NP-MRD: Showing NP-Card for ketoprofen (NP0163333)

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Record Information

Version

2.0

Created at

2022-09-02 21:56:04 UTC

Updated at

2022-09-02 21:56:04 UTC

NP-MRD ID

NP0163333

Secondary Accession Numbers

None

Natural Product Identification

Common Name

ketoprofen

Description

Ketoprofen, also known as orudis or alrheumum, belongs to the class of organic compounds known as benzophenones. These are organic compounds containing a ketone attached to two phenyl groups. Ketoprofen is a drug which is used for symptomatic treatment of acute and chronic rheumatoid arthritis, osteoarthritis, ankylosing spondylitis, primary dysmenorrhea and mild to moderate pain associated with musculotendinous trauma (sprains and strains), postoperative (including dental surgery) or postpartum pain. Ketoprofen is an extremely weak basic (essentially neutral) compound (based on its pKa). Ketoprofen exists in all living organisms, ranging from bacteria to humans. In humans, ketoprofen is involved in ketoprofen action pathway. ketoprofen is found in Homo sapiens. ketoprofen was first documented in 1986 (PMID: 3526298). An oxo monocarboxylic acid that consists of propionic acid substituted by a 3-benzoylphenyl group at position 2 (PMID: 16274258) (PMID: 11452775) (PMID: 12772856) (PMID: 18969772).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 34  0  0  0  0  0  0  0  0999 V2000
   -3.9618   -0.1027   -1.0927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5870    0.0119    0.3774 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5804    1.4496    0.7536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5147    2.0307    1.1210 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7249    2.2256    0.7240 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2106   -0.5307    0.5147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9435   -1.5977    1.3615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6513   -2.0722    1.4599 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3970   -1.5040    0.7266 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1435   -0.4434   -0.1176 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1803    0.1914   -0.9134 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7925    0.7484   -1.9966 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5770    0.2450   -0.5927 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5108    0.3575   -1.6273 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8706    0.4210   -1.4063 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3624    0.3745   -0.1310 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4494    0.2629    0.9115 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0924    0.2002    0.6813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1669   -0.0018   -0.1837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9614    0.3837   -1.2223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9957   -1.1674   -1.3991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2062    0.4256   -1.6851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2944   -0.5417    1.0204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8851    2.9776    0.0822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7671   -2.0310    1.9267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4311   -2.9134    2.1253 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4111   -1.9053    0.8228 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1339    0.3950   -2.6335 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5871    0.5084   -2.2207 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4274    0.4248    0.0300 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8657    0.2286    1.9046 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4328    0.1188    1.5278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3520    0.8299   -0.8493 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  5  1  0
  3  4  2  0
  2  6  1  0
  6 19  2  0
 19 10  1  0
 10  9  2  0
  9  8  1  0
  8  7  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
  7  6  1  0
 18 13  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  1
  5 24  1  0
 19 33  1  0
  9 27  1  0
  8 26  1  0
  7 25  1  0
 14 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
M  END

1009
  Mrv0541 02231215102D          

 19 20  0  0  1  0            999 V2000
    1.6500   -2.4256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.6995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.4256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.1880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.7755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.0495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.4620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.1880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.7755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.0495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.7755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.2870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.0130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.6995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    2.5246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.2870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    2.9371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    1.6995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    2.5246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 13  1  0  0  0  0
  2 12  2  0  0  0  0
  3 13  2  0  0  0  0
  4  5  1  0  0  0  0
  4  9  1  0  0  0  0
  4 13  1  0  0  0  0
  5  6  2  0  0  0  0
  5  8  1  0  0  0  0
  6  7  1  0  0  0  0
  7 10  2  0  0  0  0
  7 12  1  0  0  0  0
  8 11  2  0  0  0  0
 10 11  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 15 17  1  0  0  0  0
 16 18  2  0  0  0  0
 17 19  2  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0163333

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C(O)=O)C1=CC(=CC=C1)C(=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O3/c1-11(16(18)19)13-8-5-9-14(10-13)15(17)12-6-3-2-4-7-12/h2-11H,1H3,(H,18,19)

> <INCHI_KEY>
DKYWVDODHFEZIM-UHFFFAOYSA-N

> <FORMULA>
C16H14O3

> <MOLECULAR_WEIGHT>
254.2806

> <EXACT_MASS>
254.094294314

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
26.56281844636002

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(3-benzoylphenyl)propanoic acid

> <ALOGPS_LOGP>
3.29

> <JCHEM_LOGP>
3.613333421

> <ALOGPS_LOGS>
-4.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.882608970976492

> <JCHEM_PKA_STRONGEST_BASIC>
-7.457434189163898

> <JCHEM_POLAR_SURFACE_AREA>
54.37

> <JCHEM_REFRACTIVITY>
72.51560000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.13e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ketoprofen

