343    2.0783 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2054   -1.2939   -0.9212 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8073   -2.3819    0.3713 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0279   -0.4267    1.3970 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4153    0.5944   -0.0217 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7742    1.5457   -1.9802 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7669    2.9685   -1.6531 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5245    2.3313   -0.0830 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2514    0.1783    1.1972 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3103   -1.1883    0.8622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0953   -3.1165    1.7046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2595   -4.1043    1.3490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7811   -3.2282   -0.4110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0329   -1.3381   -1.7775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8377   -0.3002   -1.4499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5842    2.0105   -1.3817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0738    3.9372   -1.7232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8801    4.3907   -0.1229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1689    2.8561    1.8589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6702    0.9699    2.1479 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  3 14  1  0
 14 15  2  0
 14 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  2  0
 16 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
 23  2  1  0
 29 24  1  0
 13  8  1  0
 22 17  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  9 35  1  0
 10 36  1  0
 11 37  1  0
 12 38  1  0
 13 39  1  0
 18 40  1  0
 19 41  1  0
 20 42  1  0
 21 43  1  0
 22 44  1  0
 25 45  1  0
 26 46  1  0
 27 47  1  0
 28 48  1  0
 29 49  1  0
M  END

1138
  Mrv0541 02231215162D          

 29 32  0  0  1  0            999 V2000
    2.4705    1.7861    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.4148    0.3649    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0653   -1.3421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.6999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1848   -1.0871    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5174   -1.5721    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1049   -0.3025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6199    0.3649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9299   -0.3025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8499   -1.0871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9555    1.1186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9694   -1.3421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5174   -2.3971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5826   -0.7900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2318   -2.8096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1409   -2.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8028   -2.8096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8061    2.5397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3672   -1.0450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2318   -3.6346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9256   -2.4040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8028   -3.6346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5387   -1.8520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5174   -4.0471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6266    2.6260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3212    3.2073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9621    3.3797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6567    3.9609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4772    4.0471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  2  0  0  0  0
  1 11  1  0  0  0  0
  1 18  1  0  0  0  0
  2  9  2  0  0  0  0
  3 10  2  0  0  0  0
  5  6  1  0  0  0  0
  5  9  1  0  0  0  0
  5 12  1  0  0  0  0
  6 10  1  0  0  0  0
  6 13  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  1  0  0  0  0
  8 11  1  0  0  0  0
 12 14  2  0  0  0  0
 12 16  1  0  0  0  0
 13 15  2  0  0  0  0
 13 17  1  0  0  0  0
 14 19  1  0  0  0  0
 15 20  1  0  0  0  0
 16 21  2  0  0  0  0
 17 22  2  0  0  0  0
 18 25  2  0  0  0  0
 18 26  1  0  0  0  0
 19 23  2  0  0  0  0
 20 24  2  0  0  0  0
 21 23  1  0  0  0  0
 22 24  1  0  0  0  0
 25 27  1  0  0  0  0
 26 28  2  0  0  0  0
 27 29  2  0  0  0  0
 28 29  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015269

> <DATABASE_NAME>
hmdb

> <SMILES>
O=C1C(CCS(=O)C2=CC=CC=C2)C(=O)N(N1C1=CC=CC=C1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C23H20N2O3S/c26-22-21(16-17-29(28)20-14-8-3-9-15-20)23(27)25(19-12-6-2-7-13-19)24(22)18-10-4-1-5-11-18/h1-15,21H,16-17H2

> <INCHI_KEY>
MBGGBVCUIVRRBF-UHFFFAOYSA-N

> <FORMULA>
C23H20N2O3S

> <MOLECULAR_WEIGHT>
404.482

> <EXACT_MASS>
404.119463206

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
42.15075304404465

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[2-(benzenesulfinyl)ethyl]-1,2-diphenylpyrazolidine-3,5-dione

