2-Naphthol
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Basic Info
| Common Name | 2-Naphthol(F05170) |
| 2D Structure | |
| Description | 2-Naphthol is a colorless crystalline solid and an isomer of 1-naphthol, differing by the location of the hydroxyl group on naphthalene. The naphthols are naphthalene homologues of phenol, with the hydroxyl group being more reactive than in the phenols. 2-Naphthol has several different uses including dyes, pigments, fats, oils, insecticides, pharmaceuticals, perfumes, antiseptics, synthesis of fungicides, and antioxidants for rubber. Detection of 2-Naphthol in urine usually results from long-term persistent exposure to pesticides such as chlorpyrifos, but also due to exposure to naphthalene in older types of mothballs, fires that produce polyaromatic hydrocarbons (PAHs), and tobacco smoke. |
| FRCD ID | F05170 |
| CAS Number | 135-19-3 |
| PubChem CID | 8663 |
| Formula | C10H8O |
| IUPAC Name | naphthalen-2-ol |
| InChI Key | JWAZRIHNYRIHIV-UHFFFAOYSA-N |
| InChI | InChI=1S/C10H8O/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-7,11H |
| Canonical SMILES | C1=CC=C2C=C(C=CC2=C1)O |
| Isomeric SMILES | C1=CC=C2C=C(C=CC2=C1)O |
| Synonyms |
beta-naphthol
2-NAPHTHOL
naphthalen-2-ol
135-19-3
2-Naphthalenol
2-Hydroxynaphthalene
Betanaphthol
Isonaphthol
Developer BN
Naphthol B
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Naphthalenes |
| Subclass | Naphthols and derivatives |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Naphthols and derivatives |
| Alternative Parents | |
| Molecular Framework | Aromatic homopolycyclic compounds |
| Substituents | 2-naphthol - 1-hydroxy-2-unsubstituted benzenoid - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Aromatic homopolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as naphthols and derivatives. These are naphthalene derivatives carrying one or more hydroxyl (-OH) groups at any ring position. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 144.173 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 1 |
| Rotatable Bond Count | 0 |
| Complexity | 133 |
| Monoisotopic Mass | 144.058 |
| Exact Mass | 144.058 |
| XLogP | 2.7 |
| Formal Charge | 0 |
| Heavy Atom Count | 11 |
| 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+ | 0.9196 |
| Human Intestinal Absorption | HIA+ | 1.0000 |
| Caco-2 Permeability | Caco2+ | 0.8939 |
| P-glycoprotein Substrate | Non-substrate | 0.7077 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9393 |
| Non-inhibitor | 0.9558 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8347 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.4551 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7629 |
| CYP450 2D6 Substrate | Non-substrate | 0.9004 |
| CYP450 3A4 Substrate | Non-substrate | 0.6904 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.9600 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.8050 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9245 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.6429 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9377 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.6796 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.8343 |
| Non-inhibitor | 0.8899 | |
| AMES Toxicity | AMES toxic | 0.9106 |
| Carcinogens | Non-carcinogens | 0.8518 |
| Fish Toxicity | High FHMT | 0.9173 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9806 |
| Honey Bee Toxicity | High HBT | 0.8555 |
| Biodegradation | Not ready biodegradable | 0.7846 |
| Acute Oral Toxicity | III | 0.8093 |
| Carcinogenicity (Three-class) | Warning | 0.4595 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.1362 | LogS |
| Caco-2 Permeability | 1.6586 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.8556 | LD50, mol/kg |
| Fish Toxicity | 0.7843 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 1.2087 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Determination of Aniline, 4-Aminoazobenzene, and 2-Naphthol in the Color AdditiveD&C Red No. 17 Using Ultra-High-Performance Liquid Chromatography. | J AOAC Int | 2018 May 18 | 29808790 |
| Hydrochars from bamboo sawdust through acid assisted and two-stage hydrothermalcarbonization for removal of two organics from aqueous solution. | Bioresour Technol | 2018 Aug | 29673994 |
| Quantification of steviol glycosides in food products, Stevia leaves andformulations by planar chromatography, including proof of absence for steviol andisosteviol. | J Chromatogr A | 2017 Jul 14 | 28552425 |
| Quantum Dot Nanotoxicity Investigations Using Human Lung Cells and TOXOR Electrochemical Enzyme Assay Methodology. | ACS Sens | 2017 Jan 27 | 28722443 |
| Application of 1-(2-pyridylazo)-2-naphthol-modified nanoporous silica as a technique in simultaneous trace monitoring and removal of toxic heavy metals in food and water samples. | Environ Monit Assess | 2015 Jan | 25504188 |
| Decolourisation of Acid Orange 7 recalcitrant auto-oxidation coloured by-products using an acclimatised mixed bacterial culture. | Environ Sci Pollut Res Int | 2014 Mar | 24293297 |
| Enzymes oxidizing the azo dye 1-phenylazo-2-naphthol (Sudan I) and their contribution to its genotoxicity and carcinogenicity. | Curr Drug Metab | 2014 | 25658126 |
| [Rapid determination of six preservative residues in fruits and vegetables byhigh performance liquid chromatography using dispersive solid phase extraction]. | Se Pu | 2013 Feb | 23697184 |
| Evaluation of impact of exposure of Sudan azo dyes and their metabolites on human intestinal bacteria. | Anaerobe | 2012 Aug | 22634331 |
| Effects of Orange II and Sudan III azo dyes and their metabolites on Staphylococcus aureus. | J Ind Microbiol Biotechnol | 2011 Oct | 21451978 |
| [Effect of naphthalene and its derivatives on Candida pseudotropicalis 44 PK sensitivity to trichothecene mycotoxins]. | Mikrobiol Z | 2009 Jul-Aug | 19938611 |
| Molecular cloning, expression and characterization of a phenol sulfotransferasecDNA from mouse intestine. | Biol Pharm Bull | 1999 Mar | 10220276 |
| Effect of metanil yellow, orange II and their blend on hepatic xenobiotic metabolizing enzymes in rats. | Food Chem Toxicol | 1994 Jun | 8045463 |
| Liquid chromatographic determination of 2-chloro-4-nitroaniline, 2-naphthol, and 2,4-dinitroaniline in D&C red no. 36. | J AOAC Int | 1993 Mar-Apr | 8471855 |
| Lipid peroxidation of ultrastructural components of rat liver induced by metanil yellow and orange II: comparison with blend. | Toxicol Ind Health | 1992 Jan-Apr | 1542886 |
Targets
- 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
References
- Korhonen LE, Rahnasto M, Mahonen NJ, Wittekindt C, Poso A, Juvonen RO, Raunio H: Predictive three-dimensional quantitative structure-activity relationship of cytochrome P450 1A2 inhibitors. J Med Chem. 2005 Jun 2;48(11):3808-15. [15916432 ]
- General Function:
- Thrombospondin receptor activity
- Specific Function:
- Thrombin, which cleaves bonds after Arg and Lys, converts fibrinogen to fibrin and activates factors V, VII, VIII, XIII, and, in complex with thrombomodulin, protein C. Functions in blood homeostasis, inflammation and wound healing.
- Gene Name:
- F2
- Uniprot ID:
- P00734
- Molecular Weight:
- 70036.295 Da
References
- Sun H, Shen OX, Xu XL, Song L, Wang XR: Carbaryl, 1-naphthol and 2-naphthol inhibit the beta-1 thyroid hormone receptor-mediated transcription in vitro. Toxicology. 2008 Jul 30;249(2-3):238-42. doi: 10.1016/j.tox.2008.05.008. Epub 2008 May 23. [18584933 ]
- General Function:
- Transcription regulatory region dna binding
- Specific Function:
- Ligand-activated transcriptional activator. Binds to the XRE promoter region of genes it activates. Activates the expression of multiple phase I and II xenobiotic chemical metabolizing enzyme genes (such as the CYP1A1 gene). Mediates biochemical and toxic effects of halogenated aromatic hydrocarbons. Involved in cell-cycle regulation. Likely to play an important role in the development and maturation of many tissues. Regulates the circadian clock by inhibiting the basal and circadian expression of the core circadian component PER1. Inhibits PER1 by repressing the CLOCK-ARNTL/BMAL1 heterodimer mediated transcriptional activation of PER1.
- Gene Name:
- AHR
- Uniprot ID:
- P35869
- Molecular Weight:
- 96146.705 Da
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:
- Norepinephrine:sodium symporter activity
- Specific Function:
- Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
- Gene Name:
- SLC6A2
- Uniprot ID:
- P23975
- Molecular Weight:
- 69331.42 Da
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:
- Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA/p65 and NFKB1/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Isoform 3 is involved in activation of NOS3 and endothelial nitric oxide production. Isoforms lacking one or several functional domains are thought to modulate transcriptional activity by competitive ligand or DNA binding and/or heterodimerization with the full length receptor. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3. Isoform 3 can bind to ERE and inhibit isoform 1.
- Gene Name:
- ESR1
- Uniprot ID:
- P03372
- Molecular Weight:
- 66215.45 Da
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 ]