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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-10-17 08:34:38 UTC

Update Date

2022-03-07 02:49:25 UTC

HMDB ID

HMDB0005014

Secondary Accession Numbers

HMDB05014

Metabolite Identification

Common Name

Celecoxib

Description

Celecoxib (INN) is a non-steroidal anti-inflammatory drug (NSAID) used in the treatment of osteoarthritis, rheumatoid arthritis, acute pain, painful menstruation and menstrual symptoms, and to reduce numbers of colon and rectum polyps in patients with familial adenomatous polyposis. It is marketed by Pfizer under the brand name Celebrex. In some countries, it is branded Celebra. Celecoxib is a non-steroidal anti-inflammatory drug (NSAID) used in the treatment of osteoarthritis, rheumatoid arthritis, acute pain, painful menstruation and menstrual symptoms, and to reduce numbers of colon and rectum polyps in patients with familial adenomatous polyposis. Celecoxib is a highly selective COX-2 inhibitor and primarily inhibits this isoform of cyclooxygenase, whereas traditional NSAIDs inhibit both COX-1 and COX-2. Celecoxib is approximately 10-20 times more selective for COX-2 inhibition over COX-1. In theory, this specificity allows celecoxib and other COX-2 inhibitors to reduce inflammation (and pain) while minimizing gastrointestinal adverse drug reactions (e.g. stomach ulcers) that are common with non-selective NSAIDs. It also means that it has a reduced effect on platelet aggregation compared to traditional NSAIDs; Celecoxib is a highly selective COX-2 inhibitor and primarily inhibits this isoform of cyclooxygenase, whereas traditional NSAIDs inhibit both COX-1 and COX-2. Celecoxib is approximately 10-20 times more selective for COX-2 inhibition over COX-1. In theory, this specificity allows celecoxib and other COX-2 inhibitors to reduce inflammation (and pain) while minimizing gastrointestinal adverse drug reactions (e.g. stomach ulcers) that are common with non-selective NSAIDs. It also means that it has a reduced effect on platelet aggregation compared to traditional NSAIDs.

Structure

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

482
  Mrv0541 02231214432D          

 26 28  0  0  0  0            999 V2000
    3.2149   -2.4119    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    2.3402    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.9849    3.3101    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.8325    3.4926    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.0399   -2.4119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3899   -2.4119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2149    0.8882    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5475    1.3731    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2149   -3.2369    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8824    1.3731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2149    0.0632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6670    1.1181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6274    2.1578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8024    2.1578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9294   -0.3493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5005   -0.3493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2149   -1.5868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8386    0.3112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2801    1.6702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9294   -1.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5005   -1.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2363    0.6083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6232    0.0563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0648    1.4152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3175    2.8252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0209    0.3534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  2  0  0  0  0
  1  6  2  0  0  0  0
  1  9  1  0  0  0  0
  1 17  1  0  0  0  0
  2 25  1  0  0  0  0
  3 25  1  0  0  0  0
  4 25  1  0  0  0  0
  7  8  1  0  0  0  0
  7 10  1  0  0  0  0
  7 11  1  0  0  0  0
  8 14  2  0  0  0  0
 10 12  1  0  0  0  0
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 11 15  2  0  0  0  0
 11 16  1  0  0  0  0
 12 18  2  0  0  0  0
 12 19  1  0  0  0  0
 13 14  1  0  0  0  0
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 17 21  1  0  0  0  0
 18 23  1  0  0  0  0
 19 24  2  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 22 26  1  0  0  0  0
M  END

