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Showing NP-Card for Terephthalic acid (NP0000290)

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Record Information
Version1.0
Created at2006-05-22 14:17:53 UTC
Updated at2021-10-07 20:40:50 UTC
NP-MRD IDNP0000290
Secondary Accession NumbersNone
Natural Product Identification
Common NameTerephthalic acid
DescriptionTerephthalic acid is a benzenedicarboxylic acid carrying carboxy groups at positions 1 and 4. One of three possible isomers of benzenedicarboxylic acid, the others being phthalic and isophthalic acids. It is a conjugate acid of a terephthalate(1-). Terephthalic acid is one isomer of the three phthalic acids. It finds important use as a commodity chemical, principally as a starting compound for the manufacture of polyester (specifically PET), used in clothing and to make plastic bottles. It is also known as 1,4-benzenedicarboxylic acid, and it has the chemical formula C6H4(COOH)2.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000290 (Terephthalic acid)


  Mrv1652305271900302D          

 12 12  0  0  0  0            999 V2000
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  6  9  1  0  0  0  0
  9 10  2  0  0  0  0
  8  3  1  0  0  0  0
 11  1  1  0  0  0  0
 12  9  1  0  0  0  0
M  END
Download

3D MOL for NP0000290 (Terephthalic acid)

HMDB0002428
     RDKit          3D
Terephthalic acid
 18 18  0  0  0  0  0  0  0  0999 V2000
   -3.1218   -0.8230   -1.6126 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7836   -0.4056   -0.4809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7794   -0.1429    0.4410 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3665   -0.2251   -0.2119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9081    0.2336    1.0167 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4400    0.4000    1.2575 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3895    0.1218    0.2993 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8191    0.2948    0.5446 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2581    0.7085    1.6483 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7496    0.0061   -0.4403 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9307   -0.3330   -0.9181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4172   -0.5033   -1.1699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8143    0.7391    0.9268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6635    0.4483    1.7600 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7840    0.7543    2.2081 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5636    0.1542   -1.4229 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6700   -0.5610   -1.6967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7502   -0.8668   -2.1490 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  7 11  1  0
 11 12  2  0
 12  4  1  0
  3 13  1  0
  5 14  1  0
  6 15  1  0
 10 16  1  0
 11 17  1  0
 12 18  1  0
M  END
Download

3D SDF for NP0000290 (Terephthalic acid)


  Mrv1652305271900302D          

 12 12  0  0  0  0            999 V2000
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  6  9  1  0  0  0  0
  9 10  2  0  0  0  0
  8  3  1  0  0  0  0
 11  1  1  0  0  0  0
 12  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000290

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C8H6O4/c9-7(10)5-1-2-6(4-3-5)8(11)12/h1-4H,(H,9,10)(H,11,12)

> <INCHI_KEY>
KKEYFWRCBNTPAC-UHFFFAOYSA-N

> <FORMULA>
C8H6O4

> <MOLECULAR_WEIGHT>
166.1308

> <EXACT_MASS>
166.02660868

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
15.196395864564241

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
benzene-1,4-dicarboxylic acid

> <ALOGPS_LOGP>
1.01

> <JCHEM_LOGP>
1.2884116319999999

> <ALOGPS_LOGS>
-1.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.56360221460787

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3203665007464127

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
40.57040000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.29e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
terephthalic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000290 (Terephthalic acid)

HMDB0002428
     RDKit          3D
Terephthalic acid
 18 18  0  0  0  0  0  0  0  0999 V2000
   -3.1218   -0.8230   -1.6126 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7836   -0.4056   -0.4809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7794   -0.1429    0.4410 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3665   -0.2251   -0.2119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9081    0.2336    1.0167 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4400    0.4000    1.2575 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3895    0.1218    0.2993 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8191    0.2948    0.5446 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2581    0.7085    1.6483 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7496    0.0061   -0.4403 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9307   -0.3330   -0.9181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4172   -0.5033   -1.1699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8143    0.7391    0.9268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6635    0.4483    1.7600 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7840    0.7543    2.2081 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5636    0.1542   -1.4229 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6700   -0.5610   -1.6967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7502   -0.8668   -2.1490 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  7 11  1  0
 11 12  2  0
 12  4  1  0
  3 13  1  0
  5 14  1  0
  6 15  1  0
 10 16  1  0
 11 17  1  0
 12 18  1  0
M  END
Download

