(E)-11-isonitrosostrychnine

ID: ALA4089150

PubChem CID: 99118914

Max Phase: Preclinical

Molecular Formula: C21H21N3O3

Molecular Weight: 363.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1/C(=N/O)[C@@H]2OCC=C3CN4CC[C@]56c7ccccc7N1[C@H]5[C@H]2[C@H]3C[C@H]46

Standard InChI:  InChI=1S/C21H21N3O3/c25-20-17(22-26)18-16-12-9-15-21(6-7-23(15)10-11(12)5-8-27-18)13-3-1-2-4-14(13)24(20)19(16)21/h1-5,12,15-16,18-19,26H,6-10H2/b22-17+/t12-,15-,16-,18+,19-,21+/m0/s1

Standard InChI Key:  CMOAVMXESDVBSR-SJOSXICLSA-N

Molfile:  

     RDKit          2D

 32 38  0  0  0  0  0  0  0  0999 V2000
    1.6594  -11.5936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3784  -11.9869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3328  -10.3506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6379  -10.7788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0565  -10.7418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0770  -11.5636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8318  -10.4685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4546  -10.2628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9583   -9.6109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1437   -9.7133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3281  -11.1204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8648  -11.7947    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3391  -12.5207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2034  -12.4920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.8949   -8.8075    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6956   -8.8694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9007  -10.0457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2564   -9.5793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6237   -8.8075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9926  -13.2608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7298  -11.8245    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5482  -10.4171    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1578  -10.6689    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9226  -11.2261    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0092  -12.4807    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6265  -13.1912    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4435  -13.1743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  6  1  0
  5  3  1  0
  3  4  2  0
  4  1  1  0
  5  6  2  0
  6 12  1  0
  7  5  1  0
  7 11  1  0
  7 10  1  0
 11 16  1  0
 16  8  1  0
  8  9  1  0
  9 10  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 18  1  0
 18 17  1  0
  8 19  1  0
 10 20  1  0
 20 21  1  0
 21 19  1  0
 19 22  2  0
 22 17  1  0
  7 23  1  1
 23 24  1  0
 24 20  1  0
 13 25  2  0
 11 26  1  1
 10 27  1  6
  8 28  1  6
 16 29  1  6
 15 30  1  6
 14 31  2  0
 31 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4089150

   (4aR,5aS,8aR,13aS,15E,15aR,15bR)-15-hydroxyimino-2,4a,5,5a,7,8,13a,15a,15b,16-decahydro4,6-methanoindolo[3,2,1-ij]oxepino[2,3,4-de]pyrrolo[2,3-h]quinolin-14-one

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: 363.42

Molecular Weight (Monoisotopic): 363.1583

AlogP: 1.53

#Rotatable Bonds: ┄

Polar Surface Area: 65.37

Molecular Species: BASE

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.56

CX Basic pKa: 9.29

CX LogP: 1.14

CX LogD: -0.75

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.43

Np Likeness Score: 2.48

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