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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (6)transporters (1) Show 7 proteins XML

enzymes (6)transporters (1) Show 7 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:00:46 UTC

Update Date

2020-02-26 21:39:19 UTC

HMDB ID

HMDB0013995

Secondary Accession Numbers

HMDB13995

Metabolite Identification

Common Name

Hydroxycelecoxib

Description

Hydroxycelecoxib is a metabolite of celecoxib and is only found in individuals that have used or taken this drug (PMID: 10681375 ). Hydroxycelecoxib belongs to the family of phenylpyrazoles. These are compounds containing a phenylpyrazole skeleton which consists of a pyrazole bound to a phenyl group. Celecoxib (trade name: Celebrex) is a sulfa non-steroidal anti-inflammatory drug (NSAID) and selective COX-2 inhibitor 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. Celecoxib is available by prescription in capsule form (Wikipedia).

Structure

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


  Mrv1652311011916212D          

 27 29  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
    7.6043    0.9368    0.0000 O   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
 10 13  2  0  0  0  0
 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
 14 25  1  0  0  0  0
 15 20  1  0  0  0  0
 16 21  2  0  0  0  0
 17 20  2  0  0  0  0
 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
 26 27  1  0  0  0  0
M  END

HMDB0013995
     RDKit          3D
Hydroxycelecoxib
 41 43  0  0  0  0  0  0  0  0999 V2000
    6.0996   -1.6978   -0.7801 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0010   -1.6779    0.5756 S   0  0  0  0  0  6  0  0  0  0  0  0
    5.7988   -0.9395    1.6665 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6639   -3.0200    1.0854 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6120   -0.6617    0.2713 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7499   -0.9421   -0.7998 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6163   -0.1842   -1.0332 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2833    0.8758   -0.2280 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1570    1.6739   -0.4235 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2850    2.9580   -0.8362 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8725    3.5636   -0.9796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1066    5.0011   -1.4037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2433    5.7928   -0.2634 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0276    5.4828   -2.1076 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2344    5.0580   -2.1737 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8371    2.6475   -0.6504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1596    1.4839   -0.3082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8351    0.2868    0.0851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2112   -0.8163    0.5653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8879   -1.9702    0.8694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2578   -2.0639    0.7019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0139   -3.3141    1.0145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5907   -3.3043    2.2745 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9056   -0.9587    0.2205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1962    0.1903   -0.0797 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1543    1.1429    0.8350 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2801    0.4000    1.0772 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8591   -2.3961   -0.5037 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5551   -2.0659   -1.6051 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9829   -1.7643   -1.4554 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9483   -0.3932   -1.8558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8930    2.7825   -0.6490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1590   -0.8230    0.7677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3568   -2.8514    1.2548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8040   -3.4076    0.2447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3489   -4.2022    0.9469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1879   -2.5079    2.3033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9672   -1.0184    0.0946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8154    1.0208   -0.4589 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9396    1.9924    1.5146 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9258    0.6276    1.9130 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  2  0
  2  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 12 15  1  0
 11 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 21 24  1  0
 24 25  2  0
  8 26  1  0
 26 27  2  0
 27  5  1  0
 17  9  1  0
 25 18  1  0
  1 28  1  0
  1 29  1  0
  6 30  1  0
  7 31  1  0
 16 32  1  0
 19 33  1  0
 20 34  1  0
 22 35  1  0
 22 36  1  0
 23 37  1  0
 24 38  1  0
 25 39  1  0
 26 40  1  0
 27 41  1  0
M  END


  Mrv1652311011916212D          

 27 29  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
    7.6043    0.9368    0.0000 O   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
 10 13  2  0  0  0  0
 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
 14 25  1  0  0  0  0
 15 20  1  0  0  0  0
 16 21  2  0  0  0  0
 17 20  2  0  0  0  0
 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
 26 27  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0013995

