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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 21:01:27 UTC

Update Date

2021-09-26 23:16:25 UTC

HMDB ID

HMDB0259082

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Ticrynafen

Description

Tienilic acid, also known as ticrynafen or acide tienilique, 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. Tienilic acid is a drug which is used for the treatment of hypertension. Based on a literature review a significant number of articles have been published on Tienilic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). Ticrynafen is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Ticrynafen is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

4831
  Mrv0541 02231217572D          

 20 21  0  0  0  0            999 V2000
    1.6500    1.2035    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.4465    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.8797    3.2615    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -1.2715    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    2.4410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -2.9215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -2.9215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    1.2035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -0.4465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.7910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.7910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    2.0285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.0340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.0340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    2.4410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5471    2.1054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.6840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0992    2.7186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6867    3.4330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.5090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 10  1  0  0  0  0
  2 13  1  0  0  0  0
  3 15  1  0  0  0  0
  3 19  1  0  0  0  0
  4  9  1  0  0  0  0
  4 17  1  0  0  0  0
  5 12  2  0  0  0  0
  6 20  1  0  0  0  0
  7 20  2  0  0  0  0
  8 10  2  0  0  0  0
  8 11  1  0  0  0  0
  8 12  1  0  0  0  0
  9 13  2  0  0  0  0
  9 14  1  0  0  0  0
 10 13  1  0  0  0  0
 11 14  2  0  0  0  0
 12 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 18  1  0  0  0  0
 17 20  1  0  0  0  0
 18 19  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0259082

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)COC1=C(Cl)C(Cl)=C(C=C1)C(=O)C1=CC=CS1

> <INCHI_IDENTIFIER>
InChI=1S/C13H8Cl2O4S/c14-11-7(13(18)9-2-1-5-20-9)3-4-8(12(11)15)19-6-10(16)17/h1-5H,6H2,(H,16,17)

> <INCHI_KEY>
AGHANLSBXUWXTB-UHFFFAOYSA-N

> <FORMULA>
C13H8Cl2O4S

> <MOLECULAR_WEIGHT>
331.171

> <EXACT_MASS>
329.952034848

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
30.445744499098673

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[2,3-dichloro-4-(thiophene-2-carbonyl)phenoxy]acetic acid

> <ALOGPS_LOGP>
4.09

> <JCHEM_LOGP>
3.8738816216666665

> <ALOGPS_LOGS>
-5.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.2171626547226753

> <JCHEM_PKA_STRONGEST_BASIC>
-4.964762193339346

> <JCHEM_POLAR_SURFACE_AREA>
63.6

> <JCHEM_REFRACTIVITY>
75.6808

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.54e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ticrynafen

