N-(4-chlorophenethyl)-2-((5-methoxy-7-methyl-1H-indol-3-yl)methylene)hydrazinecarboximidamide

ID: ALA4546426

PubChem CID: 155552669

Max Phase: Preclinical

Molecular Formula: C20H22ClN5O

Molecular Weight: 383.88

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cc(C)c2[nH]cc(/C=N/NC(=N)NCCc3ccc(Cl)cc3)c2c1

Standard InChI:  InChI=1S/C20H22ClN5O/c1-13-9-17(27-2)10-18-15(11-24-19(13)18)12-25-26-20(22)23-8-7-14-3-5-16(21)6-4-14/h3-6,9-12,24H,7-8H2,1-2H3,(H3,22,23,26)/b25-12+

Standard InChI Key:  XQIIZGJSJOEPKG-BRJLIKDPSA-N

Molfile:  

 
     RDKit          2D

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    3.9772  -18.8655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9761  -19.6851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6841  -20.0940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6823  -18.4567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3910  -18.8619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3958  -19.6805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1758  -19.9290    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6531  -19.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1680  -18.6045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6852  -20.9112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2694  -18.4571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4160  -17.8258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2143  -17.6512    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4623  -16.8726    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2606  -16.6980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5086  -15.9193    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8110  -17.3020    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.6093  -17.1274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1597  -17.7315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9580  -17.5569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5043  -18.1609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3020  -17.9869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5506  -17.2075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9955  -16.6021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1999  -16.7793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3487  -17.0318    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.5618  -18.8659    0.0000 C   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  1  0
  8  9  2  0
  9  5  1  0
  3 10  1  0
  1 11  1  0
  9 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 23 26  1  0
 11 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4546426

   ---

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: 383.88

Molecular Weight (Monoisotopic): 383.1513

AlogP: 3.83

#Rotatable Bonds: 6

Polar Surface Area: 85.29

Molecular Species: NEUTRAL

HBA: 3

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.17

CX LogP: 4.32

CX LogD: 3.48

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.30

Np Likeness Score: -0.74

References

1. DeChristopher B, Park SH, Vong L, Bamford D, Cho HH, Duvadie R, Fedolak A, Hogan C, Honda T, Pandey P, Rozhitskaya O, Su L, Tomlinson E, Wallace I..  (2019)  Discovery of a small molecule RXFP3/4 agonist that increases food intake in rats upon acute central administration.,  29  (8): [PMID:30824200] [10.1016/j.bmcl.2019.02.013]

2. Guan D, Rahman MT, Gay EA, Vasukuttan V, Mathews KM, Decker AM, Williams AH, Zhan CG, Jin C..  (2021)  Indole-Containing Amidinohydrazones as Nonpeptide, Dual RXFP3/4 Agonists: Synthesis, Structure-Activity Relationship, and Molecular Modeling Studies.,  64  (24.0): [PMID:34855388] [10.1021/acs.jmedchem.1c01081]

Source

Source(1):

• Scientific Literature