Monomethyl phthalate (T3D3886)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (7)XML
Targets (7)
Record Information
Version2.0
Creation Date2013-04-25 07:56:53 UTC
Update Date2014-12-24 20:26:33 UTC
Accession NumberT3D3886
Identification
Common NameMonomethyl phthalate
ClassSmall Molecule
DescriptionMonomethyl phthalate is a metabolite, or breakdown product, of dimethyl phthalate, used in insect repellant, plastic, and as a rocket propellant.
Compound Type
  • Ester
  • Ether
  • Food Toxin
  • Household Toxin
  • Industrial/Workplace Toxin
  • Metabolite
  • Organic Compound
  • Plastic
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
2-(Methoxycarbonyl)benzoate
2-(Methoxycarbonyl)benzoic acid
Methyl hydrogen phthalate
Methyl phthalate
Monomethyl 1,2-benzenedicarboxylate
Monomethyl phthalic acid
O-(Methoxycarbonyl)benzoate
O-(Methoxycarbonyl)benzoic acid
Chemical FormulaC9H8O4
Average Molecular Mass180.157 g/mol
Monoisotopic Mass180.042 g/mol
CAS Registry Number4376-18-5
IUPAC Name2-(methoxycarbonyl)benzoic acid
Traditional Namemethyl hydrogen phthalate
SMILESCOC(=O)C1=CC=CC=C1C(O)=O
InChI IdentifierInChI=1S/C9H8O4/c1-13-9(12)7-5-3-2-4-6(7)8(10)11/h2-5H,1H3,(H,10,11)
InChI KeyInChIKey=FNJSWIPFHMKRAT-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentBenzoic acid esters
Alternative Parents
Substituents
  • Benzoate ester
  • Benzoic acid
  • Benzoyl
  • Dicarboxylic acid or derivatives
  • Methyl ester
  • Carboxylic acid ester
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point82 - 84°C
Boiling PointNot Available
SolubilityNot Available
LogP1.13
Predicted Properties
PropertyValueSource
Water Solubility1.76 g/LALOGPS
logP1.5ALOGPS
logP1.63ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)3.09ChemAxon
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.6 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity45.34 m³·mol⁻¹ChemAxon
Polarizability16.88 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-06rt-4900000000-7ecedc5a0ae37b95fb892017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dr-9740000000-01768b5a1dd9f429bc592017-10-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-01ot-0900000000-65098170b3784885cf3e2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-0002-1900000000-eb93036cba5677f432e42021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-01ot-0900000000-6757db1ade89e1c39c0f2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-01ot-0900000000-bfa80ccf09eb7547a4212021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-00r2-6900000000-7e7becd99ce7a415a27a2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-014j-9300000000-85d661af2d78119733282021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0a4i-0900000000-e16e03b30bfbb5c3e6f02021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 90V, Negativesplash10-00b9-9400000000-d46f471c7dd86ce167d82021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Negativesplash10-00fu-9800000000-94470b2ac4d094b659562021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Negativesplash10-0a4i-0900000000-f0a6ee4ef8d00d6650662021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Negativesplash10-0a4i-0900000000-f5d8dcb50914d6dec34c2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Negativesplash10-0abc-3900000000-4cbbe5ea3080e1835e8b2021-09-20View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-a30afed48b4abca44a752016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001j-0900000000-6c900681bbe7b512eb7b2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-3900000000-894c68b2baa026fb0ba02016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-9ffa6bd1a11cb78d8eeb2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002r-0900000000-56be31444cf112d7c4a32016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udr-2900000000-bba5768c32c4e6274e8d2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ot-0900000000-cc0e0c22916327043a552021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052b-0900000000-782a28b988f8b2a279d72021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-3900000000-3b0ed44720a2090fc9b02021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004r-3900000000-6ec50e9028830ab6da822021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9500000000-da5c1bf0509aad0449372021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-79b57c4c262a25bff4312021-09-22View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0ufr-9400000000-0563d9ffe58f40e5046c2014-09-20View Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesMonomethyl phthalate is a metabolite, or breakdown product, of dimethyl phthalate, used in insect repellant, plastic, and as a rocket propellant.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB02130
PubChem Compound ID20392
ChEMBL IDCHEMBL243609
ChemSpider ID19207
KEGG IDNot Available
UniProt IDNot Available
OMIM ID
ChEBI ID491486
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkD3
References
Synthesis ReferenceMedonos, Vladimir; Pasek, Josef; Ruzicka, Vlastimil. Preparation of methyl phthalate by addition of dimethyl ether to phthalic anhydride. Chemicky Prumysl (1957), 7 281-5.
MSDSLink
General References
  1. Silva MJ, Reidy JA, Samandar E, Herbert AR, Needham LL, Calafat AM: Detection of phthalate metabolites in human saliva. Arch Toxicol. 2005 Nov;79(11):647-52. Epub 2005 Jul 2. [15995852 ]
  2. Liang DW, Zhang T, Fang HH: Denitrifying degradation of dimethyl phthalate. Appl Microbiol Biotechnol. 2007 Feb;74(1):221-9. Epub 2006 Nov 10. [17096122 ]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

Target Details
1. Peroxisome proliferator-activated receptor alpha
General Function:
Zinc ion binding
Specific Function:
Ligand-activated transcription factor. Key regulator of lipid metabolism. Activated by the endogenous ligand 1-palmitoyl-2-oleoyl-sn-glycerol-3-phosphocholine (16:0/18:1-GPC). Activated by oleylethanolamide, a naturally occurring lipid that regulates satiety. Receptor for peroxisome proliferators such as hypolipidemic drugs and fatty acids. Regulates the peroxisomal beta-oxidation pathway of fatty acids. Functions as transcription activator for the ACOX1 and P450 genes. Transactivation activity requires heterodimerization with RXRA and is antagonized by NR2C2. May be required for the propagation of clock information to metabolic pathways regulated by PER2.
Gene Name:
PPARA
Uniprot ID:
Q07869
Molecular Weight:
52224.595 Da
References
  1. Sarath Josh MK, Pradeep S, Vijayalekshmi Amma KS, Balachandran S, Abdul Jaleel UC, Doble M, Spener F, Benjamin S: Phthalates efficiently bind to human peroxisome proliferator activated receptor and retinoid X receptor alpha, beta, gamma subtypes: an in silico approach. J Appl Toxicol. 2014 Jul;34(7):754-65. doi: 10.1002/jat.2902. Epub 2013 Jul 11. [23843199 ]
Target Details
2. Peroxisome proliferator-activated receptor delta
General Function:
Zinc ion binding
Specific Function:
Ligand-activated transcription factor. Receptor that binds peroxisome proliferators such as hypolipidemic drugs and fatty acids. Has a preference for poly-unsaturated fatty acids, such as gamma-linoleic acid and eicosapentanoic acid. Once activated by a ligand, the receptor binds to promoter elements of target genes. Regulates the peroxisomal beta-oxidation pathway of fatty acids. Functions as transcription activator for the acyl-CoA oxidase gene. Decreases expression of NPC1L1 once activated by a ligand.
Gene Name:
PPARD
Uniprot ID:
Q03181
Molecular Weight:
49902.99 Da
References
  1. Sarath Josh MK, Pradeep S, Vijayalekshmi Amma KS, Balachandran S, Abdul Jaleel UC, Doble M, Spener F, Benjamin S: Phthalates efficiently bind to human peroxisome proliferator activated receptor and retinoid X receptor alpha, beta, gamma subtypes: an in silico approach. J Appl Toxicol. 2014 Jul;34(7):754-65. doi: 10.1002/jat.2902. Epub 2013 Jul 11. [23843199 ]
Target Details
3. Peroxisome proliferator-activated receptor gamma
General Function:
Zinc ion binding
Specific Function:
Nuclear receptor that binds peroxisome proliferators such as hypolipidemic drugs and fatty acids. Once activated by a ligand, the nuclear receptor binds to DNA specific PPAR response elements (PPRE) and modulates the transcription of its target genes, such as acyl-CoA oxidase. It therefore controls the peroxisomal beta-oxidation pathway of fatty acids. Key regulator of adipocyte differentiation and glucose homeostasis. ARF6 acts as a key regulator of the tissue-specific adipocyte P2 (aP2) enhancer. Acts as a critical regulator of gut homeostasis by suppressing NF-kappa-B-mediated proinflammatory responses. Plays a role in the regulation of cardiovascular circadian rhythms by regulating the transcription of ARNTL/BMAL1 in the blood vessels (By similarity).
Gene Name:
PPARG
Uniprot ID:
P37231
Molecular Weight:
57619.58 Da
References
  1. Sarath Josh MK, Pradeep S, Vijayalekshmi Amma KS, Balachandran S, Abdul Jaleel UC, Doble M, Spener F, Benjamin S: Phthalates efficiently bind to human peroxisome proliferator activated receptor and retinoid X receptor alpha, beta, gamma subtypes: an in silico approach. J Appl Toxicol. 2014 Jul;34(7):754-65. doi: 10.1002/jat.2902. Epub 2013 Jul 11. [23843199 ]
Target Details
4. Hydroxymethylglutaryl-CoA synthase, mitochondrial
General Function:
Hydroxymethylglutaryl-coa synthase activity
Specific Function:
This enzyme condenses acetyl-CoA with acetoacetyl-CoA to form HMG-CoA, which is the substrate for HMG-CoA reductase.
Gene Name:
HMGCS2
Uniprot ID:
P54868
Molecular Weight:
56634.915 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC500.05 uMCLZD_HMGCS2_6CellzDirect
AC500.05 uMCLZD_HMGCS2_6CellzDirect
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
Target Details
5. Cytochrome P450 2C9
General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular Weight:
55627.365 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC500.35 uMCLZD_CYP2C9_6CellzDirect
AC500.35 uMCLZD_CYP2C9_6CellzDirect
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
Target Details
6. Interstitial collagenase
General Function:
Zinc ion binding
Specific Function:
Cleaves collagens of types I, II, and III at one site in the helical domain. Also cleaves collagens of types VII and X. In case of HIV infection, interacts and cleaves the secreted viral Tat protein, leading to a decrease in neuronal Tat's mediated neurotoxicity.
Gene Name:
MMP1
Uniprot ID:
P03956
Molecular Weight:
54006.61 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC504.44 uMBSK_hDFCGF_MMP1_downBioSeek
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
Target Details
7. Plasminogen activator inhibitor 1
General Function:
Serine-type endopeptidase inhibitor activity
Specific Function:
Serine protease inhibitor. This inhibitor acts as 'bait' for tissue plasminogen activator, urokinase, protein C and matriptase-3/TMPRSS7. Its rapid interaction with PLAT may function as a major control point in the regulation of fibrinolysis.
Gene Name:
SERPINE1
Uniprot ID:
P05121
Molecular Weight:
45059.695 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC504.44 uMBSK_hDFCGF_PAI1_downBioSeek
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]