Monobutylphthalate
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Basic Info
| Common Name | Monobutylphthalate(F05098) |
| 2D Structure | |
| Description | Monobutyl phthalate (MBP), is an active metabolite of di-n-butyl phthalate (DBP). Dibutyl phthalate (DBP) is a commonly used plasticizer. It is also used as an additive to adhesives or printing inks. It is soluble in various organic solvents, e.g. in alcohol, ether and benzene. DBP is also used as an ectoparasiticide.. DBP was added to the California Proposition 65 (1986) list of suspected teratogens in November 2006. It is a suspected endocrine disruptor. It was used in some nail polishes; all major producers began eliminating this chemical from nail polishes in the Fall of 2006. DBP was permanently banned in children's toys, Monobutyl phthalate inhibits steroidogenesis by downregulating steroidogenic acute regulatory protein expression. |
| FRCD ID | F05098 |
| CAS Number | 131-70-4 |
| PubChem CID | 8575 |
| Formula | C12H14O4 |
| IUPAC Name | 2-butoxycarbonylbenzoic acid |
| InChI Key | YZBOVSFWWNVKRJ-UHFFFAOYSA-N |
| InChI | InChI=1S/C12H14O4/c1-2-3-8-16-12(15)10-7-5-4-6-9(10)11(13)14/h4-7H,2-3,8H2,1H3,(H,13,14) |
| Canonical SMILES | CCCCOC(=O)C1=CC=CC=C1C(=O)O |
| Isomeric SMILES | CCCCOC(=O)C1=CC=CC=C1C(=O)O |
| Synonyms |
MONOBUTYL PHTHALATE
Phthalic acid, monobutyl ester
131-70-4
Mono-n-butyl phthalate
Butyl hydrogen phthalate
2-(Butoxycarbonyl)benzoic acid
Monobutylphthalate
1,2-Benzenedicarboxylic acid, monobutyl ester
UNII-ZI46LWZ45G
NSC 8479
|
| Classifies |
Illegal Additives
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Benzene and substituted derivatives |
| Subclass | Benzoic acids and derivatives |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Benzoic acid esters |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | Benzoate ester - Benzoic acid - Benzoyl - Dicarboxylic acid or derivatives - Carboxylic acid ester - Carboxylic acid - Carboxylic acid derivative - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 222.24 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 6 |
| Complexity | 249 |
| Monoisotopic Mass | 222.089 |
| Exact Mass | 222.089 |
| XLogP | 3.1 |
| Formal Charge | 0 |
| Heavy Atom Count | 16 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9196 |
| Human Intestinal Absorption | HIA+ | 0.9636 |
| Caco-2 Permeability | Caco2+ | 0.6861 |
| P-glycoprotein Substrate | Non-substrate | 0.5683 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.8800 |
| Non-inhibitor | 0.9661 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8722 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.9097 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7725 |
| CYP450 2D6 Substrate | Non-substrate | 0.8998 |
| CYP450 3A4 Substrate | Non-substrate | 0.6812 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.5534 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.7757 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9118 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.6651 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9431 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9166 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9533 |
| Non-inhibitor | 0.9362 | |
| AMES Toxicity | Non AMES toxic | 0.9387 |
| Carcinogens | Non-carcinogens | 0.8129 |
| Fish Toxicity | High FHMT | 0.9465 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9980 |
| Honey Bee Toxicity | High HBT | 0.5271 |
| Biodegradation | Ready biodegradable | 0.9402 |
| Acute Oral Toxicity | III | 0.9119 |
| Carcinogenicity (Three-class) | Non-required | 0.5829 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.9855 | LogS |
| Caco-2 Permeability | 0.9925 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.9197 | LD50, mol/kg |
| Fish Toxicity | 0.7022 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 1.4133 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Hapten-Grafted Programmed Probe as a Corecognition Element for a CompetitiveImmunosensor to Detect Acetamiprid Residue in Agricultural Products. | J Agric Food Chem | 2018 Jul 25 | 29944365 |
| miRNA-200c mediates mono-butyl phthalate-disrupted steroidogenesis by targetingvimentin in Leydig tumor cells and murine adrenocortical tumor cells. | Toxicol Lett | 2016 Jan 22 | 26581634 |
| Soluble expression and purification of receptor activator of nuclear factor-kappaB ligand using Escherichia coli. | J Microbiol Biotechnol | 2015 Feb | 25248982 |
| Single-step purification and immobilization of MBP-phytase fusion on starch agar beads: application in dephytination of soy milk. | Appl Biochem Biotechnol | 2012 Jul | 22371061 |
| Pea lectin receptor-like kinase promotes high salinity stress tolerance inbacteria and expresses in response to stress in planta. | Glycoconj J | 2010 Jan | 19898933 |
| Randomized clinical trial of effect of synbiotics, neomycin and mechanical bowel preparation on intestinal barrier function in patients undergoing colectomy. | Br J Surg | 2007 May | 17443852 |
| Milk basic protein promotes bone formation and suppresses bone resorption inhealthy adult men. | Biosci Biotechnol Biochem | 2001 Jun | 11471735 |
Targets
- 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
- 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 ]
- General Function:
- Ubiquitin protein ligase binding
- Specific Function:
- Receptor tyrosine kinase binding ligands of the EGF family and activating several signaling cascades to convert extracellular cues into appropriate cellular responses. Known ligands include EGF, TGFA/TGF-alpha, amphiregulin, epigen/EPGN, BTC/betacellulin, epiregulin/EREG and HBEGF/heparin-binding EGF. Ligand binding triggers receptor homo- and/or heterodimerization and autophosphorylation on key cytoplasmic residues. The phosphorylated receptor recruits adapter proteins like GRB2 which in turn activates complex downstream signaling cascades. Activates at least 4 major downstream signaling cascades including the RAS-RAF-MEK-ERK, PI3 kinase-AKT, PLCgamma-PKC and STATs modules. May also activate the NF-kappa-B signaling cascade. Also directly phosphorylates other proteins like RGS16, activating its GTPase activity and probably coupling the EGF receptor signaling to the G protein-coupled receptor signaling. Also phosphorylates MUC1 and increases its interaction with SRC and CTNNB1/beta-catenin.Isoform 2 may act as an antagonist of EGF action.
- Gene Name:
- EGFR
- Uniprot ID:
- P00533
- Molecular Weight:
- 134276.185 Da
References
- 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 ]
- General Function:
- Urokinase plasminogen activator receptor activity
- Specific Function:
- Acts as a receptor for urokinase plasminogen activator. Plays a role in localizing and promoting plasmin formation. Mediates the proteolysis-independent signal transduction activation effects of U-PA. It is subject to negative-feedback regulation by U-PA which cleaves it into an inactive form.
- Gene Name:
- PLAUR
- Uniprot ID:
- Q03405
- Molecular Weight:
- 36977.62 Da
References
- 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 ]
- General Function:
- Serine-type endopeptidase activity
- Specific Function:
- Specifically cleaves the zymogen plasminogen to form the active enzyme plasmin.
- Gene Name:
- PLAU
- Uniprot ID:
- P00749
- Molecular Weight:
- 48507.09 Da
References
- 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 ]
- 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
- 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 ]
- 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
- 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 ]