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

ID: ALA195107

PubChem CID: 11351043

Max Phase: Preclinical

Molecular Formula: C24H25N3O5

Molecular Weight: 435.48

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C24H25N3O5/c1-13(2)25-5-6-27-23-16-9-21-22(32-12-31-21)10-18(16)26-11-17(23)14-7-19(29-3)20(30-4)8-15(14)24(27)28/h7-11,13,25H,5-6,12H2,1-4H3

Standard InChI Key:  YUJFXDQDMGPPLM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    0.2000    0.4458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5208   -0.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5208    0.8583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9167    1.6833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.5208    1.6833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6292    2.0958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3417    0.8583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.5208   -1.6250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1292    0.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1292    1.9375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6125    1.2708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9167   -0.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6167   -2.0417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3833    0.8625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3833   -0.8042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9125   -1.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6292   -2.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1000    0.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1000   -0.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9125   -3.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3417   -3.2917    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
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  8  7  2  0
  9  7  1  0
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 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 27  1  0
 25 17  1  0
 26 18  1  0
 27 23  1  0
 28 24  1  0
 29 25  1  0
 30 26  1  0
 31 28  1  0
 32 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:

   

   ALA195107

   16,17-Dimethoxy-21-[2-(propan-2-ylamino)ethyl]-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: 435.48

Molecular Weight (Monoisotopic): 435.1794

AlogP: 3.45

#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: 9.35

CX LogP: 2.48

CX LogD: 0.54

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.46

Np Likeness Score: -0.40

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