NAV

2-[4-(4-Chlorophenyl)Cyclohexylidene]-3,4-Dihydroxy-1(2h)-Naphthalenone

Identification

Generic Name
2-[4-(4-Chlorophenyl)Cyclohexylidene]-3,4-Dihydroxy-1(2h)-Naphthalenone
DrugBank Accession Number
DB04281
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Similar Structures
Weight
Average: 366.837
Monoisotopic: 366.102272181
Chemical Formula
C22H19ClO3
Synonyms
Not Available
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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
TargetActionsOrganism
UDihydroorotate dehydrogenase (quinone), mitochondrialNot AvailableHumans
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
Not Available
Classification
Not classified
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
HKIDMHSZRQSXJE-XEMYWUMJSA-N
InChI
InChI=1S/C22H19ClO3/c23-16-11-9-14(10-12-16)13-5-7-15(8-6-13)19-20(24)17-3-1-2-4-18(17)21(25)22(19)26/h1-4,9-13,25-26H,5-8H2/b19-15-/t13-/m0/s1
IUPAC Name
2-[4-(4-chlorophenyl)cyclohexylidene]-3,4-dihydroxy-1,2-dihydronaphthalen-1-one
SMILES
[H]C1(CCC(CC1)=C1C(O)=C(O)C2=CC=CC=C2C1=O)C1=CC=C(Cl)C=C1

References

General References
Not Available
PubChem Compound
5287621
PubChem Substance
46505520
ChemSpider
64873348
PDBe Ligand
AFI

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 Solubility0.00227 mg/mLALOGPS
logP4.14ALOGPS
logP4.55Chemaxon
logS-5.2ALOGPS
pKa (Strongest Acidic)7.37Chemaxon
pKa (Strongest Basic)-5.8Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area57.53 Å2Chemaxon
Rotatable Bond Count1Chemaxon
Refractivity105.01 m3·mol-1Chemaxon
Polarizability39.5 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier-0.6507
Caco-2 permeable+0.5942
P-glycoprotein substrateSubstrate0.6432
P-glycoprotein inhibitor INon-inhibitor0.8895
P-glycoprotein inhibitor IINon-inhibitor0.8958
Renal organic cation transporterNon-inhibitor0.834
CYP450 2C9 substrateNon-substrate0.821
CYP450 2D6 substrateNon-substrate0.8961
CYP450 3A4 substrateNon-substrate0.5
CYP450 1A2 substrateInhibitor0.8714
CYP450 2C9 inhibitorInhibitor0.8199
CYP450 2D6 inhibitorNon-inhibitor0.8721
CYP450 2C19 inhibitorNon-inhibitor0.7799
CYP450 3A4 inhibitorNon-inhibitor0.8406
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5343
Ames testNon AMES toxic0.672
CarcinogenicityNon-carcinogens0.909
BiodegradationNot ready biodegradable0.9955
Rat acute toxicity2.8751 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8835
hERG inhibition (predictor II)Non-inhibitor0.613
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 MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-0009000000-61ea92a0c89b7c1c4f77
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-0309000000-1d152182cc49ff174eec
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-0049000000-a610a9b34b844f2db8fb
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-9003000000-411c163d3745fd91b2a6
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-0935000000-97c97180eebce78e3649
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-9553000000-257a6e4f4121353ed7d1
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]-188.75865
predicted
DeepCCS 1.0 (2019)
[M+H]+191.11667
predicted
DeepCCS 1.0 (2019)
[M+Na]+198.13022
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Dihydroorotate dehydrogenase (quinone), mitochondrial
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Ubiquinone binding
Specific Function
Catalyzes the conversion of dihydroorotate to orotate with quinone as electron acceptor.
Gene Name
DHODH
Uniprot ID
Q02127
Uniprot Name
Dihydroorotate dehydrogenase (quinone), mitochondrial
Molecular Weight
42866.93 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 June 13, 2005 13:24 / Updated at June 12, 2020 16:52