2-Amino-4-(3-cyanophenyl)-4H-benzo[h]chromene-3-carbonitrile

ID: ALA4475290

PubChem CID: 155537648

Max Phase: Preclinical

Molecular Formula: C21H13N3O

Molecular Weight: 323.36

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  N#CC1=C(N)Oc2c(ccc3ccccc23)C1c1cccc(C#N)c1

Standard InChI:  InChI=1S/C21H13N3O/c22-11-13-4-3-6-15(10-13)19-17-9-8-14-5-1-2-7-16(14)20(17)25-21(24)18(19)12-23/h1-10,19H,24H2

Standard InChI Key:  WYJRTCSRJMUVRR-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
    4.7892  -18.2034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4972  -18.6124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7903  -17.3838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4944  -16.9762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4923  -16.1645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7870  -15.7595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0823  -16.1721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0877  -16.9825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2040  -17.3802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2029  -18.2009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9091  -18.6099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6209  -18.2029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6221  -17.3823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9114  -16.9687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3308  -16.9754    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3269  -18.6083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0334  -19.0188    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9054  -19.4241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1949  -19.8301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1923  -20.6465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8994  -21.0579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6106  -20.6469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6097  -19.8318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3176  -21.0519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0256  -21.4599    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0
  1  2  1  0
  2 10  2  0
  9  4  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  3  1  0
  9 10  1  0
  9 14  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 16 17  3  0
 12 16  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 11 18  1  0
 24 25  3  0
 22 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4475290

   ---

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: 323.36

Molecular Weight (Monoisotopic): 323.1059

AlogP: 3.93

#Rotatable Bonds: 1

Polar Surface Area: 82.83

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 1.68

CX LogP: 3.88

CX LogD: 3.88

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.74

Np Likeness Score: -1.08

References

1. Schmitt F, Gold M, Rothemund M, Andronache I, Biersack B, Schobert R, Mueller T..  (2019)  New naphthopyran analogues of LY290181 as potential tumor vascular-disrupting agents.,  163  [PMID:30503940] [10.1016/j.ejmech.2018.11.055]

Source

Source(1):

• Scientific Literature