2-(5-(Benzyloxy)-1H-indol-1-yl)-N,N-dimethylethan-1-amine Fumarate Salt

ID: ALA4578971

PubChem CID: 155565476

Max Phase: Preclinical

Molecular Formula: C23H26N2O5

Molecular Weight: 294.40

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CN(C)CCn1ccc2cc(OCc3ccccc3)ccc21.O=C(O)/C=C/C(=O)O

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

Standard InChI Key:  DAPQPRCEMGSRGD-WLHGVMLRSA-N

Molfile:  

     RDKit          2D

 30 31  0  0  0  0  0  0  0  0999 V2000
    8.2089  -29.5057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9234  -29.0932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6379  -29.5057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3523  -29.0932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0668  -29.5057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3523  -28.2682    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4945  -29.0932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2089  -30.3307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5652  -26.6040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5640  -27.4314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2789  -27.8442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2771  -26.1912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9924  -26.6003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9926  -27.4314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7831  -27.6880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2714  -27.0154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7827  -26.3434    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0374  -25.5587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8444  -25.3868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3966  -25.9997    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.2034  -25.8280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1419  -26.7845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8493  -27.8433    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1351  -27.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4204  -27.8422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7118  -27.4305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9927  -27.8418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9939  -28.6676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7164  -29.0805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4199  -28.6669    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
 10 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  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: 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: 9.24

CX LogP: 3.88

CX LogD: 2.04

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.69

Np Likeness Score: -1.30

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