1,3-Benzenediol
(right click,save link as to download,it is a temp file,please download as soon as possible, you can also use CTRL+S to save the whole html page)
Basic Info
| Common Name | 1,3-Benzenediol(F05462) |
| 2D Structure | |
| Description | 1,3-Benzenediol is found in alcoholic beverages. 1,3-Benzenediol is present in roasted barley, cane molasses, coffee, beer and wine. 1,3-Benzenediol is a flavouring ingredient1,3-Benzenediol belongs to the family of Resorcinols. These are compounds containing a resorcinol moiety, which is a benzene ring bearing two hydrocyl groups at positions 1 and 3. |
| FRCD ID | F05462 |
| CAS Number | 108-46-3 |
| PubChem CID | 5054 |
| Formula | C6H6O2 |
| IUPAC Name | benzene-1,3-diol |
| InChI Key | GHMLBKRAJCXXBS-UHFFFAOYSA-N |
| InChI | InChI=1S/C6H6O2/c7-5-2-1-3-6(8)4-5/h1-4,7-8H |
| Canonical SMILES | C1=CC(=CC(=C1)O)O |
| Isomeric SMILES | C1=CC(=CC(=C1)O)O |
| Wikipedia | 1,3-Benzenediol |
| Synonyms |
resorcinol
m-Hydroquinone
108-46-3
1,3-Benzenediol
Resorcin
1,3-Dihydroxybenzene
benzene-1,3-diol
3-Hydroxyphenol
Resorcine
m-Dihydroxybenzene
|
| Classifies |
Plant Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Phenols |
| Subclass | Benzenediols |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Resorcinols |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | Resorcinol - 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 resorcinols. These are compounds containing a resorcinol moiety, which is a benzene ring bearing two hydroxyl groups at positions 1 and 3. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 110.112 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 0 |
| Complexity | 64.9 |
| Monoisotopic Mass | 110.037 |
| Exact Mass | 110.037 |
| XLogP | 0.8 |
| 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+ | 0.6978 |
| Human Intestinal Absorption | HIA+ | 0.9872 |
| Caco-2 Permeability | Caco2+ | 0.8960 |
| P-glycoprotein Substrate | Non-substrate | 0.7660 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9792 |
| Non-inhibitor | 0.9853 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8907 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.7119 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8137 |
| CYP450 2D6 Substrate | Non-substrate | 0.9082 |
| CYP450 3A4 Substrate | Non-substrate | 0.7532 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.5873 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.8069 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9530 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.6839 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.5652 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.6378 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.8736 |
| Non-inhibitor | 0.9671 | |
| AMES Toxicity | Non AMES toxic | 0.9212 |
| Carcinogens | Non-carcinogens | 0.7588 |
| Fish Toxicity | Low FHMT | 0.6529 |
| Tetrahymena Pyriformis Toxicity | Low TPT | 0.5061 |
| Honey Bee Toxicity | High HBT | 0.7988 |
| Biodegradation | Ready biodegradable | 0.7561 |
| Acute Oral Toxicity | II | 0.6235 |
| Carcinogenicity (Three-class) | Non-required | 0.6855 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | 0.0115 | LogS |
| Caco-2 Permeability | 1.3195 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.2555 | LD50, mol/kg |
| Fish Toxicity | 1.8610 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | -0.5968 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Single nucleotide polymorphisms of ABCC2 modulate renal secretion of endogenous organic anions. | Biochem Pharmacol | 2017 Sep 15 | 28532626 |
| Antioxidant capacity of (+)-catechin visible-light photoirradiated in thepresence of vitamin B2. | Redox Rep | 2017 Nov | 27712465 |
| Laccase oxidation and removal of toxicants released during combustion processes. | Chemosphere | 2016 Feb | 26408262 |
| Biomolecule-free, selective detection of o-diphenol and its derivatives withWS2/TiO2-based photoelectrochemical platform. | Anal Chem | 2015 | 25844499 |
| Essential Structural Requirements and Additive Effects for Flavonoids to ScavengeMethylglyoxal. | J Agric Food Chem | 2014 Apr 9 | 24689984 |
| Determination of synthetic by-products and an intermediate in the colour additiveD&C Orange No. 5 using high-performance liquid chromatography. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2012 | 22779771 |