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 4831                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0       3.080   2.247   0.000  0.00  0.00          Cl+0
HETATM    2 Cl   UNK     0       3.080  -0.833   0.000  0.00  0.00          Cl+0
HETATM    3  S   UNK     0       7.242   6.088   0.000  0.00  0.00           S+0
HETATM    4  O   UNK     0       5.747  -2.373   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       4.414   4.557   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       8.415  -5.453   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       5.747  -5.453   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.747   2.247   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.747  -0.833   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.414   1.477   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.081   1.477   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.747   3.787   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.414  -0.063   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.081  -0.063   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.081   4.557   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.488   3.930   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.081  -3.143   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.519   5.075   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.749   6.408   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.081  -4.683   0.000  0.00  0.00           C+0
CONECT    1   10                                                            
CONECT    2   13                                                            
CONECT    3   15   19                                                       
CONECT    4    9   17                                                       
CONECT    5   12                                                            
CONECT    6   20                                                            
CONECT    7   20                                                            
CONECT    8   10   11   12                                                  
CONECT    9    4   13   14                                                  
CONECT   10    1    8   13                                                  
CONECT   11    8   14                                                       
CONECT   12    5    8   15                                                  
CONECT   13    2    9   10                                                  
CONECT   14    9   11                                                       
CONECT   15    3   12   16                                                  
CONECT   16   15   18                                                       
CONECT   17    4   20                                                       
CONECT   18   16   19                                                       
CONECT   19    3   18                                                       
CONECT   20    6    7   17                                                  
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0259082
HETATM    1  O1  UNL     1       4.889   2.536   0.146  1.00  0.00           O  
HETATM    2  C1  UNL     1       5.070   1.338   0.485  1.00  0.00           C  
HETATM    3  O2  UNL     1       6.327   0.980   0.928  1.00  0.00           O  
HETATM    4  C2  UNL     1       3.975   0.323   0.418  1.00  0.00           C  
HETATM    5  O3  UNL     1       2.824   0.980  -0.064  1.00  0.00           O  
HETATM    6  C3  UNL     1       1.615   0.384  -0.266  1.00  0.00           C  
HETATM    7  C4  UNL     1       1.431  -0.948  -0.005  1.00  0.00           C  
HETATM    8  C5  UNL     1       0.184  -1.528  -0.221  1.00  0.00           C  
HETATM    9  C6  UNL     1      -0.884  -0.820  -0.689  1.00  0.00           C  
HETATM   10  C7  UNL     1      -2.195  -1.380  -0.926  1.00  0.00           C  
HETATM   11  O4  UNL     1      -2.345  -2.349  -1.701  1.00  0.00           O  
HETATM   12  C8  UNL     1      -3.419  -0.854  -0.281  1.00  0.00           C  
HETATM   13  C9  UNL     1      -3.505  -0.183   0.912  1.00  0.00           C  
HETATM   14  C10 UNL     1      -4.729   0.209   1.311  1.00  0.00           C  
HETATM   15  C11 UNL     1      -5.781  -0.096   0.492  1.00  0.00           C  
HETATM   16  S1  UNL     1      -5.040  -0.915  -0.803  1.00  0.00           S  
HETATM   17  C12 UNL     1      -0.675   0.530  -0.949  1.00  0.00           C  
HETATM   18 CL1  UNL     1      -1.972   1.525  -1.553  1.00  0.00          CL  
HETATM   19  C13 UNL     1       0.547   1.131  -0.744  1.00  0.00           C  
HETATM   20 CL2  UNL     1       0.760   2.829  -1.085  1.00  0.00          CL  
HETATM   21  H1  UNL     1       6.820   0.147   0.716  1.00  0.00           H  
HETATM   22  H2  UNL     1       3.821  -0.127   1.428  1.00  0.00           H  
HETATM   23  H3  UNL     1       4.311  -0.503  -0.245  1.00  0.00           H  
HETATM   24  H4  UNL     1       2.242  -1.559   0.370  1.00  0.00           H  
HETATM   25  H5  UNL     1       0.060  -2.578  -0.009  1.00  0.00           H  
HETATM   26  H6  UNL     1      -2.581   0.012   1.502  1.00  0.00           H  
HETATM   27  H7  UNL     1      -4.906   0.761   2.265  1.00  0.00           H  
HETATM   28  H8  UNL     1      -6.842   0.155   0.674  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   21
CONECT    4    5   22   23
CONECT    5    6
CONECT    6    7    7   19
CONECT    7    8   24
CONECT    8    9    9   25
CONECT    9   10   17
CONECT   10   11   11   12
CONECT   12   13   13   16
CONECT   13   14   26
CONECT   14   15   15   27
CONECT   15   16   28
CONECT   17   18   19   19
CONECT   19   20
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(2,3-Dichloro-4-(2-thenoyl)phenoxy)acetic acid	ChEBI
(2,3-Dichloro-4-(2-thiophenecarbonyl)phenoxy)acetic acid	ChEBI
4-(2-Theonyl)-2,3-dichlorphenoxyessigsaeure	ChEBI
4-(2-Thienylketo)-2,3-dichlorophenoxyacetic acid	ChEBI
Acide tienilique	ChEBI
Acido tienilico	ChEBI
Acidum tienilicum	ChEBI
Thienylic acid	ChEBI
Ticrynafen	ChEBI
Selacryn	Kegg
(2,3-Dichloro-4-(2-thenoyl)phenoxy)acetate	Generator
(2,3-Dichloro-4-(2-thiophenecarbonyl)phenoxy)acetate	Generator
4-(2-Thienylketo)-2,3-dichlorophenoxyacetate	Generator
Thienylate	Generator
Tienilate	Generator
Acid, thienylic	MeSH
Acid, tienilic	MeSH
Tienilic acid	MeSH

