Bovine Metabolome Database: Showing metabocard for Valdecoxib (BMDB0005033)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:14:51 UTC

Update Date

2020-04-22 15:15:11 UTC

BMDB ID

BMDB0005033

Secondary Accession Numbers

BMDB05033

Metabolite Identification

Common Name

Valdecoxib

Description

Valdecoxib, also known as bextra or kudeq, belongs to the class of organic compounds known as benzenesulfonamides. These are organic compounds containing a sulfonamide group that is S-linked to a benzene ring. Valdecoxib is a drug which is used for the treatment of osteoarthritis and dysmenorrhoea. Valdecoxib is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
4-(5-Methyl-3-phenyl-4-isoxazolyl)benzenesulfonamide	ChEBI
Bextra	ChEBI
p-(5-Methyl-3-phenyl-4-isoxazolyl)benzenesulfonamide	ChEBI
Valdecoxibum	ChEBI
4-(5-Methyl-3-phenyl-4-isoxazolyl)benzenesulphonamide	Generator
p-(5-Methyl-3-phenyl-4-isoxazolyl)benzenesulphonamide	Generator
COX	HMDB
Kudeq	HMDB
Valdyn	HMDB
Valecoxib	HMDB
Pfizer brand OF valdecoxib	HMDB

Chemical Formula

C₁₆H₁₄N₂O₃S

Average Molecular Weight

314.359

Monoisotopic Molecular Weight

314.072513014

IUPAC Name

4-(5-methyl-3-phenyl-1,2-oxazol-4-yl)benzene-1-sulfonamide

Traditional Name

valdecoxib

CAS Registry Number

181695-72-7

SMILES

CC1=C(C(=NO1)C1=CC=CC=C1)C1=CC=C(C=C1)S(N)(=O)=O

InChI Identifier

InChI=1S/C16H14N2O3S/c1-11-15(12-7-9-14(10-8-12)22(17,19)20)16(18-21-11)13-5-3-2-4-6-13/h2-10H,1H3,(H2,17,19,20)

InChI Key

LNPDTQAFDNKSHK-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as benzenesulfonamides. These are organic compounds containing a sulfonamide group that is S-linked to a benzene ring.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzenesulfonamides

Direct Parent

Benzenesulfonamides

Alternative Parents

Substituents

Benzenesulfonamide
Benzenesulfonyl group
Organosulfonic acid amide
Azole
Isoxazole
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Heteroaromatic compound
Aminosulfonyl compound
Sulfonyl
Oxacycle
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

sulfonamide (CHEBI:63634 )
isoxazoles (CHEBI:63634 )

Ontology

Status

Expected but not Quantified

Origin

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cell membrane
Membrane

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	160 - 162 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.32	ALOGPS
logP	2.82	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	10.06	ChemAxon
pKa (Strongest Basic)	0.42	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	86.19 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	84.71 m³·mol⁻¹	ChemAxon
Polarizability	31.76 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-01qa-0290000000-adad99d8d7c023e6f63b	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-0089-2930000000-dac70ddadd2ffd150b22	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-014i-0439000000-984ffa23e74fb8949b56	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-014i-0439000000-8928b5e8f850f43f1430	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0089-2930000000-dac70ddadd2ffd150b22	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-001i-0941000000-0931692fec04d3e19f52	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-03di-0689000000-764e252bae3ae694704a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0019000000-596b73746ee066f35968	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0049000000-818c4a70e42df2b88f8a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0pbi-0390000000-13714d8251c6a02a4053	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0009000000-a2f711c3743b82164d6d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0029000000-2ac37e780c7fe646fc3e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9460000000-fb4b9f778483757805ea	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0009000000-fa0317e9dc89d23da23a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0009000000-fa0317e9dc89d23da23a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9611000000-28d2f85d0f3c715b52fa	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0009000000-bba9fedad3067bb6377e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0039000000-4c17bb46a939879efeea	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6r-2960000000-ea456b0a645f35565a29	View in MoNA

Biological Properties

Cellular Locations

Cell membrane
Membrane

Biospecimen Locations

Not Available

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0005033

DrugBank ID

DB00580

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023600

KNApSAcK ID

Not Available

Chemspider ID

106796

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Valdecoxib

METLIN ID

Not Available

PubChem Compound

119607

PDB ID

COX

ChEBI ID

63634

References

Synthesis Reference

Rogers, Roland S.; Talley, John J.; Brown, David L.; Nagarajan, Srinivasan; Carter, Jeffery S.; Weier, Richard M.; Stealey, Michael A.; Collins, Paul W.; Seibert, Karen; et al. Substituted isoxazoles for the treatment of inflammation. PCT Int. Appl. (1996), 171 pp. CODEN: PIXXD2 WO 9625405 A1 19960822 CAN 125:247800 AN 1996:601794

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Valdecoxib (BMDB0005033)

Structure for BMDB0005033 (Valdecoxib)