N-Propylstrychnine bromide

ID: ALA4069635

PubChem CID: 137639832

Max Phase: Preclinical

Molecular Formula: C24H29BrN2O2

Molecular Weight: 377.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC[N+]12CC[C@@]34c5ccccc5N5C(=O)C[C@@H]6OCC=C(C1)[C@H](C[C@@H]32)[C@@H]6[C@H]54.[Br-]

Standard InChI:  InChI=1S/C24H29N2O2.BrH/c1-2-9-26-10-8-24-17-5-3-4-6-18(17)25-21(27)13-19-22(23(24)25)16(12-20(24)26)15(14-26)7-11-28-19;/h3-7,16,19-20,22-23H,2,8-14H2,1H3;1H/q+1;/p-1/t16-,19-,20-,22-,23-,24+,26?;/m0./s1

Standard InChI Key:  ODEPLBNGMGYWQT-YRDDRJARSA-M

Molfile:  

     RDKit          2D

 34 39  0  0  0  0  0  0  0  0999 V2000
   16.5128   -7.9326    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   12.2084  -11.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9316  -11.6533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8858  -10.0077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1868  -10.4383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6136  -10.4011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6343  -11.2277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3933  -10.1261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0256   -9.9194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5264   -9.2636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7071   -9.3666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8925  -10.7819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4266  -11.4601    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.9035  -12.1903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7728  -12.1614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1806  -11.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7066  -10.6802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7290  -10.6017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9984  -11.4402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7992   -9.4809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4625   -8.4557    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.2678   -8.5179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4800   -9.7009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8146   -9.2319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1840   -8.4557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5550  -12.9346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2965  -11.4901    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.1138  -10.0745    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.7328  -10.3277    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.4962  -10.8881    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.5834  -12.1500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.1068   -7.9453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9870   -7.1322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4646   -6.6059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  7  1  0
  6  4  1  0
  4  5  2  0
  5  2  1  0
  6  7  2  0
  7 13  1  0
  8  6  1  0
  8 12  1  0
  8 11  1  0
 12 17  1  0
 17  9  1  0
  9 10  1  0
 10 11  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 19  1  0
 19 18  1  0
  9 20  1  0
 11 21  1  0
 21 22  1  0
 22 20  1  0
 20 23  2  0
 23 18  1  0
  8 24  1  1
 24 25  1  0
 25 21  1  0
 14 26  2  0
 12 27  1  1
 11 28  1  6
  9 29  1  6
 17 30  1  6
 16 31  1  6
 21 32  1  0
 32 33  1  0
 33 34  1  0
M  CHG  2   1  -1  21   1
M  END

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 377.51

Molecular Weight (Monoisotopic): 377.2224

AlogP: 3.02

#Rotatable Bonds: 2

Polar Surface Area: 29.54

Molecular Species: NEUTRAL

HBA: 2

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: -2.36

CX LogD: -2.36

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.59

Np Likeness Score: 2.59

References

1. Mohsen AM, Mandour YM, Sarukhanyan E, Breitinger U, Villmann C, Banoub MM, Breitinger HG, Dandekar T, Holzgrabe U, Sotriffer C, Jensen AA, Zlotos DP..  (2016)  Oxime Ethers of (E)-11-Isonitrosostrychnine as Highly Potent Glycine Receptor Antagonists.,  79  (12): [PMID:27966945] [10.1021/acs.jnatprod.6b00479]

Source

Source(1):

• Scientific Literature