> <DATABASE_NAME>
hmdb

> <SMILES>
NS(=O)(=O)C1=CC=C(C=C1)N1N=C(C=C1C1=CC=C(CO)C=C1)C(F)(F)F

> <INCHI_IDENTIFIER>
InChI=1S/C17H14F3N3O3S/c18-17(19,20)16-9-15(12-3-1-11(10-24)2-4-12)23(22-16)13-5-7-14(8-6-13)27(21,25)26/h1-9,24H,10H2,(H2,21,25,26)

> <INCHI_KEY>
ICRSYPPLGADZKA-UHFFFAOYSA-N

> <FORMULA>
C17H14F3N3O3S

> <MOLECULAR_WEIGHT>
397.372

> <EXACT_MASS>
397.070796634

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
36.11346975798021

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-{5-[4-(hydroxymethyl)phenyl]-3-(trifluoromethyl)-1H-pyrazol-1-yl}benzene-1-sulfonamide

> <ALOGPS_LOGP>
3.10

> <JCHEM_LOGP>
2.728670617666667

> <ALOGPS_LOGS>
-4.94

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.967652520594747

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.701111764241967

> <JCHEM_PKA_STRONGEST_BASIC>
0.057044299532522214

> <JCHEM_POLAR_SURFACE_AREA>
98.21000000000001

> <JCHEM_REFRACTIVITY>
94.00890000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.52e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-{5-[4-(hydroxymethyl)phenyl]-3-(trifluoromethyl)pyrazol-1-yl}benzenesulfonamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0013995
     RDKit          3D
Hydroxycelecoxib
 41 43  0  0  0  0  0  0  0  0999 V2000
    6.0996   -1.6978   -0.7801 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0010   -1.6779    0.5756 S   0  0  0  0  0  6  0  0  0  0  0  0
    5.7988   -0.9395    1.6665 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6639   -3.0200    1.0854 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6120   -0.6617    0.2713 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7499   -0.9421   -0.7998 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6163   -0.1842   -1.0332 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2833    0.8758   -0.2280 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1570    1.6739   -0.4235 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2850    2.9580   -0.8362 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8725    3.5636   -0.9796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1066    5.0011   -1.4037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2433    5.7928   -0.2634 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0276    5.4828   -2.1076 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2344    5.0580   -2.1737 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8371    2.6475   -0.6504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1596    1.4839   -0.3082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8351    0.2868    0.0851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2112   -0.8163    0.5653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8879   -1.9702    0.8694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2578   -2.0639    0.7019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0139   -3.3141    1.0145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5907   -3.3043    2.2745 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9056   -0.9587    0.2205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1962    0.1903   -0.0797 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1543    1.1429    0.8350 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2801    0.4000    1.0772 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8591   -2.3961   -0.5037 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5551   -2.0659   -1.6051 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9829   -1.7643   -1.4554 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9483   -0.3932   -1.8558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8930    2.7825   -0.6490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1590   -0.8230    0.7677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3568   -2.8514    1.2548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8040   -3.4076    0.2447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3489   -4.2022    0.9469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1879   -2.5079    2.3033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9672   -1.0184    0.0946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8154    1.0208   -0.4589 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9396    1.9924    1.5146 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9258    0.6276    1.9130 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  2  0
  2  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 12 15  1  0
 11 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 21 24  1  0
 24 25  2  0
  8 26  1  0
 26 27  2  0
 27  5  1  0
 17  9  1  0
 25 18  1  0
  1 28  1  0
  1 29  1  0
  6 30  1  0
  7 31  1  0
 16 32  1  0
 19 33  1  0
 20 34  1  0
 22 35  1  0
 22 36  1  0
 23 37  1  0
 24 38  1  0
 25 39  1  0
 26 40  1  0
 27 41  1  0
M  END

HEADER    PROTEIN                                 01-NOV-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   01-NOV-19         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
HETATM   27  O   UNK     0      14.195   1.749   0.000  0.00  0.00           O+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   27                                                       
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

