Phenol
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Basic Info
| Common Name | Phenol(F03413) |
| 2D Structure | |
| Description | Phenol, is a toxic, colourless crystalline solid with a sweet tarry odor that resembles a hospital smell. It is commonly used as an antiseptic and disinfectant. It is active against a wide range of micro-organisms including some fungi and viruses, but is only slowly effective against spores. It has been used to disinfect skin and to relieve itching. Phenol is also used in the preparation of cosmetics including sunscreens, hair dyes, and skin lightening preparations. It is also used in the production of drugs (it is the starting material in the industrial production of aspirin), weedkillers, and synthetic resins. Phenol can be found in areas with high levels of motor traffic, therefore, people living in crowded urban areas are frequently exposed to traffic-derived phenol vapor. The average (mean +/- SD) phenol concentration in urine among normal individuals living in urban areas is 7.4 +/- 2.2 mg/g of creatinine. Exposure of the skin to concentrated phenol solutions causes chemical burns which may be severe; in laboratories where it is used, it is usually recommended that polyethylene glycol solution is kept available for washing off splashes. Notwithstanding the effects of concentrated solutions, it is also used in cosmetic surgery as an exfoliant, to remove layers of dead skin (Wikipedia). In some bacteria phenol can be directly synthesized from tyrosine via the enzyme tyrosine phenol-lyase [EC:4.1.99.2]. |
| FRCD ID | F03413 |
| CAS Number | 108-95-2 |
| PubChem CID | 996 |
| Formula | C6H6O |
| IUPAC Name | phenol |
| InChI Key | ISWSIDIOOBJBQZ-UHFFFAOYSA-N |
| InChI | InChI=1S/C6H6O/c7-6-4-2-1-3-5-6/h1-5,7H |
| Canonical SMILES | C1=CC=C(C=C1)O |
| Isomeric SMILES | C1=CC=C(C=C1)O |
| Wikipedia | Phenol |
| Synonyms |
carbolic acid
phenol
Hydroxybenzene
108-95-2
Phenic acid
Phenylic acid
Oxybenzene
Benzenol
Phenyl hydrate
Monophenol
|
| Classifies |
Pollutant
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Phenols |
| Subclass | 1-hydroxy-4-unsubstituted benzenoids |
| Intermediate Tree Nodes | Not available |
| Direct Parent | 1-hydroxy-4-unsubstituted benzenoids |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Monocyclic benzene moiety - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as 1-hydroxy-4-unsubstituted benzenoids. These are phenols that are unsubstituted at the 4-position. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 94.113 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 1 |
| Rotatable Bond Count | 0 |
| Complexity | 46.1 |
| Monoisotopic Mass | 94.042 |
| Exact Mass | 94.042 |
| XLogP | 1.5 |
| Formal Charge | 0 |
| Heavy Atom Count | 7 |
| 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+ | 0.9076 |
| Human Intestinal Absorption | HIA+ | 0.9931 |
| Caco-2 Permeability | Caco2+ | 0.9326 |
| P-glycoprotein Substrate | Non-substrate | 0.8082 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9790 |
| Non-inhibitor | 0.9917 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8704 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.7339 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7898 |
| CYP450 2D6 Substrate | Non-substrate | 0.9116 |
| CYP450 3A4 Substrate | Non-substrate | 0.7558 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.6114 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9654 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9746 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.8981 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9523 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.8695 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.8468 |
| Non-inhibitor | 0.9666 | |
| AMES Toxicity | Non AMES toxic | 0.9454 |
| Carcinogens | Non-carcinogens | 0.7594 |
| Fish Toxicity | High FHMT | 0.6721 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.8899 |
| Honey Bee Toxicity | High HBT | 0.8395 |
