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Showing metabocard for Terephthalic acid (HMDB0002428)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:53 UTC
Update Date2023-02-21 17:16:23 UTC
HMDB IDHMDB0002428
Secondary Accession Numbers
  • HMDB0061917
  • HMDB02428
  • HMDB61917
Metabolite 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
Data?1676999783
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0002428 (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 HMDB0002428 (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
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3D SDF for HMDB0002428 (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>
HMDB0002428

> <DATABASE_NAME>
hmdb

> <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 HMDB0002428 (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
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PDB for HMDB0002428 (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 HMDB0002428 (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 HMDB0002428 (Terephthalic acid)

OC(=O)C1=CC=C(C=C1)C(O)=O
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INCHI for HMDB0002428 (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 Stereo Labels
Synonyms
Chemical FormulaC8H6O4
Average Molecular Weight166.1308
Monoisotopic Molecular Weight166.02660868
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
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
Ontology
Physiological effectNot Available
Disposition
Source
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point> 300 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.015 mg/mL at 20 °CNot Available
LogP2.00HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Saliva
  • Urine
Tissue Locations
  • Fibroblasts
  • Platelet
Pathways
Normal Concentrations
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1285651
References
Synthesis ReferenceEmerson, Wm. S.; Shafer, Theodore C.; Heimsch, Robert A. A study of the conversion of p-toluic acid to terephthalic acid with high-pressure oxygen. Journal of Organic Chemistry (1951), 16 1839-45.
Material Safety Data Sheet (MSDS)Download (PDF)
General References