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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 14:25:15 UTC

Update Date

2021-09-26 23:09:23 UTC

HMDB ID

HMDB0254937

Secondary Accession Numbers

None

Metabolite Identification

Common Name

1,2,3,6-Tetrahydromethylphthalic anhydride

Description

1,2,3,6-Tetrahydromethylphthalic anhydride, also known as 3a,4,7,7a-tetrahydromethyl-1,3-isobenzofurandione or methyl tetrahydrophthalic anhydride, belongs to the class of organic compounds known as isobenzofurans. These are organic aromatic compounds containing an isobenzofuran moiety. Based on a literature review a significant number of articles have been published on 1,2,3,6-Tetrahydromethylphthalic anhydride. This compound has been identified in human blood as reported by (PMID: 31557052 ). 1,2,3,6-tetrahydromethylphthalic anhydride is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 1,2,3,6-Tetrahydromethylphthalic 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

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

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       3.429   0.999   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.650  -4.013   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       1.220  -1.303   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.126  -0.057   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.650   1.408   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7   11                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    2    8                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10    2   12                                                  
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1-Methylcyclohex-4-ene-1,2-dicarboxylic acid anhydride	ChEBI
3a,4,7,7a-Tetrahydromethyl-1,3-isobenzofurandione	ChEBI
Methyl tetrahydrophthalic anhydride	ChEBI
MTHPA	ChEBI
1-Methylcyclohex-4-ene-1,2-dicarboxylate anhydride	Generator
2-Methyl-3-(2,4,5-trihydroxyphenyl)alanine	MeSH
2-Methyl-3-(2,4,5-trihydroxyphenyl)alanine hydrochloride, (D-tyr)-isomer	MeSH
2-Methyl-3-(2,4,5-trihydroxyphenyl)alanine hydrochloride, (DL-tyr)-isomer	MeSH
2-Methyl-3-(2,4,5-trihydroxyphenyl)alanine hydrochloride, (L-tyr)-isomer	MeSH
2-Methyl-3-(2,4,5-trihydroxyphenyl)alanine, (L-tyr)-isomer	MeSH

Chemical Formula

C₉H₁₀O₃

Average Molecular Weight

166.176

Monoisotopic Molecular Weight

166.062994182

IUPAC Name

3a-methyl-1,3,3a,4,7,7a-hexahydro-2-benzofuran-1,3-dione

Traditional Name

mthpa

CAS Registry Number

Not Available

SMILES

CC12CC=CCC1C(=O)OC2=O

InChI Identifier

InChI=1S/C9H10O3/c1-9-5-3-2-4-6(9)7(10)12-8(9)11/h2-3,6H,4-5H2,1H3

InChI Key

SOOZEQGBHHIHEF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isobenzofurans. These are organic aromatic compounds containing an isobenzofuran moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isobenzofurans

Sub Class

Not Available

Direct Parent

Isobenzofurans

Alternative Parents

Substituents

Isobenzofuran
Dicarboxylic acid or derivatives
Tetrahydrofuran
Carboxylic acid anhydride
Lactone
Oxacycle
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

cyclic dicarboxylic anhydride (CHEBI:55466 )
tetrahydrofurandione (CHEBI:55466 )

Ontology

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	1.53	ALOGPS
logP	1.44	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	42.5 m³·mol⁻¹	ChemAxon
Polarizability	16.09 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-2H]-	166.65	30932474
DeepCCS	[M+Na]+	141.911	30932474
AllCCS	[M+H]+	134.8	32859911
AllCCS	[M+H-H2O]+	130.4	32859911
AllCCS	[M+NH4]+	139.0	32859911
AllCCS	[M+Na]+	140.2	32859911
AllCCS	[M-H]-	134.4	32859911
AllCCS	[M+Na-2H]-	135.2	32859911
AllCCS	[M+HCOO]-	136.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1,2,3,6-Tetrahydromethylphthalic anhydride	CC12CC=CCC1C(=O)OC2=O	2275.3	Standard polar	33892256
1,2,3,6-Tetrahydromethylphthalic anhydride	CC12CC=CCC1C(=O)OC2=O	1391.5	Standard non polar	33892256
1,2,3,6-Tetrahydromethylphthalic anhydride	CC12CC=CCC1C(=O)OC2=O	1373.4	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 - 1,2,3,6-Tetrahydromethylphthalic anhydride GC-MS (Non-derivatized) - 70eV, Positive	splash10-0g4u-9800000000-0afa2ef5666de5be89a8	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,2,3,6-Tetrahydromethylphthalic anhydride GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-25	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

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

171584

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

198243

PDB ID

Not Available

ChEBI ID

55466

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 1,2,3,6-Tetrahydromethylphthalic anhydride (HMDB0254937)

MOL for HMDB0254937 (1,2,3,6-Tetrahydromethylphthalic anhydride)

3D MOL for HMDB0254937 (1,2,3,6-Tetrahydromethylphthalic anhydride)

3D SDF for HMDB0254937 (1,2,3,6-Tetrahydromethylphthalic anhydride)

3D-SDF for HMDB0254937 (1,2,3,6-Tetrahydromethylphthalic anhydride)

PDB for HMDB0254937 (1,2,3,6-Tetrahydromethylphthalic anhydride)

3D PDB for HMDB0254937 (1,2,3,6-Tetrahydromethylphthalic anhydride)

SMILES for HMDB0254937 (1,2,3,6-Tetrahydromethylphthalic anhydride)

INCHI for HMDB0254937 (1,2,3,6-Tetrahydromethylphthalic anhydride)

Structure for HMDB0254937 (1,2,3,6-Tetrahydromethylphthalic anhydride)

3D Structure for HMDB0254937 (1,2,3,6-Tetrahydromethylphthalic anhydride)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

NMR Spectra