HMDB0005014
     RDKit          3D
Celecoxib
 40 42  0  0  0  0  0  0  0  0999 V2000
   -4.5488    2.9701    1.3050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5616    1.9198    0.9512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9542    0.6115    1.1782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1067   -0.4164    0.8503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8635   -0.1921    0.2998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0784   -1.3625   -0.1525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6336   -2.6461   -0.2879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6558   -3.5108   -0.7223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8892   -4.9762   -1.0058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2956   -5.7790   -0.0596 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3940   -5.2283   -2.2925 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2229   -5.2687   -1.0708 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.4271   -2.7812   -0.8296 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1845   -1.4888   -0.4888 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2175   -0.5092   -0.4908 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7935   -0.0475   -1.6552 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8759    0.8405   -1.6209 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3837    1.2653   -0.4215 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7956    2.2795   -0.2364 S   0  0  0  0  0  6  0  0  0  0  0  0
    6.1137    1.1727    0.1328 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1019    3.0178   -1.4912 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6502    3.2052    0.9132 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8002    0.8064    0.7552 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7525   -0.0537    0.7058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4715    1.0997    0.0788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3344    2.1673    0.4120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0838    3.9403    1.5723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2121    2.6662    2.1434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2246    3.0934    0.4183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9193    0.4098    1.6081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4417   -1.4275    1.0344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6810   -2.9075   -0.0888 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4347   -0.3841   -2.6313 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3082    1.2115   -2.5198 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8147    0.7136    1.0642 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0276    0.3781   -0.5865 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1933    1.1180    1.7406 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2664   -0.4175    1.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5381    1.3177   -0.3568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0304    3.1927    0.2315 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
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 17 18  2  0
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 19 21  2  0
 19 22  2  0
 18 23  1  0
 23 24  2  0
  5 25  1  0
 25 26  2  0
 26  2  1  0
 14  6  1  0
 24 15  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  4 31  1  0
  7 32  1  0
 16 33  1  0
 17 34  1  0
 20 35  1  0
 20 36  1  0
 23 37  1  0
 24 38  1  0
 25 39  1  0
 26 40  1  0
M  END

482
  Mrv0541 02231214432D          

 26 28  0  0  0  0            999 V2000
    3.2149   -2.4119    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    2.3402    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.9849    3.3101    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.8325    3.4926    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.0399   -2.4119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3899   -2.4119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2149    0.8882    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5475    1.3731    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2149   -3.2369    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8824    1.3731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2149    0.0632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6670    1.1181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6274    2.1578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8024    2.1578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9294   -0.3493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5005   -0.3493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2149   -1.5868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8386    0.3112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2801    1.6702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9294   -1.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5005   -1.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2363    0.6083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6232    0.0563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0648    1.4152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3175    2.8252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0209    0.3534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  2  0  0  0  0
  1  6  2  0  0  0  0
  1  9  1  0  0  0  0
  1 17  1  0  0  0  0
  2 25  1  0  0  0  0
  3 25  1  0  0  0  0
  4 25  1  0  0  0  0
  7  8  1  0  0  0  0
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  7 11  1  0  0  0  0
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 11 16  1  0  0  0  0
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 17 21  1  0  0  0  0
 18 23  1  0  0  0  0
 19 24  2  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 22 26  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0005014

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC=C(C=C1)C1=CC(=NN1C1=CC=C(C=C1)S(N)(=O)=O)C(F)(F)F

> <INCHI_IDENTIFIER>
InChI=1S/C17H14F3N3O2S/c1-11-2-4-12(5-3-11)15-10-16(17(18,19)20)22-23(15)13-6-8-14(9-7-13)26(21,24)25/h2-10H,1H3,(H2,21,24,25)

> <INCHI_KEY>
RZEKVGVHFLEQIL-UHFFFAOYSA-N

> <FORMULA>
C17H14F3N3O2S

> <MOLECULAR_WEIGHT>
381.372

> <EXACT_MASS>
381.075882012

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
35.200201261435936

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzene-1-sulfonamide

> <ALOGPS_LOGP>
3.99

> <JCHEM_LOGP>
4.009441774333333

> <ALOGPS_LOGS>
-4.88

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.70145080874998

> <JCHEM_PKA_STRONGEST_BASIC>
-0.4187111614431479

> <JCHEM_POLAR_SURFACE_AREA>
77.98

> <JCHEM_REFRACTIVITY>
92.23420000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.03e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
celecoxib

