4-Aminophenol
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Basic Info
| Common Name | 4-Aminophenol(F04875) |
| 2D Structure | |
| Description | 4-Aminophenol is an amphoteric molecule and a reducing agent. Aminophenols are intermediates in the synthesis of dyes and can thus be found in numerous cosmetics products, particularly hair dyes. 4-aminophenol is considered a minor nephrotoxic metabolite of phenacetin and acetaminophen (paracetamol) in man. 4-Aminophenol can undergo autoxidations and metal-catalyzed and enzymatic oxidations in man to produce reactive oxygen species. (A7848) (L1882) |
| FRCD ID | F04875 |
| CAS Number | 123-30-8 |
| PubChem CID | 403 |
| Formula | C6H7NO |
| IUPAC Name | 4-aminophenol |
| InChI Key | PLIKAWJENQZMHA-UHFFFAOYSA-N |
| InChI | InChI=1S/C6H7NO/c7-5-1-3-6(8)4-2-5/h1-4,8H,7H2 |
| Canonical SMILES | C1=CC(=CC=C1N)O |
| Isomeric SMILES | C1=CC(=CC=C1N)O |
| Wikipedia | 4-Aminophenol |
| Synonyms |
4-aminophenol
p-aminophenol
123-30-8
4-hydroxyaniline
p-hydroxyaniline
Phenol, 4-amino-
Paranol
4-aminobenzenol
Certinal
Citol
|
| Classifies |
Predicted: Plant Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Benzene and substituted derivatives |
| Subclass | Aniline and substituted anilines |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Aniline and substituted anilines |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | P-aminophenol - Aniline or substituted anilines - Aminophenol - 1-hydroxy-2-unsubstituted benzenoid - Phenol - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Hydrocarbon derivative - Primary amine - Organooxygen compound - Organonitrogen compound - Amine - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as aniline and substituted anilines. These are organic compounds containing an aminobenzene moiety. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 109.128 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 0 |
| Complexity | 66.9 |
| Monoisotopic Mass | 109.053 |
| Exact Mass | 109.053 |
| XLogP | 0 |
| Formal Charge | 0 |
| Heavy Atom Count | 8 |
| 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+ | 0.7269 |
| Human Intestinal Absorption | HIA+ | 0.9739 |
| Caco-2 Permeability | Caco2+ | 0.6438 |
| P-glycoprotein Substrate | Non-substrate | 0.8354 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9880 |
| Non-inhibitor | 0.9851 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8898 |
| Distribution | ||
| Subcellular localization | Nucleus | 0.3808 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8411 |
| CYP450 2D6 Substrate | Non-substrate | 0.6626 |
| CYP450 3A4 Substrate | Non-substrate | 0.7507 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.7881 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.8386 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9774 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.7637 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8334 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.8152 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9106 |
| Non-inhibitor | 0.9408 | |
| AMES Toxicity | AMES toxic | 0.6650 |
| Carcinogens | Non-carcinogens | 0.6728 |
| Fish Toxicity | High FHMT | 0.5068 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.7591 |
| Honey Bee Toxicity | Low HBT | 0.5059 |
| Biodegradation | Not ready biodegradable | 0.7851 |
| Acute Oral Toxicity | II | 0.7651 |
| Carcinogenicity (Three-class) | Non-required | 0.6087 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -0.4323 | LogS |
| Caco-2 Permeability | 1.1206 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.4324 | LD50, mol/kg |
| Fish Toxicity | 2.3390 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.0451 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Highly Uniform Gold Nanobipyramids for Ultrasensitive Colorimetric Detection ofInfluenza Virus. | Anal Chem | 2017 Feb 7 | 28208287 |
| Colorimetric Detection of Escherichia coli Based on the Enzyme-InducedMetallization of Gold Nanorods. | Small | 2016 May | 26997252 |
| Visual and colorimetric detection of p-aminophenol in environmental water andhuman urine samples based on anisotropic growth of Ag nanoshells on Au nanorods. | Talanta | 2016 | 26653424 |
| In vitro safety assessment of food ingredients in canine renal proximal tubule cells. | Toxicol In Vitro | 2015 Mar | 25458622 |
| Fibrillar networks of glycyrrhizic acid for hybrid nanomaterials with catalyticfeatures. | Angew Chem Int Ed Engl | 2015 Apr 27 | 25759108 |
