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Record Information
Version2.0
Creation Date2009-03-06 18:58:14 UTC
Update Date2014-12-24 20:21:17 UTC
Accession NumberT3D0182
Identification
Common NamePhenol
ClassSmall Molecule
DescriptionPhenol, 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].
Compound Type
  • Anti-Infective Agent, Local
  • Antipsoriatic Agent
  • Antiseptic Agent
  • Aromatic Hydrocarbon
  • Disinfectant
  • Drug
  • Food Toxin
  • Household Toxin
  • Industrial/Workplace Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
  • Pollutant
  • Sclerosing Solution
Chemical Structure
Thumb
Synonyms
Synonym
Anbesol
Benzenol
Benzophenol
Campho-phenique cold sore gel
Campho-phenique gel
Campho-phenique liquid
Carbolic acid
Carbolic acid liquid
Carbolic oil
Carbolsaeure
Carbolsaure
Cepastat lozenges
Fenol
Fenolo
Fenosmolin
Fenosmoline
Hydroxy-benzene
Hydroxybenzene
IPH
IZAL
Karbolsaeure
Liquid phenol
Liquified phenol
Monohydroxy benzene
Monohydroxybenzene
Monophenol
Oxybenzene
Paoscle
Phenic
Phenic acid
Phenic alcohol
Phenol alcohol
Phenol liquid
Phenolated water
Phenole
Phenosmolin
Phenyl alcohol
Phenyl hydroxide
Phenylic acid
Phenylic alcohol
PHOH
Synthetic phenol
Tea polyphenol
Chemical FormulaC6H6O
Average Molecular Mass94.111 g/mol
Monoisotopic Mass94.042 g/mol
CAS Registry Number108-95-2
IUPAC Namephenol
Traditional Namephenol
SMILESOC1=CC=CC=C1
InChI IdentifierInChI=1S/C6H6O/c7-6-4-2-1-3-5-6/h1-5,7H
InChI KeyInChIKey=ISWSIDIOOBJBQZ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1-hydroxy-4-unsubstituted benzenoids. These are phenols that are unsubstituted at the 4-position.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub Class1-hydroxy-4-unsubstituted benzenoids
Direct Parent1-hydroxy-4-unsubstituted benzenoids
Alternative Parents
Substituents
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue Locations
  • Adipose Tissue
  • Bladder
  • Brain
  • Epidermis
  • Fibroblasts
  • Intestine
  • Liver
  • Muscle
  • Nerve Cells
  • Platelet
  • Spleen
  • Stratum Corneum
  • Testes
  • Thyroid Gland
PathwaysNot Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point40.9°C
Boiling Point182°C (359.6°F)
Solubility82.8 mg/mL at 25°C [SOUTHWORTH,GR & KELLER,JL (1986)]
LogP1.46
Predicted Properties
PropertyValueSource
Water Solubility46.6 mg/mLALOGPS
logP1.39ALOGPS
logP1.67ChemAxon
logS-0.31ALOGPS
pKa (Strongest Acidic)10.02ChemAxon
pKa (Strongest Basic)-5.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity28.04 m3·mol-1ChemAxon
Polarizability9.81 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0udi-3900000000-97dfa3be718a9ee7ace4View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSsplash10-0006-9000000000-c35c89484e2499c62a49View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-00kf-9000000000-6fb456992902a13931f9View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-0006-9000000000-78c83ab6ff1d3dfdbec6View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-0006-9000000000-89b0c430b8924ee2afdeView in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-0006-9000000000-fc01d0ad6740cfd70e13View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-006w-9000000000-c8b41f2899ca8cc9d4bcView