NAV

1,2-Dihydroxynaphthalene

Identification

Generic Name
1,2-Dihydroxynaphthalene
DrugBank Accession Number
DB07610
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 160.1693
Monoisotopic: 160.0524295
Chemical Formula
C10H8O2
Synonyms
  • 1,2-Naphthalenediol
  • 1,2-naphthohydroquinone
  • beta-Naphthohydroquinone
  • Naphthalene-1,2-diol
  • β-naphthohydroquinone
External IDs
  • NSC-401609
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
U1,2-dihydroxynaphthalene dioxygenaseNot AvailablePseudomonas sp. (strain C18)
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Naphthalenes
Sub Class
Naphthols and derivatives
Direct Parent
Naphthols and derivatives
Alternative Parents
1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Organooxygen compounds / Hydrocarbon derivatives
Substituents
1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / 1-naphthol / 2-naphthol / Aromatic homopolycyclic compound / Hydrocarbon derivative / Organic oxygen compound / Organooxygen compound
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
naphthalenediol (CHEBI:17435) / a small molecule (NAPHTHALENE-12-DIOL)
Affected organisms
Not Available

Chemical Identifiers

UNII
2R5017T335
CAS number
574-00-5
InChI Key
NXPPAOGUKPJVDI-UHFFFAOYSA-N
InChI
InChI=1S/C10H8O2/c11-9-6-5-7-3-1-2-4-8(7)10(9)12/h1-6,11-12H
IUPAC Name
naphthalene-1,2-diol
SMILES
OC1=C(O)C2=CC=CC=C2C=C1

References

General References
Not Available
Human Metabolome Database
HMDB0060497
KEGG Compound
C03012
PubChem Compound
11318
PubChem Substance
99444081
ChemSpider
10842
BindingDB
50049067
ChEBI
17435
ChEMBL
CHEMBL204543
ZINC
ZINC000000407059
PDBe Ligand
D1N
PDB Entries
2ei1

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.71 mg/mLALOGPS
logP2.06ALOGPS
logP2.36Chemaxon
logS-2.4ALOGPS
pKa (Strongest Acidic)9.04Chemaxon
pKa (Strongest Basic)-6.3Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area40.46 Å2Chemaxon
Rotatable Bond Count0Chemaxon
Refractivity46.47 m3·mol-1Chemaxon
Polarizability16.4 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9922
Blood Brain Barrier+0.5569
Caco-2 permeable+0.7786
P-glycoprotein substrateNon-substrate0.5982
P-glycoprotein inhibitor INon-inhibitor0.9279
P-glycoprotein inhibitor IINon-inhibitor0.9747
Renal organic cation transporterNon-inhibitor0.8902
CYP450 2C9 substrateNon-substrate0.8003
CYP450 2D6 substrateNon-substrate0.8698
CYP450 3A4 substrateNon-substrate0.65
CYP450 1A2 substrateInhibitor0.8783
CYP450 2C9 inhibitorInhibitor0.638
CYP450 2D6 inhibitorNon-inhibitor0.8864
CYP450 2C19 inhibitorNon-inhibitor0.6121
CYP450 3A4 inhibitorNon-inhibitor0.9433
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5079
Ames testAMES toxic0.907
CarcinogenicityNon-carcinogens0.9086
BiodegradationNot ready biodegradable0.8429
Rat acute toxicity2.2883 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9263
hERG inhibition (predictor II)Non-inhibitor0.6828
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-01q9-0900000000-0f956a12d0643c144a3c
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-0900000000-03099c7baff7081aacc4
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-0900000000-88e1225d3a9e4a06d89d
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0900000000-c8c463c1e5f65d1f2919
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0ufr-6900000000-a2e5a4faf61a14feb533
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0900000000-f222d28e2f14cac63a03
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0ugi-3900000000-c890480f5123d46d7db8
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-133.5184234
predicted
DarkChem Lite v0.1.0
[M-H]-133.6289234
predicted
DarkChem Lite v0.1.0
[M-H]-133.4623234
predicted
DarkChem Lite v0.1.0
[M-H]-128.14412
predicted
DeepCCS 1.0 (2019)
[M+H]+134.1817234
predicted
DarkChem Lite v0.1.0
[M+H]+134.2494234
predicted
DarkChem Lite v0.1.0
[M+H]+133.8904234
predicted
DarkChem Lite v0.1.0
[M+H]+130.69713
predicted
DeepCCS 1.0 (2019)
[M+Na]+133.7738234
predicted
DarkChem Lite v0.1.0
[M+Na]+133.7799234
predicted
DarkChem Lite v0.1.0
[M+Na]+133.7851234
predicted
DarkChem Lite v0.1.0
[M+Na]+139.33961
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. 1,2-dihydroxynaphthalene dioxygenase
Kind
Protein
Organism
Pseudomonas sp. (strain C18)
Pharmacological action
Unknown
General Function
Oxidoreductase activity, acting on single donors with incorporation of molecular oxygen, incorporation of two atoms of oxygen
Specific Function
Involved in the naphthalene catabolic pathway. Catalyzes the meta-cleavage of 1,2-dihydroxynaphthalene (1,2-DHN) to yield 2-hydroxychromene-2-carboxylic acid (By similarity).
Gene Name
doxG
Uniprot ID
P0A108
Uniprot Name
1,2-dihydroxynaphthalene dioxygenase
Molecular Weight
33941.375 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

Drug created at September 15, 2010 21:24 / Updated at June 12, 2020 16:52