| Laccase-Prussian blue film-graphene doped carbon paste modified electrode forcarbamate pesticides quantification. | Biosens Bioelectron | 2013 Sep 15 | 23587791 |
| Ultra sensitive microfluidic immunosensor for determination of clenbuterol inbovine hair samples using electrodeposited gold nanoparticles and magnetic micro particles as bio-affinity platform. | Biosens Bioelectron | 2013 Mar 15 | 22975092 |
| Biosensor based on multi-walled carbon nanotubes paste electrode modified withlaccase for pirimicarb pesticide quantification. | Talanta | 2013 Mar 15 | 23598106 |
| Selective determination of catechin among phenolic antioxidants with the use of anovel optical fiber reflectance sensor based on indophenol dye formation onnano-sized TiO₂. | J Agric Food Chem | 2012 Mar 21 | 22339278 |
| Enzyme-free electrochemical immunoassay with catalytic reduction of p-nitrophenoland recycling of p-aminophenol using gold nanoparticles-coated carbon nanotubesas nanocatalysts. | Biosens Bioelectron | 2011 Mar 15 | 21216587 |
| A novel strategy for ultra-sensitive electrochemical immunoassay of biomarkers bycoupling multifunctional iridium oxide (IrO(x)) nanospheres with catalyticrecycling of self-produced reactants. | Anal Bioanal Chem | 2011 Jun | 21461861 |
| Reproductive and developmental toxicity screening study of 4-aminophenol in rats. | Drug Chem Toxicol | 2008 | 18850357 |
| Generation of quinoneimine intermediates in the bioactivation of 3-(N-phenylamino)alanine (PAA) by human liver microsomes: a potential link between eosinophilia-myalgia syndrome and toxic oil syndrome. | Chem Res Toxicol | 2007 Oct | 17892268 |
| Metabolism of (R)- and (S)-3-(phenylamino)propane-1,2-diol in C57BL/6- and A/J-strain mice. Identification of new metabolites with potential toxicological significance to the toxic oil syndrome. | Chem Res Toxicol | 2001 Aug | 11511184 |
| Analysis of the metabolites of the sodium salt of6-hydroxy-5-(phenylazo)-2-naphthalenesulfonic acid in Sprague-Dawley rat urine. | J Chromatogr B Biomed Sci Appl | 2001 Apr 25 | 11339284 |
| Effect of dietary 2(3)-tert-butyl-4-hydroxyanisole on the metabolism and actionof estradiol and estrone in female CD-1 mice. | Cancer Res | 1997 Jun 15 | 9192820 |
Targets
- General Function:
- Oxygen transporter activity
- Specific Function:
- Involved in oxygen transport from the lung to the various peripheral tissues.LVV-hemorphin-7 potentiates the activity of bradykinin, causing a decrease in blood pressure.Spinorphin: functions as an endogenous inhibitor of enkephalin-degrading enzymes such as DPP3, and as a selective antagonist of the P2RX3 receptor which is involved in pain signaling, these properties implicate it as a regulator of pain and inflammation.
- Gene Name:
- HBB
- Uniprot ID:
- P68871
- Molecular Weight:
- 15998.34 Da
- Mechanism of Action:
- Edit4-Aminophenol interacts with both adult and fetal hemoglobin, forming methemoglobin. In comparison to its isomers, 2-aminophenol and 3-aminophenol, 4-aminophenol is the second most effective in forming methemoglobin. Since methemoglobin cannot bind oxygen like hemoglobin can, elevated levels of methemoglobin cause a condition called methemoglobinemia, which can result in tissue hypoxia.
References
- Coghlin J, Gann PH, Hammond SK, Skipper PL, Taghizadeh K, Paul M, Tannenbaum SR: 4-Aminobiphenyl hemoglobin adducts in fetuses exposed to the tobacco smoke carcinogen in utero. J Natl Cancer Inst. 1991 Feb 20;83(4):274-80. [1994056 ]
- 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
- Mechanism of Action:
- 4-Aminobiphenyl requires metabolic activation in order to exert its toxicity. This is catalyzed by N-hydroxylation via cytochrome P450 1A2, then followed by O-sulfation and O-acetylation by sulfotransferase 1A1 and arylamine N-acetyltransferase 2. The metabolites of 4-aminobiphenyl then form adducts with DNA, inducing mutations. 4-Aminobiphenyl and its metabolites may also cross the placenta and have fetal effects. (1, 2, 3, 4). It is also though that the mode of action involves metabolic activation by N-hydroxylation, followed by N-esterification leading to the formation of a reactive electrophile, which binds covalently to DNA, principally to deoxyguanosine, leading to an increased rate of DNA mutations and ultimately to the development of cancer. In humans and dogs, the urinary bladder urothelium is the target organ, whereas in mice it is the bladder and liver; in other species, other tissues can be involved. Differences in organ specificity are thought to be due to differences in metabolic activation versus inactivation (, A15085).