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0005014
     RDKit          3D
Celecoxib
 40 42  0  0  0  0  0  0  0  0999 V2000
   -4.5488    2.9701    1.3050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5616    1.9198    0.9512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9542    0.6115    1.1782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1067   -0.4164    0.8503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8635   -0.1921    0.2998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0784   -1.3625   -0.1525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6336   -2.6461   -0.2879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6558   -3.5108   -0.7223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8892   -4.9762   -1.0058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2956   -5.7790   -0.0596 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3940   -5.2283   -2.2925 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2229   -5.2687   -1.0708 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.4271   -2.7812   -0.8296 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1845   -1.4888   -0.4888 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2175   -0.5092   -0.4908 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7935   -0.0475   -1.6552 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8759    0.8405   -1.6209 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3837    1.2653   -0.4215 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7956    2.2795   -0.2364 S   0  0  0  0  0  6  0  0  0  0  0  0
    6.1137    1.1727    0.1328 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1019    3.0178   -1.4912 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6502    3.2052    0.9132 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8002    0.8064    0.7552 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7525   -0.0537    0.7058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4715    1.0997    0.0788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3344    2.1673    0.4120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0838    3.9403    1.5723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2121    2.6662    2.1434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2246    3.0934    0.4183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9193    0.4098    1.6081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4417   -1.4275    1.0344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6810   -2.9075   -0.0888 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4347   -0.3841   -2.6313 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3082    1.2115   -2.5198 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8147    0.7136    1.0642 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0276    0.3781   -0.5865 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1933    1.1180    1.7406 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2664   -0.4175    1.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5381    1.3177   -0.3568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0304    3.1927    0.2315 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
  9 12  1  0
  8 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 19 22  2  0
 18 23  1  0
 23 24  2  0
  5 25  1  0
 25 26  2  0
 26  2  1  0
 14  6  1  0
 24 15  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  4 31  1  0
  7 32  1  0
 16 33  1  0
 17 34  1  0
 20 35  1  0
 20 36  1  0
 23 37  1  0
 24 38  1  0
 25 39  1  0
 26 40  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 482                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0       6.001  -4.502   0.000  0.00  0.00           S+0
HETATM    2  F   UNK     0       3.080   4.368   0.000  0.00  0.00           F+0
HETATM    3  F   UNK     0       5.572   6.179   0.000  0.00  0.00           F+0
HETATM    4  F   UNK     0       3.421   6.520   0.000  0.00  0.00           F+0
HETATM    5  O   UNK     0       7.541  -4.502   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       4.461  -4.502   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0       6.001   1.658   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0       4.755   2.563   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0       6.001  -6.042   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       7.247   2.563   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.001   0.118   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.712   2.087   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.771   4.028   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.231   4.028   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.335  -0.652   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.668  -0.652   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.001  -2.962   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.032   0.581   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.856   3.118   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.335  -2.192   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.668  -2.192   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.641   1.135   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.497   0.105   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.321   2.642   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.326   5.274   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      13.106   0.660   0.000  0.00  0.00           C+0
CONECT    1    5    6    9   17                                             
CONECT    2   25                                                            
CONECT    3   25                                                            
CONECT    4   25                                                            
CONECT    5    1                                                            
CONECT    6    1                                                            
CONECT    7    8   10   11                                                  
CONECT    8    7   14                                                       
CONECT    9    1                                                            
CONECT   10    7   12   13                                                  
CONECT   11    7   15   16                                                  
CONECT   12   10   18   19                                                  
CONECT   13   10   14                                                       
CONECT   14    8   13   25                                                  
CONECT   15   11   20                                                       
CONECT   16   11   21                                                       
CONECT   17    1   20   21                                                  
CONECT   18   12   23                                                       
CONECT   19   12   24                                                       
CONECT   20   15   17                                                       
CONECT   21   16   17                                                       
CONECT   22   23   24   26                                                  
CONECT   23   18   22                                                       
CONECT   24   19   22                                                       
CONECT   25    2    3    4   14                                             
CONECT   26   22                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