Chemical Formula

C₁₃H₈Cl₂O₄S

Average Molecular Weight

331.171

Monoisotopic Molecular Weight

329.952034848

IUPAC Name

2-[2,3-dichloro-4-(thiophene-2-carbonyl)phenoxy]acetic acid

Traditional Name

ticrynafen

CAS Registry Number

Not Available

SMILES

OC(=O)COC1=C(Cl)C(Cl)=C(C=C1)C(=O)C1=CC=CS1

InChI Identifier

InChI=1S/C13H8Cl2O4S/c14-11-7(13(18)9-2-1-5-20-9)3-4-8(12(11)15)19-6-10(16)17/h1-5H,6H2,(H,16,17)

InChI Key

AGHANLSBXUWXTB-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
Chlorophenoxyacetate
Phenoxyacetate
Phenoxy compound
1,2-dichlorobenzene
Benzoyl
Phenol ether
Thiophene carboxylic acid or derivatives
Alkyl aryl ether
Halobenzene
Chlorobenzene
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Benzenoid
Heteroaromatic compound
Vinylogous halide
Thiophene
Organoheterocyclic compound
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Ether
Organohalogen compound
Hydrocarbon derivative
Organic oxide
Organochloride
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

aromatic ether (CHEBI:9590 )
monocarboxylic acid (CHEBI:9590 )
thiophenes (CHEBI:9590 )
dichlorobenzene (CHEBI:9590 )
aromatic ketone (CHEBI:9590 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

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	4.09	ALOGPS
logP	3.87	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	3.22	ChemAxon
pKa (Strongest Basic)	-5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	75.68 m³·mol⁻¹	ChemAxon
Polarizability	30.45 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	165.633	30932474
DeepCCS	[M-H]-	163.275	30932474
DeepCCS	[M-2H]-	196.862	30932474
DeepCCS	[M+Na]+	172.089	30932474
AllCCS	[M+H]+	166.6	32859911
AllCCS	[M+H-H2O]+	163.3	32859911
AllCCS	[M+NH4]+	169.7	32859911
AllCCS	[M+Na]+	170.6	32859911
AllCCS	[M-H]-	162.0	32859911
AllCCS	[M+Na-2H]-	161.6	32859911
AllCCS	[M+HCOO]-	161.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ticrynafen	OC(=O)COC1=C(Cl)C(Cl)=C(C=C1)C(=O)C1=CC=CS1	4299.3	Standard polar	33892256
Ticrynafen	OC(=O)COC1=C(Cl)C(Cl)=C(C=C1)C(=O)C1=CC=CS1	2524.9	Standard non polar	33892256
Ticrynafen	OC(=O)COC1=C(Cl)C(Cl)=C(C=C1)C(=O)C1=CC=CS1	2759.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Ticrynafen GC-MS (Non-derivatized) - 70eV, Positive	splash10-03di-6930000000-f63fca8a05df421cff0e	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ticrynafen GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ticrynafen GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ticrynafen GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	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 - Ticrynafen 10V, Positive-QTOF	splash10-001i-0009000000-446d66363ddb92cb2d50	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ticrynafen 20V, Positive-QTOF	splash10-01q9-0009000000-a87109fb3d8db700aa54	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ticrynafen 40V, Positive-QTOF	splash10-0btc-4292000000-042781873dcaa9ab3909	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ticrynafen 10V, Negative-QTOF	splash10-004i-0009000000-c55afae4bf1556baba73	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ticrynafen 20V, Negative-QTOF	splash10-004i-0039000000-3b7e8adf4b687fe0ead5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ticrynafen 40V, Negative-QTOF	splash10-0a4i-9010000000-00db6c72a610b41c8723	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB04831

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

35204

KEGG Compound ID

C11702

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Tienilic_acid

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

9590

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Ticrynafen (HMDB0259082)

MOL for HMDB0259082 (Ticrynafen)

3D MOL for HMDB0259082 (Ticrynafen)

3D SDF for HMDB0259082 (Ticrynafen)

3D-SDF for HMDB0259082 (Ticrynafen)

PDB for HMDB0259082 (Ticrynafen)

3D PDB for HMDB0259082 (Ticrynafen)

SMILES for HMDB0259082 (Ticrynafen)

INCHI for HMDB0259082 (Ticrynafen)

Structure for HMDB0259082 (Ticrynafen)

3D Structure for HMDB0259082 (Ticrynafen)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra