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Showing metabocard for Trimellitic anhydride (HMDB0259233)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 21:43:49 UTC
Update Date2022-11-23 22:29:21 UTC
HMDB IDHMDB0259233
Secondary Accession NumbersNone
Metabolite Identification
Common NameTrimellitic anhydride
Descriptiontrimellitic anhydride, also known as anhydrotrimellic acid or TMA, belongs to the class of organic compounds known as phthalic anhydrides. Phthalic anhydrides are compounds containing a phthalic anhydride moiety (or a derivative thereof), which consists of a benzene fused to a furan-1,3-dione. Based on a literature review a significant number of articles have been published on trimellitic anhydride. This compound has been identified in human blood as reported by (PMID: 31557052 ). Trimellitic anhydride is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Trimellitic anhydride 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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0259233 (Trimellitic anhydride)

  Mrv1572004221603382D          

 14 15  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
    3.2789   -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
    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
    4.7079   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 C   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
    5.4223   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249    1.8646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249   -1.0396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  4  1  1  0  0  0  0
  4  3  2  0  0  0  0
  5  2  1  0  0  0  0
  6  3  1  0  0  0  0
  6  5  2  0  0  0  0
  7  4  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
 10  7  2  0  0  0  0
 11  7  1  0  0  0  0
 12  8  2  0  0  0  0
 13  9  2  0  0  0  0
 14  8  1  0  0  0  0
 14  9  1  0  0  0  0
M  END
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3D MOL for HMDB0259233 (Trimellitic anhydride)

HMDB0259233
     RDKit          3D
TRIMELLITIC ANHYDRIDE
 18 19  0  0  0  0  0  0  0  0999 V2000
    3.1256    1.4889   -0.4416 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7515    0.3367   -0.1681 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6361   -0.7074    0.0606 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3081    0.0669   -0.0828 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8395   -1.1948    0.2176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5228   -1.4415    0.2964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4588   -0.4486    0.0804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9921    0.8134   -0.2201 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3749    1.0587   -0.2985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1782    1.6381   -0.3930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1663    2.8588   -0.6767 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3129    0.8688   -0.1965 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9163   -0.4451    0.1025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6968   -1.4161    0.3403 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7624   -1.1176    0.9942 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5773   -1.9769    0.3877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8674   -2.4367    0.5329 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7362    2.0544   -0.5354 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
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
  9  4  1  0
 13  7  1  0
  3 15  1  0
  5 16  1  0
  6 17  1  0
  9 18  1  0
M  END
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3D SDF for HMDB0259233 (Trimellitic anhydride)

  Mrv1572004221603382D          

 14 15  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
    3.2789   -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
    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
    4.7079   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 C   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
    5.4223   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249    1.8646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249   -1.0396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  4  1  1  0  0  0  0
  4  3  2  0  0  0  0
  5  2  1  0  0  0  0
  6  3  1  0  0  0  0
  6  5  2  0  0  0  0
  7  4  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
 10  7  2  0  0  0  0
 11  7  1  0  0  0  0
 12  8  2  0  0  0  0
 13  9  2  0  0  0  0
 14  8  1  0  0  0  0
 14  9  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0259233

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)C1=CC2=C(C=C1)C(=O)OC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H4O5/c10-7(11)4-1-2-5-6(3-4)9(13)14-8(5)12/h1-3H,(H,10,11)

> <INCHI_KEY>
SRPWOOOHEPICQU-UHFFFAOYSA-N

> <FORMULA>
C9H4O5

> <MOLECULAR_WEIGHT>
192.126

> <EXACT_MASS>
192.005873229

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
16.406281662801334

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxylic acid

> <ALOGPS_LOGP>
0.98

> <JCHEM_LOGP>
1.080166550333333

> <ALOGPS_LOGS>
-1.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3836185663623586

> <JCHEM_PKA_STRONGEST_BASIC>
-6.899403827613462

> <JCHEM_POLAR_SURFACE_AREA>
80.67

> <JCHEM_REFRACTIVITY>
44.62120000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.89e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
trimellitic anhydride

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0259233 (Trimellitic anhydride)

HMDB0259233
     RDKit          3D
TRIMELLITIC ANHYDRIDE
 18 19  0  0  0  0  0  0  0  0999 V2000
    3.1256    1.4889   -0.4416 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7515    0.3367   -0.1681 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6361   -0.7074    0.0606 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3081    0.0669   -0.0828 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8395   -1.1948    0.2176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5228   -1.4415    0.2964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4588   -0.4486    0.0804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9921    0.8134   -0.2201 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3749    1.0587   -0.2985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1782    1.6381   -0.3930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1663    2.8588   -0.6767 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3129    0.8688   -0.1965 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9163   -0.4451    0.1025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6968   -1.4161    0.3403 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7624   -1.1176    0.9942 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5773   -1.9769    0.3877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8674   -2.4367    0.5329 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7362    2.0544   -0.5354 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
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
  9  4  1  0
 13  7  1  0
  3 15  1  0
  5 16  1  0
  6 17  1  0
  9 18  1  0
M  END
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PDB for HMDB0259233 (Trimellitic anhydride)