| Biodegradation | Ready biodegradable | 0.7488 |
| Acute Oral Toxicity | II | 0.7632 |
| Carcinogenicity (Three-class) | Non-required | 0.6029 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -0.1541 | LogS |
| Caco-2 Permeability | 1.7116 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.5044 | LD50, mol/kg |
| Fish Toxicity | 1.4802 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | -0.0634 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Screening of potential bioremediation enzymes from hot spring bacteria using conventional plate assays and liquid chromatography - Tandem mass spectrometry (Lc-Ms/Ms). | J Environ Manage | 2018 Oct 1 | 29986326 |
| Evaluation of Probiotic Potential and Safety Assessment of Lactobacillus pentosusMMP4 Isolated From Mare's Lactation. | Probiotics Antimicrob Proteins | 2018 May 30 | 29846884 |
| Agronomical, biochemical and histological response of resistant and susceptiblewheat and barley under BYDV stress. | PeerJ | 2018 May 28 | 29868264 |
| Exotoxin diversity of Staphylococcus aureus isolated from milk of cows with subclinical mastitis in Central Russia. | J Dairy Sci | 2018 May | 29477514 |
| Chromatographic fingerprinting through chemometric techniques for herbal slimming pills: A way of adulterant identification. | Forensic Sci Int | 2018 May | 29602149 |
| Rhodomyrtone (Rom) is a membrane-active compound. | Biochim Biophys Acta | 2018 May | 29317198 |
| Bifunctional supported ionic liquid-based smart films for dyes adsorption andphotodegradation. | J Colloid Interface Sci | 2018 Jun 30 | 29982022 |
| Low-cost iron-doped catalyst for phenol degradation by heterogeneous Fenton. | J Hazard Mater | 2018 Jul 9 | 30014919 |
| Degradation and decolourization potential of an ligninolytic enzyme producingAeromonas hydrophila for crystal violet dye and its phytotoxicity evaluation. | Ecotoxicol Environ Saf | 2018 Jul 30 | 29550434 |
| Influence of inherent hierarchical porous char with alkali and alkaline earthmetallic species on lignin pyrolysis. | Bioresour Technol | 2018 Jul 25 | 30092486 |
| Phytochemical, Free Radical Scavenging and Antifungal Profile of Cuscutacampestris Yunck. Seeds. | Chem Biodivers | 2018 Jul 19:e1800174 | 29874415 |
| Persistence of thiacloprid and deltamethrin residues in tea grown at differentlocations of North-East India. | Food Chem | 2018 Jul 1 | 29502848 |
| Extended internal standard method for quantitative 1H NMR assisted bychromatography (EIC) for analyte overlapping impurity on 1H NMR spectra. | Talanta | 2018 Jul 1 | 29674072 |
| Fast and simple determination and exposure assessment of bisphenol A, phenol,p-tert-butylphenol, and diphenylcarbonate transferred from polycarbonatefood-contact materials to food simulants. | Chemosphere | 2018 Jul | 29625319 |
| Extracts from the edible seaweed, Ascophyllum nodosum, inhibit lipase activity invitro: contributions of phenolic and polysaccharide components. | Food Funct | 2018 Jan 24 | 29243753 |
| Anaerobic detoxification fermentation by Rhodospirillum rubrum for rice straw as feed with moderate pretreatment. | Prep Biochem Biotechnol | 2018 Jan 2 | 29194020 |
| Semisynthetic Phenol Derivatives Obtained from Natural Phenols: AntimicrobialActivity and Molecular Properties. | J Agric Food Chem | 2018 Jan 10 | 29286652 |
| Necrotic enteritis challenge and high dietary sodium level affect odorantcomposition or emission from broilers. | Poult Sci | 2018 Jan 1 | 29077885 |
| [A new strategy for enhancing acanthamoebicidal activity with synthesis of nanoflower of Laurocerausus officinalis Roemer (cherry laurel) fruit extracts]. | Mikrobiyol Bul | 2018 Jan | 29642830 |
| Subacute Inhalation Toxicity of Cyclohexanone in B6C3F1 Mice. | Toxicol Res | 2018 Jan | 29372001 |
Targets
- General Function:
- Zinc ion binding
- Specific Function:
- Reversible hydration of carbon dioxide.
- Gene Name:
- CA12
- Uniprot ID:
- O43570
- Molecular Weight:
- 39450.615 Da
- Mechanism of Action:
- Phenol acts as an effective, low micromolar inhibitor of isozyme hCAXII.
