PHENOL
Relevant Data
Food Additives Approved by WHO:
Flavouring Substances Approved by European Union:
General Information
| Mainterm | PHENOL |
| Doc Type | ASP |
| CAS Reg.No.(or other ID) | 108-95-2 |
| Regnum |
175.105 175.300 176.170 175.380 175.390 177.1210 177.2600 177.2410 177.1580 |
From www.fda.gov
Computed Descriptors
Download SDF| 2D Structure | |
| CID | 996 |
| IUPAC Name | phenol |
| InChI | InChI=1S/C6H6O/c7-6-4-2-1-3-5-6/h1-5,7H |
| InChI Key | ISWSIDIOOBJBQZ-UHFFFAOYSA-N |
| Canonical SMILES | C1=CC=C(C=C1)O |
| Molecular Formula | C6H6O |
| Wikipedia | phenol |
From Pubchem
Computed 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 |
| CACTVS Substructure Key Fingerprint | A A A D c Y B g I A A A A A A A A A A A A A A A A A A A A A A A A A A w A A A A A A A A A A A B A A A A G g A A C A A A C A S A k A A w B o A A A g C A A C B C A A A C A A A g I A A I i A A G C I g I J i K C E R K A c A A k w B E I m A e A Q A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A = = |
| Topological Polar Surface Area | 20.2 |
| Monoisotopic Mass | 94.042 |
| Exact Mass | 94.042 |
| Compound Is Canonicalized | True |
| 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 |
From Pubchem
Food Additives Biosynthesis/Degradation
ADMET Predicted Profile --- Classification
| 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 |
From admetSAR
ADMET Predicted Profile --- Regression
| 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 |
From admetSAR
Toxicity Profile
| Route of Exposure | Inhalation ; oral ; dermal ; eye contact |
|---|---|
| Mechanism of Toxicity | Phenol is irritating and corrosive at high concentrations. Phenol impairs the stratum corneum and produces coagulation necrosis by denaturing and precipitating proteins. It is suggested that dermal application of phenol increases the formation of free radicals in the skin, and that the redox cycling of these radicals reduces antioxidant capacity, leading to significant oxidative damage of protein, DNA, and lipids. Phenol also act as a cyclooxygenase inhibitor. |
| Metabolism | When it is absorbed through the lungs, gut, or skin, phenol conjugated at the portal-of-entry and free phenol enter the bloodstream where it can then be distributed throughout the body. The dilution of phenol in water enhances the dermal absorption of phenol. Three different enzymes systems catalyze the reactions that transform phenol. Cytosolic phenol sulfotransferases catalyze the transfer of inorganic sulfur from the activated 3'-phosphoadenosine-5'phosphosulfate donor molecule to the hydroxyl group on phenol. Microsomal membrane-located uridine diphosphate (UDP) glucuronosyltransferases catalyze the transfer of an activated glucuronic acid molecule to the hydroxyl moiety of phenol to form an O-glucuronide conjugate. Cytochrome P4502E1, also microsomally located, catalyzes the hydroxylation of phenol to form hydroquinone (and to a much lesser extent, catechol), which is then acted upon by the phase II enzymes. Hydroquinone can, in turn, form conjugates, undergo peroxidation to form benzoquinone, or undergo further oxidation to form trihydroxybenzene. All three enzyme systems that metabolize phenol are found in multiple tissues and there is competition among them not only for phenol, but also for subsequent oxidative products, like hydroquinone. As a consequence, the relative amount of the products formed can vary based on species, dose and route of administration. Cytochromes other than CYP2E1, such as CYP2F2 are suggested to participate in the phenol metabolism in the liver. Tyrosinase also catalyzes the oxidation of phenols. The gastrointestinal tract, liver, lung, and kidney appear to be the major sites of phenol sulfate and glucuronide conjugation of simple phenols. Phenol, in its free and conjugated forms, is a normal constituent of human urine. |
| Toxicity Values | LD50: 400 mg/kg/day (Oral, Rat) LD50: 669 mg/cm2/day (Dermal, Rat) LD50: 1400 mg/cm2/day (Dermal, Rabbit) |
| Lethal Dose | None |
| Carcinogenicity (IARC Classification) | 3, not classifiable as to its carcinogenicity to humans. |
| Minimum Risk Level | Acute Oral: 1 mg/kg/day (Rat) |
| Health Effects | Long-term exposure to phenol at work has been associated with cardiovascular disease, irritation of the respiratory tract and muscle twitching depedning of the route of exposure. Ingestion of liquid products containing concentrated phenol can cause serious gastrointestinal damage and even death. Application of concentrated phenol to the skin can cause severe skin damage. Longer-term exposure to high levels of phenol caused damaged to the heart, kidneys, liver, and lungs. Liver effects, as judged by increased serum activities of alanine aminotransferase (ALT) and aspartate amino transferase (AST), were also reported in a case of prolonged inhalation exposure to phenol. (L624) |
| Treatment | None |
| Reference |
|
From T3DB
Taxonomic Classification
| 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. |
From ClassyFire
Targets
- General Function:
- Zinc ion binding
- Specific Function:
- Reversible hydration of carbon dioxide.
- Gene Name:
- CA13
- Uniprot ID:
- Q8N1Q1
- Molecular Weight:
- 29442.895 Da
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
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:
- CA12
- Uniprot ID:
- O43570
- Molecular Weight:
- 39450.615 Da
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
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:
- 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
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
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
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
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
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
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
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
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:
- Metalloendopeptidase activity
- Specific Function:
- Extracellular zinc metalloprotease.
- Gene Name:
- nprS
- Uniprot ID:
- P43133
- Molecular Weight:
- 60616.22 Da
- General Function:
- Lysozyme activity
- Specific Function:
- Endolysin with lysozyme activity that degrades host peptidoglycans and participates with the holin and spanin proteins in the sequential events which lead to the programmed host cell lysis releasing the mature viral particles. Once the holin has permeabilized the host cell membrane, the endolysin can reach the periplasm and break down the peptidoglycan layer.
- Gene Name:
- E
- Uniprot ID:
- P00720
- Molecular Weight:
- 18691.385 Da
- General Function:
- Nicotinate-nucleotide-dimethylbenzimidazole phosphoribosyltransferase activity
- Specific Function:
- Catalyzes the synthesis of alpha-ribazole-5'-phosphate from nicotinate mononucleotide (NAMN) and 5,6-dimethylbenzimidazole (DMB).
- Gene Name:
- cobT
- Uniprot ID:
- Q05603
- Molecular Weight:
- 36612.305 Da
- General Function:
- Toxic substance binding
- Specific Function:
- Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloidal osmotic pressure of blood. Major zinc transporter in plasma, typically binds about 80% of all plasma zinc.
- Gene Name:
- ALB
- Uniprot ID:
- P02768
- Molecular Weight:
- 69365.94 Da
From T3DB