13,23-diazahexacyclo[14.7.0.0^{2,10}.0^{3,8}.0^{11,15}.0^{17,22}]tricosa-1(16),2(10),3(8),4,6,11(15),17(22),18,20-nonaen-14-one

ID: ALA374353

PubChem CID: 9796714

Max Phase: Preclinical

Molecular Formula: C21H14N2O

Molecular Weight: 310.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1NCc2c3c(c4[nH]c5ccccc5c4c21)-c1ccccc1C3

Standard InChI:  InChI=1S/C21H14N2O/c24-21-19-15(10-22-21)14-9-11-5-1-2-6-12(11)17(14)20-18(19)13-7-3-4-8-16(13)23-20/h1-8,23H,9-10H2,(H,22,24)

Standard InChI Key:  TXAHISLWNLQNMW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 29  0  0  0  0  0  0  0  0999 V2000
    1.1272  -13.4567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9522  -13.4636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2137  -12.6811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5503  -12.1906    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8789  -12.6700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0003  -12.4327    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3603  -14.1797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9457  -14.8925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4955  -15.5071    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1664  -14.3538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2463  -15.1715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9931  -15.5095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6606  -15.0307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5763  -14.2104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8293  -13.8761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1137  -14.8886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7053  -14.1633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1109  -14.3274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5499  -15.5011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2045  -15.1534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8807  -15.6324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8040  -16.4594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0450  -16.8048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6281  -16.3237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
 10 11  2  0
  3  4  1  0
 11 12  1  0
  4  5  1  0
 12 13  2  0
  5  1  1  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
 16 17  2  0
  3  6  2  0
  7  8  2  0
  1 17  1  0
 17 18  1  0
 18 20  1  0
 19 16  1  0
 16  8  1  0
  7  2  1  0
 19 20  2  0
  8  9  1  0
 20 21  1  0
  9 11  1  0
 21 22  2  0
 10  7  1  0
 22 23  1  0
  1  2  2  0
 23 24  2  0
 24 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA374353

   13,23-Diazahexacyclo[14.7.0.02,10.03,8.011,15.017,22]tricosa-1,3,5,7,10,15,17,19,21-nonaen-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: 310.36

Molecular Weight (Monoisotopic): 310.1106

AlogP: 4.14

#Rotatable Bonds: ┄

Polar Surface Area: 44.89

Molecular Species: NEUTRAL

HBA: 1

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.35

CX Basic pKa: ┄

CX LogP: 3.68

CX LogD: 3.68

Aromatic Rings: 4

Heavy Atoms: 24

QED Weighted: 0.44

Np Likeness Score: 0.56

References

1. Hudkins RL, Johnson NW, Angeles TS, Gessner GW, Mallamo JP..  (2007)  Synthesis and mixed lineage kinase activity of pyrrolocarbazole and isoindolone analogs of (+)K-252a.,  50  (3): [PMID:17266195] [10.1021/jm051074u]

Source

Source(1):

• Scientific Literature