5-Methoxy-3-((S)-1-methyl-pyrrolidin-2-ylmethyl)-1H-indole

ID: ALA133939

PubChem CID: 10105889

Max Phase: Preclinical

Molecular Formula: C15H20N2O

Molecular Weight: 244.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc2[nH]cc(C[C@@H]3CCCN3C)c2c1

Standard InChI:  InChI=1S/C15H20N2O/c1-17-7-3-4-12(17)8-11-10-16-15-6-5-13(18-2)9-14(11)15/h5-6,9-10,12,16H,3-4,7-8H2,1-2H3/t12-/m0/s1

Standard InChI Key:  MKEGUJPBCIXABO-LBPRGKRZSA-N

Molfile:  

     RDKit          2D

 19 21  0  0  1  0  0  0  0  0999 V2000
    2.5417   -2.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9750   -2.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5417   -3.2667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875   -2.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5625   -1.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7292   -1.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9750   -3.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3167   -1.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4500   -2.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4500   -3.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9292   -2.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9292   -3.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1542   -1.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2625   -0.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -2.1917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7625   -2.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2792   -1.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1083   -2.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3125   -2.2125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  4  1  0
  4  1  2  0
  5  8  1  0
  6  1  1  0
  7  2  2  0
  8  6  1  0
  9  2  1  0
 10  7  1  0
 11  9  2  0
 12 11  1  0
 13  5  1  0
 14  5  1  0
 15 11  1  0
 16  8  1  0
 17 16  1  0
 18 15  1  0
  8 19  1  6
  3  7  1  0
 13 17  1  0
 12 10  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA133939

   (S)-5-Methoxy-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 244.34

Molecular Weight (Monoisotopic): 244.1576

AlogP: 2.81

#Rotatable Bonds: 3

Polar Surface Area: 28.26

Molecular Species: BASE

HBA: 2

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.69

CX LogP: 2.61

CX LogD: 0.34

Aromatic Rings: 2

Heavy Atoms: 18

QED Weighted: 0.90

Np Likeness Score: -0.09

References

1. Gerasimov M, Marona-Lewicka D, Kurrasch-Orbaugh DM, Qandil AM, Nichols DE..  (1999)  Further studies on oxygenated tryptamines with LSD-like activity incorporating a chiral pyrrolidine moiety into the side chain.,  42  (20): [PMID:10514296] [10.1021/jm990325u]

2. Macor JE, Blake J, Fox CB, Johnson C, Koe BK, Lebel LA, Morrone JM, Ryan K, Schmidt AW, Schulz DW..  (1992)  Synthesis and serotonergic pharmacology of the enantiomers of 3-[(N-methylpyrrolidin-2-yl)methyl]-5-methoxy-1H-indole: discovery of stereogenic differentiation in the aminoethyl side chain of the neurotransmitter serotonin.,  35  (23): [PMID:1447752] [10.1021/jm00101a032]

Source

Source(1):

• Scientific Literature