in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-0006-9000000000-db80d8b605e20595c679View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-0udi-3900000000-97dfa3be718a9ee7ace4View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS)splash10-0g4i-9300000000-afd565a878ea36c74defView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0006-9000000000-e67da0571423f0e6b4b8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0006-9000000000-e0f57b1e970d0d46597eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0006-9000000000-e67da0571423f0e6b4b8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-00kf-9000000000-7bfe3b897e928a8f3a2cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-01-SG-2) , Positivesplash10-0006-9000000000-78c83ab6ff1d3dfdbec6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6L) , Positivesplash10-0006-9000000000-89b0c430b8924ee2afdeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-D-3000) , Positivesplash10-0006-9000000000-fc01d0ad6740cfd70e13View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0006-9000000000-ca4fa5905cccbfeab33aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9000000000-2c7201e803e029dd1aefView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9000000000-3fb3990dfbfbde2b8d57View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gba-9000000000-d3da8db6579f32d02c6cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9000000000-a74494cda18ab9fb8055View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-a74494cda18ab9fb8055View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-03a61ff7da92cb08edf8View in MoNA
MSMass Spectrum (Electron Ionization)splash10-00kf-9000000000-40b376f4e58c23369a01View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Toxicity Profile
Route of ExposureInhalation (29) ; oral (29) ; dermal (29) ; eye contact (29)
Mechanism of ToxicityPhenol 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. (5, 30)
MetabolismWhen 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. (30, 2, 4, 1, 3)
Toxicity ValuesLD50: 400 mg/kg/day (Oral, Rat) (30) LD50: 669 mg/cm2/day (Dermal, Rat) (30) LD50: 1400 mg/cm2/day (Dermal, Rabbit) (30)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)3, not classifiable as to its carcinogenicity to humans. (31)
Uses/SourcesPhenol is used to make plastics. Phenol is also used as a disinfectant in household cleaning products and in consumer products such as mouthwashes, gargles, throat sprays. Exposure may result from breathing air containing phenol and drinking contaminated water or eating food contaminated with phenol. Exposure also occurs through dermal contact with contaminated air or by skin contact with products containing phenol. Dermal contact can occur through the use of general disinfectants and ointments containing phenol. Ingestion can occur through the use of products such as throat lozenges or sore throat sprays that contain phenol. (30)
Minimum Risk LevelAcute Oral: 1 mg/kg/day (Rat) (30)
Health EffectsLong-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. (30)
SymptomsBurning pain in mouth and throat; white necrotic lesions in mouth; abdominal pain, vomiting, bloody diarrhea, pallor, sweating, weakness, headache, dizziness, tinnitus can result from phenol poisoning. Phenol absorption can lead to weak irregular pulse, hypotension, shallow respirations, cyanosis, pallor, a profound fall in body temperature, muscle tremors, and difficulty walking. Possibly fleeting excitement and confusion, followed by unconsciousness. (27, 30)
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDDB03255
HMDB IDHMDB00228
PubChem Compound ID996
ChEMBL IDNot Available
ChemSpider ID971
KEGG IDC00146
UniProt IDNot Available
OMIM ID147450 , 147460 , 171150 , 191740 , 600641 , 601292
ChEBI ID15882
BioCyc ID24-DICHLOROPHENOL
CTD IDD019800
Stitch IDPhenol
PDB IDIPH
ACToR ID1148
Wikipedia LinkPhenol
References
Synthesis Reference

http://en.wikipedia.org/wiki/Phenols#Synthesis_of_phenols

MSDSLink
General References
  1. Land EJ, Ramsden CA, Riley PA: The mechanism of suicide-inactivation of tyrosinase: a substrate structure investigation. Tohoku J Exp Med. 2007 Aug;212(4):341-8. [17660699 ]
  2. Tyapochkin E, Cook PF, Chen G: Isotope exchange at equilibrium indicates a steady state ordered kinetic mechanism for human sulfotransferase. Biochemistry. 2008 Nov 11;47(45):11894-9. doi: 10.1021/bi801211t. Epub 2008 Oct 18. [18928301 ]
  3. Li D, Fournel-Gigleux S, Barre L, Mulliert G, Netter P, Magdalou J, Ouzzine M: Identification of aspartic acid and histidine residues mediating the reaction mechanism and the substrate specificity of the human UDP-glucuronosyltransferases 1A. J Biol Chem. 2007 Dec 14;282(50):36514-24. Epub 2007 Oct 23. [17956868 ]
  4. Meinl W, Ebert B, Glatt H, Lampen A: Sulfotransferase forms expressed in human intestinal Caco-2 and TC7 cells at varying stages of differentiation and role in benzo[a]pyrene metabolism. Drug Metab Dispos. 2008 Feb;36(2):276-83. Epub 2007 Oct 29. [17967930 ]
  5. Oliveira HM, Sallam HS, Espana-Tenorio J, Chinkes D, Chung DH, Chen JD, Herndon DN: Gastric and small bowel ileus after severe burn in rats: the effect of cyclooxygenase-2 inhibitors. Burns. 2009 Dec;35(8):1180-4. doi: 10.1016/j.burns.2009.02.022. Epub 2009 May 22. [19464805 ]
  6. Chen X, Chen M, Xu B, Tang R, Han X, Qin Y, Xu B, Hang B, Mao Z, Huo W, Xia Y, Xu Z, Wang X: Parental phenols exposure and spontaneous abortion in Chinese population residing in the middle and lower reaches of the Yangtze River. Chemosphere. 2013 Sep;93(2):217-22. doi: 10.1016/j.chemosphere.2013.04.067. Epub 2013 May 25. [23714150 ]
  7. Gracies JM, Elovic E, McGuire J, Simpson DM: Traditional pharmacological treatments for spasticity. Part I: Local treatments. Muscle Nerve Suppl. 1997;6:S61-91. [9826983 ]
  8. Kilic SS, Aydin S, Kilic N, Erman F, Aydin S, Celik I: Serum arylesterase and paraoxonase activity in patients with chronic hepatitis. World J Gastroenterol. 2005 Dec 14;11(46):7351-4. [16437641 ]
  9. Tanaka T, Kasai K, Kita T, Tanaka N: Distribution of phenol in a fatal poisoning case determined by gas chromatography/mass spectrometry. J Forensic Sci. 1998 Sep;43(5):1086-8. [9729832 ]
  10. McDonald TA, Holland NT, Skibola C, Duramad P, Smith MT: Hypothesis: phenol and hydroquinone derived mainly from diet and gastrointestinal flora activity are causal factors in leukemia. Leukemia. 2001 Jan;15(1):10-20. [11243376 ]
  11. Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. [8087979 ]
  12. Blades KJ, Patel S: The dynamics of tear flow within a phenol red impregnated thread. Ophthalmic Physiol Opt. 1996 Sep;16(5):409-15. [8944185 ]
  13. Miller WL, Doughty MJ, Narayanan S, Leach NE, Tran A, Gaume AL, Bergmanson JP: A comparison of tear volume (by tear meniscus height and phenol red thread test) and tear fluid osmolality measures in non-lens wearers and in contact lens wearers. Eye Contact Lens. 2004 Jul;30(3):132-7. [15499232 ]
  14. Hume R, Barker EV, Coughtrie MW: Differential expression and immunohistochemical localisation of the phenol and hydroxysteroid sulphotransferase enzyme families in the developing lung. Histochem Cell Biol. 1996 Feb;105(2):147-52. [8852436 ]
  15. Slatkin NE, Rhiner M: Phenol saddle blocks for intractable pain at end of life: report of four cases and literature review. Am J Hosp Palliat Care. 2003 Jan-Feb;20(1):62-6. [12568439 ]
  16. Bauer M, Patzelt D: A method for simultaneous RNA and DNA isolation from dried blood and semen stains. Forensic Sci Int. 2003 Sep 9;136(1-3):76-8. [12969623 ]
  17. Norberg J, Emneus JA, Jonsson JA, Mathiasson L, Burestedt E, Knutsson M, Marko-Varga G: On-line supported liquid membrane-liquid chromatography with a phenol oxidase-based biosensor as a selective detection unit for the determination of phenols in blood plasma. J Chromatogr B Biomed Sci Appl. 1997 Nov 7;701(1):39-46. [9389336 ]
