Chemistry:Monastrol

Monastrol

Names
IUPAC name ethyl 4-(3-hydroxyphenyl)-6-methyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxylate
Other names Monastrol
Identifiers
CAS Number	329689-23-8 N
3D model (JSmol)	Interactive image
ChEBI	CHEBI:75382 Y
ChEMBL	ChEMBL236789 Y
ChemSpider	2259791 Y
PubChem CID	2987927
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) 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
SMILES CCOC(=O)C1=C(NC(=S)NC1C2=CC(=CC=C2)O)C
Properties
Chemical formula	C14H16N2O3S
Molar mass	292.35344
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Tracking categories (test):

• SizeSet

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.

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

References

{{Navbox | name = GABA receptor modulators | title = GABA receptor modulators | state = collapsed | bodyclass = hlist | groupstyle = text-align:center;

 | group1 = Ionotropic
 |  list1 = {{Navbox|subgroup
 | groupstyle = text-align:center
 | groupwidth = 5em

   | group1 = GABAA
   | list1  = 

• Agonists: (+)-Catechin
• Bamaluzole
• Barbiturates (e.g., phenobarbital)
• BL-1020
• DAVA
• Dihydromuscimol
• GABA
• Gabamide
• GABOB
• Gaboxadol (THIP)
• Homotaurine (tramiprosate, 3-APS)
• Ibotenic acid
• iso-THAZ
• iso-THIP
• Isoguvacine
• Isomuscimol
• Isonipecotic acid
• Kojic amine
• Lignans (e.g., honokiol)
• Methylglyoxal
• Monastrol
• Muscimol
• Nefiracetam
• Neuroactive steroids (e.g., allopregnanolone)
• Org 20599
• PF-6372865
• Phenibut
• Picamilon
• P4S
• Progabide
• Propofol
• Quisqualamine
• SL-75102
• TACA
• TAMP
• Terpenoids (e.g., borneol)
• Thiomuscimol
• Tolgabide
• ZAPA

• Positive modulators (abridged; see here for a full list): α-EMTBL
• Alcohols (e.g., ethanol)
• 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)<!--PMID: 9776662-->
• Lanthanum
• Loreclezole
• Monastrol
• Neuroactive steroids (e.g., allopregnanolone, [[Chemistry:Cholecholesterol]], THDOC)
• Niacin
• Nicotinamide (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
• Piperidinediones (e.g., glutethimide)
• Propanidid
• Pyrazolopyridines (e.g., etazolate)
• Quinazolinones (e.g., methaqualone)
• Retigabine (ezogabine)
• ROD-188
• Skullcap constituents (e.g., baicalin)
• Stiripentol
• Sulfonylalkanes (e.g., sulfonmethane (sulfonal))
• Topiramate
• Valerian constituents (e.g., valerenic acid)
• Volatiles/gases (e.g., chloral hydrate, chloroform, [[Chemistry:Diethyl diethyl ether, Parparaldehyde]], sevoflurane)

• Antagonists: Bicuculline
• Coriamyrtin
• Dihydrosecurinine
• Gabazine (SR-95531)
• Hydrastine
• Hyenachin (mellitoxin)
• PHP-501
• Pitrazepin
• Securinine
• Sinomenine
• SR-42641
• SR-95103
• Thiocolchicoside
• Tutin

• Negative modulators: 1,3M1B
• 3M2B
• 11-Ketoprogesterone
• 17-Phenylandrostenol
• α5IA (LS-193,268)
• β-CCB
• β-CCE
• β-CCM
• β-CCP
• β-EMGBL
• Anabolic steroids
• Amiloride
• Anisatin
• β-Lactams (e.g., penicillins, cephalosporins, carbapenems)
• Basmisanil
• Bemegride
• Bicyclic phosphates (TBPS, TBPO, IPTBO)
• BIDN
• Bilobalide
• Bupropion
• CHEB
• Chlorophenylsilatrane
• Cicutoxin
• Cloflubicyne
• Cyclothiazide
• DHEA
• DHEA-S
• Dieldrin
• (+)-DMBB
• DMCM
• DMPC
• EBOB
• Etbicyphat
• FG-7142 (ZK-31906)
• Fiproles (e.g., fipronil)
• Flavonoids (e.g., amentoflavone, oroxylin A)
• Flumazenil
• Fluoroquinolones (e.g., ciprofloxacin)
• Flurothyl
• Furosemide
• Golexanolone
• Iomazenil (¹²³I)
• IPTBO
• Isopregnanolone (sepranolone)
• L-655,708
• Laudanosine
• Leptazol
• Lindane
• MaxiPost
• Morphine
• Morphine-3-glucuronide
• MRK-016
• Naloxone
• Naltrexone
• Nicardipine
• Nonsteroidal antiandrogens (e.g., [[apalutamide, [[Chemistry:Bicalutbicalutamide, Enzalutenzalutamide, Chemistry:Flutamide|flut]]amide]], nilutamide)
• Oenanthotoxin
• Pentylenetetrazol (pentetrazol)
• Phenylsilatrane
• Picrotoxin (i.e., picrotin, picrotoxinin and dihydropicrotoxinin)
• Pregnenolone sulfate
• Propybicyphat
• 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

   | group2 = GABAA-ρ
   | list2  = 

• Agonists: BL-1020
• CACA
• CAMP
• Homohypotaurine
• GABA
• GABOB
• Ibotenic acid
• Isoguvacine
• Muscimol
• N⁴-Chloroacetylcytosine arabinoside
• Picamilon
• Progabide
• TACA
• TAMP
• Thiomuscimol
• Tolgabide

• Positive modulators: Allopregnanolone
• Alphaxolone
• ATHDOC
• Lanthanides

• Antagonists: (S)-2-MeGABA
• (S)-4-ACPBPA
• (S)-4-ACPCA
• 2-MeTACA
• 3-APMPA
• 4-ACPAM
• 4-GBA
• cis-3-ACPBPA
• CGP-36742 (SGS-742)
• DAVA
• Gabazine (SR-95531)
• Gaboxadol (THIP)
• I4AA
• Isonipecotic acid
• Loreclezole
• P4MPA
• P4S
• SKF-97541
• SR-95318
• SR-95813
• TPMPA
• trans-3-ACPBPA
• ZAPA

• Negative modulators: 5α-Dihydroprogesterone
• Bilobalide
• Loreclezole
• Picrotoxin (picrotin, picrotoxinin)
• Pregnanolone
• ROD-188
• THDOC
• Zinc

 }}

 | group2 = Metabotropic

| list2 =

GABAB

Agonists: 1,4-Butanediol 4-Fluorophenibut Aceburic acid Arbaclofen Arbaclofen placarbil Baclofen BL-1020 GABA Gabamide GABOB GBL GHB GHBAL GHV GVL Isovaline Lesogaberan Phenibut Picamilon Progabide Sodium oxybate SKF-97,541 SL 75102 Tolgabide Tolibut Positive modulators: ADX-71441 BHF-177 BHFF BSPP CGP-7930 CGP-13501 GS-39783 rac-BHFF KK-92A Antagonists: 2-Hydroxysaclofen CGP-35348 CGP-46381 CGP-52432 CGP-54626 CGP-55845 CGP-64213 DAVA Homotaurine (tramiprosate, 3-APS) Phaclofen Saclofen SCH-50911 SKF-97541 Negative modulators: Compound 14

 | below = 

See also

Receptor/signaling modulators

GABA_A receptor positive modulators

GABA metabolism/transport modulators

}}