PDB for NP0000290 (Terephthalic acid)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   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   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2    3   11                                                  
CONECT    2    1                                                            
CONECT    3    1    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    9                                                  
CONECT    7    6    8                                                       
CONECT    8    7    3                                                       
CONECT    9    6   10   12                                                  
CONECT   10    9                                                            
CONECT   11    1                                                            
CONECT   12    9                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END
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3D PDB for NP0000290 (Terephthalic acid)

COMPND    HMDB0002428
HETATM    1  O1  UNL     1      -3.122  -0.823  -1.613  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.784  -0.406  -0.481  1.00  0.00           C  
HETATM    3  O2  UNL     1      -3.779  -0.143   0.441  1.00  0.00           O  
HETATM    4  C2  UNL     1      -1.366  -0.225  -0.212  1.00  0.00           C  
HETATM    5  C3  UNL     1      -0.908   0.234   1.017  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.440   0.400   1.257  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.389   0.122   0.299  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.819   0.295   0.545  1.00  0.00           C  
HETATM    9  O3  UNL     1       3.258   0.708   1.648  1.00  0.00           O  
HETATM   10  O4  UNL     1       3.750   0.006  -0.440  1.00  0.00           O  
HETATM   11  C7  UNL     1       0.931  -0.333  -0.918  1.00  0.00           C  
HETATM   12  C8  UNL     1      -0.417  -0.503  -1.170  1.00  0.00           C  
HETATM   13  H1  UNL     1      -3.814   0.739   0.927  1.00  0.00           H  
HETATM   14  H2  UNL     1      -1.664   0.448   1.760  1.00  0.00           H  
HETATM   15  H3  UNL     1       0.784   0.754   2.208  1.00  0.00           H  
HETATM   16  H4  UNL     1       3.564   0.154  -1.423  1.00  0.00           H  
HETATM   17  H5  UNL     1       1.670  -0.561  -1.697  1.00  0.00           H  
HETATM   18  H6  UNL     1      -0.750  -0.867  -2.149  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   13
CONECT    4    5    5   12
CONECT    5    6   14
CONECT    6    7    7   15
CONECT    7    8   11
CONECT    8    9    9   10
CONECT   10   16
CONECT   11   12   12   17
CONECT   12   18
END
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SMILES for NP0000290 (Terephthalic acid)

OC(=O)C1=CC=C(C=C1)C(O)=O
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INCHI for NP0000290 (Terephthalic acid)

