Benzophenone
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Basic Info
| Common Name | Benzophenone(F05175) |
| 2D Structure | |
| Description | Benzophenone is found in fruits. Benzophenone is present in grapes. Benzophenone is a flavouring agent Benzophenone is a common photosensitizer in photochemistry. It crosses from the S1 state into the triplet state with nearly 100% yield. The resulting diradical will abstract a hydrogen atom from a suitable hydrogen donor to form a ketyl radical. Benzophenone is the organic compound with the formula (C6H5)2CO, generally abbreviated Ph2CO. Benzophenone is a widely used building block in organic chemistry, being the parent diarylketone. Benzophenone has been shown to exhibit anti-inflammatory function Benzophenone belongs to the family of Benzophenones. These are organic compounds containing a ketone attached to two phenyl groups. (A3203). |
| FRCD ID | F05175 |
| CAS Number | 119-61-9 |
| PubChem CID | 3102 |
| Formula | C13H10O |
| IUPAC Name | diphenylmethanone |
| InChI Key | RWCCWEUUXYIKHB-UHFFFAOYSA-N |
| InChI | InChI=1S/C13H10O/c14-13(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10H |
| Canonical SMILES | C1=CC=C(C=C1)C(=O)C2=CC=CC=C2 |
| Isomeric SMILES | C1=CC=C(C=C1)C(=O)C2=CC=CC=C2 |
| Wikipedia | Benzophenone |
| Synonyms |
diphenylmethanone
alpha-Oxoditane
BENZOPHENONE
Diphenyl ketone
119-61-9
Benzoylbenzene
Methanone, diphenyl-
Phenyl ketone
Ketone, diphenyl
Benzene, benzoyl-
|
| Classifies |
Plant Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| 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. |
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 |
| Monoisotopic Mass | 182.073 |
| Exact Mass | 182.073 |
| XLogP | 3.4 |
| 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 |
ADMET
| 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 |
| 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 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Determination of diffusion and partition coefficients of model migrants by directcontact and vapour phase transfer from low-density polyethylene films into cake. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2018Mar | 29067891 |
| Antifungal effect of phenolic extract of fermented rice bran with Rhizopus oryzaeand its potential use in loaf bread shelf life extension. | J Sci Food Agric | 2018 Mar 30 | 29602173 |
| Effects of steaming on contaminants of emerging concern levels in seafood. | Food Chem Toxicol | 2018 Aug | 29787848 |
| Reaction of diazepam and related benzodiazepines with chlorine. Kinetics, transformation products and in-silico toxicological assessment. | Water Res | 2017 Sep 1 | 28549311 |
| Comparison of the In Vivo Biotransformation of Two Emerging Estrogenic Contaminants, BP2 and BPS, in Zebrafish Embryos and Adults. | Int J Mol Sci | 2017 Mar 25 | 28346357 |
| A mechanistic insight into hydrogen peroxide-mediated elicitation of bioactivexanthones in Hoppea fastigiata shoot cultures. | Planta | 2016 Jul | 27059029 |
| Determination of key diffusion and partition parameters and their use inmigration modelling of benzophenone from low-density polyethylene (LDPE) intodifferent foodstuffs. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2016 | 26892649 |
| Occurrences, toxicities, and ecological risks of benzophenone-3, a common component of organic sunscreen products: a mini-review. | Environ Int | 2014 Sep | 24934855 |
| Direct interaction of garcinol and related polyisoprenylated benzophenones of Garcinia cambogia fruits with the transcription factor STAT-1 as a likely mechanism of their inhibitory effect on cytokine signaling pathways. | J Nat Prod | 2014 Mar 28 | 24417609 |
| Endocrine disruptors in food contact materials; is there a health threat? | Rocz Panstw Zakl Hig | 2014 | 25247795 |
| Model studies of migration from paper and board into fruit and vegetables andinto Tenax as a food simulant. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2014 | 24823503 |
| 4-Methylbenzophenone and benzophenone are inactive in the micronucleus assay. | Toxicol Lett | 2011 Mar 25 | 21238557 |
| Photoinduced reduction of divalent mercury in ice by organic matter. | Chemosphere | 2011 Jan | 21044797 |
| Effect of 2,4-dihydroxybenzophenone (BP1) on early life-stage development of the marine copepod Acartia tonsa at different temperatures and salinities. | Environ Toxicol Chem | 2011 Apr | 21194178 |
| Rapid multi-analyte quantification of benzophenone, 4-methylbenzophenone andrelated derivatives from paperboard food packaging. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2010Oct | 20640959 |
| Importance of prey and predator feeding behaviors for trophic transfer and secondary poisoning. | Environ Sci Technol | 2009 Oct 15 | 19921914 |
| Photostability and phytotoxicity of selected sunscreen agents and their degradation mixtures in water. | Anal Bioanal Chem | 2009 Nov | 19768642 |
| Benzophenone derivatives from the fruits of Garcinia multiflora and their anti-inflammatory activity. | J Nat Prod | 2009 Feb 27 | 19203247 |
| 1,3-diene probes for detection of triplet carbonyls in biological systems. | Chem Res Toxicol | 2007 Aug | 17630714 |
| Effectiveness of polypropylene film as a barrier to migration from recycledpaperboard packaging to fatty and high-moisture food. | Food Addit Contam | 2003 Sep | 13129783 |
Targets
- 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:
- 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:
- 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. 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 ]
- 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 ]