> <ALOGPS_LOGP>
2.92

> <JCHEM_LOGP>
3.1874085596666673

> <ALOGPS_LOGS>
-3.10

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
16.363817426055114

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.4136141519969105

> <JCHEM_PKA_STRONGEST_BASIC>
-6.722072173688344

> <JCHEM_POLAR_SURFACE_AREA>
57.690000000000005

> <JCHEM_REFRACTIVITY>
113.61550000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.23e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sulfinpyrazone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015269
     RDKit          3D
Sulfinpyrazone
 49 52  0  0  0  0  0  0  0  0999 V2000
    0.4231    1.4235    0.8146 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2087    0.3484    0.7854 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3228   -1.0021    0.9954 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5034   -1.3395    0.1256 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6712   -0.4270    0.3463 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0000   -0.9647   -0.7754 S   0  0  0  0  0  4  0  0  0  0  0  0
    4.4138   -2.3976   -0.4790 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4220    0.0723   -0.5642 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5341    1.2380   -1.2809 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6499    2.0403   -1.1006 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6578    1.7102   -0.2245 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5269    0.5265    0.4918 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4057   -0.2840    0.3140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8111   -1.8494    0.5555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6986   -3.0981    0.3652 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9808   -1.0512    0.3943 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2677   -1.6096    0.1513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6993   -2.6769    0.9166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9480   -3.2665    0.7303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7908   -2.7837   -0.2414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3575   -1.7103   -1.0119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1133   -1.1371   -0.8126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6119    0.2677    0.5311 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5295    1.3546    0.4164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3793    2.1977   -0.6622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2083    3.2844   -0.8698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2310    3.5333    0.0458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3946    2.7031    1.1255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5464    1.6273    1.2993 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5464   -1.1343    2.0783 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2054   -1.2939   -0.9212 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8073   -2.3819    0.3713 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0279   -0.4267    1.3970 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4153    0.5944   -0.0217 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7742    1.5457   -1.9802 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7669    2.9685   -1.6531 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5245    2.3313   -0.0830 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2514    0.1783    1.1972 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3103   -1.1883    0.8622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0953   -3.1165    1.7046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2595   -4.1043    1.3490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7811   -3.2282   -0.4110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0329   -1.3381   -1.7775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8377   -0.3002   -1.4499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5842    2.0105   -1.3817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0738    3.9372   -1.7232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8801    4.3907   -0.1229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1689    2.8561    1.8589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6702    0.9699    2.1479 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  3 14  1  0
 14 15  2  0
 14 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  2  0
 16 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
 23  2  1  0
 29 24  1  0
 13  8  1  0
 22 17  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  9 35  1  0
 10 36  1  0
 11 37  1  0
 12 38  1  0
 13 39  1  0
 18 40  1  0
 19 41  1  0
 20 42  1  0
 21 43  1  0
 22 44  1  0
 25 45  1  0
 26 46  1  0
 27 47  1  0
 28 48  1  0
 29 49  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1138                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0       4.612   3.334   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0       8.241   0.681   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       3.855  -2.505   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       3.080   3.173   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       7.812  -2.029   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       6.566  -2.935   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       5.796  -0.565   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.890   0.681   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.336  -0.565   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.320  -2.029   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.517   2.088   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.276  -2.505   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.566  -4.475   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.421  -1.475   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.899  -5.245   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.596  -4.012   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.232  -5.245   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.238   4.741   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.885  -1.951   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.899  -6.785   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.061  -4.487   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.232  -6.785   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.206  -3.457   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.566  -7.555   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.770   4.902   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.333   5.987   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.396   6.309   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.959   7.394   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.491   7.555   0.000  0.00  0.00           C+0
CONECT    1    4   11   18                                                  
CONECT    2    9                                                            
CONECT    3   10                                                            
CONECT    4    1                                                            
CONECT    5    6    9   12                                                  
CONECT    6    5   10   13                                                  
CONECT    7    8    9   10                                                  
CONECT    8    7   11                                                       
CONECT    9    2    5    7                                                  
CONECT   10    3    6    7                                                  
CONECT   11    1    8                                                       
CONECT   12    5   14   16                                                  
CONECT   13    6   15   17                                                  
CONECT   14   12   19                                                       
CONECT   15   13   20                                                       
CONECT   16   12   21                                                       
CONECT   17   13   22                                                       
CONECT   18    1   25   26                                                  
CONECT   19   14   23                                                       
CONECT   20   15   24                                                       
CONECT   21   16   23                                                       
CONECT   22   17   24                                                       
CONECT   23   19   21                                                       
CONECT   24   20   22                                                       
CONECT   25   18   27                                                       
CONECT   26   18   28                                                       
CONECT   27   25   29                                                       
CONECT   28   26   29                                                       
CONECT   29   27   28                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

