4-Aminobiphenyl
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Basic Info
| Common Name | 4-Aminobiphenyl(F03444) |
| 2D Structure | |
| Description | 4-Aminobiphenyl is an amine derivative of biphenyl. It is used to manufacture azo dyes. It is a known human carcinogen and so it has been largely replaced by less toxic compounds. It is similar to benzidine. |
| FRCD ID | F03444 |
| CAS Number | 92-67-1 |
| PubChem CID | 7102 |
| Formula | C12H11N |
| IUPAC Name | 4-phenylaniline |
| InChI Key | DMVOXQPQNTYEKQ-UHFFFAOYSA-N |
| InChI | InChI=1S/C12H11N/c13-12-8-6-11(7-9-12)10-4-2-1-3-5-10/h1-9H,13H2 |
| Canonical SMILES | C1=CC=C(C=C1)C2=CC=C(C=C2)N |
| Isomeric SMILES | C1=CC=C(C=C1)C2=CC=C(C=C2)N |
| Wikipedia | 4-Aminobiphenyl |
| Synonyms |
4-BIPHENYLAMINE
4-Aminobiphenyl
92-67-1
4-Phenylaniline
4-Aminodiphenyl
Biphenyl-4-ylamine
[1,1'-Biphenyl]-4-amine
biphenyl-4-amine
Xenylamine
p-Phenylaniline
|
| Classifies |
Pollutant
|
| 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 - Aniline or substituted anilines - Organic nitrogen compound - Organopnictogen compound - Hydrocarbon derivative - Primary amine - Organonitrogen compound - Amine - 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 | 169.227 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 1 |
| Rotatable Bond Count | 1 |
| Complexity | 141 |
| Monoisotopic Mass | 169.089 |
| Exact Mass | 169.089 |
| XLogP | 2.9 |
| Formal Charge | 0 |
| Heavy Atom Count | 13 |
| 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+ | 0.9601 |
| Human Intestinal Absorption | HIA+ | 0.9962 |
| Caco-2 Permeability | Caco2+ | 0.8513 |
| P-glycoprotein Substrate | Non-substrate | 0.8706 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9561 |
| Non-inhibitor | 0.9153 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8485 |
| Distribution | ||
| Subcellular localization | Lysosome | 0.6595 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8260 |
| CYP450 2D6 Substrate | Non-substrate | 0.9140 |
| CYP450 3A4 Substrate | Non-substrate | 0.7622 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.7969 |
| CYP450 2C9 Inhibitor | Inhibitor | 0.5990 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.8415 |
| CYP450 2C19 Inhibitor | Inhibitor | 0.8637 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8657 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.7562 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9753 |
| Non-inhibitor | 0.8422 | |
| AMES Toxicity | AMES toxic | 0.9107 |
| Carcinogens | Carcinogens | 0.5719 |
| Fish Toxicity | High FHMT | 0.9348 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9880 |
| Honey Bee Toxicity | Low HBT | 0.6652 |
| Biodegradation | Not ready biodegradable | 0.8880 |
| Acute Oral Toxicity | III | 0.8418 |
| Carcinogenicity (Three-class) | Danger | 0.4316 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.0713 | LogS |
| Caco-2 Permeability | 1.7222 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.4979 | LD50, mol/kg |
| Fish Toxicity | 0.8393 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.8865 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Strong impact of sulfotransferases on DNA adduct formation by 4-aminobiphenyl in bladder and liver in mice. | Cancer Med | 2018 Oct 10 | 30306738 |
| Laccase oxidation and removal of toxicants released during combustion processes. | Chemosphere | 2016 Feb | 26408262 |
| Differential mutagenicity of aflatoxin B1 in the liver of neonatal and adult mice. | Environ Mol Mutagen | 2010 Mar | 19642212 |
| Cytochrome P4501A2: enzyme induction and genetic control in determining 4-aminobiphenyl-hemoglobin adduct levels. | Cancer Epidemiol Biomarkers Prev | 1996 Sep | 8877060 |
Targets
- Specific Function:
- Keratin-binding protein required for epithelial cell polarization. Involved in apical junction complex (AJC) assembly via its interaction with PARD3. Required for ciliogenesis.
- Gene Name:
- FBF1
- Uniprot ID:
- Q8TES7
- Molecular Weight:
- 125445.19 Da
References
- Thier R, Lewalter J, Selinski S, Bolt HM: Biological monitoring in workers in a nitrobenzene reduction plant: haemoglobin versus serum albumin adducts. Int Arch Occup Environ Health. 2001 Sep;74(7):483-8. [11697451 ]