  18. Tucker IG: A method to study the kinetics of oral mucosal drug absorption from solutions. J Pharm Pharmacol. 1988 Oct;40(10):679-83. [2907532 ]
  19. Achterrath-Tuckermann U, Saano V, Minker E, Stroman F, Arny I, Joki S, Nuutinen J, Szelenyi I: Influence of azelastine and some selected drugs on mucociliary clearance. Lung. 1992;170(4):201-9. [1522740 ]
  20. Tatsumi H, Shimada N, Kuramoto R, Mochizuki Y, Nishizima M, Arai M, Osanai K, Ishihara K, Goso K, Hotta K: [The phenol turbidity test for measurement of pulmonary surfactants in amniotic fluid--rapid test for fetal lung maturity (author's transl)]. Acta Obstet Gynaecol Jpn. 1981 May;33(5):643-50. [6894513 ]
  21. Jones AL, Hagen M, Coughtrie MW, Roberts RC, Glatt H: Human platelet phenolsulfotransferases: cDNA cloning, stable expression in V79 cells and identification of a novel allelic variant of the phenol-sulfating form. Biochem Biophys Res Commun. 1995 Mar 17;208(2):855-62. [7695643 ]
  22. Bartholomew LE, Bartholomew FN: Antigenic bacterial polysaccharide in rheumatoid synovial effusions. Arthritis Rheum. 1979 Sep;22(9):969-77. [314293 ]
  23. Le Poole IC, Yang F, Brown TL, Cornelius J, Babcock GF, Das PK, Boissy RE: Altered gene expression in melanocytes exposed to 4-tertiary butyl phenol (4-TBP): upregulation of the A2b adenosine receptor 1. J Invest Dermatol. 1999 Nov;113(5):725-31. [10571726 ]
  24. Bukowska B, Kowalska S: Phenol and catechol induce prehemolytic and hemolytic changes in human erythrocytes. Toxicol Lett. 2004 Aug 30;152(1):73-84. [15294349 ]
  25. Asai Y, Ohyama Y, Taiji Y, Makimura Y, Tamai R, Hashimoto M, Ogawa T: Treponema medium glycoconjugate inhibits activation of human gingival fibroblasts stimulated with phenol-water extracts of periodontopathic bacteria. J Dent Res. 2005 May;84(5):456-61. [15840783 ]
  26. Rumack BH (2009). POISINDEX(R) Information System. Englewood, CO: Micromedex, Inc. CCIS Volume 141, edition expires Aug, 2009.
  27. Gosselin RE, Smith RP, and Hodge HC (1984). Clinical Toxicology of Commercial Products. 5th ed. Baltimore: Williams and Wilkins.
  28. H. Babich, D.L. Davis, Phenol: A review of environmental and health risks. Regulatory Toxicology and Pharmacology, Volume 1, Issue 1, June 1981, Pages 90–109.
  29. ATSDR - Agency for Toxic Substances and Disease Registry (1999). Toxicological profile for chlorophenols. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  30. ATSDR - Agency for Toxic Substances and Disease Registry (2008). Toxicological profile for phenol. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  31. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
Gene Regulation
Up-Regulated Genes
GeneGene SymbolGene IDInteractionChromosomeDetails
Down-Regulated Genes
GeneGene SymbolGene IDInteractionChromosomeDetails

Targets

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
  1. 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
  1. 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
References
  1. 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
  1. 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
  1. 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
  1. 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
  1. 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
  1. 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
  1. 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
  1. 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
  1. 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
  1. 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:
Not Available
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
  1. 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 ]