COMPND    HMDB0005014
HETATM    1  C1  UNL     1      -4.549   2.970   1.305  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.562   1.920   0.951  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.954   0.612   1.178  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.107  -0.416   0.850  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.863  -0.192   0.300  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.078  -1.362  -0.153  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.634  -2.646  -0.288  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.656  -3.511  -0.722  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.889  -4.976  -1.006  1.00  0.00           C  
HETATM   10  F1  UNL     1      -0.296  -5.779  -0.060  1.00  0.00           F  
HETATM   11  F2  UNL     1      -0.394  -5.228  -2.293  1.00  0.00           F  
HETATM   12  F3  UNL     1      -2.223  -5.269  -1.071  1.00  0.00           F  
HETATM   13  N1  UNL     1       0.427  -2.781  -0.830  1.00  0.00           N  
HETATM   14  N2  UNL     1       0.185  -1.489  -0.489  1.00  0.00           N  
HETATM   15  C10 UNL     1       1.218  -0.509  -0.491  1.00  0.00           C  
HETATM   16  C11 UNL     1       1.793  -0.047  -1.655  1.00  0.00           C  
HETATM   17  C12 UNL     1       2.876   0.840  -1.621  1.00  0.00           C  
HETATM   18  C13 UNL     1       3.384   1.265  -0.421  1.00  0.00           C  
HETATM   19  S1  UNL     1       4.796   2.280  -0.236  1.00  0.00           S  
HETATM   20  N3  UNL     1       6.114   1.173   0.133  1.00  0.00           N  
HETATM   21  O1  UNL     1       5.102   3.018  -1.491  1.00  0.00           O  
HETATM   22  O2  UNL     1       4.650   3.205   0.913  1.00  0.00           O  
HETATM   23  C14 UNL     1       2.800   0.806   0.755  1.00  0.00           C  
HETATM   24  C15 UNL     1       1.753  -0.054   0.706  1.00  0.00           C  
HETATM   25  C16 UNL     1      -1.472   1.100   0.079  1.00  0.00           C  
HETATM   26  C17 UNL     1      -2.334   2.167   0.412  1.00  0.00           C  
HETATM   27  H1  UNL     1      -4.084   3.940   1.572  1.00  0.00           H  
HETATM   28  H2  UNL     1      -5.212   2.666   2.143  1.00  0.00           H  
HETATM   29  H3  UNL     1      -5.225   3.093   0.418  1.00  0.00           H  
HETATM   30  H4  UNL     1      -4.919   0.410   1.608  1.00  0.00           H  
HETATM   31  H5  UNL     1      -3.442  -1.427   1.034  1.00  0.00           H  
HETATM   32  H6  UNL     1      -2.681  -2.907  -0.089  1.00  0.00           H  
HETATM   33  H7  UNL     1       1.435  -0.384  -2.631  1.00  0.00           H  
HETATM   34  H8  UNL     1       3.308   1.211  -2.520  1.00  0.00           H  
HETATM   35  H9  UNL     1       5.815   0.714   1.064  1.00  0.00           H  
HETATM   36  H10 UNL     1       6.028   0.378  -0.587  1.00  0.00           H  
HETATM   37  H11 UNL     1       3.193   1.118   1.741  1.00  0.00           H  
HETATM   38  H12 UNL     1       1.266  -0.417   1.614  1.00  0.00           H  
HETATM   39  H13 UNL     1      -0.538   1.318  -0.357  1.00  0.00           H  
HETATM   40  H14 UNL     1      -2.030   3.193   0.231  1.00  0.00           H  
CONECT    1    2   27   28   29
CONECT    2    3    3   26
CONECT    3    4   30
CONECT    4    5    5   31
CONECT    5    6   25
CONECT    6    7    7   14
CONECT    7    8   32
CONECT    8    9   13   13
CONECT    9   10   11   12
CONECT   13   14
CONECT   14   15
CONECT   15   16   16   24
CONECT   16   17   33
CONECT   17   18   18   34
CONECT   18   19   23
CONECT   19   20   21   21   22
CONECT   19   22
CONECT   20   35   36
CONECT   23   24   24   37
CONECT   24   38
CONECT   25   26   26   39
CONECT   26   40
END

