2-(4-(Benzyloxy)-1H-indol-1-yl)-N,N-dimethylethan-1-amine Fumarate Salt

ID: ALA4465660

PubChem CID: 155531081

Max Phase: Preclinical

Molecular Formula: C23H26N2O5

Molecular Weight: 294.40

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CN(C)CCn1ccc2c(OCc3ccccc3)cccc21.O=C(O)/C=C/C(=O)O

Standard InChI:  InChI=1S/C19H22N2O.C4H4O4/c1-20(2)13-14-21-12-11-17-18(21)9-6-10-19(17)22-15-16-7-4-3-5-8-16;5-3(6)1-2-4(7)8/h3-12H,13-15H2,1-2H3;1-2H,(H,5,6)(H,7,8)/b;2-1+

Standard InChI Key:  RGVAVLCOONBWRG-WLHGVMLRSA-N

Molfile:  

     RDKit          2D

 30 31  0  0  0  0  0  0  0  0999 V2000
   -3.4702    2.0081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4713    1.1808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7566    0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7584    2.4209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0429    2.0117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0427    1.1807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2522    0.9240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7639    1.5966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2527    2.2687    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9979    3.0534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1911    3.2252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3611    2.6123    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1681    2.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1065    1.8276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7563   -0.0571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4706   -0.4698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1853   -0.0575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1826    0.7654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8962    1.1776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6116    0.7649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6088   -0.0643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8944   -0.4728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3281   -0.8012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3865   -0.3887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1009   -0.8012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8154   -0.3887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5298   -0.8012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8154    0.4363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0426   -0.3887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3281   -1.6262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9  5  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
  3 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 26 28  2  0
 23 29  1  0
 23 30  2  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: 294.40

Molecular Weight (Monoisotopic): 294.1732

AlogP: 3.78

#Rotatable Bonds: 6

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: 3.88

CX LogD: 2.03

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.69

Np Likeness Score: -1.22

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