COMPND    HMDB0013995
HETATM    1  N1  UNL     1       6.100  -1.698  -0.780  1.00  0.00           N  
HETATM    2  S1  UNL     1       5.001  -1.678   0.576  1.00  0.00           S  
HETATM    3  O1  UNL     1       5.799  -0.940   1.666  1.00  0.00           O  
HETATM    4  O2  UNL     1       4.664  -3.020   1.085  1.00  0.00           O  
HETATM    5  C1  UNL     1       3.612  -0.662   0.271  1.00  0.00           C  
HETATM    6  C2  UNL     1       2.750  -0.942  -0.800  1.00  0.00           C  
HETATM    7  C3  UNL     1       1.616  -0.184  -1.033  1.00  0.00           C  
HETATM    8  C4  UNL     1       1.283   0.876  -0.228  1.00  0.00           C  
HETATM    9  N2  UNL     1       0.157   1.674  -0.423  1.00  0.00           N  
HETATM   10  N3  UNL     1       0.285   2.958  -0.836  1.00  0.00           N  
HETATM   11  C5  UNL     1      -0.872   3.564  -0.980  1.00  0.00           C  
HETATM   12  C6  UNL     1      -1.107   5.001  -1.404  1.00  0.00           C  
HETATM   13  F1  UNL     1      -1.243   5.793  -0.263  1.00  0.00           F  
HETATM   14  F2  UNL     1      -0.028   5.483  -2.108  1.00  0.00           F  
HETATM   15  F3  UNL     1      -2.234   5.058  -2.174  1.00  0.00           F  
HETATM   16  C7  UNL     1      -1.837   2.648  -0.650  1.00  0.00           C  
HETATM   17  C8  UNL     1      -1.160   1.484  -0.308  1.00  0.00           C  
HETATM   18  C9  UNL     1      -1.835   0.287   0.085  1.00  0.00           C  
HETATM   19  C10 UNL     1      -1.211  -0.816   0.565  1.00  0.00           C  
HETATM   20  C11 UNL     1      -1.888  -1.970   0.869  1.00  0.00           C  
HETATM   21  C12 UNL     1      -3.258  -2.064   0.702  1.00  0.00           C  
HETATM   22  C13 UNL     1      -4.014  -3.314   1.014  1.00  0.00           C  
HETATM   23  O3  UNL     1      -4.591  -3.304   2.274  1.00  0.00           O  
HETATM   24  C14 UNL     1      -3.906  -0.959   0.220  1.00  0.00           C  
HETATM   25  C15 UNL     1      -3.196   0.190  -0.080  1.00  0.00           C  
HETATM   26  C16 UNL     1       2.154   1.143   0.835  1.00  0.00           C  
HETATM   27  C17 UNL     1       3.280   0.400   1.077  1.00  0.00           C  
HETATM   28  H1  UNL     1       6.859  -2.396  -0.504  1.00  0.00           H  
HETATM   29  H2  UNL     1       5.555  -2.066  -1.605  1.00  0.00           H  
HETATM   30  H3  UNL     1       2.983  -1.764  -1.455  1.00  0.00           H  
HETATM   31  H4  UNL     1       0.948  -0.393  -1.856  1.00  0.00           H  
HETATM   32  H5  UNL     1      -2.893   2.783  -0.649  1.00  0.00           H  
HETATM   33  H6  UNL     1      -0.159  -0.823   0.768  1.00  0.00           H  
HETATM   34  H7  UNL     1      -1.357  -2.851   1.255  1.00  0.00           H  
HETATM   35  H8  UNL     1      -4.804  -3.408   0.245  1.00  0.00           H  
HETATM   36  H9  UNL     1      -3.349  -4.202   0.947  1.00  0.00           H  
HETATM   37  H10 UNL     1      -5.188  -2.508   2.303  1.00  0.00           H  
HETATM   38  H11 UNL     1      -4.967  -1.018   0.095  1.00  0.00           H  
HETATM   39  H12 UNL     1      -3.815   1.021  -0.459  1.00  0.00           H  
HETATM   40  H13 UNL     1       1.940   1.992   1.515  1.00  0.00           H  
HETATM   41  H14 UNL     1       3.926   0.628   1.913  1.00  0.00           H  
CONECT    1    2   28   29
CONECT    2    3    3    4    4
CONECT    2    5
CONECT    5    6    6   27
CONECT    6    7   30
CONECT    7    8    8   31
CONECT    8    9   26
CONECT    9   10   17
CONECT   10   11   11
CONECT   11   12   16
CONECT   12   13   14   15
CONECT   16   17   17   32
CONECT   17   18
CONECT   18   19   19   25
CONECT   19   20   33
CONECT   20   21   21   34
CONECT   21   22   24
CONECT   22   23   35   36
CONECT   23   37
CONECT   24   25   25   38
CONECT   25   39
CONECT   26   27   27   40
CONECT   27   41
END

