12-(2-Ethylamino-ethyl)-2,3-dimethoxy-12H-8,10-dioxa-6,12-diaza-cyclopenta[b]chrysen-13-one

ID: ALA363340

PubChem CID: 11316140

Max Phase: Preclinical

Molecular Formula: C23H23N3O5

Molecular Weight: 421.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCNCCn1c(=O)c2cc(OC)c(OC)cc2c2cnc3cc4c(cc3c21)OCO4

Standard InChI:  InChI=1S/C23H23N3O5/c1-4-24-5-6-26-22-15-9-20-21(31-12-30-20)10-17(15)25-11-16(22)13-7-18(28-2)19(29-3)8-14(13)23(26)27/h7-11,24H,4-6,12H2,1-3H3

Standard InChI Key:  GMUDTVNHMSFVLQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 35  0  0  0  0  0  0  0  0999 V2000
    0.2292   -0.4875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2292    0.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4833   -0.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4833    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2000    0.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2000   -0.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9417    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9417    1.5833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6542    0.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9083    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9083   -0.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2292    1.9958    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4833    1.5833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6542    1.9958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3792    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3792    1.5833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6333    0.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6333   -0.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4833   -1.7250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1542    0.5000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1542    1.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6417    1.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9542   -0.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3458    0.7625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3458   -0.9167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6542   -2.1500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9417   -1.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6542   -2.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0708    0.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0708   -0.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3667   -3.4000    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  9  2  0
 16 15  1  0
 17 18  2  0
 18 11  1  0
 19  3  2  0
 20 15  1  0
 21 16  1  0
 22 20  1  0
 23  1  1  0
 24 17  1  0
 25 18  1  0
 26 27  1  0
 27 23  1  0
 28 26  1  0
 29 24  1  0
 30 25  1  0
 31 28  1  0
  5  4  1  0
 12 13  2  0
 17 10  1  0
 16 14  2  0
 22 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA363340

   21-[2-(Ethylamino)ethyl]-16,17-dimethoxy-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: 421.45

Molecular Weight (Monoisotopic): 421.1638

AlogP: 3.06

#Rotatable Bonds: 6

Polar Surface Area: 83.84

Molecular Species: BASE

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.26

CX LogP: 2.06

CX LogD: 0.21

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.38

Np Likeness Score: -0.41

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