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Lawsone

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Identification

Generic Name
Lawsone
DrugBank Accession Number
DB04744
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Similar Structures
Weight
Average: 174.1528
Monoisotopic: 174.031694058
Chemical Formula
C10H6O3
Synonyms
  • 2-hydroxy-1,4-naphthalenedione
  • 2-hydroxy-1,4-naphthoquinone
  • 2-hydroxynaphthoquinone
  • Lawsone
External IDs
  • NSC-27285
  • NSC-52500
  • NSC-8625
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
Not Available
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.
DrugInteraction
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interactions in your software
AcenocoumarolThe therapeutic efficacy of Acenocoumarol can be increased when used in combination with Lawsone.
DicoumarolThe therapeutic efficacy of Dicoumarol can be increased when used in combination with Lawsone.
FluindioneThe therapeutic efficacy of Fluindione can be increased when used in combination with Lawsone.
PhenindioneThe therapeutic efficacy of Phenindione can be increased when used in combination with Lawsone.
PhenprocoumonThe therapeutic efficacy of Phenprocoumon can be increased when used in combination with Lawsone.
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as naphthoquinones. These are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone).
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Naphthalenes
Sub Class
Naphthoquinones
Direct Parent
Naphthoquinones
Alternative Parents
Quinones / Aryl ketones / Vinylogous acids / Enols / Organic oxides / Hydrocarbon derivatives
Substituents
Aromatic homopolycyclic compound / Aryl ketone / Enol / Hydrocarbon derivative / Ketone / Naphthoquinone / Organic oxide / Organic oxygen compound / Organooxygen compound / Quinone
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
naphthoquinone (CHEBI:44401) / alpha-Naphthoquinones (C10368)
Affected organisms
Not Available

Chemical Identifiers

UNII
TLH4A6LV1W
CAS number
83-72-7
InChI Key
CSFWPUWCSPOLJW-UHFFFAOYSA-N
InChI
InChI=1S/C10H6O3/c11-8-5-9(12)10(13)7-4-2-1-3-6(7)8/h1-5,12H
IUPAC Name
2-hydroxy-1,4-dihydronaphthalene-1,4-dione
SMILES
OC1=CC(=O)C2=CC=CC=C2C1=O

References

General References
Not Available
KEGG Compound
C10368
PubChem Compound
6755
PubChem Substance
46509125
ChemSpider
10430995
BindingDB
50049066
ChEBI
44401
ChEMBL
CHEMBL240963
ZINC
ZINC000004632115
PDBe Ligand
NQ
Wikipedia
Lawsone
PDB Entries
2d0e

Clinical Trials

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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 Solubility1.8 mg/mLALOGPS
logP0.99ALOGPS
logP0.98Chemaxon
logS-2ALOGPS
pKa (Strongest Acidic)5.32Chemaxon
pKa (Strongest Basic)-5.4Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area54.37 Å2Chemaxon
Rotatable Bond Count0Chemaxon
Refractivity48.15 m3·mol-1Chemaxon
Polarizability16.42 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.8282
Caco-2 permeable+0.7343
P-glycoprotein substrateNon-substrate0.5873
P-glycoprotein inhibitor IInhibitor0.5
P-glycoprotein inhibitor IINon-inhibitor0.8995
Renal organic cation transporterNon-inhibitor0.8735
CYP450 2C9 substrateNon-substrate0.7873
CYP450 2D6 substrateNon-substrate0.9245
CYP450 3A4 substrateNon-substrate0.6861
CYP450 1A2 substrateInhibitor0.9206
CYP450 2C9 inhibitorInhibitor0.7177
CYP450 2D6 inhibitorNon-inhibitor0.8078
CYP450 2C19 inhibitorNon-inhibitor0.7624
CYP450 3A4 inhibitorNon-inhibitor0.9078
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5311
Ames testAMES toxic0.9107
CarcinogenicityNon-carcinogens0.9077
BiodegradationNot ready biodegradable0.8819
Rat acute toxicity3.0215 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9541
hERG inhibition (predictor II)Non-inhibitor0.931
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-MSsplash10-0f6t-1900000000-7f32546cfae1991babd5
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-0900000000-efa6aaef290b8df5cf0a
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-0900000000-57b71348177b5af4993e
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-0900000000-baf7151f89001b2b5998
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00dl-5900000000-01a1b906ee81d3cb39ee
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-9700000000-0e656b9edc2255a2af75
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-002f-9000000000-ce81a7897cecec0bf6d8
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]-137.9365829
predicted
DarkChem Lite v0.1.0
[M-H]-137.9626829
predicted
DarkChem Lite v0.1.0
[M-H]-126.9478
predicted
DeepCCS 1.0 (2019)
[M+H]+138.6313829
predicted
DarkChem Lite v0.1.0
[M+H]+138.6201829
predicted
DarkChem Lite v0.1.0
[M+H]+130.59474
predicted
DeepCCS 1.0 (2019)
[M+Na]+138.1501829
predicted
DarkChem Lite v0.1.0
[M+Na]+138.1227829
predicted
DarkChem Lite v0.1.0
[M+Na]+139.86617
predicted
DeepCCS 1.0 (2019)

Drug created at September 11, 2007 17:49 / Updated at June 12, 2020 16:52