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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2022-09-09 19:28:31 UTC

Update Date

2022-09-22 18:35:04 UTC

HMDB ID

HMDB0341169

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Ketorolac (tromethamine salt)

Description

ketorolac tromethamine, also known as acular or toradol, belongs to the class of organic compounds known as aryl-phenylketones. These are aromatic compounds containing a ketone substituted by one aryl group, and a phenyl group. ketorolac tromethamine is a drug. ketorolac tromethamine is an extremely weak basic (essentially neutral) compound (based on its pKa). An organoammonium salt resulting from the mixture of equimolar amounts of ketorolac and tromethamine (tris). It is used in the short-term management of post-operative pain, and in eye drops to relieve the ocular itching associated with seasonal allergic conjunctivitis. It has potent non-sedating analgesic and moderate anti-inflammatory effects.

Structure

MOL SDF PDB SMILES InChI


  Mrv1572004051622032D          

 27 28  0  0  0  0            999 V2000
   -0.0611   -0.2401    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0611    0.5959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8421   -0.4959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7243    0.8820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8612    0.8382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3326    0.1650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1710   -1.2522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0577    1.6686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7518   -0.4998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2276    0.2036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6677   -1.9307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0075   -1.3606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5020    2.4038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9166    1.7818    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -2.4980   -0.6997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3364   -2.1169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1556   -2.2124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3301   -0.7776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6460   -1.5514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7889   -1.4029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5032   -1.8154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2174   -1.4029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9317   -1.8154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6460   -1.4029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2174   -0.5783    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    2.4384   -2.1980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2370   -2.4038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  9  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  2  2  0  0  0  0
  6  3  2  0  0  0  0
  7  3  1  0  0  0  0
  4  8  1  0  0  0  0
 10  4  1  0  0  0  0
  6  5  1  0  0  0  0
 11  7  2  0  0  0  0
 12  7  1  0  0  0  0
 13  8  2  0  0  0  0
 14  8  1  0  0  0  0
 10  9  1  0  0  0  0
 15 12  2  0  0  0  0
 16 12  1  0  0  0  0
 18 15  1  0  0  0  0
 17 16  2  0  0  0  0
 19 17  1  0  0  0  0
 19 18  2  0  0  0  0
 21 20  1  0  0  0  0
 22 21  1  0  0  0  0
 23 22  1  0  0  0  0
 24 23  1  0  0  0  0
 22 25  1  0  0  0  0
 22 26  1  0  0  0  0
 26 27  1  0  0  0  0
M  CHG  2  14  -1  25   1
M  END


  Mrv1572004051622032D          

 27 28  0  0  0  0            999 V2000
   -0.0611   -0.2401    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0611    0.5959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8421   -0.4959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7243    0.8820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8612    0.8382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3326    0.1650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1710   -1.2522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0577    1.6686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7518   -0.4998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2276    0.2036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6677   -1.9307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0075   -1.3606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5020    2.4038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9166    1.7818    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -2.4980   -0.6997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3364   -2.1169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1556   -2.2124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3301   -0.7776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6460   -1.5514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7889   -1.4029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5032   -1.8154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2174   -1.4029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9317   -1.8154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6460   -1.4029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2174   -0.5783    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    2.4384   -2.1980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2370   -2.4038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  9  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  2  2  0  0  0  0
  6  3  2  0  0  0  0
  7  3  1  0  0  0  0
  4  8  1  0  0  0  0
 10  4  1  0  0  0  0
  6  5  1  0  0  0  0
 11  7  2  0  0  0  0
 12  7  1  0  0  0  0
 13  8  2  0  0  0  0
 14  8  1  0  0  0  0
 10  9  1  0  0  0  0
 15 12  2  0  0  0  0
 16 12  1  0  0  0  0
 18 15  1  0  0  0  0
 17 16  2  0  0  0  0
 19 17  1  0  0  0  0
 19 18  2  0  0  0  0
 21 20  1  0  0  0  0
 22 21  1  0  0  0  0
 23 22  1  0  0  0  0
 24 23  1  0  0  0  0
 22 25  1  0  0  0  0
 22 26  1  0  0  0  0
 26 27  1  0  0  0  0
M  CHG  2  14  -1  25   1
M  END
> <DATABASE_ID>
HMDB0341169

> <DATABASE_NAME>
hmdb

> <SMILES>
[NH3+]C(CO)(CO)CO.[O-]C(=O)C1CCN2C1=CC=C2C(=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H13NO3.C4H11NO3/c17-14(10-4-2-1-3-5-10)13-7-6-12-11(15(18)19)8-9-16(12)13;5-4(1-6,2-7)3-8/h1-7,11H,8-9H2,(H,18,19);6-8H,1-3,5H2

> <INCHI_KEY>
BWHLPLXXIDYSNW-UHFFFAOYSA-N

> <FORMULA>
C19H24N2O6

> <MOLECULAR_WEIGHT>
376.409

> <EXACT_MASS>
376.163436501

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
26.42084801037099

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,3-dihydroxy-2-(hydroxymethyl)propan-2-aminium 5-benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylate

> <ALOGPS_LOGP>
-0.92

> <JCHEM_LOGP>
2.283362963666667

> <ALOGPS_LOGS>
-2.64

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.835179403731399

> <JCHEM_PKA_STRONGEST_BASIC>
-7.792088517190788

> <JCHEM_POLAR_SURFACE_AREA>
62.129999999999995

> <JCHEM_REFRACTIVITY>
81.03160000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.61e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
htris 5-benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-APR-16         0                                  
HETATM    1  N   UNK     0      -0.114  -0.448   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      -0.114   1.112   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.572  -0.926   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.352   1.646   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.608   1.565   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.487   0.308   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.186  -2.337   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.974   3.115   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.403  -0.933   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.292   0.380   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.246  -3.604   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -3.747  -2.540   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.937   4.487   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       3.578   3.326   0.000  0.00  0.00           O-1
HETATM   15  C   UNK     0      -4.663  -1.306   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.361  -3.952   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.890  -4.130   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -6.216  -1.452   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -6.806  -2.896   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.473  -2.619   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.806  -3.389   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.139  -2.619   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.473  -3.389   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       6.806  -2.619   0.000  0.00  0.00           O+0
HETATM   25  N   UNK     0       4.139  -1.079   0.000  0.00  0.00           N+1
HETATM   26  C   UNK     0       4.552  -4.103   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       6.042  -4.487   0.000  0.00  0.00           O+0
CONECT    1    2    3    9                                                  
CONECT    2    1    4    5                                                  
CONECT    3    1    6    7                                                  
CONECT    4    2    8   10                                                  
CONECT    5    2    6                                                       
CONECT    6    3    5                                                       
CONECT    7    3   11   12                                                  
CONECT    8    4   13   14                                                  
CONECT    9    1   10                                                       
CONECT   10    4    9                                                       
CONECT   11    7                                                            
CONECT   12    7   15   16                                                  
CONECT   13    8                                                            
CONECT   14    8                                                            
CONECT   15   12   18                                                       
CONECT   16   12   17                                                       
CONECT   17   16   19                                                       
CONECT   18   15   19                                                       
CONECT   19   17   18                                                       
CONECT   20   21                                                            
CONECT   21   20   22                                                       
CONECT   22   21   23   25   26                                             
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   22                                                            
CONECT   26   22   27                                                       
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   56    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Acular	ChEBI
Acuvail	ChEBI
Dolac	ChEBI
Lixidol	ChEBI
Sprix	ChEBI
Toradol	ChEBI
2-amino-2-(Hydroxymethyl)propane-1,3-diol;5-benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylate	Generator
Ketorolac tromethamine	MeSH
Tromethamine, ketorolac	MeSH

Chemical Formula

C₁₉H₂₄N₂O₆

Average Molecular Weight

376.409

Monoisotopic Molecular Weight

376.163436501

IUPAC Name

1,3-dihydroxy-2-(hydroxymethyl)propan-2-aminium 5-benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylate

Traditional Name

htris 5-benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylate

CAS Registry Number

Not Available

SMILES

[NH3+]C(CO)(CO)CO.[O-]C(=O)C1CCN2C1=CC=C2C(=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C15H13NO3.C4H11NO3/c17-14(10-4-2-1-3-5-10)13-7-6-12-11(15(18)19)8-9-16(12)13;5-4(1-6,2-7)3-8/h1-7,11H,8-9H2,(H,18,19);6-8H,1-3,5H2

InChI Key

BWHLPLXXIDYSNW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aryl-phenylketones. These are aromatic compounds containing a ketone substituted by one aryl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Aryl-phenylketones

Alternative Parents

Substituents

Aryl-phenylketone
Benzoyl
Pyrrolizine
Monocyclic benzene moiety
Substituted pyrrole
Benzenoid
Pyrrole
Heteroaromatic compound
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organoheterocyclic compound
Azacycle
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organonitrogen compound
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Not Available

External Descriptors

organoammonium salt (CHEBI:6130 )

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
logP	-0.92	ALOGPS
logP	2.28	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	3.84	ChemAxon
pKa (Strongest Basic)	-7.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	62.13 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	81.03 m³·mol⁻¹	ChemAxon
Polarizability	26.42 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	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Not Available

Spectra

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	34436864	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	34436864	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DBSALT001045

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ketorolac

METLIN ID

Not Available

PubChem Compound

84003

PDB ID

Not Available

ChEBI ID

6130

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

Neto FC, Raftery D: Expanding Urinary Metabolite Annotation through Integrated Mass Spectral Similarity Networking. Anal Chem. 2021 Sep 7;93(35):12001-12010. doi: 10.1021/acs.analchem.1c02041. Epub 2021 Aug 26. [PubMed:34436864 ]

Showing metabocard for Ketorolac (tromethamine salt) (HMDB0341169)

MOL for HMDB0341169 (Ketorolac (tromethamine salt))

3D MOL for HMDB0341169 (Ketorolac (tromethamine salt))

3D SDF for HMDB0341169 (Ketorolac (tromethamine salt))

3D-SDF for HMDB0341169 (Ketorolac (tromethamine salt))

PDB for HMDB0341169 (Ketorolac (tromethamine salt))

3D PDB for HMDB0341169 (Ketorolac (tromethamine salt))

SMILES for HMDB0341169 (Ketorolac (tromethamine salt))

INCHI for HMDB0341169 (Ketorolac (tromethamine salt))

Structure for HMDB0341169 (Ketorolac (tromethamine salt))

3D Structure for HMDB0341169 (Ketorolac (tromethamine salt))

Predicted Kovats Retention Indices