COMPND    HMDB0015269
HETATM    1  O1  UNL     1       0.423   1.424   0.815  1.00  0.00           O  
HETATM    2  C1  UNL     1      -0.209   0.348   0.785  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.323  -1.002   0.995  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.503  -1.340   0.126  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.671  -0.427   0.346  1.00  0.00           C  
HETATM    6  S1  UNL     1       4.000  -0.965  -0.775  1.00  0.00           S  
HETATM    7  O2  UNL     1       4.414  -2.398  -0.479  1.00  0.00           O  
HETATM    8  C5  UNL     1       5.422   0.072  -0.564  1.00  0.00           C  
HETATM    9  C6  UNL     1       5.534   1.238  -1.281  1.00  0.00           C  
HETATM   10  C7  UNL     1       6.650   2.040  -1.101  1.00  0.00           C  
HETATM   11  C8  UNL     1       7.658   1.710  -0.224  1.00  0.00           C  
HETATM   12  C9  UNL     1       7.527   0.527   0.492  1.00  0.00           C  
HETATM   13  C10 UNL     1       6.406  -0.284   0.314  1.00  0.00           C  
HETATM   14  C11 UNL     1      -0.811  -1.849   0.556  1.00  0.00           C  
HETATM   15  O3  UNL     1      -0.699  -3.098   0.365  1.00  0.00           O  
HETATM   16  N1  UNL     1      -1.981  -1.051   0.394  1.00  0.00           N  
HETATM   17  C12 UNL     1      -3.268  -1.610   0.151  1.00  0.00           C  
HETATM   18  C13 UNL     1      -3.699  -2.677   0.917  1.00  0.00           C  
HETATM   19  C14 UNL     1      -4.948  -3.266   0.730  1.00  0.00           C  
HETATM   20  C15 UNL     1      -5.791  -2.784  -0.241  1.00  0.00           C  
HETATM   21  C16 UNL     1      -5.358  -1.710  -1.012  1.00  0.00           C  
HETATM   22  C17 UNL     1      -4.113  -1.137  -0.813  1.00  0.00           C  
HETATM   23  N2  UNL     1      -1.612   0.268   0.531  1.00  0.00           N  
HETATM   24  C18 UNL     1      -2.530   1.355   0.416  1.00  0.00           C  
HETATM   25  C19 UNL     1      -2.379   2.198  -0.662  1.00  0.00           C  
HETATM   26  C20 UNL     1      -3.208   3.284  -0.870  1.00  0.00           C  
HETATM   27  C21 UNL     1      -4.231   3.533   0.046  1.00  0.00           C  
HETATM   28  C22 UNL     1      -4.395   2.703   1.126  1.00  0.00           C  
HETATM   29  C23 UNL     1      -3.546   1.627   1.299  1.00  0.00           C  
HETATM   30  H1  UNL     1       0.546  -1.134   2.078  1.00  0.00           H  
HETATM   31  H2  UNL     1       1.205  -1.294  -0.921  1.00  0.00           H  
HETATM   32  H3  UNL     1       1.807  -2.382   0.371  1.00  0.00           H  
HETATM   33  H4  UNL     1       3.028  -0.427   1.397  1.00  0.00           H  
HETATM   34  H5  UNL     1       2.415   0.594  -0.022  1.00  0.00           H  
HETATM   35  H6  UNL     1       4.774   1.546  -1.980  1.00  0.00           H  
HETATM   36  H7  UNL     1       6.767   2.969  -1.653  1.00  0.00           H  
HETATM   37  H8  UNL     1       8.525   2.331  -0.083  1.00  0.00           H  
HETATM   38  H9  UNL     1       8.251   0.178   1.197  1.00  0.00           H  
HETATM   39  H10 UNL     1       6.310  -1.188   0.862  1.00  0.00           H  
HETATM   40  H11 UNL     1      -3.095  -3.116   1.705  1.00  0.00           H  
HETATM   41  H12 UNL     1      -5.259  -4.104   1.349  1.00  0.00           H  
HETATM   42  H13 UNL     1      -6.781  -3.228  -0.411  1.00  0.00           H  
HETATM   43  H14 UNL     1      -6.033  -1.338  -1.777  1.00  0.00           H  
HETATM   44  H15 UNL     1      -3.838  -0.300  -1.450  1.00  0.00           H  
HETATM   45  H16 UNL     1      -1.584   2.010  -1.382  1.00  0.00           H  
HETATM   46  H17 UNL     1      -3.074   3.937  -1.723  1.00  0.00           H  
HETATM   47  H18 UNL     1      -4.880   4.391  -0.123  1.00  0.00           H  
HETATM   48  H19 UNL     1      -5.169   2.856   1.859  1.00  0.00           H  
HETATM   49  H20 UNL     1      -3.670   0.970   2.148  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   23
CONECT    3    4   14   30
CONECT    4    5   31   32
CONECT    5    6   33   34
CONECT    6    7    7    8
CONECT    8    9    9   13
CONECT    9   10   35
CONECT   10   11   11   36
CONECT   11   12   37
CONECT   12   13   13   38
CONECT   13   39
CONECT   14   15   15   16
CONECT   16   17   23
CONECT   17   18   18   22
CONECT   18   19   40
CONECT   19   20   20   41
CONECT   20   21   42
CONECT   21   22   22   43
CONECT   22   44
CONECT   23   24
CONECT   24   25   25   29
CONECT   25   26   45
CONECT   26   27   27   46
CONECT   27   28   47
CONECT   28   29   29   48
CONECT   29   49
END