InChI=1S/C8H6O4/c9-7(10)5-1-2-6(4-3-5)8(11)12/h1-4H,(H,9,10)(H,11,12)
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View in JSmolView NMR Assignments
Synonyms
ValueSource
1,4-Benzenedicarboxylic acidChEBI
p-Benzenedicarboxylic acidChEBI
Para-benzenedicarboxylic acidChEBI
TPAChEBI
1,4-BenzenedicarboxylateGenerator
p-BenzenedicarboxylateGenerator
Para-benzenedicarboxylateGenerator
TerephthalateGenerator
Benzene-p-dicarboxylateHMDB
Benzene-p-dicarboxylic acidHMDB
Kyselina terftalovaHMDB
p-DicarboxybenzeneHMDB
p-PhthalateHMDB
p-Phthalic acidHMDB
p-PhthelateHMDB
p-Phthelic acidHMDB
Disodium terephthalateHMDB
Terephthalic acidKEGG
Chemical FormulaC8H6O4
Average Mass166.1308 Da
Monoisotopic Mass166.02661 Da
IUPAC Namebenzene-1,4-dicarboxylic acid
Traditional Nameterephthalic acid
CAS Registry Number100-21-0
SMILES
OC(=O)C1=CC=C(C=C1)C(O)=O
InChI Identifier
InChI=1S/C8H6O4/c9-7(10)5-1-2-6(4-3-5)8(11)12/h1-4H,(H,9,10)(H,11,12)
InChI KeyKKEYFWRCBNTPAC-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
Cassia roxburghiiLOTUS Database
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Homo sapiensLOTUS Database
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Pinus pinasterLOTUS Database
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as p-phthalic acid and derivatives. P-phthalic acid and derivatives are compounds containing a benzene ring bearing a carboxylic acid group at ring carbon atoms 1 and 4.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentP-phthalic acid and derivatives
Alternative Parents
Substituents
  • Para_phthalic_acid
  • Benzoic acid
  • Benzoyl
  • Dicarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point> 300 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.015 mg/mL at 20 °CNot Available
LogP2.00Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted Properties
PropertyValueSource
Water Solubility2.29 g/LALOGPS
logP1.01ALOGPS
logP1.29ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)3.32ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity40.57 m³·mol⁻¹ChemAxon
Polarizability15.2 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0002428
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023000
KNApSAcK IDNot Available
Chemspider ID7208
KEGG Compound IDC06337
BioCyc IDTEREPHTHALATE
BiGG IDNot Available
Wikipedia LinkTerephthalic_acid
METLIN ID6676
PubChem Compound7489
PDB IDNot Available
ChEBI ID15702
Good Scents IDrw1285651
References
General References
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  2. Iwasaki Y, Yamasaki A, Ishihara K: Platelet compatible blood filtration fabrics using a phosphorylcholine polymer having high surface mobility. Biomaterials. 2003 Sep;24(20):3599-604. [PubMed:12809789 ]
  3. Bot I, von der Thusen JH, Donners MM, Lucas A, Fekkes ML, de Jager SC, Kuiper J, Daemen MJ, van Berkel TJ, Heeneman S, Biessen EA: Serine protease inhibitor Serp-1 strongly impairs atherosclerotic lesion formation and induces a stable plaque phenotype in ApoE-/-mice. Circ Res. 2003 Sep 5;93(5):464-71. Epub 2003 Aug 14. [PubMed:12919945 ]
  4. Yepes M, Sandkvist M, Moore EG, Bugge TH, Strickland DK, Lawrence DA: Tissue-type plasminogen activator induces opening of the blood-brain barrier via the LDL receptor-related protein. J Clin Invest. 2003 Nov;112(10):1533-40. [PubMed:14617754 ]
  5. Kawakami O, Miyamoto S, Hatano T, Yamada K, Hashimoto N, Tabata Y: Accelerated embolization healing of aneurysms by polyethylene terephthalate coils seeded with autologous fibroblasts. Neurosurgery. 2005 May;56(5):1075-81; discussion 1075-81. [PubMed:15854257 ]
  6. Kim YH, Park JH, Hong SH, Koh JY: Nonproteolytic neuroprotection by human recombinant tissue plasminogen activator. Science. 1999 Apr 23;284(5414):647-50. [PubMed:10213688 ]
  7. Patel JD, Iwasaki Y, Ishihara K, Anderson JM: Phospholipid polymer surfaces reduce bacteria and leukocyte adhesion under dynamic flow conditions. J Biomed Mater Res A. 2005 Jun 1;73(3):359-66. [PubMed:15800952 ]
  8. Tremaine LM, Quebbemann AJ: The renal handling of terephthalic acid. Toxicol Appl Pharmacol. 1985 Jan;77(1):165-74. [PubMed:3966238 ]
  9. Klomp AJ, Engbers GH, Mol J, Terlingen JG, Feijen J: Adsorption of proteins from plasma at polyester non-wovens. Biomaterials. 1999 Jul;20(13):1203-11. [PubMed:10395389 ]
  10. Roald HE, Barstad RM, Bakken IJ, Roald B, Lyberg T, Sakariassen KS: Initial interactions of platelets and plasma proteins in flowing non-anticoagulated human blood with the artificial surfaces Dacron and PTFE. Blood Coagul Fibrinolysis. 1994 Jun;5(3):355-63. [PubMed:8075307 ]
  11. Gappa-Fahlenkamp H, Lewis RS: Improved hemocompatibility of poly(ethylene terephthalate) modified with various thiol-containing groups. Biomaterials. 2005 Jun;26(17):3479-85. [PubMed:15621237 ]