References
- Innocenti A, Vullo D, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: interactions of phenols with the 12 catalytically active mammalian isoforms (CA I-XIV). Bioorg Med Chem Lett. 2008 Mar 1;18(5):1583-7. doi: 10.1016/j.bmcl.2008.01.077. Epub 2008 Jan 26. [18242985 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Reversible hydration of carbon dioxide.
- Gene Name:
- CA13
- Uniprot ID:
- Q8N1Q1
- Molecular Weight:
- 29442.895 Da
- Mechanism of Action:
- Phenol acts as an effective, low inhibitor(in the millimolar range) of isozyme hCAXIV.
References
- Innocenti A, Vullo D, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: interactions of phenols with the 12 catalytically active mammalian isoforms (CA I-XIV). Bioorg Med Chem Lett. 2008 Mar 1;18(5):1583-7. doi: 10.1016/j.bmcl.2008.01.077. Epub 2008 Jan 26. [18242985 ]
- General Function:
- Metal ion binding
- Specific Function:
- Reversible hydration of carbon dioxide.
- Gene Name:
- CA14
- Uniprot ID:
- Q9ULX7
- Molecular Weight:
- 37667.37 Da
- Mechanism of Action:
- Phenol acts as an effective, low micromolar inhibitor of isozyme hCAXIV.
References
- Innocenti A, Vullo D, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: interactions of phenols with the 12 catalytically active mammalian isoforms (CA I-XIV). Bioorg Med Chem Lett. 2008 Mar 1;18(5):1583-7. doi: 10.1016/j.bmcl.2008.01.077. Epub 2008 Jan 26. [18242985 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Reversible hydration of carbon dioxide.
- Gene Name:
- CA3
- Uniprot ID:
- P07451
- Molecular Weight:
- 29557.215 Da
- Mechanism of Action:
- Phenol acts as an effective, low micromolar inhibitor of isozyme hCAIII.
References
- Innocenti A, Vullo D, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: interactions of phenols with the 12 catalytically active mammalian isoforms (CA I-XIV). Bioorg Med Chem Lett. 2008 Mar 1;18(5):1583-7. doi: 10.1016/j.bmcl.2008.01.077. Epub 2008 Jan 26. [18242985 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Reversible hydration of carbon dioxide. Can hydrates cyanamide to urea.
- Gene Name:
- CA1
- Uniprot ID:
- P00915
- Molecular Weight:
- 28870.0 Da
- Mechanism of Action:
- Phenol acts as an effective, low micromolar inhibitor of isozyme hCAI.
References
- Innocenti A, Vullo D, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: interactions of phenols with the 12 catalytically active mammalian isoforms (CA I-XIV). Bioorg Med Chem Lett. 2008 Mar 1;18(5):1583-7. doi: 10.1016/j.bmcl.2008.01.077. Epub 2008 Jan 26. [18242985 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Reversible hydration of carbon dioxide. May stimulate the sodium/bicarbonate transporter activity of SLC4A4 that acts in pH homeostasis. It is essential for acid overload removal from the retina and retina epithelium, and acid release in the choriocapillaris in the choroid.
- Gene Name:
- CA4
- Uniprot ID:
- P22748
- Molecular Weight:
- 35032.075 Da
- Mechanism of Action:
- Phenol acts as an effective, low micromolar inhibitor of isozyme hCAIV.
References
- Innocenti A, Vullo D, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: interactions of phenols with the 12 catalytically active mammalian isoforms (CA I-XIV). Bioorg Med Chem Lett. 2008 Mar 1;18(5):1583-7. doi: 10.1016/j.bmcl.2008.01.077. Epub 2008 Jan 26. [18242985 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Reversible hydration of carbon dioxide. Low activity.
- Gene Name:
- CA5A
- Uniprot ID:
- P35218
- Molecular Weight:
- 34750.21 Da
- Mechanism of Action:
- Phenol acts as an effective, low inhibitor(in the millimolar range) of isozyme hCAVA.