HMDB0015269
     RDKit          3D
Sulfinpyrazone
 49 52  0  0  0  0  0  0  0  0999 V2000
    0.4231    1.4235    0.8146 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2087    0.3484    0.7854 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3228   -1.0021    0.9954 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5034   -1.3395    0.1256 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6712   -0.4270    0.3463 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0000   -0.9647   -0.7754 S   0  0  0  0  0  4  0  0  0  0  0  0
    4.4138   -2.3976   -0.4790 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4220    0.0723   -0.5642 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5341    1.2380   -1.2809 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6499    2.0403   -1.1006 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6578    1.7102   -0.2245 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5269    0.5265    0.4918 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4057   -0.2840    0.3140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8111   -1.8494    0.5555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6986   -3.0981    0.3652 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9808   -1.0512    0.3943 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2677   -1.6096    0.1513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6993   -2.6769    0.9166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9480   -3.2665    0.7303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7908   -2.7837   -0.2414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3575   -1.7103   -1.0119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1133   -1.1371   -0.8126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6119    0.2677    0.5311 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5295    1.3546    0.4164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3793    2.1977   -0.6622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2083    3.2844   -0.8698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2310    3.5333    0.0458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3946    2.7031    1.1255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5464    1.6273    1.2993 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5464   -1.1343    2.0783 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2054   -1.2939   -0.9212 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8073   -2.3819    0.3713 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0279   -0.4267    1.3970 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4153    0.5944   -0.0217 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7742    1.5457   -1.9802 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7669    2.9685   -1.6531 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5245    2.3313   -0.0830 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2514    0.1783    1.1972 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3103   -1.1883    0.8622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0953   -3.1165    1.7046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2595   -4.1043    1.3490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7811   -3.2282   -0.4110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0329   -1.3381   -1.7775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8377   -0.3002   -1.4499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5842    2.0105   -1.3817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0738    3.9372   -1.7232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8801    4.3907   -0.1229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1689    2.8561    1.8589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6702    0.9699    2.1479 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  3 14  1  0
 14 15  2  0
 14 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  2  0
 16 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
 23  2  1  0
 29 24  1  0
 13  8  1  0
 22 17  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  9 35  1  0
 10 36  1  0
 11 37  1  0
 12 38  1  0
 13 39  1  0
 18 40  1  0
 19 41  1  0
 20 42  1  0
 21 43  1  0
 22 44  1  0
 25 45  1  0
 26 46  1  0
 27 47  1  0
 28 48  1  0
 29 49  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,2-Diphenyl-3,5-dioxo-4-(2-phenylsulfinylethyl)pyrazolidine	ChEBI
1,2-Diphenyl-4-(2'-phenylsulfinethyl)-3,5-pyrazolidinedione	ChEBI
4-(2-Benzenesulfinylethyl)-1,2-diphenylpyrazolidine-3,5-dione	ChEBI
Anturane	ChEBI
Sulfoxyphenylpyrazolidine	ChEBI
1,2-Diphenyl-3,5-dioxo-4-(2-phenylsulphinylethyl)pyrazolidine	Generator
1,2-Diphenyl-4-(2'-phenylsulphinethyl)-3,5-pyrazolidinedione	Generator
4-(2-Benzenesulphinylethyl)-1,2-diphenylpyrazolidine-3,5-dione	Generator
Sulphoxyphenylpyrazolidine	Generator
Sulphinpyrazone	Generator
Diphenylpyrazone	HMDB
Sulfinpyrazine	HMDB
Sulfinpyrazon	HMDB
Usaf ge-13	HMDB
Apo sulfinpyrazone	HMDB
Nu pharm brand OF sulfinpyrazone	HMDB
Nu sulfinpyrazone	HMDB
Nu-pharm brand OF sulfinpyrazone	HMDB
Nu-sulfinpyrazone	HMDB
Sulfoxyphenylpyrazolidin	HMDB
Anturan	HMDB
Apo-sulfinpyrazone	HMDB
Apotex brand OF sulfinpyrazone	HMDB
Novartis brand OF sulfinpyrazone	HMDB