HMDB0013995
     RDKit          3D
Hydroxycelecoxib
 41 43  0  0  0  0  0  0  0  0999 V2000
    6.0996   -1.6978   -0.7801 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0010   -1.6779    0.5756 S   0  0  0  0  0  6  0  0  0  0  0  0
    5.7988   -0.9395    1.6665 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6639   -3.0200    1.0854 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6120   -0.6617    0.2713 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7499   -0.9421   -0.7998 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6163   -0.1842   -1.0332 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2833    0.8758   -0.2280 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1570    1.6739   -0.4235 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2850    2.9580   -0.8362 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8725    3.5636   -0.9796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1066    5.0011   -1.4037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2433    5.7928   -0.2634 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0276    5.4828   -2.1076 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2344    5.0580   -2.1737 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8371    2.6475   -0.6504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1596    1.4839   -0.3082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8351    0.2868    0.0851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2112   -0.8163    0.5653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8879   -1.9702    0.8694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2578   -2.0639    0.7019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0139   -3.3141    1.0145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5907   -3.3043    2.2745 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9056   -0.9587    0.2205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1962    0.1903   -0.0797 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1543    1.1429    0.8350 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2801    0.4000    1.0772 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8591   -2.3961   -0.5037 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5551   -2.0659   -1.6051 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9829   -1.7643   -1.4554 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9483   -0.3932   -1.8558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8930    2.7825   -0.6490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1590   -0.8230    0.7677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3568   -2.8514    1.2548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8040   -3.4076    0.2447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3489   -4.2022    0.9469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1879   -2.5079    2.3033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9672   -1.0184    0.0946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8154    1.0208   -0.4589 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9396    1.9924    1.5146 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9258    0.6276    1.9130 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  2  0
  2  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 12 15  1  0
 11 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 21 24  1  0
 24 25  2  0
  8 26  1  0
 26 27  2  0
 27  5  1  0
 17  9  1  0
 25 18  1  0
  1 28  1  0
  1 29  1  0
  6 30  1  0
  7 31  1  0
 16 32  1  0
 19 33  1  0
 20 34  1  0
 22 35  1  0
 22 36  1  0
 23 37  1  0
 24 38  1  0
 25 39  1  0
 26 40  1  0
 27 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4'-Hydroxycelecoxib	HMDB
4’-Hydroxycelecoxib	HMDB
Hydroxycelecoxib	HMDB

Chemical Formula

C₁₇H₁₄F₃N₃O₃S

Average Molecular Weight

397.372

Monoisotopic Molecular Weight

397.070796634

IUPAC Name

4-{5-[4-(hydroxymethyl)phenyl]-3-(trifluoromethyl)-1H-pyrazol-1-yl}benzene-1-sulfonamide

Traditional Name

4-{5-[4-(hydroxymethyl)phenyl]-3-(trifluoromethyl)pyrazol-1-yl}benzenesulfonamide

