2,3-Dimethoxy-12-(2-piperazin-1-yl-ethyl)-12H-8,10-dioxa-6,12-diaza-cyclopenta[b]chrysen-13-one

ID: ALA195792

PubChem CID: 11305763

Max Phase: Preclinical

Molecular Formula: C25H26N4O5

Molecular Weight: 462.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc2c(=O)n(CCN3CCNCC3)c3c4cc5c(cc4ncc3c2cc1OC)OCO5

Standard InChI:  InChI=1S/C25H26N4O5/c1-31-20-9-15-16(10-21(20)32-2)25(30)29(8-7-28-5-3-26-4-6-28)24-17-11-22-23(34-14-33-22)12-19(17)27-13-18(15)24/h9-13,26H,3-8,14H2,1-2H3

Standard InChI Key:  OOEHOPSGXVHFSJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 34 39  0  0  0  0  0  0  0  0999 V2000
   -0.0208   -0.2875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0208    0.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7458   -0.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7458    0.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4583    0.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4583   -0.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7000    0.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7000    1.7833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4042    0.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1708    0.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1708   -0.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0333    2.1958    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7458    1.7833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4042    2.1958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7000   -0.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1167    0.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1167    1.7833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8833    0.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8833   -0.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4042   -1.9500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7458   -1.5250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9042    0.7000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9042    2.0375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3917    1.3708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8417   -2.7792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7000   -1.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6000   -0.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6000    0.9625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4042   -2.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1167   -1.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8417   -1.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1167   -3.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3208   -0.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3208    0.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  2  2  0
  5  6  1  0
  6  3  1  0
  7  2  1  0
  8  7  2  0
  9  7  1  0
 10  5  2  0
 11  6  2  0
 12  8  1  0
 13  4  1  0
 14  8  1  0
 15  1  1  0
 16  9  2  0
 17 16  1  0
 18 19  2  0
 19 11  1  0
 20 26  1  0
 21  3  2  0
 22 16  1  0
 23 17  1  0
 24 22  1  0
 25 31  1  0
 26 15  1  0
 27 19  1  0
 28 18  1  0
 29 20  1  0
 30 20  1  0
 31 30  1  0
 32 29  1  0
 33 27  1  0
 34 28  1  0
  5  4  1  0
 12 13  2  0
 25 32  1  0
 18 10  1  0
 17 14  2  0
 24 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA195792

   16,17-Dimethoxy-21-(2-piperazin-1-ylethyl)-5,7-dioxa-11,21-diazapentacyclo[11.8.0.02,10.04,8.014,19]henicosa-1(13),2,4(8),9,11,14,16,18-octaen-20-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: 462.51

Molecular Weight (Monoisotopic): 462.1903

AlogP: 2.35

#Rotatable Bonds: 5

Polar Surface Area: 87.08

Molecular Species: BASE

HBA: 9

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.22

CX LogP: 1.55

CX LogD: -0.26

Aromatic Rings: 4

Heavy Atoms: 34

QED Weighted: 0.45

Np Likeness Score: -0.51

References

1. Ruchelman AL, Houghton PJ, Zhou N, Liu A, Liu LF, LaVoie EJ..  (2005)  5-(2-aminoethyl)dibenzo[c,h][1,6]naphthyridin-6-ones: variation of n-alkyl substituents modulates sensitivity to efflux transporters associated with multidrug resistance.,  48  (3): [PMID:15689163] [10.1021/jm049447z]

2. Zhou W, Dai Z, Chen Y, Yuan Z.  (2013)  Computational QSAR models with high-dimensional descriptor selection improve antitumor activity design of ARC-111 analogues,  22  (1): [10.1007/s00044-012-0034-x]

Source

Source(1):

• Scientific Literature