Chemical Formula

C₂₃H₂₀N₂O₃S

Average Molecular Weight

404.482

Monoisotopic Molecular Weight

404.119463206

IUPAC Name

4-[2-(benzenesulfinyl)ethyl]-1,2-diphenylpyrazolidine-3,5-dione

Traditional Name

sulfinpyrazone

CAS Registry Number

57-96-5

SMILES

O=C1C(CCS(=O)C2=CC=CC=C2)C(=O)N(N1C1=CC=CC=C1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C23H20N2O3S/c26-22-21(16-17-29(28)20-14-8-3-9-15-20)23(27)25(19-12-6-2-7-13-19)24(22)18-10-4-1-5-11-18/h1-15,21H,16-17H2

InChI Key

MBGGBVCUIVRRBF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenyl sulfoxides. These are organosulfur compounds containing a sulfoxide group substituted with a phenyl group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenyl sulfoxides

Direct Parent

Phenyl sulfoxides

Alternative Parents

Substituents

Phenyl sulfoxide
Pyrazolidinone
1,3-dicarbonyl compound
Pyrazolidine
Carboxylic acid hydrazide
Sulfoxide
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Sulfinyl compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

sulfoxide (CHEBI:9342 )
pyrazolidines (CHEBI:9342 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0015269)
Membrane (HMDB: HMDB0015269)

Source

Exogenous

Exogenous (HMDB: HMDB0015269)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	136 - 137 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.32 g/L	Not Available
LogP	2.4	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	193.452	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000823