CAS Registry Number

170571-00-3

SMILES

NS(=O)(=O)C1=CC=C(C=C1)N1N=C(C=C1C1=CC=C(CO)C=C1)C(F)(F)F

InChI Identifier

InChI=1S/C17H14F3N3O3S/c18-17(19,20)16-9-15(12-3-1-11(10-24)2-4-12)23(22-16)13-5-7-14(8-6-13)27(21,25)26/h1-9,24H,10H2,(H2,21,25,26)

InChI Key

ICRSYPPLGADZKA-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
Benzyl alcohol
Monocyclic benzene moiety
Benzenoid
Organosulfonic acid amide
Organic sulfonic acid or derivatives
Heteroaromatic compound
Organosulfonic acid or derivatives
Aminosulfonyl compound
Sulfonyl
Azacycle
Alcohol
Hydrocarbon derivative
Primary alcohol
Organic oxide
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organofluoride
Organohalogen compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Alkyl halide
Alkyl fluoride
Aromatic alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0045 g/L	ALOGPS
logP	3.1	ALOGPS
logP	2.73	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	10.7	ChemAxon
pKa (Strongest Basic)	0.057	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	98.21 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	94.01 m³·mol⁻¹	ChemAxon
Polarizability	36.11 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]+	179.962	30932474
DeepCCS	[M-H]-	177.604	30932474
DeepCCS	[M-2H]-	210.987	30932474
DeepCCS	[M+Na]+	186.15	30932474
AllCCS	[M+H]+	187.5	32859911
AllCCS	[M+H-H2O]+	184.6	32859911
AllCCS	[M+NH4]+	190.1	32859911
AllCCS	[M+Na]+	190.8	32859911
AllCCS	[M-H]-	182.4	32859911
AllCCS	[M+Na-2H]-	181.8	32859911
AllCCS	[M+HCOO]-	181.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Hydroxycelecoxib	NS(=O)(=O)C1=CC=C(C=C1)N1N=C(C=C1C1=CC=C(CO)C=C1)C(F)(F)F	4925.9	Standard polar	33892256
Hydroxycelecoxib	NS(=O)(=O)C1=CC=C(C=C1)N1N=C(C=C1C1=CC=C(CO)C=C1)C(F)(F)F	2915.9	Standard non polar	33892256
Hydroxycelecoxib	NS(=O)(=O)C1=CC=C(C=C1)N1N=C(C=C1C1=CC=C(CO)C=C1)C(F)(F)F	3200.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Hydroxycelecoxib,1TMS,isomer #1	C[Si](C)(C)OCC1=CC=C(C2=CC(C(F)(F)F)=NN2C2=CC=C(S(N)(=O)=O)C=C2)C=C1	3192.9	Semi standard non polar	33892256
Hydroxycelecoxib,1TMS,isomer #2	C[Si](C)(C)NS(=O)(=O)C1=CC=C(N2N=C(C(F)(F)F)C=C2C2=CC=C(CO)C=C2)C=C1	3147.3	Semi standard non polar	33892256
Hydroxycelecoxib,2TMS,isomer #1	C[Si](C)(C)NS(=O)(=O)C1=CC=C(N2N=C(C(F)(F)F)C=C2C2=CC=C(CO[Si](C)(C)C)C=C2)C=C1	3153.7	Semi standard non polar	33892256
Hydroxycelecoxib,2TMS,isomer #1	C[Si](C)(C)NS(=O)(=O)C1=CC=C(N2N=C(C(F)(F)F)C=C2C2=CC=C(CO[Si](C)(C)C)C=C2)C=C1	3154.0	Standard non polar	33892256
Hydroxycelecoxib,2TMS,isomer #1	C[Si](C)(C)NS(=O)(=O)C1=CC=C(N2N=C(C(F)(F)F)C=C2C2=CC=C(CO[Si](C)(C)C)C=C2)C=C1	3598.0	Standard polar	33892256
Hydroxycelecoxib,2TMS,isomer #2	C[Si](C)(C)N([Si](C)(C)C)S(=O)(=O)C1=CC=C(N2N=C(C(F)(F)F)C=C2C2=CC=C(CO)C=C2)C=C1	3111.2	Semi standard non polar	33892256
Hydroxycelecoxib,2TMS,isomer #2	C[Si](C)(C)N([Si](C)(C)C)S(=O)(=O)C1=CC=C(N2N=C(C(F)(F)F)C=C2C2=CC=C(CO)C=C2)C=C1	3323.9	Standard non polar	33892256
Hydroxycelecoxib,2TMS,isomer #2	C[Si](C)(C)N([Si](C)(C)C)S(=O)(=O)C1=CC=C(N2N=C(C(F)(F)F)C=C2C2=CC=C(CO)C=C2)C=C1	3868.6	Standard polar	33892256
Hydroxycelecoxib,3TMS,isomer #1	C[Si](C)(C)OCC1=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	3156.7	Semi standard non polar	33892256
Hydroxycelecoxib,3TMS,isomer #1	C[Si](C)(C)OCC1=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	3323.9	Standard non polar	33892256
Hydroxycelecoxib,3TMS,isomer #1	C[Si](C)(C)OCC1=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	3553.1	Standard polar	33892256
Hydroxycelecoxib,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1=CC=C(C2=CC(C(F)(F)F)=NN2C2=CC=C(S(N)(=O)=O)C=C2)C=C1	3448.1	Semi standard non polar	33892256