HMDB0005014
     RDKit          3D
Celecoxib
 40 42  0  0  0  0  0  0  0  0999 V2000
   -4.5488    2.9701    1.3050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5616    1.9198    0.9512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9542    0.6115    1.1782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1067   -0.4164    0.8503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8635   -0.1921    0.2998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0784   -1.3625   -0.1525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6336   -2.6461   -0.2879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6558   -3.5108   -0.7223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8892   -4.9762   -1.0058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2956   -5.7790   -0.0596 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3940   -5.2283   -2.2925 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2229   -5.2687   -1.0708 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.4271   -2.7812   -0.8296 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1845   -1.4888   -0.4888 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2175   -0.5092   -0.4908 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7935   -0.0475   -1.6552 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8759    0.8405   -1.6209 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3837    1.2653   -0.4215 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7956    2.2795   -0.2364 S   0  0  0  0  0  6  0  0  0  0  0  0
    6.1137    1.1727    0.1328 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1019    3.0178   -1.4912 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6502    3.2052    0.9132 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8002    0.8064    0.7552 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7525   -0.0537    0.7058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4715    1.0997    0.0788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3344    2.1673    0.4120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0838    3.9403    1.5723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2121    2.6662    2.1434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2246    3.0934    0.4183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9193    0.4098    1.6081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4417   -1.4275    1.0344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6810   -2.9075   -0.0888 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4347   -0.3841   -2.6313 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3082    1.2115   -2.5198 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8147    0.7136    1.0642 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0276    0.3781   -0.5865 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1933    1.1180    1.7406 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2664   -0.4175    1.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5381    1.3177   -0.3568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0304    3.1927    0.2315 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
  9 12  1  0
  8 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 19 22  2  0
 18 23  1  0
 23 24  2  0
  5 25  1  0
 25 26  2  0
 26  2  1  0
 14  6  1  0
 24 15  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  4 31  1  0
  7 32  1  0
 16 33  1  0
 17 34  1  0
 20 35  1  0
 20 36  1  0
 23 37  1  0
 24 38  1  0
 25 39  1  0
 26 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Celebrex	ChEBI
Celecoxibum	ChEBI
p-(5-p-Tolyl-3-(trifluoromethyl)pyrazol-1-yl)benzenesulfonamide	ChEBI
Onsenal	Kegg
p-(5-p-Tolyl-3-(trifluoromethyl)pyrazol-1-yl)benzenesulphonamide	Generator
Celocoxib	HMDB
4-(5-(4-Methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)benzenesulfonamide	HMDB

Chemical Formula

C₁₇H₁₄F₃N₃O₂S

Average Molecular Weight

381.372

Monoisotopic Molecular Weight

381.075882012

IUPAC Name

4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzene-1-sulfonamide

Traditional Name

celecoxib

CAS Registry Number

169590-42-5

SMILES

CC1=CC=C(C=C1)C1=CC(=NN1C1=CC=C(C=C1)S(N)(=O)=O)C(F)(F)F

InChI Identifier

InChI=1S/C17H14F3N3O2S/c1-11-2-4-12(5-3-11)15-10-16(17(18,19)20)22-23(15)13-6-8-14(9-7-13)26(21,24)25/h2-10H,1H3,(H2,21,24,25)

InChI Key

RZEKVGVHFLEQIL-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpyrazoles. Phenylpyrazoles are compounds containing a phenylpyrazole skeleton, which consists of a pyrazole bound to a phenyl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azoles

