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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 20:21:57 UTC

Update Date

2021-09-26 23:15:47 UTC

HMDB ID

HMDB0258677

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Tafamidis

Description

Tafamidis, also known as FX-1006 or vyndamax, belongs to the class of organic compounds known as phenyl-1,3-oxazoles. These are aromatic heterocyclic compounds containing a 1,3-oxazole substituted at one or more positions by a phenyl group. Based on a literature review a significant number of articles have been published on Tafamidis. This compound has been identified in human blood as reported by (PMID: 31557052 ). Tafamidis is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Tafamidis 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


  Mrv0541 05031421482D          

 20 22  0  0  0  0            999 V2000
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0574   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0574    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1801    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4699    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7676   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7676    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1801   -1.0164    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.1801    1.8414    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  7  1  1  0  0  0  0
  7  5  2  0  0  0  0
  8  3  2  0  0  0  0
  8  4  1  0  0  0  0
  9  3  1  0  0  0  0
  9  6  2  0  0  0  0
 10  4  2  0  0  0  0
 10  6  1  0  0  0  0
 11  2  1  0  0  0  0
 12  5  1  0  0  0  0
 12 11  2  0  0  0  0
 13  8  1  0  0  0  0
 14  7  1  0  0  0  0
 15  9  1  0  0  0  0
 16 10  1  0  0  0  0
 17 11  1  0  0  0  0
 17 13  2  0  0  0  0
 18 14  2  0  0  0  0
 19 14  1  0  0  0  0
 20 12  1  0  0  0  0
 20 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0258677

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)C1=CC2=C(C=C1)N=C(O2)C1=CC(Cl)=CC(Cl)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H7Cl2NO3/c15-9-3-8(4-10(16)6-9)13-17-11-2-1-7(14(18)19)5-12(11)20-13/h1-6H,(H,18,19)

> <INCHI_KEY>
TXEIIPDJKFWEEC-UHFFFAOYSA-N

> <FORMULA>
C14H7Cl2NO3

> <MOLECULAR_WEIGHT>
308.116

> <EXACT_MASS>
306.980298509

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
29.7419386504683

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(3,5-dichlorophenyl)-1,3-benzoxazole-6-carboxylic acid

> <ALOGPS_LOGP>
3.91

> <JCHEM_LOGP>
4.210307916666666

> <ALOGPS_LOGS>
-3.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.731895088691083

> <JCHEM_PKA_STRONGEST_BASIC>
-0.4052775803497598

> <JCHEM_POLAR_SURFACE_AREA>
63.33

> <JCHEM_REFRACTIVITY>
84.69049999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.23e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tafamidis