Hydroxycelecoxib,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NS(=O)(=O)C1=CC=C(N2N=C(C(F)(F)F)C=C2C2=CC=C(CO)C=C2)C=C1	3412.9	Semi standard non polar	33892256
Hydroxycelecoxib,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NS(=O)(=O)C1=CC=C(N2N=C(C(F)(F)F)C=C2C2=CC=C(CO[Si](C)(C)C(C)(C)C)C=C2)C=C1	3607.5	Semi standard non polar	33892256
Hydroxycelecoxib,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NS(=O)(=O)C1=CC=C(N2N=C(C(F)(F)F)C=C2C2=CC=C(CO[Si](C)(C)C(C)(C)C)C=C2)C=C1	3632.1	Standard non polar	33892256
Hydroxycelecoxib,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NS(=O)(=O)C1=CC=C(N2N=C(C(F)(F)F)C=C2C2=CC=C(CO[Si](C)(C)C(C)(C)C)C=C2)C=C1	3683.0	Standard polar	33892256
Hydroxycelecoxib,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(N2N=C(C(F)(F)F)C=C2C2=CC=C(CO)C=C2)C=C1	3663.2	Semi standard non polar	33892256
Hydroxycelecoxib,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(N2N=C(C(F)(F)F)C=C2C2=CC=C(CO)C=C2)C=C1	3741.3	Standard non polar	33892256
Hydroxycelecoxib,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(N2N=C(C(F)(F)F)C=C2C2=CC=C(CO)C=C2)C=C1	3863.8	Standard polar	33892256
Hydroxycelecoxib,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1=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	3863.3	Semi standard non polar	33892256
Hydroxycelecoxib,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1=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	3990.4	Standard non polar	33892256
Hydroxycelecoxib,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1=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	3660.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxycelecoxib GC-MS (Non-derivatized) - 70eV, Positive	splash10-0159-0219000000-75437073bbbdaf5d4daa	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxycelecoxib GC-MS (1 TMS) - 70eV, Positive	splash10-00ei-6219200000-3f22c3b291fe5a80e34c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxycelecoxib GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxycelecoxib 10V, Positive-QTOF	splash10-0002-0009000000-719c96498b40762e673f	2016-06-20	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxycelecoxib 20V, Positive-QTOF	splash10-0002-0019000000-35706f03cc1e8e27a4d9	2016-06-20	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxycelecoxib 40V, Positive-QTOF	splash10-014j-2195000000-cbb3525c9f48b9b78c61	2016-06-20	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxycelecoxib 10V, Negative-QTOF	splash10-0002-0009000000-4e2b2f45a804b673392d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxycelecoxib 20V, Negative-QTOF	splash10-016s-1019000000-c1f5f514fa613d4f4df7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxycelecoxib 40V, Negative-QTOF	splash10-004i-9012000000-0fdfa368188026f491e1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxycelecoxib 10V, Positive-QTOF	splash10-0002-0009000000-2cca6189ad9818927ffd	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxycelecoxib 20V, Positive-QTOF	splash10-0002-0009000000-64b8142194a011996565	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxycelecoxib 40V, Positive-QTOF	splash10-0ge9-0049000000-3b6aa050f18b1c799a12	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxycelecoxib 10V, Negative-QTOF	splash10-0002-1009000000-eb5f4ee5947cfedea62a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxycelecoxib 20V, Negative-QTOF	splash10-014j-4009000000-918311500994c904fd1c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxycelecoxib 40V, Negative-QTOF	splash10-00ou-9004000000-73d51e91d09b45542ee6	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

