Biphenyl
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Basic Info
| Common Name | Biphenyl(F03555) |
| 2D Structure | |
| Description | Biphenyl is found in alcoholic beverages. Fungistat, especially for citrus fruits. Biphenyl is used as food preservative and flavouring agent. Biphenyl is detected in bilberry, wine grape, carrot, peas, rum, potato, bell pepper, tomato, butter, milk, smoked fatty fish, cocoa, coffee, roast peanuts, olive, buckwheat and tamarind. Generally, the fruit packaging is impregnated with biphenyl, which evaporates into the air space surrounding the fruit. Some biphenyl is absorbed by the fruit skins Biphenyl has been shown to exhibit anti-coagulant and catabolic functions (A7741, A7742). Biphenyl belongs to the family of Biphenyls and Derivatives. These are organic compounds containing to benzene rings linked together by a C-C bond. |
| FRCD ID | F03555 |
| CAS Number | 92-52-4 |
| PubChem CID | 7095 |
| Formula | C12H10 |
| IUPAC Name | 1,1'-biphenyl |
| InChI Key | ZUOUZKKEUPVFJK-UHFFFAOYSA-N |
| InChI | InChI=1S/C12H10/c1-3-7-11(8-4-1)12-9-5-2-6-10-12/h1-10H |
| Canonical SMILES | C1=CC=C(C=C1)C2=CC=CC=C2 |
| Isomeric SMILES | C1=CC=C(C=C1)C2=CC=CC=C2 |
| Synonyms |
Biphenyl
1,1'-Biphenyl
Phenylbenzene
92-52-4
DIPHENYL
Bibenzene
Lemonene
Xenene
1,1'-Diphenyl
Phenador-X
|
| Classifies |
Illegal Additives
Pollutant
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Benzene and substituted derivatives |
| Subclass | Biphenyls and derivatives |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Biphenyls and derivatives |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | Biphenyl - Aromatic hydrocarbon - Unsaturated hydrocarbon - Hydrocarbon - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as biphenyls and derivatives. These are organic compounds containing to benzene rings linked together by a C-C bond. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 154.212 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 0 |
| Rotatable Bond Count | 1 |
| Complexity | 100 |
| Monoisotopic Mass | 154.078 |
| Exact Mass | 154.078 |
| XLogP | 4 |
| Formal Charge | 0 |
| Heavy Atom Count | 12 |
| 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+ | 0.9735 |
| Human Intestinal Absorption | HIA+ | 1.0000 |
| Caco-2 Permeability | Caco2+ | 0.8926 |
| P-glycoprotein Substrate | Non-substrate | 0.8067 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9398 |
| Non-inhibitor | 0.9477 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8309 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.6269 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7929 |
| CYP450 2D6 Substrate | Non-substrate | 0.9191 |
| CYP450 3A4 Substrate | Non-substrate | 0.7884 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.5656 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.7950 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9652 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.7489 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9586 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.7077 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9623 |
| Non-inhibitor | 0.9084 | |
| AMES Toxicity | Non AMES toxic | 0.9280 |
| Carcinogens | Non-carcinogens | 0.5233 |
| Fish Toxicity | High FHMT | 0.9678 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9981 |
| Honey Bee Toxicity | High HBT | 0.7014 |
| Biodegradation | Not ready biodegradable | 0.7578 |
| Acute Oral Toxicity | III | 0.8330 |
| Carcinogenicity (Three-class) | Warning | 0.4112 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -5.0135 | LogS |
| Caco-2 Permeability | 2.0284 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.9506 | LD50, mol/kg |
| Fish Toxicity | 0.2361 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 1.1751 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Citrus fruits | 0110000 | European Union | 0.01* | 05/10/2011 | |
| Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,) | 0110010 | European Union | 0.01* | 05/10/2011 | |
| Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,) | 0110020 | European Union | 0.01* | 05/10/2011 | |
| Lemons (Buddha's hands/Buddha's fingers, Citrons,) | 0110030 | European Union | 0.01* | 05/10/2011 | |
| Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,) | 0110040 | European Union | 0.01* | 05/10/2011 | |
| Mandarins (Calamondins, Clementines, Cleopatra mandarins, Minneolas, Satsumas/clausellinas, Tangerines/dancy mandarins, Tangors, Other hybrids of Citrus reticulata, not elsewhere mentioned,) | 0110050 | European Union | 0.01* | 05/10/2011 | |
| Others (2) | 0110990 | European Union | 0.01* | 05/10/2011 | |
| Tree nuts | 0120000 | European Union | 0.01* | 05/10/2011 | |
| Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,) | 0120010 | European Union | 0.01* | 05/10/2011 | |
| Brazil nuts | 0120020 | European Union | 0.01* | 05/10/2011 | |
| Cashew nuts | 0120030 | European Union | 0.01* | 05/10/2011 | |
| Chestnuts | 0120040 | European Union | 0.01* | 05/10/2011 | |
| Coconuts (Areca nuts/betel nuts,) | 0120050 | European Union | 0.01* | 05/10/2011 | |
| Hazelnuts/cobnuts (Acorns, Filberts,) | 0120060 | European Union | 0.01* | 05/10/2011 | |
| Macadamias | 0120070 | European Union | 0.01* | 05/10/2011 | |
| Pecans (Hickory nuts,) | 0120080 | European Union | 0.01* | 05/10/2011 | |
| Pistachios | 0120100 | European Union | 0.01* | 05/10/2011 | |
| Walnuts | 0120110 | European Union | 0.01* | 05/10/2011 | |
| Others (2) | 0120990 | European Union | 0.01* | 05/10/2011 | |
| Pome fruits | 0130000 | European Union | 0.01* | 05/10/2011 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Development and validation of an LC-MS/MS method for the quantification oftiamulin, trimethoprim, tylosin, sulfadiazine and sulfamethazine in medicatedfeed. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2018May | 29324179 |
| Comparison of migration disturbance potency of epigallocatechin gallate (EGCG) synthetic analogs and EGCG PEGylated PLGA nanoparticles in rat neurospheres. | Food Chem Toxicol | 2018 Oct 24 | 30367911 |
| Enantioselective Toxicity in Adult Zebrafish ( Danio rerio) Induced by Chiral PCB91 through Multiple Pathways. | Environ Sci Technol | 2018 May 1 | 29641891 |
| Polychlorinated biphenyl concentrations in pooled serum from people in different age groups from five Chinese cities. | Chemosphere | 2018 May | 29421746 |
| Concentrations and trophic magnification of polychlorinated naphthalenes (PCNs) in marine fish from the Bohai coastal area, China. | Environ Pollut | 2018 Mar | 29248855 |
| Acute and subchronic toxicities in dogs and genotoxicity of honokiol microemulsion. | Regul Toxicol Pharmacol | 2018 Jun | 29655856 |
| Multi-elemental composition and antioxidant properties of strawberry tree (Arbutus unedo L.) honey from the coastal region of Croatia: Risk-benefit analysis. | J Trace Elem Med Biol | 2018 Jan | 29173488 |
| Simultaneous determination of eight cyclopolypeptide antibiotics in feed by high performance liquid chromatography coupled with evaporation light scatteringdetection. | J Chromatogr B Analyt Technol Biomed Life Sci | 2018 Feb 15 | 29406023 |
| Temporal trends in dioxin-like polychlorinated biphenyl concentrations in serum from the general population of Shandong Province, China: A longitudinal study from 2011 to 2017. | Environ Pollut | 2018 Dec | 30172124 |
| Covalent triazine-based framework for micro solid-phase extraction of parabens. | J Chromatogr A | 2018 Aug 31 | 29921466 |
| Integrated transcriptomics and metabolomics reveal signatures of lipid metabolism dysregulation in HepaRG liver cells exposed to PCB 126. | Arch Toxicol | 2018 Aug | 29947894 |
| Sources of polychlorinated dibenzo-p-dioxins and dibenzofurans, and biphenyls in Chinese mitten crabs. | Chemosphere | 2018 Apr | 29329084 |
| Enantioseparation and identification for the rationalization of the environmental impact of 4 polychlorinated biphenyls. | Chirality | 2018 Apr | 29315818 |
| New Insights into SN-38 Glucuronidation: Evidence for the Important Role of UDP Glucuronosyltransferase 1A9. | Basic Clin Pharmacol Toxicol | 2018 Apr | 29076612 |
| Formulation and physiochemical study of α-tocopherol based oil in water nanoemulsion stabilized with non toxic, biodegradable surfactant: Sodium stearoyl lactate. | Ultrason Sonochem | 2017 Sep | 27566966 |
| Insights into the genomic plasticity of Pseudomonas putida KF715, a strain withunique biphenyl-utilizing activity and genome instability properties. | Environ Microbiol Rep | 2017 Oct | 28631340 |
| Deciphering the influence of column chemistry and mass spectrometry settings for the analyses of geometrical isomers of L-chicoric acid. | J Chromatogr B Analyt Technol Biomed Life Sci | 2017 May 1 | 28364699 |
| Bacteria Associated to Plants Naturally Selected in a Historical PCB PollutedSoil Show Potential to Sustain Natural Attenuation. | Front Microbiol | 2017 Jul 25 | 28790991 |
| Phyto-rhizoremediation of polychlorinated biphenyl contaminated soils: An outlook on plant-microbe beneficial interactions. | Sci Total Environ | 2017 Jan 1 | 27717569 |
| Structure-Antioxidative and Anti-Inflammatory Activity Relationships of Purpurin and Related Anthraquinones in Chemical and Cell Assays. | Molecules | 2017 Feb 10 | 28208613 |
Targets
- 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
- Mechanism of Action:
- Causes endocrine disruption in humans by binding to and inhibiting the estrogen receptor.