| Automated determination of seven phenolic compounds in mainstream tobacco smoke. | Nicotine Tob Res | 2008 Jul | 18629737 |
| Plastic components affect the activation of the aryl hydrocarbon and the androgenreceptor. | Toxicology | 2008 Apr 18 | 18294747 |
| Determination of 2,4,6-triiodoresorcinol and other side reaction products andintermediates in the colour additive FD&C Red No. 3 (erythrosine) usinghigh-performance liquid chromatography. | Food Addit Contam | 2006 Jun | 16766453 |
| Effect of tea polyphenols on histamine release from rat basophilic leukemia(RBL-2H3) cells: the structure-inhibitory activity relationship. | Allergy | 1997 Jan | 9062630 |
| Mechanism-based inactivation of lactoperoxidase and thyroid peroxidase byresorcinol derivatives. | Biochemistry | 1994 Aug 16 | 8068644 |
| Detection of GD3 ganglioside in childhood acute lymphoblastic leukemia withmonoclonal antibody to GD3: restriction to immunophenotypically defined T-celldisease. | J Cell Biochem | 1988 May | 3292545 |
Targets
- 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: inhibition of mammalian isoforms I-XIV with a series of substituted phenols including paracetamol and salicylic acid. Bioorg Med Chem. 2008 Aug 1;16(15):7424-8. doi: 10.1016/j.bmc.2008.06.013. Epub 2008 Jun 13. [18579385 ]
- 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: inhibition of mammalian isoforms I-XIV with a series of substituted phenols including paracetamol and salicylic acid. Bioorg Med Chem. 2008 Aug 1;16(15):7424-8. doi: 10.1016/j.bmc.2008.06.013. Epub 2008 Jun 13. [18579385 ]
- 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: inhibition of mammalian isoforms I-XIV with a series of substituted phenols including paracetamol and salicylic acid. Bioorg Med Chem. 2008 Aug 1;16(15):7424-8. doi: 10.1016/j.bmc.2008.06.013. Epub 2008 Jun 13. [18579385 ]
- 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: inhibition of mammalian isoforms I-XIV with a series of substituted phenols including paracetamol and salicylic acid. Bioorg Med Chem. 2008 Aug 1;16(15):7424-8. doi: 10.1016/j.bmc.2008.06.013. Epub 2008 Jun 13. [18579385 ]
- 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: inhibition of mammalian isoforms I-XIV with a series of substituted phenols including paracetamol and salicylic acid. Bioorg Med Chem. 2008 Aug 1;16(15):7424-8. doi: 10.1016/j.bmc.2008.06.013. Epub 2008 Jun 13. [18579385 ]
- 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: inhibition of mammalian isoforms I-XIV with a series of substituted phenols including paracetamol and salicylic acid. Bioorg Med Chem. 2008 Aug 1;16(15):7424-8. doi: 10.1016/j.bmc.2008.06.013. Epub 2008 Jun 13. [18579385 ]
- 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: inhibition of mammalian isoforms I-XIV with a series of substituted phenols including paracetamol and salicylic acid. Bioorg Med Chem. 2008 Aug 1;16(15):7424-8. doi: 10.1016/j.bmc.2008.06.013. Epub 2008 Jun 13. [18579385 ]
- 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: inhibition of mammalian isoforms I-XIV with a series of substituted phenols including paracetamol and salicylic acid. Bioorg Med Chem. 2008 Aug 1;16(15):7424-8. doi: 10.1016/j.bmc.2008.06.013. Epub 2008 Jun 13. [18579385 ]
- 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: inhibition of mammalian isoforms I-XIV with a series of substituted phenols including paracetamol and salicylic acid. Bioorg Med Chem. 2008 Aug 1;16(15):7424-8. doi: 10.1016/j.bmc.2008.06.013. Epub 2008 Jun 13. [18579385 ]
- 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: inhibition of mammalian isoforms I-XIV with a series of substituted phenols including paracetamol and salicylic acid. Bioorg Med Chem. 2008 Aug 1;16(15):7424-8. doi: 10.1016/j.bmc.2008.06.013. Epub 2008 Jun 13. [18579385 ]
- Uniprot ID:
- P05184
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- 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: inhibition of mammalian isoforms I-XIV with a series of substituted phenols including paracetamol and salicylic acid. Bioorg Med Chem. 2008 Aug 1;16(15):7424-8. doi: 10.1016/j.bmc.2008.06.013. Epub 2008 Jun 13. [18579385 ]