HEADER    PROTEIN                                 22-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-16         0                                  
HETATM    1  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.788  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.322   2.016   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.322  -0.476   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       8.788  -2.310   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      10.122  -0.000   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       2.846   3.481   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       2.846  -1.941   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       2.417   0.770   0.000  0.00  0.00           O+0
CONECT    1    2    4                                                       
CONECT    2    1    5                                                       
CONECT    3    4    6                                                       
CONECT    4    1    3    7                                                  
CONECT    5    2    6    8                                                  
CONECT    6    3    5    9                                                  
CONECT    7    4   10   11                                                  
CONECT    8    5   12   14                                                  
CONECT    9    6   13   14                                                  
CONECT   10    7                                                            
CONECT   11    7                                                            
CONECT   12    8                                                            
CONECT   13    9                                                            
CONECT   14    8    9                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END
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3D PDB for HMDB0259233 (Trimellitic anhydride)

COMPND    HMDB0259233
HETATM    1  O1  UNL     1       3.126   1.489  -0.442  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.751   0.337  -0.168  1.00  0.00           C  
HETATM    3  O2  UNL     1       3.636  -0.707   0.061  1.00  0.00           O  
HETATM    4  C2  UNL     1       1.308   0.067  -0.083  1.00  0.00           C  
HETATM    5  C3  UNL     1       0.840  -1.195   0.218  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.523  -1.442   0.296  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.459  -0.449   0.080  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.992   0.813  -0.220  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.375   1.059  -0.298  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.178   1.638  -0.393  1.00  0.00           C  
HETATM   11  O3  UNL     1      -2.166   2.859  -0.677  1.00  0.00           O  
HETATM   12  O4  UNL     1      -3.313   0.869  -0.196  1.00  0.00           O  
HETATM   13  C9  UNL     1      -2.916  -0.445   0.102  1.00  0.00           C  
HETATM   14  O5  UNL     1      -3.697  -1.416   0.340  1.00  0.00           O  
HETATM   15  H1  UNL     1       3.762  -1.118   0.994  1.00  0.00           H  
HETATM   16  H2  UNL     1       1.577  -1.977   0.388  1.00  0.00           H  
HETATM   17  H3  UNL     1      -0.867  -2.437   0.533  1.00  0.00           H  
HETATM   18  H4  UNL     1       0.736   2.054  -0.535  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   15
CONECT    4    5    5    9
CONECT    5    6   16
CONECT    6    7    7   17
CONECT    7    8   13
CONECT    8    9    9   10
CONECT    9   18
CONECT   10   11   11   12
CONECT   12   13
CONECT   13   14   14
END
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SMILES for HMDB0259233 (Trimellitic anhydride)

OC(=O)C1=CC2=C(C=C1)C(=O)OC2=O
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INCHI for HMDB0259233 (Trimellitic anhydride)

InChI=1S/C9H4O5/c10-7(11)4-1-2-5-6(3-4)9(13)14-8(5)12/h1-3H,(H,10,11)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
Chemical FormulaC9H4O5
Average Molecular Weight192.126
Monoisotopic Molecular Weight192.005873229
IUPAC Name1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxylic acid
Traditional Nametrimellitic anhydride
CAS Registry NumberNot Available
SMILES
OC(=O)C1=CC2=C(C=C1)C(=O)OC2=O
InChI Identifier
InChI=1S/C9H4O5/c10-7(11)4-1-2-5-6(3-4)9(13)14-8(5)12/h1-3H,(H,10,11)
InChI KeySRPWOOOHEPICQU-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phthalic anhydrides. Phthalic anhydrides are compounds containing a phthalic anhydride moiety (or a derivative thereof), which consists of a benzene fused to a furan-1,3-dione.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzofurans
Sub ClassBenzofuranones
Direct ParentPhthalic anhydrides
Alternative Parents
Substituents
  • Phthalic anhydride
  • Phthalic_anhydride
  • Isobenzofuranone
  • Isocoumaran
  • Tricarboxylic acid or derivatives
  • Benzenoid
  • Carboxylic acid anhydride
  • Oxacycle
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID10618
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTrimellitic anhydride
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID53050
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1385081
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]