(1R,9S)-1-methyl-16-azatetracyclo[7.6.1.02,7.010,15]hexadeca-2,4,6,10(15),11,13-hexaene; but-2-enedioic acid

• ChemBase ID: 155361
• Molecular Formular: C20H19NO4
• Molecular Mass: 337.36916
• Monoisotopic Mass: 337.13140809
• SMILES: C[C@]12c3ccccc3C[C@H](N1)c1c2cccc1.C(=C\C(=O)O)/C(=O)O
• Canonical SMILES: C[C@@]12N[C@H](c3c2cccc3)Cc2c1cccc2.OC(=O)/C=C/C(=O)O
• InChI: InChI=1S/C16H15N.C4H4O4/c1-16-13-8-4-2-6-11(13)10-15(17-16)12-7-3-5-9-14(12)16;5-3(6)1-2-4(7)8/h2-9,15,17H,10H2,1H3;1-2H,(H,5,6)(H,7,8)/t15-,16+;/m0./s1
• InChIKey: QLTXKCWMEZIHBJ-IDVLALEDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,9S)-1-methyl-16-azatetracyclo[7.6.1.0^2,^7.0^1^0,^1^5]hexadeca-2,4,6,10(15),11,13-hexaene; but-2-enedioic acid
• IUPAC Traditional name: (1R,9S)-1-methyl-16-azatetracyclo[7.6.1.0^2,^7.0^1^0,^1^5]hexadeca-2,4,6,10(15),11,13-hexaene; butenedioic acid
• Synonyms: (5R,10S)-(-)-5-Methyl-10,11-dihydro-5H-dibenzo-[a,d]-cyclo-hepten-5,10-imine hydrogen maleate; (-)-MK-801 hydrogen maleate

Database IDs

• CAS Number: 77086-19-2
• MDL Number: MFCD00082466
• PubChem SID: 162249499; 24277961
• PubChem CID: 71312123

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 0.44438058
• LogD (pH = 7.4): 2.0864916
• Log P: 3.3085747
• Molar Refractivity: 69.9624 cm^3
• Polarizability: 27.347187 Å^3
• Polar Surface Area: 12.03 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >20 mg/mL
• Apperance: white solid
• Optical Rotation: [α]25/D -117.7°, c = 1 in methanol(lit.)

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: room temp

Pharmacology Properties

• Gene Information: human ... GRIN1(2902), GRIN2C(2905), GRIN2D(2906), GRIN3A(116443), GRIN3B(116444), GRINA(2907)mouse ... GRIN1(14810), GRIN2C(14813), GRIN2D(14814), GRIN3A(242443), GRIN3B(170483), GRINA(66168)rat ... GRIN1(24408), GRIN2C(24411), GRIN2D(24412), GRIN3A(191573), GRIN3B(170796), GRINA(266668)

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C16H15N · C4H4O4

DETAILS

Sigma Aldrich - M108

Biochem/physiol Actions
Less active enantiomer of (+)-MK-801 hydrogen maleate