References
- Taccone-Gallucci M, Manca-di-Villahermosa S, Battistini L, Stuffler RG, Tedesco M, Maccarrone M: N-3 PUFAs reduce oxidative stress in ESRD patients on maintenance HD by inhibiting 5-lipoxygenase activity. Kidney Int. 2006 Apr;69(8):1450-4. [16531984 ]
- General Function:
- Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
- 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. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
- Gene Name:
- CYP1A2
- Uniprot ID:
- P05177
- Molecular Weight:
- 58293.76 Da
References
- Korhonen LE, Rahnasto M, Mahonen NJ, Wittekindt C, Poso A, Juvonen RO, Raunio H: Predictive three-dimensional quantitative structure-activity relationship of cytochrome P450 1A2 inhibitors. J Med Chem. 2005 Jun 2;48(11):3808-15. [15916432 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Binds to an ERR-alpha response element (ERRE) containing a single consensus half-site, 5'-TNAAGGTCA-3'. Can bind to the medium-chain acyl coenzyme A dehydrogenase (MCAD) response element NRRE-1 and may act as an important regulator of MCAD promoter. Binds to the C1 region of the lactoferrin gene promoter. Requires dimerization and the coactivator, PGC-1A, for full activity. The ERRalpha/PGC1alpha complex is a regulator of energy metabolism. Induces the expression of PERM1 in the skeletal muscle.
- Gene Name:
- ESRRA
- Uniprot ID:
- P11474
- Molecular Weight:
- 45509.11 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
- Mechanism of Action:
- Causes endocrine disruption in humans by binding to and inhibiting the estrogen receptor.
References
- Taccone-Gallucci M, Manca-di-Villahermosa S, Battistini L, Stuffler RG, Tedesco M, Maccarrone M: N-3 PUFAs reduce oxidative stress in ESRD patients on maintenance HD by inhibiting 5-lipoxygenase activity. Kidney Int. 2006 Apr;69(8):1450-4. [16531984 ]
- General Function:
- Oxygen binding
- 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, retinoid and xenobiotics. Preferentially oxidizes 17beta-estradiol to the carcinogenic 4-hydroxy derivative, and a variety of procarcinogenic compounds to their activated forms, including polycyclic aromatic hydrocarbons. Promotes angiogenesis by removing cellular oxygenation products, thereby decreasing oxidative stress, release of antiangiogenic factor THBS2, then allowing endothelial cells migration, cell adhesion and capillary morphogenesis. These changes are concommitant with the endothelial nitric oxide synthase activity and nitric oxide synthesis. Plays an important role in the regulation of perivascular cell proliferation, migration, and survival through modulation of the intracellular oxidative state and NF-kappa-B expression and/or activity, during angiogenesis. Contributes to oxidative homeostasis and ultrastructural organization and function of trabecular meshwork tissue through modulation of POSTN expression.
- Gene Name:
- CYP1B1
- Uniprot ID:
- Q16678
- Molecular Weight:
- 60845.33 Da
References
- Shimada T, Tanaka K, Takenaka S, Foroozesh MK, Murayama N, Yamazaki H, Guengerich FP, Komori M: Reverse type I binding spectra of human cytochrome P450 1B1 induced by flavonoid, stilbene, pyrene, naphthalene, phenanthrene, and biphenyl derivatives that inhibit catalytic activity: a structure-function relationship study. Chem Res Toxicol. 2009 Jul;22(7):1325-33. doi: 10.1021/tx900127s. [19563207 ]