References
- Innocenti A, Vullo D, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: interactions of phenols with the 12 catalytically active mammalian isoforms (CA I-XIV). Bioorg Med Chem Lett. 2008 Mar 1;18(5):1583-7. doi: 10.1016/j.bmcl.2008.01.077. Epub 2008 Jan 26. [18242985 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Reversible hydration of carbon dioxide.
- Gene Name:
- CA5B
- Uniprot ID:
- Q9Y2D0
- Molecular Weight:
- 36433.43 Da
- Mechanism of Action:
- Phenol acts as an effective, low inhibitor(in the millimolar range) of isozyme hCAVB.
References
- Innocenti A, Vullo D, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: interactions of phenols with the 12 catalytically active mammalian isoforms (CA I-XIV). Bioorg Med Chem Lett. 2008 Mar 1;18(5):1583-7. doi: 10.1016/j.bmcl.2008.01.077. Epub 2008 Jan 26. [18242985 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Reversible hydration of carbon dioxide. Its role in saliva is unknown.
- Gene Name:
- CA6
- Uniprot ID:
- P23280
- Molecular Weight:
- 35366.615 Da
- Mechanism of Action:
- Phenol acts as an effective, low inhibitor(in the millimolar range) of isozyme hCAVI.
References
- Innocenti A, Vullo D, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: interactions of phenols with the 12 catalytically active mammalian isoforms (CA I-XIV). Bioorg Med Chem Lett. 2008 Mar 1;18(5):1583-7. doi: 10.1016/j.bmcl.2008.01.077. Epub 2008 Jan 26. [18242985 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Reversible hydration of carbon dioxide.
- Gene Name:
- CA7
- Uniprot ID:
- P43166
- Molecular Weight:
- 29658.235 Da
- Mechanism of Action:
- Phenol acts as an effective, low inhibitor(in the millimolar range) of isozyme hCAVII.
References
- Innocenti A, Vullo D, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: interactions of phenols with the 12 catalytically active mammalian isoforms (CA I-XIV). Bioorg Med Chem Lett. 2008 Mar 1;18(5):1583-7. doi: 10.1016/j.bmcl.2008.01.077. Epub 2008 Jan 26. [18242985 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Reversible hydration of carbon dioxide. Participates in pH regulation. May be involved in the control of cell proliferation and transformation. Appears to be a novel specific biomarker for a cervical neoplasia.
- Gene Name:
- CA9
- Uniprot ID:
- Q16790
- Molecular Weight:
- 49697.36 Da
- Mechanism of Action:
- Phenol acts as an effective, low micromolar inhibitor of isozyme hCAIX.
References
- Innocenti A, Vullo D, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: interactions of phenols with the 12 catalytically active mammalian isoforms (CA I-XIV). Bioorg Med Chem Lett. 2008 Mar 1;18(5):1583-7. doi: 10.1016/j.bmcl.2008.01.077. Epub 2008 Jan 26. [18242985 ]
- 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
- Ogata N, Shibata T: Binding of alkyl- and alkoxy-substituted simple phenolic compounds to human serum proteins. Res Commun Mol Pathol Pharmacol. 2000;107(1-2):167-73. [11334365 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Essential for bone resorption and osteoclast differentiation (By similarity). Reversible hydration of carbon dioxide. Can hydrate cyanamide to urea. Involved in the regulation of fluid secretion into the anterior chamber of the eye. Contributes to intracellular pH regulation in the duodenal upper villous epithelium during proton-coupled peptide absorption. Stimulates the chloride-bicarbonate exchange activity of SLC26A6.
- Gene Name:
- CA2
- Uniprot ID:
- P00918
- Molecular Weight:
- 29245.895 Da
- Mechanism of Action:
- Phenol acts as an effective, low micromolar inhibitor of isozyme hCAII.
References
- Innocenti A, Vullo D, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: interactions of phenols with the 12 catalytically active mammalian isoforms (CA I-XIV). Bioorg Med Chem Lett. 2008 Mar 1;18(5):1583-7. doi: 10.1016/j.bmcl.2008.01.077. Epub 2008 Jan 26. [18242985 ]