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1009                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       3.080  -4.528   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       5.748   3.172   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       5.748  -4.528   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       4.414  -2.218   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.748  -1.448   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.748   0.092   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.081   0.862   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.081  -2.218   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.080  -1.448   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.415   0.092   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.415  -1.448   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.081   2.402   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.414  -3.758   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.415   3.172   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.415   4.713   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.748   2.402   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.748   5.483   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.082   3.172   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.082   4.713   0.000  0.00  0.00           C+0
CONECT    1   13                                                            
CONECT    2   12                                                            
CONECT    3   13                                                            
CONECT    4    5    9   13                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6   10   12                                                  
CONECT    8    5   11                                                       
CONECT    9    4                                                            
CONECT   10    7   11                                                       
CONECT   11    8   10                                                       
CONECT   12    2    7   14                                                  
CONECT   13    1    3    4                                                  
CONECT   14   12   15   16                                                  
CONECT   15   14   17                                                       
CONECT   16   14   18                                                       
CONECT   17   15   19                                                       
CONECT   18   16   19                                                       
CONECT   19   17   18                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

View in JSmol

Synonyms

Value	Source
2-(3-Benzoylphenyl)propionic acid	ChEBI
3-Benzoyl-alpha-methylbenzeneacetic acid	ChEBI
3-Benzoylhydratropic acid	ChEBI
L'acide (benzoyl-3-phenyl)-2-propionique	ChEBI
m-Benzoylhydratropic acid	ChEBI
Orudis	ChEBI
2-(3-Benzoylphenyl)propionate	Generator
3-Benzoyl-a-methylbenzeneacetate	Generator
3-Benzoyl-a-methylbenzeneacetic acid	Generator
3-Benzoyl-alpha-methylbenzeneacetate	Generator
3-Benzoyl-α-methylbenzeneacetate	Generator
3-Benzoyl-α-methylbenzeneacetic acid	Generator
3-Benzoylhydratropate	Generator
m-Benzoylhydratropate	Generator
Alrheumum	HMDB
Profenid	HMDB
Benzoylhydratropic acid	HMDB
Alrheumat	HMDB

Chemical Formula

C₁₆H₁₄O₃

Average Mass

254.2806 Da

Monoisotopic Mass

254.09429 Da

IUPAC Name

2-(3-benzoylphenyl)propanoic acid

Traditional Name

ketoprofen

CAS Registry Number

Not Available

SMILES

CC(C(O)=O)C1=CC(=CC=C1)C(=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C16H14O3/c1-11(16(18)19)13-8-5-9-14(10-13)15(17)12-6-3-2-4-7-12/h2-11H,1H3,(H,18,19)

InChI Key

DKYWVDODHFEZIM-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Homo sapiens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzophenones. These are organic compounds containing a ketone attached to two phenyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzophenones

Direct Parent

Benzophenones

Alternative Parents

Substituents

Benzophenone
Aryl-phenylketone
Diphenylmethane
2-phenylpropanoic-acid
Benzoyl
Aryl ketone
Ketone
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

benzophenones (CHEBI:6128 )
oxo monocarboxylic acid (CHEBI:6128 )

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	3.29	ALOGPS
logP	3.61	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	3.88	ChemAxon
pKa (Strongest Basic)	-7.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	72.52 m³·mol⁻¹	ChemAxon
Polarizability	26.56 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0015144

DrugBank ID

DB01009

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3693

KEGG Compound ID

C01716

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ketoprofen

METLIN ID

Not Available

PubChem Compound

3825

PDB ID

Not Available

ChEBI ID

6128

Good Scents ID

Not Available

References

General References

Kantor TG: Ketoprofen: a review of its pharmacologic and clinical properties. Pharmacotherapy. 1986 May-Jun;6(3):93-103. doi: 10.1002/j.1875-9114.1986.tb03459.x. [PubMed:3526298 ]
Mazieres B: Topical ketoprofen patch. Drugs R D. 2005;6(6):337-44. doi: 10.2165/00126839-200506060-00003. [PubMed:16274258 ]
Osipova NA, Beresnev VA, Vetsheva MS, Dolgopolova TV: [Ketoprofen (ketonal): a drug for preventing and treating postoperative pain]. Anesteziol Reanimatol. 1999 Nov-Dec;(6):71-4. [PubMed:11452775 ]
Ting ST, Earley B, Hughes JM, Crowe MA: Effect of ketoprofen, lidocaine local anesthesia, and combined xylazine and lidocaine caudal epidural anesthesia during castration of beef cattle on stress responses, immunity, growth, and behavior. J Anim Sci. 2003 May;81(5):1281-93. doi: 10.2527/2003.8151281x. [PubMed:12772856 ]
Fan Y, Feng YQ, Da SL, Wang ZH: In-tube solid phase microextraction using a beta-cyclodextrin coated capillary coupled to high performance liquid chromatography for determination of non-steroidal anti-inflammatory drugs in urine samples. Talanta. 2005 Jan 15;65(1):111-7. doi: 10.1016/j.talanta.2004.05.040. [PubMed:18969772 ]
LOTUS database [Link]

Showing NP-Card for ketoprofen (NP0163333)

MOL for NP0163333 (ketoprofen)

3D MOL for NP0163333 (ketoprofen)

3D SDF for NP0163333 (ketoprofen)

3D-SDF for NP0163333 (ketoprofen)

PDB for NP0163333 (ketoprofen)

3D PDB for NP0163333 (ketoprofen)

SMILES for NP0163333 (ketoprofen)

INCHI for NP0163333 (ketoprofen)

Structure for NP0163333 (ketoprofen)

3D Structure for NP0163333 (ketoprofen)