2-(6-Fluoro-1H-indol-1-yl)-N,N-dimethylethan-1-amine Fumarate Salt

ID: ALA4474326

PubChem CID: 155536894

Max Phase: Preclinical

Molecular Formula: C16H19FN2O4

Molecular Weight: 206.26

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CN(C)CCn1ccc2ccc(F)cc21.O=C(O)/C=C/C(=O)O

Standard InChI:  InChI=1S/C12H15FN2.C4H4O4/c1-14(2)7-8-15-6-5-10-3-4-11(13)9-12(10)15;5-3(6)1-2-4(7)8/h3-6,9H,7-8H2,1-2H3;1-2H,(H,5,6)(H,7,8)/b;2-1+

Standard InChI Key:  XJDJVUPYWGQYAB-WLHGVMLRSA-N

Molfile:  

     RDKit          2D

 23 23  0  0  0  0  0  0  0  0999 V2000
   11.7415   -5.7833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4560   -5.3708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1704   -5.7833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8850   -5.3708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5994   -5.7833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8850   -4.5458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0271   -5.3708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7415   -6.6083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6526   -3.2583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6515   -4.0856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3663   -4.4985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3645   -2.8455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0799   -3.2547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0801   -4.0856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8706   -4.3423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3589   -3.6698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8702   -2.9976    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1249   -2.2129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9317   -2.0412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4840   -2.6541    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.2909   -2.4823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2294   -3.4388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9381   -2.8459    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  1  7  1  0
  1  8  2  0
  9 10  2  0
 10 11  1  0
 11 14  2  0
 13 12  2  0
 12  9  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 13  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
  9 23  1  0
M  END

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 206.26

Molecular Weight (Monoisotopic): 206.1219

AlogP: 2.34

#Rotatable Bonds: 3

Polar Surface Area: 8.17

Molecular Species: BASE

HBA: 2

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.24

CX LogP: 2.46

CX LogD: 0.62

Aromatic Rings: 2

Heavy Atoms: 15

QED Weighted: 0.75

Np Likeness Score: -1.95

References

1. Dunlap LE, Azinfar A, Ly C, Cameron LP, Viswanathan J, Tombari RJ, Myers-Turnbull D, Taylor JC, Grodzki AC, Lein PJ, Kokel D, Olson DE..  (2020)  Identification of Psychoplastogenic N,N-Dimethylaminoisotryptamine (isoDMT) Analogues through Structure-Activity Relationship Studies.,  63  (3): [PMID:31977208] [10.1021/acs.jmedchem.9b01404]

Source

Source(1):

• Scientific Literature