BENZOPHENONE
Relevant Data
Food Additives Approved by WHO:
Flavouring Substances Approved by European Union:
General Information
| Mainterm | BENZOPHENONE |
| Doc Type | ASP |
| CAS Reg.No.(or other ID) | 119-61-9 |
| Regnum |
177.2600 172.515 |
From www.fda.gov
Computed Descriptors
Download SDF| 2D Structure | |
| CID | 3102 |
| IUPAC Name | diphenylmethanone |
| InChI | InChI=1S/C13H10O/c14-13(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10H |
| InChI Key | RWCCWEUUXYIKHB-UHFFFAOYSA-N |
| Canonical SMILES | C1=CC=C(C=C1)C(=O)C2=CC=CC=C2 |
| Molecular Formula | C13H10O |
| Wikipedia | benzophenone |
From Pubchem
Computed Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 182.222 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 1 |
| Rotatable Bond Count | 2 |
| Complexity | 165.0 |
| CACTVS Substructure Key Fingerprint | A A A D c c B w I A A A A A A A A A A A A A A A A A A A A A A A A A A w Y A A A A A A A A A A B Q A A A G g A A A A A A D A S A m A A w A I A A A A C I A q B S A A A C A A A k A A A I i A E A A M g I I D K A F R C A I Q A g g A A I i Y c I i M C O A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A = = |
| Topological Polar Surface Area | 17.1 |
| Monoisotopic Mass | 182.073 |
| Exact Mass | 182.073 |
| Compound Is Canonicalized | True |
| Formal Charge | 0 |
| Heavy Atom Count | 14 |
| 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 |
From Pubchem
ADMET Predicted Profile --- Classification
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9841 |
| Human Intestinal Absorption | HIA+ | 0.9974 |
| Caco-2 Permeability | Caco2+ | 0.9389 |
| P-glycoprotein Substrate | Non-substrate | 0.7743 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.8819 |
| Non-inhibitor | 0.9486 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.7907 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.6815 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8005 |
| CYP450 2D6 Substrate | Non-substrate | 0.9528 |
| CYP450 3A4 Substrate | Non-substrate | 0.7820 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.8099 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.8791 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9505 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.5414 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9524 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.6136 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9253 |
| Non-inhibitor | 0.9292 | |
| AMES Toxicity | Non AMES toxic | 0.9741 |
| Carcinogens | Non-carcinogens | 0.6164 |
| Fish Toxicity | High FHMT | 0.7970 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9967 |
| Honey Bee Toxicity | High HBT | 0.7129 |
| Biodegradation | Ready biodegradable | 0.6106 |
| Acute Oral Toxicity | IV | 0.5950 |
| Carcinogenicity (Three-class) | Non-required | 0.6436 |
From admetSAR
ADMET Predicted Profile --- Regression
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.1826 | LogS |
| Caco-2 Permeability | 2.1205 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.8492 | LD50, mol/kg |
| Fish Toxicity | 1.2765 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.7448 | pIGC50, ug/L |
From admetSAR
Toxicity Profile
| Route of Exposure | None |
|---|---|
| Mechanism of Toxicity | Benzophenone is a cholinesterase or acetylcholinesterase (AChE) inhibitor. A cholinesterase inhibitor (or 'anticholinesterase') suppresses the action of acetylcholinesterase. Because of its essential function, chemicals that interfere with the action of acetylcholinesterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses, followed by muscle spasms and ultimately death. Nerve gases and many substances used in insecticides have been shown to act by binding a serine in the active site of acetylcholine esterase, inhibiting the enzyme completely. Acetylcholine esterase breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions, in order to allow the muscle or organ to relax. The result of acetylcholine esterase inhibition is that acetylcholine builds up and continues to act so that any nerve impulses are continually transmitted and muscle contractions do not stop. Among the most common acetylcholinesterase inhibitors are phosphorus-based compounds, which are designed to bind to the active site of the enzyme. The structural requirements are a phosphorus atom bearing two lipophilic groups, a leaving group (such as a halide or thiocyanate), and a terminal oxygen. |