References
- Landi MT, Zocchetti C, Bernucci I, Kadlubar FF, Tannenbaum S, Skipper P, Bartsch H, Malaveille C, Shields P, Caporaso NE, Vineis P: Cytochrome P4501A2: enzyme induction and genetic control in determining 4-aminobiphenyl-hemoglobin adduct levels. Cancer Epidemiol Biomarkers Prev. 1996 Sep;5(9):693-8. [8877060 ]
- General Function:
- Oxygen transporter activity
- Specific Function:
- Involved in oxygen transport from the lung to the various peripheral tissues.
- Gene Name:
- HBA1
- Uniprot ID:
- P69905
- Molecular Weight:
- 15257.405 Da
- Mechanism of Action:
- 4-Aminophenol interacts with both adult and fetal hemoglobin, forming methemoglobin. In comparison to its isomers, 2-aminophenol and 3-aminophenol, 4-aminophenol is the second most effective in forming methemoglobin. Since methemoglobin cannot bind oxygen like hemoglobin can, elevated levels of methemoglobin cause a condition called methemoglobinemia, which can result in tissue hypoxia.
References
- Coghlin J, Gann PH, Hammond SK, Skipper PL, Taghizadeh K, Paul M, Tannenbaum SR: 4-Aminobiphenyl hemoglobin adducts in fetuses exposed to the tobacco smoke carcinogen in utero. J Natl Cancer Inst. 1991 Feb 20;83(4):274-80. [1994056 ]
- General Function:
- Arylamine n-acetyltransferase activity
- Specific Function:
- Participates in the detoxification of a plethora of hydrazine and arylamine drugs. Catalyzes the N- or O-acetylation of various arylamine and heterocyclic amine substrates and is able to bioactivate several known carcinogens.
- Gene Name:
- NAT2
- Uniprot ID:
- P11245
- Molecular Weight:
- 33542.235 Da
- Mechanism of Action:
- 4-Aminobiphenyl requires metabolic activation in order to exert its toxicity. This is catalyzed by N-hydroxylation via cytochrome P450 1A2, then followed by O-sulfation and O-acetylation by sulfotransferase 1A1 and arylamine N-acetyltransferase 2. The metabolites of 4-aminobiphenyl then form adducts with DNA, inducing mutations. 4-Aminobiphenyl and its metabolites may also cross the placenta and have fetal effects. (1, 2, 3, 4). It is also though that the mode of action involves metabolic activation by N-hydroxylation, followed by N-esterification leading to the formation of a reactive electrophile, which binds covalently to DNA, principally to deoxyguanosine, leading to an increased rate of DNA mutations and ultimately to the development of cancer. In humans and dogs, the urinary bladder urothelium is the target organ, whereas in mice it is the bladder and liver; in other species, other tissues can be involved. Differences in organ specificity are thought to be due to differences in metabolic activation versus inactivation (, A15085).
References
- Jiang X, Yuan JM, Skipper PL, Tannenbaum SR, Yu MC: Environmental tobacco smoke and bladder cancer risk in never smokers of Los Angeles County. Cancer Res. 2007 Aug 1;67(15):7540-5. [17671226 ]
- General Function:
- Sulfotransferase activity
- Specific Function:
- Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of catecholamines, phenolic drugs and neurotransmitters. Has also estrogen sulfotransferase activity. responsible for the sulfonation and activation of minoxidil. Is Mediates the metabolic activation of carcinogenic N-hydroxyarylamines to DNA binding products and could so participate as modulating factor of cancer risk.
- Gene Name:
- SULT1A1
- Uniprot ID:
- P50225
- Molecular Weight:
- 34165.13 Da
- Mechanism of Action:
- 4-Aminobiphenyl requires metabolic activation in order to exert its toxicity. This is catalyzed by N-hydroxylation via cytochrome P450 1A2, then followed by O-sulfation and O-acetylation by sulfotransferase 1A1 and arylamine N-acetyltransferase 2. The metabolites of 4-aminobiphenyl then form adducts with DNA, inducing mutations. 4-Aminobiphenyl and its metabolites may also cross the placenta and have fetal effects. (1, 2, 3, 4). It is also though that the mode of action involves metabolic activation by N-hydroxylation, followed by N-esterification leading to the formation of a reactive electrophile, which binds covalently to DNA, principally to deoxyguanosine, leading to an increased rate of DNA mutations and ultimately to the development of cancer. In humans and dogs, the urinary bladder urothelium is the target organ, whereas in mice it is the bladder and liver; in other species, other tissues can be involved. Differences in organ specificity are thought to be due to differences in metabolic activation versus inactivation
References
- Ozawa S, Katoh T, Inatomi H, Imai H, Kuroda Y, Ichiba M, Ohno Y: Association of genotypes of carcinogen-activating enzymes, phenol sulfotransferase SULT1A1 (ST1A3) and arylamine N-acetyltransferase NAT2, with urothelial cancer in a Japanese population. Int J Cancer. 2002 Dec 1;102(4):418-21. [12402313 ]