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.32 g/L	ALOGPS
logP	2.92	ALOGPS
logP	3.19	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	3.41	ChemAxon
pKa (Strongest Basic)	-6.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	57.69 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	113.62 m³·mol⁻¹	ChemAxon
Polarizability	42.15 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	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	199.261	30932474
DeepCCS	[M-H]-	196.877	30932474
DeepCCS	[M-2H]-	231.194	30932474
DeepCCS	[M+Na]+	206.422	30932474
AllCCS	[M+H]+	195.3	32859911
AllCCS	[M+H-H2O]+	192.8	32859911
AllCCS	[M+NH4]+	197.5	32859911
AllCCS	[M+Na]+	198.2	32859911
AllCCS	[M-H]-	187.5	32859911
AllCCS	[M+Na-2H]-	187.1	32859911
AllCCS	[M+HCOO]-	186.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	7.51 minutes	32390414
Predicted by Siyang on May 30, 2022	15.5783 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.21 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	29.5 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3108.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	366.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	197.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	191.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	217.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	629.4 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	554.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	65.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1362.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	563.2 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	1652.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	386.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	410.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	208.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	97.0 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	11.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Sulfinpyrazone	O=C1C(CCS(=O)C2=CC=CC=C2)C(=O)N(N1C1=CC=CC=C1)C1=CC=CC=C1	4791.5	Standard polar	33892256
Sulfinpyrazone	O=C1C(CCS(=O)C2=CC=CC=C2)C(=O)N(N1C1=CC=CC=C1)C1=CC=CC=C1	3649.5	Standard non polar	33892256
Sulfinpyrazone	O=C1C(CCS(=O)C2=CC=CC=C2)C(=O)N(N1C1=CC=CC=C1)C1=CC=CC=C1	3415.3	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 - Sulfinpyrazone GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-2962000000-94e8774039d3f0fcca8f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sulfinpyrazone 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sulfinpyrazone LC-ESI-qTof , Positive-QTOF	splash10-004i-0002900000-472e293a011d716bb5a8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sulfinpyrazone LC-ESI-qTof , Positive-QTOF	splash10-0550-2930000000-70abc4e49a7459cc1980	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sulfinpyrazone , positive-QTOF	splash10-0a6r-0591500000-4b27d64be1dee69f96e6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sulfinpyrazone , positive-QTOF	splash10-004i-0002900000-472e293a011d716bb5a8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sulfinpyrazone , positive-QTOF	splash10-0550-2930000000-70abc4e49a7459cc1980	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfinpyrazone 10V, Positive-QTOF	splash10-0a4i-0121900000-c9fce22e4f1bf8639c5f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfinpyrazone 20V, Positive-QTOF	splash10-0aor-1982700000-265219a2340547ed8bbd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfinpyrazone 40V, Positive-QTOF	splash10-0296-8980000000-1a7f9e1d8816c5ac0085	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfinpyrazone 10V, Negative-QTOF	splash10-0ufr-0611900000-4d4b16dafcc3e3c35c10	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfinpyrazone 20V, Negative-QTOF	splash10-004i-0900000000-6ced63b6018b3dc056eb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfinpyrazone 40V, Negative-QTOF	splash10-004i-4900000000-d6a82452b72bf2aa7d3f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfinpyrazone 10V, Positive-QTOF	splash10-0a4i-0010900000-c22c20a4b5ae18de64c5	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfinpyrazone 20V, Positive-QTOF	splash10-0a70-0091500000-79c6d2d2234f9c7c03c9	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfinpyrazone 40V, Positive-QTOF	splash10-01ri-3981000000-e2a706d32b4166dcf98f	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfinpyrazone 10V, Negative-QTOF	splash10-0fb9-0590700000-e4fb976008c18fe00f50	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfinpyrazone 20V, Negative-QTOF	splash10-004i-2951100000-ccd7d87659eeb242040e	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfinpyrazone 40V, Negative-QTOF	splash10-004l-8910000000-8627304c89a73101a237	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01138	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01138	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01138

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5149

KEGG Compound ID

C07317

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Sulfinpyrazone

METLIN ID

Not Available

PubChem Compound

5342

PDB ID

Not Available

ChEBI ID

9342

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Only showing the first 10 proteins. There are 11 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

2. Cytochrome P450 2C9

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular weight:: 55627.365

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

3. Cytochrome P450 2B6

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:: CYP2B6
Uniprot ID:: P20813
Molecular weight:: 56277.81

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

4. Cytochrome P450 2C8

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti-cancer drug paclitaxel (taxol).
Gene Name:: CYP2C8
Uniprot ID:: P10632
Molecular weight:: 55824.275

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Transporters

Enzyme Details

1. Canalicular multispecific organic anion transporter 1

General function:: Involved in ATP binding
Specific function:: Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter
Gene Name:: ABCC2
Uniprot ID:: Q92887
Molecular weight:: 174205.6

