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Monastrol
Names
IUPAC name
ethyl 4-(3-hydroxyphenyl)-6-methyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxylate
Other names
Monastrol
Identifiers
ChEBI
ChEMBL
ChemSpider
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)
N Key: LOBCDGHHHHGHFA-UHFFFAOYSA-N
Y InChI=1/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)
Key: LOBCDGHHHHGHFA-UHFFFAOYAO
CCOC(=O)C1=C(NC(=S)NC1C2=CC(=CC=C2)O)C
Properties
C14 H16 N2 O3 S
Molar mass
292.35344
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
Monastrol is a cell-permeable small molecule inhibitor discovered by Thomas U. Mayer in the lab of Tim Mitchison . Monastrol was shown to inhibit the kinesin -5 (also known as KIF11 , Kinesin Eg5), a motor protein important for spindle bipolarity.[ 1]
Mechanism of action
Monastrol inhibits Eg5
Monastrol binds to a long loop that is specific to the Eg5 (also known as KIF11 or kinesin-5) kinesin family, and allosterically inhibits ATPase activity of the kinesin [ 2]
References
Ionotropic
GABAA Tooltip γ-Aminobutyric acid A receptor
Positive modulators (abridged; see here for a full list): α-EMTBL
Alcohols (e.g., drinking alcohol , 2M2B )
Anabolic steroids
Avermectins (e.g., ivermectin )
Barbiturates (e.g., phenobarbital )
Benzodiazepines (e.g., diazepam )
Bromide compounds (e.g., potassium bromide )
Carbamates (e.g., meprobamate )
Carbamazepine
Chloralose
Chlormezanone
Clomethiazole
Dihydroergolines (e.g., ergoloid (dihydroergotoxine) )
Etazepine
Etifoxine
Fenamates (e.g., mefenamic acid )
Flavonoids (e.g., apigenin , hispidulin )
Fluoxetine
Flupirtine
Imidazoles (e.g., etomidate )
Kava constituents (e.g., kavain )
Lanthanum
Loreclezole
Monastrol
Neuroactive steroids (e.g., allopregnanolone , cholesterol , THDOC )
Niacin
Niacinamide
Nonbenzodiazepines (e.g., β-carbolines (e.g., abecarnil ), cyclopyrrolones (e.g., zopiclone ), imidazopyridines (e.g., zolpidem ), pyrazolopyrimidines (e.g., zaleplon ))
Norfluoxetine
Petrichloral
Phenols (e.g., propofol )
Phenytoin
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Quinazolinones (e.g., methaqualone )
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ROD-188
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Stiripentol
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Topiramate
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Volatiles /gases (e.g., chloral hydrate , chloroform , diethyl ether , paraldehyde , sevoflurane )
Negative modulators: 1,3M1B
3M2B
11-Ketoprogesterone
17-Phenylandrostenol
α3IA
α5IA (LS-193,268)
β-CCB
β-CCE
β-CCM
β-CCP
β-EMGBL
Anabolic steroids
Amiloride
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β-Lactams (e.g., penicillins , cephalosporins , carbapenems )
Basmisanil
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BIDN
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FG-7142 (ZK-31906)
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Flumazenil
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IPTBO
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L-655,708
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Morphine
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MRK-016
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PWZ-029
Radequinil
Ro 15-4513
Ro 19-4603
RO4882224
RO4938581
Sarmazenil
SCS
Suritozole
TB-21007
TBOB
TBPS
TCS-1105
Terbequinil
TETS
Thujone
U-93631
Zinc
ZK-93426
GABAA -ρ Tooltip γ-Aminobutyric acid A-rho receptor
Metabotropic
GABAB Tooltip γ-Aminobutyric acid B receptor
Receptor (ligands )
GHBR Tooltip GHB receptor GABAB Tooltip γ-Aminobutyric acid B receptor
Transporter (blockers )
MCTs Tooltip Monocarboxylate transporters SMCTs Tooltip Sodium-coupled monocarboxylate transporters VIATT Tooltip Vesicular inhibitory amino acid transporter
Enzyme (inhibitors )
SSR Tooltip Succinic semialdehyde reductase GHBDH Tooltip 4-Hydroxybutyrate dehydrogenase HOT Tooltip Hydroxyacid-oxoacid transhydrogenase ADH Tooltip Alcohol dehydrogenase ALDH Tooltip Aldehyde dehydrogenase