| Metabolism | Paraoxonase (PON1) is a key enzyme in the metabolism of organophosphates. PON1 can inactivate some organophosphates through hydrolysis. PON1 hydrolyzes the active metabolites in several organophosphates insecticides as well as, nerve agents such as soman, sarin, and VX. The presence of PON1 polymorphisms causes there to be different enzyme levels and catalytic efficiency of this esterase, which in turn suggests that different individuals may be more susceptible to the toxic effect of OP exposure. |
| Toxicity Values | None |
| Lethal Dose | None |
| Carcinogenicity (IARC Classification) | 2B, possibly carcinogenic to humans. |
| Minimum Risk Level | None |
| Health Effects | Acute exposure to cholinesterase inhibitors can cause a cholinergic crisis characterized by severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Accumulation of ACh at motor nerves causes overstimulation of nicotinic expression at the neuromuscular junction. When this occurs symptoms such as muscle weakness, fatigue, muscle cramps, fasciculation, and paralysis can be seen. When there is an accumulation of ACh at autonomic ganglia this causes overstimulation of nicotinic expression in the sympathetic system. Symptoms associated with this are hypertension, and hypoglycemia. Overstimulation of nicotinic acetylcholine receptors in the central nervous system, due to accumulation of ACh, results in anxiety, headache, convulsions, ataxia, depression of respiration and circulation, tremor, general weakness, and potentially coma. When there is expression of muscarinic overstimulation due to excess acetylcholine at muscarinic acetylcholine receptors symptoms of visual disturbances, tightness in chest, wheezing due to bronchoconstriction, increased bronchial secretions, increased salivation, lacrimation, sweating, peristalsis, and urination can occur. Certain reproductive effects in fertility, growth, and development for males and females have been linked specifically to organophosphate pesticide exposure. Most of the research on reproductive effects has been conducted on farmers working with pesticides and insecticdes in rural areas. In females menstrual cycle disturbances, longer pregnancies, spontaneous abortions, stillbirths, and some developmental effects in offspring have been linked to organophosphate pesticide exposure. Prenatal exposure has been linked to impaired fetal growth and development. Neurotoxic effects have also been linked to poisoning with OP pesticides causing four neurotoxic effects in humans: cholinergic syndrome, intermediate syndrome, organophosphate-induced delayed polyneuropathy (OPIDP), and chronic organophosphate-induced neuropsychiatric disorder (COPIND). These syndromes result after acute and chronic exposure to OP pesticides. |
| Treatment | If the compound has been ingested, rapid gastric lavage should be performed using 5% sodium bicarbonate. For skin contact, the skin should be washed with soap and water. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. In serious cases, atropine and/or pralidoxime should be administered. Anti-cholinergic drugs work to counteract the effects of excess acetylcholine and reactivate AChE. Atropine can be used as an antidote in conjunction with pralidoxime or other pyridinium oximes (such as trimedoxime or obidoxime), though the use of '-oximes' has been found to be of no benefit, or possibly harmful, in at least two meta-analyses. Atropine is a muscarinic antagonist, and thus blocks the action of acetylcholine peripherally. |
| Reference |
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From T3DB
Taxonomic Classification
| Kingdom | Organic compounds |
|---|---|
| Superclass | Benzenoids |
| Class | Benzene and substituted derivatives |
| Subclass | Benzophenones |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Benzophenones |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | Benzophenone - Aryl-phenylketone - Diphenylmethane - Aryl ketone - Benzoyl - Ketone - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as benzophenones. These are organic compounds containing a ketone attached to two phenyl groups. |
From ClassyFire
Targets
- General Function:
- Proteoglycan binding
- Specific Function:
- Thiol protease which is believed to participate in intracellular degradation and turnover of proteins. Has also been implicated in tumor invasion and metastasis.
- Gene Name:
- CTSB
- Uniprot ID:
- P07858
- Molecular Weight:
- 37821.35 Da
References
- Martins FT, Assis DM, Dos Santos MH, Camps I, Veloso MP, Juliano MA, Alves LC, Doriguetto AC: Natural polyprenylated benzophenones inhibiting cysteine and serine proteases. Eur J Med Chem. 2009 Mar;44(3):1230-9. doi: 10.1016/j.ejmech.2008.09.018. Epub 2008 Sep 24. [18995931 ]
- General Function:
- Serine hydrolase activity
- Specific Function:
- Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis.
