3-{12-ethynyl-8-methyl-9-oxo-2,4,8-triazatricyclo[8.4.0.02,6]tetradeca-1(14),3,5,10,12-pentaene-5-carbonyloxy}propyl 12-ethynyl-8-methyl-9-oxo-2,4,8-triazatricyclo[8.4.0.02,6]tetradeca-1(14),3,5,10,12-pentaene-5-carboxylate hydrate

• ChemBase ID: 153946
• Molecular Formular: C33H28N6O7
• Molecular Mass: 620.61142
• Monoisotopic Mass: 620.20194727
• SMILES: CN1Cc2c(ncn2c2ccc(cc2C1=O)C#C)C(=O)OCCCOC(=O)c1c2n(cn1)c1ccc(cc1C(=O)N(C2)C)C#C.O
• Canonical SMILES: C#Cc1ccc2c(c1)C(=O)N(C)Cc1n2cnc1C(=O)OCCCOC(=O)c1ncn2c1CN(C)C(=O)c1c2ccc(c1)C#C.O
• InChI: InChI=1S/C33H26N6O6.H2O/c1-5-20-8-10-24-22(14-20)30(40)36(3)16-26-28(34-18-38(24)26)32(42)44-12-7-13-45-33(43)29-27-17-37(4)31(41)23-15-21(6-2)9-11-25(23)39(27)19-35-29;/h1-2,8-11,14-15,18-19H,7,12-13,16-17H2,3-4H3;1H2
• InChIKey: KMNXXZIAPMJRKU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-{12-ethynyl-8-methyl-9-oxo-2,4,8-triazatricyclo[8.4.0.0^2,^6]tetradeca-1(14),3,5,10,12-pentaene-5-carbonyloxy}propyl 12-ethynyl-8-methyl-9-oxo-2,4,8-triazatricyclo[8.4.0.0^2,^6]tetradeca-1(14),3,5,10,12-pentaene-5-carboxylate hydrate
• IUPAC Traditional name: 3-{12-ethynyl-8-methyl-9-oxo-2,4,8-triazatricyclo[8.4.0.0^2,^6]tetradeca-1(14),3,5,10,12-pentaene-5-carbonyloxy}propyl 12-ethynyl-8-methyl-9-oxo-2,4,8-triazatricyclo[8.4.0.0^2,^6]tetradeca-1(14),3,5,10,12-pentaene-5-carboxylate hydrate
• Synonyms: Bis[8-ethynyl-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylic acid] 1,3-propanediyl ester hydrate; Xli 093 hydrate

Database IDs

• CAS Number: 646066-59-3(anhydrous)
• MDL Number: MFCD08705422
• PubChem SID: 162248085; 24724668
• PubChem CID: 16079020

CALCULATED PROPERTIES

• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): -0.075581126
• LogD (pH = 7.4): -0.07076163
• Log P: -0.0707
• Molar Refractivity: 179.1682 cm^3
• Polarizability: 61.5638 Å^3
• Polar Surface Area: 128.86 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: ~16 mg/mL; H2O: insoluble
• Apperance: off-white powder

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C33H26N6O6 · xH2O

DETAILS

Sigma Aldrich - X4628

Biochem/physiol Actions
Xli 093 is α5 subtype selective benzodiazepine/GABAA receptor antagonist. Xli 093 shows Ki = 5 nM at the α5 receptor in Ltk- cell membranes expressing human α5β3γ2 receptors; little or no affinity at other BDZ/ GABAA subtypes; does not trigger chloride currents in any subtype of tested subtypes, up to 1 μM in concentration; dose-dependently and completely inhibits diazepam stimulated currents in α5β3γ2 receptors.