tris(N-cyclohexyl-11-{[(2-methoxyethyl)(methyl)amino]methyl}-N-methyl-5-thia-2,7-diazatricyclo[6.4.0.02,6]dodeca-1(12),3,6,8,10-pentaene-4-carboxamide) bis(but-2-enedioic acid) hydrate

• ChemBase ID: 154474
• Molecular Formular: C74H100N12O15S3
• Molecular Mass: 1493.8522
• Monoisotopic Mass: 1492.65932356
• SMILES: CN(Cc1cc2n3c(sc(c3)C(=O)N(C3CCCCC3)C)nc2cc1)CCOC.CN(Cc1cc2n3c(sc(c3)C(=O)N(C3CCCCC3)C)nc2cc1)CCOC.CN(Cc1cc2n3c(sc(c3)C(=O)N(C3CCCCC3)C)nc2cc1)CCOC.C(=C\C(=O)O)/C(=O)O.C(=C\C(=O)O)/C(=O)O.O
• Canonical SMILES: OC(=O)/C=C/C(=O)O.OC(=O)/C=C/C(=O)O.COCCN(Cc1ccc2c(c1)n1cc(sc1n2)C(=O)N(C1CCCCC1)C)C.COCCN(Cc1ccc2c(c1)n1cc(sc1n2)C(=O)N(C1CCCCC1)C)C.COCCN(Cc1ccc2c(c1)n1cc(sc1n2)C(=O)N(C1CCCCC1)C)C.O
• InChI: InChI=1S/3C22H30N4O2S.2C4H4O4.H2O/c3*1-24(11-12-28-3)14-16-9-10-18-19(13-16)26-15-20(29-22(26)23-18)21(27)25(2)17-7-5-4-6-8-17;2*5-3(6)1-2-4(7)8;/h3*9-10,13,15,17H,4-8,11-12,14H2,1-3H3;2*1-2H,(H,5,6)(H,7,8);1H2
• InChIKey: MCGFIZFYSARKON-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tris(N-cyclohexyl-11-{[(2-methoxyethyl)(methyl)amino]methyl}-N-methyl-5-thia-2,7-diazatricyclo[6.4.0.0^2,^6]dodeca-1(12),3,6,8,10-pentaene-4-carboxamide) bis(but-2-enedioic acid) hydrate
• IUPAC Traditional name: tris(N-cyclohexyl-11-{[(2-methoxyethyl)(methyl)amino]methyl}-N-methyl-5-thia-2,7-diazatricyclo[6.4.0.0^2,^6]dodeca-1(12),3,6,8,10-pentaene-4-carboxamide) bis(butenedioic acid) hydrate
• Synonyms: N-cyclohexyl-6-{[(2-methoxyethyl)(methyl)amino]methyl}-N-methylthiazolo[3,2-a]benzimidazole-2-carboxamide; YM 202074; YM202074; YM-202074 sesquifumarate salt hydrate

Database IDs

• CAS Number: 299900-84-8(anhydrous)
• MDL Number: MFCD16879020
• PubChem SID: 162248613
• PubChem CID: 71311875

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): -0.006459068
• LogD (pH = 7.4): 1.8034005
• Log P: 2.9423
• Molar Refractivity: 128.7244 cm^3
• Polarizability: 45.91182 Å^3
• Polar Surface Area: 50.08 Å^2
• Rotatable Bonds: 25
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: >20 mg/mL; H2O: >5 mg/mL
• Apperance: white to off-white powder

Safety Information

• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 25-36
• Safety Statements: 26-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H319
• GHS Precautionary statements: P301 + P310-P305 + P351 + P338
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: room temp

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C22H30N4O2S · 1.5C4H4O4 · xH2O

DETAILS

Sigma Aldrich - Y1271

Biochem/physiol Actions
YM-202074 is a potent and selective allosteric metabotropic glutamate receptor type 1 (mGluR1) antagonist. It bound an allosteric site of rat mGluR1 with a Ki value of 4.8 nM. It also inhibited the mGluR1-mediated inositol phosphates production in rat cerebellar granule cells with an IC50 value of 8.6 nM, while showing selectivity over mGluR(2-7).