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	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8084428

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9908776

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Paulson SK, Hribar JD, Liu NW, Hajdu E, Bible RH Jr, Piergies A, Karim A: Metabolism and excretion of [(14)C]celecoxib in healthy male volunteers. Drug Metab Dispos. 2000 Mar;28(3):308-14. [PubMed:10681375 ]

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

References

Sigthorsson G, Simpson RJ, Walley M, Anthony A, Foster R, Hotz-Behoftsitz C, Palizban A, Pombo J, Watts J, Morham SG, Bjarnason I: COX-1 and 2, intestinal integrity, and pathogenesis of nonsteroidal anti-inflammatory drug enteropathy in mice. Gastroenterology. 2002 Jun;122(7):1913-23. [PubMed:12055598 ]
Scheiman JM: Outcomes studies of the gastrointestinal safety of cyclooxygenase-2 inhibitors. Cleve Clin J Med. 2002;69 Suppl 1:SI40-6. [PubMed:12086292 ]
Reddy BS, Rao CV: Novel approaches for colon cancer prevention by cyclooxygenase-2 inhibitors. J Environ Pathol Toxicol Oncol. 2002;21(2):155-64. [PubMed:12086402 ]
Ahmad SR, Kortepeter C, Brinker A, Chen M, Beitz J: Renal failure associated with the use of celecoxib and rofecoxib. Drug Saf. 2002;25(7):537-44. [PubMed:12093311 ]
Lu S, Zhang X, Badawi AF, El-Sohemy A, Archer MC: Cyclooxygenase-2 inhibitor celecoxib inhibits promotion of mammary tumorigenesis in rats fed a high fat diet rich in n-6 polyunsaturated fatty acids. Cancer Lett. 2002 Oct 8;184(1):7-12. [PubMed:12104042 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

2. 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

3. 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

Davies NM, McLachlan AJ, Day RO, Williams KM: Clinical pharmacokinetics and pharmacodynamics of celecoxib: a selective cyclo-oxygenase-2 inhibitor. Clin Pharmacokinet. 2000 Mar;38(3):225-42. [PubMed:10749518 ]
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 ]
Mo SL, Zhou ZW, Yang LP, Wei MQ, Zhou SF: New insights into the structural features and functional relevance of human cytochrome P450 2C9. Part I. Curr Drug Metab. 2009 Dec;10(10):1075-126. [PubMed:20167001 ]
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 ]
Lin Y, Lu P, Tang C, Mei Q, Sandig G, Rodrigues AD, Rushmore TH, Shou M: Substrate inhibition kinetics for cytochrome P450-catalyzed reactions. Drug Metab Dispos. 2001 Apr;29(4 Pt 1):368-74. [PubMed:11259318 ]