References

Bakos E, Evers R, Sinko E, Varadi A, Borst P, Sarkadi B: Interactions of the human multidrug resistance proteins MRP1 and MRP2 with organic anions. Mol Pharmacol. 2000 Apr;57(4):760-8. [PubMed:10727523 ]
Evers R, de Haas M, Sparidans R, Beijnen J, Wielinga PR, Lankelma J, Borst P: Vinblastine and sulfinpyrazone export by the multidrug resistance protein MRP2 is associated with glutathione export. Br J Cancer. 2000 Aug;83(3):375-83. [PubMed:10917554 ]
Morrow CS, Smitherman PK, Townsend AJ: Role of multidrug-resistance protein 2 in glutathione S-transferase P1-1-mediated resistance to 4-nitroquinoline 1-oxide toxicities in HepG2 cells. Mol Carcinog. 2000 Nov;29(3):170-8. [PubMed:11108662 ]
Ito K, Oleschuk CJ, Westlake C, Vasa MZ, Deeley RG, Cole SP: Mutation of Trp1254 in the multispecific organic anion transporter, multidrug resistance protein 2 (MRP2) (ABCC2), alters substrate specificity and results in loss of methotrexate transport activity. J Biol Chem. 2001 Oct 12;276(41):38108-14. Epub 2001 Aug 10. [PubMed:11500505 ]
Flanagan SD, Cummins CL, Susanto M, Liu X, Takahashi LH, Benet LZ: Comparison of furosemide and vinblastine secretion from cell lines overexpressing multidrug resistance protein (P-glycoprotein) and multidrug resistance-associated proteins (MRP1 and MRP2). Pharmacology. 2002;64(3):126-34. [PubMed:11834888 ]
Hagos Y, Stein D, Ugele B, Burckhardt G, Bahn A: Human renal organic anion transporter 4 operates as an asymmetric urate transporter. J Am Soc Nephrol. 2007 Feb;18(2):430-9. Epub 2007 Jan 17. [PubMed:17229912 ]

Enzyme Details

2. Multidrug resistance-associated protein 1

General function:: Involved in ATP binding
Specific function:: Mediates export of organic anions and drugs from the cytoplasm. Mediates ATP-dependent transport of glutathione and glutathione conjugates, leukotriene C4, estradiol-17-beta-o- glucuronide, methotrexate, antiviral drugs and other xenobiotics. Confers resistance to anticancer drugs. Hydrolyzes ATP with low efficiency
Gene Name:: ABCC1
Uniprot ID:: P33527
Molecular weight:: 171589.5

References

Evers R, de Haas M, Sparidans R, Beijnen J, Wielinga PR, Lankelma J, Borst P: Vinblastine and sulfinpyrazone export by the multidrug resistance protein MRP2 is associated with glutathione export. Br J Cancer. 2000 Aug;83(3):375-83. [PubMed:10917554 ]
Morrow CS, Smitherman PK, Diah SK, Schneider E, Townsend AJ: Coordinated action of glutathione S-transferases (GSTs) and multidrug resistance protein 1 (MRP1) in antineoplastic drug detoxification. Mechanism of GST A1-1- and MRP1-associated resistance to chlorambucil in MCF7 breast carcinoma cells. J Biol Chem. 1998 Aug 7;273(32):20114-20. [PubMed:9685354 ]
Bakos E, Evers R, Sinko E, Varadi A, Borst P, Sarkadi B: Interactions of the human multidrug resistance proteins MRP1 and MRP2 with organic anions. Mol Pharmacol. 2000 Apr;57(4):760-8. [PubMed:10727523 ]
Depeille P, Cuq P, Mary S, Passagne I, Evrard A, Cupissol D, Vian L: Glutathione S-transferase M1 and multidrug resistance protein 1 act in synergy to protect melanoma cells from vincristine effects. Mol Pharmacol. 2004 Apr;65(4):897-905. [PubMed:15044619 ]
Raggers RJ, van Helvoort A, Evers R, van Meer G: The human multidrug resistance protein MRP1 translocates sphingolipid analogs across the plasma membrane. J Cell Sci. 1999 Feb;112 ( Pt 3):415-22. [PubMed:9885294 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