Sub Class

Pyrazoles

Direct Parent

Phenylpyrazoles

Alternative Parents

Substituents

Phenylpyrazole
Benzenesulfonamide
Benzenesulfonyl group
Toluene
Monocyclic benzene moiety
Organosulfonic acid amide
Benzenoid
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Sulfonyl
Aminosulfonyl compound
Heteroaromatic compound
Azacycle
Organic oxide
Alkyl halide
Alkyl fluoride
Organopnictogen compound
Organosulfur compound
Organonitrogen compound
Organofluoride
Organohalogen compound
Hydrocarbon derivative
Organic nitrogen compound
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

organofluorine compound (CHEBI:41423 )
pyrazoles (CHEBI:41423 )
sulfonamide (CHEBI:41423 )

Ontology

Physiological effect

Health effect

Observation

Breathing difficulties (HMDB: HMDB0005014)
Vomiting (HMDB: HMDB0005014)
Nausea (HMDB: HMDB0005014)
Pain (HMDB: HMDB0005014)
Drowsiness (HMDB: HMDB0005014)
Bleeding (HMDB: HMDB0005014)

Nervous system disorder

Coma (HMDB: HMDB0005014)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 16580269)

Cellular substructure

Membrane (HMDB: HMDB0005014)
Cell membrane (HMDB: HMDB0005014)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0005014)
Gastrointestinal (HMDB: HMDB0005014)

Source

Exogenous

Exogenous (HMDB: HMDB0005014)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Celecoxib Action Pathway (HMDB: HMDB0005014)
Celecoxib Action Pathway (PathBank: SMP0000096)

Metabolic pathway

Celecoxib Metabolism Pathway (HMDB: HMDB0005014)
Celecoxib Metabolism Pathway (PathBank: SMP0000644)

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0005014)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	101.7 - 103.9 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	186.4	30932474
[M+H]+	Not Available	186.121	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001044