- Gene Name:
- ACHE
- Uniprot ID:
- P22303
- Molecular Weight:
- 67795.525 Da
References
- Wadkins RM, Hyatt JL, Wei X, Yoon KJ, Wierdl M, Edwards CC, Morton CL, Obenauer JC, Damodaran K, Beroza P, Danks MK, Potter PM: Identification and characterization of novel benzil (diphenylethane-1,2-dione) analogues as inhibitors of mammalian carboxylesterases. J Med Chem. 2005 Apr 21;48(8):2906-15. [15828829 ]
- General Function:
- Methylumbelliferyl-acetate deacetylase activity
- Specific Function:
- Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Shows high catalytic efficiency for hydrolysis of cocaine, 4-methylumbelliferyl acetate, heroin and 6-monoacetylmorphine.
- Gene Name:
- CES2
- Uniprot ID:
- O00748
- Molecular Weight:
- 61806.41 Da
References
- Wadkins RM, Hyatt JL, Wei X, Yoon KJ, Wierdl M, Edwards CC, Morton CL, Obenauer JC, Damodaran K, Beroza P, Danks MK, Potter PM: Identification and characterization of novel benzil (diphenylethane-1,2-dione) analogues as inhibitors of mammalian carboxylesterases. J Med Chem. 2005 Apr 21;48(8):2906-15. [15828829 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA/p65 and NFKB1/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Isoform 3 is involved in activation of NOS3 and endothelial nitric oxide production. Isoforms lacking one or several functional domains are thought to modulate transcriptional activity by competitive ligand or DNA binding and/or heterodimerization with the full length receptor. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3. Isoform 3 can bind to ERE and inhibit isoform 1.
- Gene Name:
- ESR1
- Uniprot ID:
- P03372
- Molecular Weight:
- 66215.45 Da
References
- Matsumoto H, Adachi S, Suzuki Y: [Estrogenic activity of ultraviolet absorbers and the related compounds]. Yakugaku Zasshi. 2005 Aug;125(8):643-52. [16079615 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear hormone receptor. Binds estrogens with an affinity similar to that of ESR1, and activates expression of reporter genes containing estrogen response elements (ERE) in an estrogen-dependent manner (PubMed:20074560). Isoform beta-cx lacks ligand binding ability and has no or only very low ere binding activity resulting in the loss of ligand-dependent transactivation ability. DNA-binding by ESR1 and ESR2 is rapidly lost at 37 degrees Celsius in the absence of ligand while in the presence of 17 beta-estradiol and 4-hydroxy-tamoxifen loss in DNA-binding at elevated temperature is more gradual.
- Gene Name:
- ESR2
- Uniprot ID:
- Q92731
- Molecular Weight:
- 59215.765 Da
References
- Matsumoto H, Adachi S, Suzuki Y: [Estrogenic activity of ultraviolet absorbers and the related compounds]. Yakugaku Zasshi. 2005 Aug;125(8):643-52. [16079615 ]
- General Function:
- Triglyceride lipase activity
- Specific Function:
- Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acyl-CoA ester. Hydrolyzes the methyl ester group of cocaine to form benzoylecgonine. Catalyzes the transesterification of cocaine to form cocaethylene. Displays fatty acid ethyl ester synthase activity, catalyzing the ethyl esterification of oleic acid to ethyloleate.
- Gene Name:
- CES1
- Uniprot ID:
- P23141
- Molecular Weight:
- 62520.62 Da
References
- Wadkins RM, Hyatt JL, Wei X, Yoon KJ, Wierdl M, Edwards CC, Morton CL, Obenauer JC, Damodaran K, Beroza P, Danks MK, Potter PM: Identification and characterization of novel benzil (diphenylethane-1,2-dione) analogues as inhibitors of mammalian carboxylesterases. J Med Chem. 2005 Apr 21;48(8):2906-15. [15828829 ]
- Gene Name:
- TP53
- Uniprot ID:
- P04637
- Molecular Weight:
- 43652.79 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 ]
From T3DB