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-MAY-14         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15 Cl   UNK     0       0.000   0.000   0.000  0.00  0.00          Cl+0
HETATM   16 Cl   UNK     0       0.000   0.000   0.000  0.00  0.00          Cl+0
HETATM   17  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   18  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    2    7                                                       
CONECT    2    1   11                                                       
CONECT    3    8    9                                                       
CONECT    4    8   10                                                       
CONECT    5    7   12                                                       
CONECT    6    9   10                                                       
CONECT    7    1    5   14                                                  
CONECT    8    3    4   13                                                  
CONECT    9    3    6   15                                                  
CONECT   10    4    6   16                                                  
CONECT   11    2   12   17                                                  
CONECT   12    5   11   20                                                  
CONECT   13    8   17   20                                                  
CONECT   14    7   18   19                                                  
CONECT   15    9                                                            
CONECT   16   10                                                            
CONECT   17   11   13                                                       
CONECT   18   14                                                            
CONECT   19   14                                                            
CONECT   20   12   13                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0304883
HETATM    1  O1  UNL     1       5.941   0.808  -0.231  1.00  0.00           O  
HETATM    2  C1  UNL     1       5.017   0.097   0.226  1.00  0.00           C  
HETATM    3  O2  UNL     1       5.373  -0.996   1.016  1.00  0.00           O  
HETATM    4  C2  UNL     1       3.632   0.410  -0.063  1.00  0.00           C  
HETATM    5  C3  UNL     1       3.350   1.503  -0.850  1.00  0.00           C  
HETATM    6  C4  UNL     1       2.030   1.839  -1.153  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.994   1.076  -0.664  1.00  0.00           C  
HETATM    8  N1  UNL     1      -0.342   1.110  -0.754  1.00  0.00           N  
HETATM    9  C6  UNL     1      -0.875   0.074  -0.048  1.00  0.00           C  
HETATM   10  C7  UNL     1      -2.301  -0.240   0.104  1.00  0.00           C  
HETATM   11  C8  UNL     1      -3.276   0.528  -0.487  1.00  0.00           C  
HETATM   12  C9  UNL     1      -4.630   0.243  -0.352  1.00  0.00           C  
HETATM   13 CL1  UNL     1      -5.824   1.262  -1.132  1.00  0.00          CL  
HETATM   14  C10 UNL     1      -4.987  -0.858   0.408  1.00  0.00           C  
HETATM   15  C11 UNL     1      -4.009  -1.638   1.008  1.00  0.00           C  
HETATM   16 CL2  UNL     1      -4.388  -3.040   1.980  1.00  0.00          CL  
HETATM   17  C12 UNL     1      -2.668  -1.322   0.850  1.00  0.00           C  
HETATM   18  O3  UNL     1       0.125  -0.574   0.459  1.00  0.00           O  
HETATM   19  C13 UNL     1       1.267  -0.028   0.130  1.00  0.00           C  
HETATM   20  C14 UNL     1       2.582  -0.328   0.406  1.00  0.00           C  
HETATM   21  H1  UNL     1       5.097  -1.926   0.715  1.00  0.00           H  
HETATM   22  H2  UNL     1       4.135   2.143  -1.264  1.00  0.00           H  
HETATM   23  H3  UNL     1       1.827   2.701  -1.772  1.00  0.00           H  
HETATM   24  H4  UNL     1      -2.969   1.392  -1.083  1.00  0.00           H  
HETATM   25  H5  UNL     1      -6.026  -1.116   0.539  1.00  0.00           H  
HETATM   26  H6  UNL     1      -1.884  -1.924   1.315  1.00  0.00           H  
HETATM   27  H7  UNL     1       2.810  -1.196   1.032  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   21
CONECT    4    5    5   20
CONECT    5    6   22
CONECT    6    7    7   23
CONECT    7    8   19
CONECT    8    9    9
CONECT    9   10   18
CONECT   10   11   11   17
CONECT   11   12   24
CONECT   12   13   14   14
CONECT   14   15   25
CONECT   15   16   17   17
CONECT   17   26
CONECT   18   19
CONECT   19   20   20
CONECT   20   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-(3,5-Dichlorophenyl)benzoxazole-6-carboxylic acid	ChEBI
FX-1006	ChEBI
Tafamidisum	ChEBI
Vyndamax	Kegg
Vynmac	Kegg
2-(3,5-Dichlorophenyl)benzoxazole-6-carboxylate	Generator
Tafamidis meglumine	MeSH
Vyndaqel	KEGG, MeSH

Chemical Formula

C₁₄H₇Cl₂NO₃

Average Molecular Weight

308.116

Monoisotopic Molecular Weight

306.980298509

IUPAC Name

2-(3,5-dichlorophenyl)-1,3-benzoxazole-6-carboxylic acid

Traditional Name

tafamidis

CAS Registry Number

Not Available

SMILES

OC(=O)C1=CC2=C(C=C1)N=C(O2)C1=CC(Cl)=CC(Cl)=C1

InChI Identifier

InChI=1S/C14H7Cl2NO3/c15-9-3-8(4-10(16)6-9)13-17-11-2-1-7(14(18)19)5-12(11)20-13/h1-6H,(H,18,19)

InChI Key

TXEIIPDJKFWEEC-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenyl-1,3-oxazoles. These are aromatic heterocyclic compounds containing a 1,3-oxazole substituted at one or more positions by a phenyl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azoles