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.005 g/L	ALOGPS
logP	3.99	ALOGPS
logP	4.01	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	10.7	ChemAxon
pKa (Strongest Basic)	-0.42	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	77.98 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	92.23 m³·mol⁻¹	ChemAxon
Polarizability	35.2 Å³	ChemAxon
Number of Rings	3	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]+	184.384	30932474
DeepCCS	[M-H]-	182.026	30932474
DeepCCS	[M-2H]-	216.295	30932474
DeepCCS	[M+Na]+	191.466	30932474
AllCCS	[M+H]+	185.7	32859911
AllCCS	[M+H-H2O]+	182.7	32859911
AllCCS	[M+NH4]+	188.5	32859911
AllCCS	[M+Na]+	189.3	32859911
AllCCS	[M-H]-	178.7	32859911
AllCCS	[M+Na-2H]-	177.8	32859911
AllCCS	[M+HCOO]-	177.1	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.	7.19 minutes	32390414
Predicted by Siyang on May 30, 2022	15.3911 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.32 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	27.9 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2004.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	419.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	192.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	234.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	327.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	670.0 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	654.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	91.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1400.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	511.4 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	1525.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	421.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	461.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	300.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	226.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	39.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Celecoxib	CC1=CC=C(C=C1)C1=CC(=NN1C1=CC=C(C=C1)S(N)(=O)=O)C(F)(F)F	4575.6	Standard polar	33892256
Celecoxib	CC1=CC=C(C=C1)C1=CC(=NN1C1=CC=C(C=C1)S(N)(=O)=O)C(F)(F)F	2882.8	Standard non polar	33892256
Celecoxib	CC1=CC=C(C=C1)C1=CC(=NN1C1=CC=C(C=C1)S(N)(=O)=O)C(F)(F)F	2842.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Celecoxib,1TMS,isomer #1	CC1=CC=C(C2=CC(C(F)(F)F)=NN2C2=CC=C(S(=O)(=O)N[Si](C)(C)C)C=C2)C=C1	2895.1	Semi standard non polar	33892256
Celecoxib,1TMS,isomer #1	CC1=CC=C(C2=CC(C(F)(F)F)=NN2C2=CC=C(S(=O)(=O)N[Si](C)(C)C)C=C2)C=C1	2886.6	Standard non polar	33892256
Celecoxib,1TMS,isomer #1	CC1=CC=C(C2=CC(C(F)(F)F)=NN2C2=CC=C(S(=O)(=O)N[Si](C)(C)C)C=C2)C=C1	3504.4	Standard polar	33892256
Celecoxib,2TMS,isomer #1	CC1=CC=C(C2=CC(C(F)(F)F)=NN2C2=CC=C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)C=C2)C=C1	2871.0	Semi standard non polar	33892256
Celecoxib,2TMS,isomer #1	CC1=CC=C(C2=CC(C(F)(F)F)=NN2C2=CC=C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)C=C2)C=C1	3036.8	Standard non polar	33892256
Celecoxib,2TMS,isomer #1	CC1=CC=C(C2=CC(C(F)(F)F)=NN2C2=CC=C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)C=C2)C=C1	3438.5	Standard polar	33892256
Celecoxib,1TBDMS,isomer #1	CC1=CC=C(C2=CC(C(F)(F)F)=NN2C2=CC=C(S(=O)(=O)N[Si](C)(C)C(C)(C)C)C=C2)C=C1	3135.6	Semi standard non polar	33892256
Celecoxib,1TBDMS,isomer #1	CC1=CC=C(C2=CC(C(F)(F)F)=NN2C2=CC=C(S(=O)(=O)N[Si](C)(C)C(C)(C)C)C=C2)C=C1	3122.7	Standard non polar	33892256
Celecoxib,1TBDMS,isomer #1	CC1=CC=C(C2=CC(C(F)(F)F)=NN2C2=CC=C(S(=O)(=O)N[Si](C)(C)C(C)(C)C)C=C2)C=C1	3498.7	Standard polar	33892256
Celecoxib,2TBDMS,isomer #1	CC1=CC=C(C2=CC(C(F)(F)F)=NN2C2=CC=C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)C=C1	3378.8	Semi standard non polar	33892256
Celecoxib,2TBDMS,isomer #1	CC1=CC=C(C2=CC(C(F)(F)F)=NN2C2=CC=C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)C=C1	3470.6	Standard non polar	33892256
Celecoxib,2TBDMS,isomer #1	CC1=CC=C(C2=CC(C(F)(F)F)=NN2C2=CC=C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)C=C1	3470.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Celecoxib GC-MS (Non-derivatized) - 70eV, Positive	splash10-0uy0-0729000000-75ddea9acd30a029b25b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Celecoxib GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Celecoxib 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 - Celecoxib LC-ESI-qTof , Positive-QTOF	splash10-0aou-3960000000-2bd7d8539498dde5c2f5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Celecoxib LC-ESI-QFT , negative-QTOF	splash10-001i-0029000000-1a5ed66ff895eeb127ce	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Celecoxib , positive-QTOF	splash10-001i-0129000000-a967b7f9e88a461e3db4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Celecoxib , positive-QTOF	splash10-01q9-2598000000-f71f4f9eb7c83ddf79f4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Celecoxib LC-ESI-QFT , positive-QTOF	splash10-001i-0029000000-13ff69b3abd31dde6bae	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Celecoxib 75V, Negative-QTOF	splash10-014i-9100000000-9a8cd0b75d276f108651	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Celecoxib 10V, Positive-QTOF	splash10-001i-0009000000-41eaecd214cbc50e645e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Celecoxib 20V, Positive-QTOF	splash10-001i-0009000000-f2376e3bc87d5951988c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Celecoxib 90V, Negative-QTOF	splash10-02vi-9100000000-3b8e53549d02c7db5cba	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Celecoxib 60V, Negative-QTOF	splash10-014i-9220000000-e1d41283ce6235c1de0d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Celecoxib 40V, Positive-QTOF	splash10-0gx0-0059000000-9e48db23da1b4b859e68	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Celecoxib 30V, Positive-QTOF	splash10-001i-0009000000-25406fbf853a86a41e2f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Celecoxib 45V, Negative-QTOF	splash10-016r-7292000000-0c298e1f9b51823232c7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Celecoxib 20V, Negative-QTOF	splash10-001i-0009000000-57c7836793a5363fda3d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Celecoxib 30V, Negative-QTOF	splash10-017j-0198000000-927a7c09840b934e4cea	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Celecoxib 10V, Negative-QTOF	splash10-001i-0009000000-e3bce1b4f36e339f9f39	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Celecoxib 50V, Positive-QTOF	splash10-001i-0293000000-c8b94b6bd1da23395b78	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Celecoxib 15V, Negative-QTOF	splash10-001i-0009000000-72b8641321f8f9f0f2b3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Celecoxib 40V, Negative-QTOF	splash10-004i-0490000000-0b6fde7d96dea087de34	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Celecoxib 10V, Positive-QTOF	splash10-001i-0009000000-23d25f88a0e277e47c54	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Celecoxib 20V, Positive-QTOF	splash10-001i-0009000000-a933645e1cf7fb8edf4f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Celecoxib 40V, Positive-QTOF	splash10-0ufr-3289000000-7c03de47cb9bd124fa0c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Celecoxib 10V, Negative-QTOF	splash10-001i-0009000000-9d1a9c471dc123cee735	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Celecoxib 20V, Negative-QTOF	splash10-001i-0009000000-bdb3f0787c9e831e7530	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Celecoxib 40V, Negative-QTOF	splash10-004i-9125000000-ad5803f68fece8f76b2a	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Celecoxib Action Pathway		Not Available
Celecoxib Metabolism Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.0257 +/- 1.33 uM	Adult (>18 years old)	Both	Normal	16580269	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00482

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023586

KNApSAcK ID

Not Available

Chemspider ID

2562

KEGG Compound ID

C07589

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Celecoxib

METLIN ID

Not Available

PubChem Compound

2662

PDB ID

Not Available

ChEBI ID

41423

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Talley, John J.; Penning, Thomas D.; Collins, Paul W.; Rogier, Donald J., Jr.; Malecha, James W.; Miyashiro, Julie M.; Bertenshaw, Stephen R.; Khanna, Ish K.; Granets, Matthew J.; et al. Preparation of pyrazolylbenzenesulfonamides as antiinflammatories. PCT Int. Appl. (1995), 254 pp. CODEN: PIXXD2 WO 9515316 A1 19950608 CAN 123:340112 AN 1995:931246

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Not Available

Enzymes

Enzyme Details

1. Prostaglandin G/H synthase 2

General function:: Involved in peroxidase activity
Specific function:: Mediates the formation of prostaglandins from arachidonate. May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity.
Gene Name:: PTGS2
Uniprot ID:: P35354
Molecular weight:: 68995.625

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

Enzyme Details

3. 3-phosphoinositide-dependent protein kinase 1

General function:: Involved in protein kinase activity
Specific function:: Phosphorylates and activates not only PKB/AKT, but also PKA, PKC-zeta, RPS6KA1 and RPS6KB1. May play a general role in signaling processes and in development. Isoform 3 is catalytically inactive
Gene Name:: PDPK1
Uniprot ID:: O15530
Molecular weight:: 63151.3

Enzyme Details

4. Cytochrome P450 2D6

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:: CYP2D6
Uniprot ID:: P10635
Molecular weight:: 55768.94

Showing metabocard for Celecoxib (HMDB0005014)

MOL for HMDB0005014 (Celecoxib)

3D MOL for HMDB0005014 (Celecoxib)

3D SDF for HMDB0005014 (Celecoxib)

3D-SDF for HMDB0005014 (Celecoxib)

PDB for HMDB0005014 (Celecoxib)

3D PDB for HMDB0005014 (Celecoxib)

SMILES for HMDB0005014 (Celecoxib)

INCHI for HMDB0005014 (Celecoxib)

Structure for HMDB0005014 (Celecoxib)

3D Structure for HMDB0005014 (Celecoxib)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes