T3DB: 2-Naphthol

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Gene Regulation Targets (5)XML

Targets (5)

Record Information

Version

2.0

Creation Date

2014-08-29 04:48:15 UTC

Update Date

2014-12-24 20:26:35 UTC

Accession Number

T3D3970

Identification

Common Name

2-Naphthol

Class

Small Molecule

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.

Compound Type

Dye
Food Toxin
Fungicide
Metabolite
Organic Compound
Pesticide
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym
2-Hydroxynaphthalene
2-Naftol
2-Naftolo
2-Naphthalenol
2-Naphtol
Antioxygene BN
Azogen developer a
beta-Hydroxynaphthalene
beta-Monoxynaphthalene
beta-Naftol
beta-Naftolo
beta-Naphthol
beta-Naphthyl alcohol
beta-Naphthyl hydroxide
beta-Naphtol
beta-Napthol
beta.-Hydroxynaphthalene
Betanaphthol
Developer BN
Hydronaphthol
Isonaphthol
Naphthol b
Trimetin

Chemical Formula

C₁₀H₈O

Average Molecular Mass

144.170 g/mol

Monoisotopic Mass

144.058 g/mol

CAS Registry Number

135-19-3

IUPAC Name

naphthalen-2-ol

Traditional Name

β naphthol

SMILES

OC1=CC2=CC=CC=C2C=C1

InChI Identifier

InChI=1S/C10H8O/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-7,11H

InChI Key

InChIKey=JWAZRIHNYRIHIV-UHFFFAOYSA-N

Chemical Taxonomy

Description

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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Naphthalenes

Sub Class

Naphthols and derivatives

Direct Parent

Naphthols and derivatives

Alternative Parents

Substituents

2-naphthol
1-hydroxy-2-unsubstituted benzenoid
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

naphthol (CHEBI:10432 )
a small molecule (CPD-8131 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

antinematodal drug

Biological Roles

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	123°C
Boiling Point	Not Available
Solubility	Not Available
LogP	2.7

Predicted Properties

Property	Value	Source
Water Solubility	0.72 g/L	ALOGPS
logP	2.93	ALOGPS
logP	2.66	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	9.78	ChemAxon
pKa (Strongest Basic)	-5.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	44.49 m³·mol⁻¹	ChemAxon
Polarizability	15.56 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-2900000000-59876f73d937e3fff0c1	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-2900000000-59876f73d937e3fff0c1	2018-05-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-0900000000-2b4afdf032e4268cf0db	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0fk9-8950000000-be69afc3a0e419124c04	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, positive	splash10-0002-0900000000-150b753c58953122f7a0	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, positive	splash10-0002-0900000000-3ed11eab13f522e296d0	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 4V, positive	splash10-0002-0900000000-76ad2ee08369a5c72727	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 5V, positive	splash10-014j-0900000000-668149fa5169e936b8cc	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 6V, positive	splash10-014i-0900000000-818a664d833b009956ca	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 7V, positive	splash10-014i-1900000000-cfdbc5ded35ac6d127e8	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 8V, positive	splash10-016u-3900000000-7581b81c891ce2121e30	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 10V, positive	splash10-016u-6900000000-ecc855690e59bfdd5598	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 12V, positive	splash10-016u-9800000000-68d9b962e8fe93336126	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 14V, positive	splash10-016r-9400000000-9eeb688197da71b8a3bc	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 10V, positive	splash10-014i-0900000000-820d3a81dfc9463584eb	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 10V, positive	splash10-000i-9000000000-41143d019e9e3192e3a9	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Negative	splash10-014i-0900000000-8a33e2a4035f1d5db4c6	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Negative	splash10-00kf-0900000000-b57369b32440fe60da1d	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Negative	splash10-0006-0900000000-95369892ad06085feeaa	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Negative	splash10-0006-0900000000-4359d09beb852a6b4d8d	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-014j-1900000000-3f45d855eafad75b3a67	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-014j-2900000000-949ec470c0e3ac2ca5b2	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Negative	splash10-0006-0900000000-ec57dc12ddf60a2741f0	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0900000000-7b3aeb4e0f86148dab68	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0900000000-a5c6a08b3ea484ba1d0d	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014j-2900000000-ecd1849d7a9f7a9bcac8	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0900000000-e1a1f37ba96a4bf71d70	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0900000000-e1a1f37ba96a4bf71d70	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-0900000000-019880a3b2ccbcc83a87	2016-08-03	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00kf-3900000000-9ba2c98085c1cfb979ae	2014-09-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, experimental)	Not Available	2014-09-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Not Available	2014-09-23	View Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

This is a man-made compound that is used as a pesticide.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

PubChem Compound ID

ChEMBL ID

ChemSpider ID

KEGG ID

UniProt ID

Not Available

OMIM ID

ChEBI ID

10432

BioCyc ID

CPD-8131

CTD ID

Not Available

Stitch ID

Not Available

PDB ID

03V

ACToR ID

Not Available

Wikipedia Link

Not Available

References

Synthesis Reference

Not Available

MSDS

Link

General References

COLOMB D, TISSOT A: [2nd Case of dermatitis from betanaphthol with reticular reactions]. Lyon Med. 1956 Nov 4;88(45):423-4. [13386410 ]
PATTERSON SJ, LERRIGO AF: Betanaphthol in gelatin capsules; its use as a preservative, with a method for its determination. Q J Pharm Pharmacol. 1947 Apr-Jun;20(2):83-6. [20260560 ]
VORONEOV II: [Effect of temperature in the sulphonating of betanaphtol for production of 2,6,8-naphtaldisulphonic acid]. Zhurnal Prikl Him. 1947 May;20(5):464-6. [18856458 ]

Gene Regulation

Up-Regulated Genes

Not Available

Down-Regulated Genes

Not Available

Targets

Target Details

1. Cytochrome P450 1A2

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

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
IC50	17 uM	Not Available	BindingDB 50159250

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 ]

Target Details

2. Prothrombin

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 ]

Target Details

3. Aryl hydrocarbon receptor

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

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	1.22 uM	ATG_Ahr_CIS	Attagene

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 ]

Target Details

4. Estrogen receptor

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

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	3.86 uM	NVS_NR_hER	Novascreen

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 ]

Target Details

5. Sodium-dependent noradrenaline transporter

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

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	8.66 uM	NVS_TR_hNET	Novascreen

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 ]

2-Naphthol (T3D3970)

Structure for T3D3970: 2-Naphthol

Targets

Binding/Activity Constants

References

References

Binding/Activity Constants

References

Binding/Activity Constants

References

Binding/Activity Constants

References