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(+)-[(11)C]galanthamine

ID: ALA3099483

PubChem CID: 73056462

Max Phase: Preclinical

Molecular Formula: C17H21NO3

Molecular Weight: 287.36

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Canonical SMILES:  COc1ccc2c3c1O[C@@H]1C[C@H](O)C=C[C@]31CCN([11CH3])C2

Standard InChI:  InChI=1S/C17H21NO3/c1-18-8-7-17-6-5-12(19)9-14(17)21-16-13(20-2)4-3-11(10-18)15(16)17/h3-6,12,14,19H,7-10H2,1-2H3/t12-,14-,17-/m1/s1/i1-1

Standard InChI Key:  ASUTZQLVASHGKV-CTPQCZGMSA-N

Molfile:  

     RDKit          2D

 22 25  0  0  0  0  0  0  0  0999 V2000
   19.0344   -4.3597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1379   -5.1431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3488   -4.3879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3331   -5.1338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7472   -3.9709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9101   -5.8330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3458   -3.9431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5011   -5.3712    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.2582   -4.1120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7792   -3.1606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0979   -5.9397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5402   -5.8496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3616   -3.1278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3067   -6.5408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1348   -6.5594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5770   -4.5681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0765   -2.7354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3584   -5.8526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0987   -1.9095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7342   -5.6501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7677   -6.5633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4749   -3.5815    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  1  0
  3  5  1  0
  4  1  1  0
  5  1  1  0
  6  4  2  0
  7  1  1  0
  8 16  1  0
  1  9  1  6
 10  5  1  0
 11  6  1  0
 12  2  2  0
 13  7  2  0
 14  6  1  0
 15 14  2  0
 16  9  1  0
 17 13  1  0
 18 12  1  0
 17 19  1  1
 20  8  1  0
 21 18  1  0
  5 22  1  6
  3  2  1  0
 17 10  1  0
 11  8  1  0
 15 12  1  0
M  ISO  1  20  11
M  END

Associated Targets(non-human)

Cerebellum (165 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Striatum (23 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Brain (4203 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Ache Acetylcholinesterase (2577 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 287.36Molecular Weight (Monoisotopic): 287.1521AlogP: 1.85#Rotatable Bonds: 1
Polar Surface Area: 41.93Molecular Species: BASEHBA: 4HBD: 1
#RO5 Violations: HBA (Lipinski): 4HBD (Lipinski): 1#RO5 Violations (Lipinski):
CX Acidic pKa: CX Basic pKa: 8.58CX LogP: 1.16CX LogD: -0.04
Aromatic Rings: 1Heavy Atoms: 21QED Weighted: 0.80Np Likeness Score: 2.11

References

1. Kimura H, Kawai T, Hamashima Y, Kawashima H, Miura K, Nakaya Y, Hirasawa M, Arimitsu K, Kajimoto T, Ohmomo Y, Ono M, Node M, Saji H..  (2014)  Synthesis and evaluation of (-)- and (+)-[¹¹C]galanthamine as PET tracers for cerebral acetylcholinesterase imaging.,  22  (1): [PMID:24315193] [10.1016/j.bmc.2013.11.026]

Source