Sub Class

Oxazoles

Direct Parent

Phenyl-1,3-oxazoles

Alternative Parents

Substituents

Phenyl-1,3-oxazole
Benzoxazole
1,3-dichlorobenzene
Chlorobenzene
Halobenzene
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Benzenoid
Heteroaromatic compound
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Azacycle
Monocarboxylic acid or derivatives
Organopnictogen compound
Organic oxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Organic oxide
Organohalogen compound
Organochloride
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

1,3-benzoxazoles (CHEBI:78538 )
monocarboxylic acid (CHEBI:78538 )
dichlorobenzene (CHEBI:78538 )

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	3.91	ALOGPS
logP	4.21	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	3.73	ChemAxon
pKa (Strongest Basic)	-0.41	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.33 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	84.69 m³·mol⁻¹	ChemAxon
Polarizability	29.74 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]+	165.145	30932474
DeepCCS	[M-H]-	162.786	30932474
DeepCCS	[M-2H]-	196.083	30932474
DeepCCS	[M+Na]+	171.31	30932474
AllCCS	[M+H]+	162.8	32859911
AllCCS	[M+H-H2O]+	159.4	32859911
AllCCS	[M+NH4]+	166.0	32859911
AllCCS	[M+Na]+	166.9	32859911
AllCCS	[M-H]-	158.5	32859911
AllCCS	[M+Na-2H]-	157.5	32859911
AllCCS	[M+HCOO]-	156.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Tafamidis	OC(=O)C1=CC2=C(C=C1)N=C(O2)C1=CC(Cl)=CC(Cl)=C1	3723.3	Standard polar	33892256
Tafamidis	OC(=O)C1=CC2=C(C=C1)N=C(O2)C1=CC(Cl)=CC(Cl)=C1	2654.0	Standard non polar	33892256
Tafamidis	OC(=O)C1=CC2=C(C=C1)N=C(O2)C1=CC(Cl)=CC(Cl)=C1	2637.9	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 - Tafamidis GC-MS (Non-derivatized) - 70eV, Positive	splash10-052r-2093000000-6c9eda1b616978583c87	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tafamidis GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tafamidis GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tafamidis 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 - Tafamidis 10V, Positive-QTOF	splash10-0a4i-0009000000-9bea728c413bdb9daee6	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tafamidis 20V, Positive-QTOF	splash10-0a4i-0029000000-b3ca4475b9dd9b1a6eda	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tafamidis 40V, Positive-QTOF	splash10-03dl-4193000000-1e48f0ff8a348c8f07ab	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tafamidis 10V, Negative-QTOF	splash10-0a4i-0039000000-ae2507840cb55bce1387	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tafamidis 20V, Negative-QTOF	splash10-08fr-0095000000-8b9dd17bac76b66e22b4	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tafamidis 40V, Negative-QTOF	splash10-03dr-0190000000-e94e174d249641c4645e	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tafamidis 10V, Positive-QTOF	splash10-0a4r-0059000000-c0d8ab35b64658841939	2021-10-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tafamidis 20V, Positive-QTOF	splash10-0a4i-0039000000-29608bd9590174e0dc4c	2021-10-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tafamidis 40V, Positive-QTOF	splash10-000i-0090000000-bc5904847fec2c65ec50	2021-10-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tafamidis 10V, Negative-QTOF	splash10-0bt9-0069000000-87dedd5cb0a6ca0fa264	2021-10-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tafamidis 20V, Negative-QTOF	splash10-03di-0092000000-f3903dc96102fd561848	2021-10-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tafamidis 40V, Negative-QTOF	splash10-08fr-0098000000-5094b7495b0c94fcffa7	2021-10-22	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

DB11644

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9176510

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Tafamidis

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

78538

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 Tafamidis (HMDB0258677)

MOL for HMDB0258677 (Tafamidis)

3D MOL for HMDB0258677 (Tafamidis)

3D SDF for HMDB0258677 (Tafamidis)

3D-SDF for HMDB0258677 (Tafamidis)

PDB for HMDB0258677 (Tafamidis)

3D PDB for HMDB0258677 (Tafamidis)

SMILES for HMDB0258677 (Tafamidis)

INCHI for HMDB0258677 (Tafamidis)

Structure for HMDB0258677 (Tafamidis)

3D Structure for HMDB0258677 (Tafamidis)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra