NAV

Monastrol

Identification

Generic Name
Monastrol
DrugBank Accession Number
DB04331
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 292.353
Monoisotopic: 292.088163078
Chemical Formula
C14H16N2O3S
Synonyms
  • (+)-Monastrol
  • (4S)-Monastrol
  • (S)-monastrol
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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
UKinesin-like protein KIF11Not 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 Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
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.
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AmbroxolThe risk or severity of methemoglobinemia can be increased when Monastrol is combined with Ambroxol.
ArticaineThe risk or severity of methemoglobinemia can be increased when Monastrol is combined with Articaine.
BenzocaineThe risk or severity of methemoglobinemia can be increased when Monastrol is combined with Benzocaine.
Benzyl alcoholThe risk or severity of methemoglobinemia can be increased when Monastrol is combined with Benzyl alcohol.
BupivacaineThe risk or severity of methemoglobinemia can be increased when Monastrol is combined with Bupivacaine.
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as hydropyrimidine carboxylic acids and derivatives. These are compounds containing a hydrogenated pyrimidine ring which bears a carboxylic acid group.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Diazines
Sub Class
Pyrimidines and pyrimidine derivatives
Direct Parent
Hydropyrimidine carboxylic acids and derivatives
Alternative Parents
Pyrimidinethiones / 2-Thiopyrimidines / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Benzene and substituted derivatives / Vinylogous amides / Enoate esters / Thioureas / Monocarboxylic acids and derivatives / Azacyclic compounds
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Substituents
1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / 2-thiopyrimidine / Alpha,beta-unsaturated carboxylic ester / Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester
show 17 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
monastrol (CHEBI:75384)
Affected organisms
Not Available

Chemical Identifiers

UNII
6BSM97YZ8G
CAS number
254753-54-3
InChI Key
LOBCDGHHHHGHFA-LBPRGKRZSA-N
InChI
InChI=1S/C14H16N2O3S/c1-3-19-13(18)11-8(2)15-14(20)16-12(11)9-5-4-6-10(17)7-9/h4-7,12,17H,3H2,1-2H3,(H2,15,16,20)/t12-/m0/s1
IUPAC Name
ethyl (4S)-4-(3-hydroxyphenyl)-6-methyl-2-sulfanylidene-1,2,3,4-tetrahydropyrimidine-5-carboxylate
SMILES
CCOC(=O)C1=C(C)NC(=S)N[C@H]1C1=CC=CC(O)=C1

References

General References
Not Available
PubChem Compound
794323
PubChem Substance
46508959
ChemSpider
694709
ChEBI
75384
ChEMBL
CHEMBL254432
ZINC
ZINC000004425506
PDBe Ligand
NAT
Wikipedia
Monastrol
PDB Entries
1q0b / 1x88

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
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 Solubility0.0603 mg/mLALOGPS
logP2.11ALOGPS
logP1.83Chemaxon
logS-3.7ALOGPS
pKa (Strongest Acidic)9.37Chemaxon
pKa (Strongest Basic)-6Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area70.59 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity81.41 m3·mol-1Chemaxon
Polarizability30.22 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.8805
Blood Brain Barrier-0.9108
Caco-2 permeable-0.5425
P-glycoprotein substrateSubstrate0.5619
P-glycoprotein inhibitor IInhibitor0.5817
P-glycoprotein inhibitor IINon-inhibitor0.8551
Renal organic cation transporterNon-inhibitor0.8409
CYP450 2C9 substrateNon-substrate0.7354
CYP450 2D6 substrateNon-substrate0.8222
CYP450 3A4 substrateNon-substrate0.5795
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorInhibitor0.6529
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorInhibitor0.8994
CYP450 3A4 inhibitorNon-inhibitor0.6004
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.9141
Ames testNon AMES toxic0.6574
CarcinogenicityNon-carcinogens0.8282
BiodegradationNot ready biodegradable0.9848
Rat acute toxicity2.4622 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9605
hERG inhibition (predictor II)Non-inhibitor0.7884
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-MSsplash10-004j-5290000000-921ed1e316073e67929f
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0005-0490000000-599d281925a5d84eac59
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-01ox-0090000000-0720d9afb1e7b2c2c861
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0ged-0390000000-5e06799ce537be951565
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-1090000000-532ca815b616805f7988
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-05a2-2970000000-fbc2f30cc1451441e5fb
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0gbc-6790000000-73911edc21196e22b4ec
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]-166.62859
predicted
DeepCCS 1.0 (2019)
[M+H]+168.98659
predicted
DeepCCS 1.0 (2019)
[M+Na]+175.64032
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Kinesin-like protein KIF11
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Protein kinase binding
Specific Function
Motor protein required for establishing a bipolar spindle. Blocking of KIF11 prevents centrosome migration and arrest cells in mitosis with monoastral microtubule arrays.
Gene Name
KIF11
Uniprot ID
P52732
Uniprot Name
Kinesin-like protein KIF11
Molecular Weight
119158.025 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. 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