Enzyme Details

4. 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

References

Kulp SK, Yang YT, Hung CC, Chen KF, Lai JP, Tseng PH, Fowble JW, Ward PJ, Chen CS: 3-phosphoinositide-dependent protein kinase-1/Akt signaling represents a major cyclooxygenase-2-independent target for celecoxib in prostate cancer cells. Cancer Res. 2004 Feb 15;64(4):1444-51. [PubMed:14973075 ]
Zhu J, Huang JW, Tseng PH, Yang YT, Fowble J, Shiau CW, Shaw YJ, Kulp SK, Chen CS: From the cyclooxygenase-2 inhibitor celecoxib to a novel class of 3-phosphoinositide-dependent protein kinase-1 inhibitors. Cancer Res. 2004 Jun 15;64(12):4309-18. [PubMed:15205346 ]
Tong Z, Wu X, Ovcharenko D, Zhu J, Chen CS, Kehrer JP: Neutrophil gelatinase-associated lipocalin as a survival factor. Biochem J. 2005 Oct 15;391(Pt 2):441-8. [PubMed:16060857 ]
Li J, Zhu J, Melvin WS, Bekaii-Saab TS, Chen CS, Muscarella P: A structurally optimized celecoxib derivative inhibits human pancreatic cancer cell growth. J Gastrointest Surg. 2006 Feb;10(2):207-14. [PubMed:16455452 ]
Tseng PH, Wang YC, Weng SC, Weng JR, Chen CS, Brueggemeier RW, Shapiro CL, Chen CY, Dunn SE, Pollak M, Chen CS: Overcoming trastuzumab resistance in HER2-overexpressing breast cancer cells by using a novel celecoxib-derived phosphoinositide-dependent kinase-1 inhibitor. Mol Pharmacol. 2006 Nov;70(5):1534-41. Epub 2006 Aug 3. [PubMed:16887935 ]

Enzyme Details

5. 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

References

Werner U, Werner D, Rau T, Fromm MF, Hinz B, Brune K: Celecoxib inhibits metabolism of cytochrome P450 2D6 substrate metoprolol in humans. Clin Pharmacol Ther. 2003 Aug;74(2):130-7. [PubMed:12891223 ]
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

6. 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

Rodrigues AD: Impact of CYP2C9 genotype on pharmacokinetics: are all cyclooxygenase inhibitors the same? Drug Metab Dispos. 2005 Nov;33(11):1567-75. Epub 2005 Aug 23. [PubMed:16118328 ]
Martinez C, Blanco G, Garcia-Martin E, Agundez JA: [Clinical pharmacogenomics for CYP2C8 and CYP2C9: general concepts and application to the use of NSAIDs]. Farm Hosp. 2006 Jul-Aug;30(4):240-8. [PubMed:17022718 ]

Transporters

Enzyme Details

1. 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

Reid G, Wielinga P, Zelcer N, van der Heijden I, Kuil A, de Haas M, Wijnholds J, Borst P: The human multidrug resistance protein MRP4 functions as a prostaglandin efflux transporter and is inhibited by nonsteroidal antiinflammatory drugs. Proc Natl Acad Sci U S A. 2003 Aug 5;100(16):9244-9. Epub 2003 Jun 30. [PubMed:12835412 ]

Showing metabocard for Hydroxycelecoxib (HMDB0013995)

MOL for HMDB0013995 (Hydroxycelecoxib)

3D MOL for HMDB0013995 (Hydroxycelecoxib)

3D SDF for HMDB0013995 (Hydroxycelecoxib)

3D-SDF for HMDB0013995 (Hydroxycelecoxib)

PDB for HMDB0013995 (Hydroxycelecoxib)

3D PDB for HMDB0013995 (Hydroxycelecoxib)

SMILES for HMDB0013995 (Hydroxycelecoxib)

INCHI for HMDB0013995 (Hydroxycelecoxib)

Structure for HMDB0013995 (Hydroxycelecoxib)

3D Structure for HMDB0013995 (Hydroxycelecoxib)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

References

References

Transporters

References