3. Multidrug resistance-associated protein 6

General function:: Involved in ATP binding
Specific function:: May participate directly in the active transport of drugs into subcellular organelles or influence drug distribution indirectly. Transports glutathione conjugates as leukotriene-c4 (LTC4) and N-ethylmaleimide S-glutathione (NEM-GS)
Gene Name:: ABCC6
Uniprot ID:: O95255
Molecular weight:: 164904.8

References

Chen ZS, Hopper-Borge E, Belinsky MG, Shchaveleva I, Kotova E, Kruh GD: Characterization of the transport properties of human multidrug resistance protein 7 (MRP7, ABCC10). Mol Pharmacol. 2003 Feb;63(2):351-8. [PubMed:12527806 ]

Enzyme Details

4. Canalicular multispecific organic anion transporter 2

General function:: Involved in ATP binding
Specific function:: May act as an inducible transporter in the biliary and intestinal excretion of organic anions. Acts as an alternative route for the export of bile acids and glucuronides from cholestatic hepatocytes
Gene Name:: ABCC3
Uniprot ID:: O15438
Molecular weight:: 169341.1

References

Zelcer N, Saeki T, Reid G, Beijnen JH, Borst P: Characterization of drug transport by the human multidrug resistance protein 3 (ABCC3). J Biol Chem. 2001 Dec 7;276(49):46400-7. [PubMed:11581266 ]

Enzyme Details

5. Multidrug resistance protein 1

General function:: Involved in ATP binding
Specific function:: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:: ABCB1
Uniprot ID:: P08183
Molecular weight:: 141477.3

References

Honda Y, Ushigome F, Koyabu N, Morimoto S, Shoyama Y, Uchiumi T, Kuwano M, Ohtani H, Sawada Y: Effects of grapefruit juice and orange juice components on P-glycoprotein- and MRP2-mediated drug efflux. Br J Pharmacol. 2004 Dec;143(7):856-64. Epub 2004 Oct 25. [PubMed:15504753 ]

Enzyme Details

6. Multidrug resistance-associated protein 4

General function:: Involved in ATP binding
Specific function:: May be an organic anion pump relevant to cellular detoxification
Gene Name:: ABCC4
Uniprot ID:: O15439
Molecular weight:: 149525.3

References

Chen ZS, Lee K, Walther S, Raftogianis RB, Kuwano M, Zeng H, Kruh GD: Analysis of methotrexate and folate transport by multidrug resistance protein 4 (ABCC4): MRP4 is a component of the methotrexate efflux system. Cancer Res. 2002 Jun 1;62(11):3144-50. [PubMed:12036927 ]

Enzyme Details

7. Multidrug resistance-associated protein 5

General function:: Involved in ATP binding
Specific function:: Acts as a multispecific organic anion pump which can transport nucleotide analogs
Gene Name:: ABCC5
Uniprot ID:: O15440
Molecular weight:: 160658.8

References

Wijnholds J, Mol CA, van Deemter L, de Haas M, Scheffer GL, Baas F, Beijnen JH, Scheper RJ, Hatse S, De Clercq E, Balzarini J, Borst P: Multidrug-resistance protein 5 is a multispecific organic anion transporter able to transport nucleotide analogs. Proc Natl Acad Sci U S A. 2000 Jun 20;97(13):7476-81. [PubMed:10840050 ]

Only showing the first 10 proteins. There are 11 proteins in total.

Show all enzymes and transporters

Showing metabocard for Sulfinpyrazone (HMDB0015269)

MOL for HMDB0015269 (Sulfinpyrazone)

3D MOL for HMDB0015269 (Sulfinpyrazone)

3D SDF for HMDB0015269 (Sulfinpyrazone)

3D-SDF for HMDB0015269 (Sulfinpyrazone)

PDB for HMDB0015269 (Sulfinpyrazone)

3D PDB for HMDB0015269 (Sulfinpyrazone)

SMILES for HMDB0015269 (Sulfinpyrazone)

INCHI for HMDB0015269 (Sulfinpyrazone)

Structure for HMDB0015269 (Sulfinpyrazone)

3D Structure for HMDB0015269 (Sulfinpyrazone)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

Transporters

References

References

References

References

References

References

References