2-(7-Methoxy-1H-indol-1-yl)-N,N-dimethylethan-1-amine Fumarate Salt

ID: ALA4459661

PubChem CID: 155527381

Max Phase: Preclinical

Molecular Formula: C17H22N2O5

Molecular Weight: 218.30

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cccc2ccn(CCN(C)C)c12.O=C(O)/C=C/C(=O)O

Standard InChI:  InChI=1S/C13H18N2O.C4H4O4/c1-14(2)9-10-15-8-7-11-5-4-6-12(16-3)13(11)15;5-3(6)1-2-4(7)8/h4-8H,9-10H2,1-3H3;1-2H,(H,5,6)(H,7,8)/b;2-1+

Standard InChI Key:  SPNQCEAJUVSITN-WLHGVMLRSA-N

Molfile:  

     RDKit          2D

 24 24  0  0  0  0  0  0  0  0999 V2000
   25.0151  -21.3255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7296  -20.9130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4440  -21.3255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1585  -20.9130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8730  -21.3255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.1585  -20.0881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.3007  -20.9130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.0151  -22.1505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6776  -19.6790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6764  -20.5063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3912  -20.9192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3894  -19.2662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1048  -19.6753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1051  -20.5063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8954  -20.7629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3839  -20.0905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8950  -19.4183    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.1497  -18.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9567  -18.4619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5089  -19.0748    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.3158  -18.9029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2542  -19.8595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3870  -18.4412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1001  -18.0266    0.0000 C   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
 12 23  1  0
 23 24  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: 218.30

Molecular Weight (Monoisotopic): 218.1419

AlogP: 2.21

#Rotatable Bonds: 4

Polar Surface Area: 17.40

Molecular Species: BASE

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.26

CX LogP: 2.16

CX LogD: 0.30

Aromatic Rings: 2

Heavy Atoms: 16

QED Weighted: 0.78

Np Likeness Score: -0.95

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