1-Naphthol
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Basic Info
| Common Name | 1-Naphthol(F05168) |
| 2D Structure | |
| Description | 1-naphthol (1N) is a metabolite of carbaryl and naphthalene that is an intermediate in Metabolism of xenobiotics by cytochrome P450. It is generated by spontaneous reaction from (1R,2S)-Naphthalene epoxide then is it converted to 1,4-Dihydroxynaphthalene. Although 1-Naphthol is not persistent in the body, a single urine sample may adequately predict exposure over several months to chlorpyrifos, which is a broad-spectrum organophosphate insecticide. In adult men, TCPY and 1N were associated with reduced testosterone levels (A3198, A3199). |
| FRCD ID | F05168 |
| CAS Number | 90-15-3 |
| PubChem CID | 7005 |
| Formula | C10H8O |
| IUPAC Name | naphthalen-1-ol |
| InChI Key | KJCVRFUGPWSIIH-UHFFFAOYSA-N |
| InChI | InChI=1S/C10H8O/c11-10-7-3-5-8-4-1-2-6-9(8)10/h1-7,11H |
| Canonical SMILES | C1=CC=C2C(=C1)C=CC=C2O |
| Isomeric SMILES | C1=CC=C2C(=C1)C=CC=C2O |
| Wikipedia | 1-Naphthol |
| Synonyms |
Tertral ERN
1-NAPHTHOL
naphthalen-1-ol
90-15-3
1-Naphthalenol
alpha-naphthol
1-Hydroxynaphthalene
NAPHTHOL
Fouramine ERN
Fourrine ERN
|
| Classifies |
Animal Toxin
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 | 1-naphthol - 1-hydroxy-4-unsubstituted benzenoid - 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 | 2.8 |
| 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 |
|---|---|---|---|
| Broad-specificity photoelectrochemical immunoassay for the simultaneous detection of ochratoxin A, ochratoxin B and ochratoxin C. | Biosens Bioelectron | 2018 May 30 | 29428592 |
| In vitro interactions of malachite green and leucomalachite green with hepaticdrug-metabolizing enzyme systems in the rainbow trout (Onchorhyncus mykiss). | Toxicol Lett | 2017 Oct 5 | 28802653 |
| Amplified impedimetric immunosensor based on instant catalyst for sensitive determination of ochratoxin A. | Biosens Bioelectron | 2016 Dec 15 | 27419906 |
| Metabolism of chamaechromone in vitro with human liver microsomes and recombinanthuman drug-metabolizing enzymes. | Planta Med | 2014 Apr | 24687737 |
| [Effect of naphthalene and its derivatives on Candida pseudotropicalis 44 PK sensitivity to trichothecene mycotoxins]. | Mikrobiol Z | 2009 Jul-Aug | 19938611 |
| Biocatalyzed deposition amplification for detection of aflatoxin B1 based on quartz crystal microbalance. | Anal Chim Acta | 2009 Jul 10 | 19481636 |
| Determination of pesticides in honey using excitation-emission matrixfluorescence coupled with second-order calibration and second-order standardaddition methods. | Anal Chim Acta | 2008 Jul 7 | 18558109 |
| Liquid chromatographic determination of N-methyl carbamate pesticide residues at low parts-per-billion levels in eggs. | J AOAC Int | 2006 Jan-Feb | 16512248 |
| ELISA as an affordable methodology for monitoring groundwater contamination bypesticides in low-income countries. | Environ Sci Technol | 2005 Jun 1 | 15984762 |
| Application of micellar electrokinetic capillary chromatography to the analysisof uncharged pesticides of environmental impact. | J Agric Food Chem | 2004 Sep 22 | 15366822 |
| Development of a membrane-based immunofiltration assay for the detection of T-2 toxin. | Anal Chem | 2004 Jul 15 | 15253669 |
| An analytical device for on-site immunoassay. Demonstration of its applicability in semiquantitative detection of aflatoxin B1 in a batch of samples with ultrahigh sensitivity. | Anal Chem | 2004 Jan 1 | 14697037 |
| Hydrolysis of carbaryl by carbonate impurities in reference clay SWy-2. | J Agric Food Chem | 2004 Dec 29 | 15612797 |
| Nuclear receptor, pregname X receptor, is required for induction ofUDP-glucuronosyltranferases in mouse liver by pregnenolone-16 alpha-carbonitrile. | Drug Metab Dispos | 2003 Jul | 12814968 |
| Dissipation of 14C carbaryl and quinalphos in soil under a groundnut crop(Arachis hypogaea L.) in semi-arid India. | Chemosphere | 2003 Dec | 14505725 |
| A simple method for the determination of carbaryl and 1-naphthol in fruit juices by high-performance liquid chromatography-diode-array detection. | J Food Prot | 2003 Aug | 12929849 |
| Investigation of the relation between self-reported food consumption andhousehold chemical exposures with urinary levels of selected nonpersistentpesticides. | J Expo Anal Environ Epidemiol | 2002 Nov | 12415488 |
| Kuwait's total diet study: dietary intake of organochlorine, carbamate,benzimidazole and phenylurea pesticide residues. | J AOAC Int | 1999 Nov-Dec | 10589497 |
| Spectrophotometric determination of carbaryl pesticide and its hydrolysis productin soil and strawberry samples. | Sci Total Environ | 1998 Sep 18 | 9810730 |
| Effects of 1-isothiocyanato-3-(methylsulfinyl)-propane on xenobiotic metabolizingenzymes in rats. | Food Chem Toxicol | 1993 Oct | 8225130 |
Targets
- 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:
- Zinc ion binding
- Specific Function:
- Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism and secretion of potentially harmful xenobiotics, drugs and endogenous compounds. Activated by the antibiotic rifampicin and various plant metabolites, such as hyperforin, guggulipid, colupulone, and isoflavones. Response to specific ligands is species-specific. Activated by naturally occurring steroids, such as pregnenolone and progesterone. Binds to a response element in the promoters of the CYP3A4 and ABCB1/MDR1 genes.
- Gene Name:
- NR1I2
- Uniprot ID:
- O75469
- Molecular Weight:
- 49761.245 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:
- 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:
- Signal transducer activity
- Specific Function:
- Stress-activated serine/threonine-protein kinase involved in cytokines production, endocytosis, reorganization of the cytoskeleton, cell migration, cell cycle control, chromatin remodeling, DNA damage response and transcriptional regulation. Following stress, it is phosphorylated and activated by MAP kinase p38-alpha/MAPK14, leading to phosphorylation of substrates. Phosphorylates serine in the peptide sequence, Hyd-X-R-X(2)-S, where Hyd is a large hydrophobic residue. Phosphorylates ALOX5, CDC25B, CDC25C, ELAVL1, HNRNPA0, HSF1, HSP27/HSPB1, KRT18, KRT20, LIMK1, LSP1, PABPC1, PARN, PDE4A, RCSD1, RPS6KA3, TAB3 and TTP/ZFP36. Mediates phosphorylation of HSP27/HSPB1 in response to stress, leading to dissociate HSP27/HSPB1 from large small heat-shock protein (sHsps) oligomers and impair their chaperone activities and ability to protect against oxidative stress effectively. Involved in inflammatory response by regulating tumor necrosis factor (TNF) and IL6 production post-transcriptionally: acts by phosphorylating AU-rich elements (AREs)-binding proteins ELAVL1, HNRNPA0, PABPC1 and TTP/ZFP36, leading to regulate the stability and translation of TNF and IL6 mRNAs. Phosphorylation of TTP/ZFP36, a major post-transcriptional regulator of TNF, promotes its binding to 14-3-3 proteins and reduces its ARE mRNA affinity leading to inhibition of dependent degradation of ARE-containing transcript. Also involved in late G2/M checkpoint following DNA damage through a process of post-transcriptional mRNA stabilization: following DNA damage, relocalizes from nucleus to cytoplasm and phosphorylates HNRNPA0 and PARN, leading to stabilize GADD45A mRNA. Involved in toll-like receptor signaling pathway (TLR) in dendritic cells: required for acute TLR-induced macropinocytosis by phosphorylating and activating RPS6KA3.
- Gene Name:
- MAPKAPK2
- Uniprot ID:
- P49137
- Molecular Weight:
- 45567.415 Da
References
- Constantine KL, Mueller L, Metzler WJ, McDonnell PA, Todderud G, Goldfarb V, Fan Y, Newitt JA, Kiefer SE, Gao M, Tortolani D, Vaccaro W, Tokarski J: Multiple and single binding modes of fragment-like kinase inhibitors revealed by molecular modeling, residue type-selective protonation, and nuclear overhauser effects. J Med Chem. 2008 Oct 9;51(19):6225-9. doi: 10.1021/jm800747w. Epub 2008 Sep 5. [18771253 ]
- 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 ]