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

ID: ALA195377

PubChem CID: 11487723

Max Phase: Preclinical

Molecular Formula: C25H27N3O5

Molecular Weight: 449.51

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C25H27N3O5/c1-25(2,3)27-6-7-28-23-16-10-21-22(33-13-32-21)11-18(16)26-12-17(23)14-8-19(30-4)20(31-5)9-15(14)24(28)29/h8-12,27H,6-7,13H2,1-5H3

Standard InChI Key:  NMPAWLAPMZAWFZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 37  0  0  0  0  0  0  0  0999 V2000
    0.1542   -0.2917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1542    0.5333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5625   -0.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5625    0.9458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2833    0.5333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2833   -0.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8625    0.9458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8625    1.7708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5792    0.5333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9958    0.9458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9958   -0.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1542    2.1833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5625    1.7708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5792    2.1833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3000    0.9458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3000    1.7708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7125    0.5333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7125   -0.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5458   -1.5292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0792    0.6958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0792    2.0333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5625    1.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8792   -0.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5792   -2.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5792   -1.9667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4250    0.9583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4250   -0.7167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8625   -1.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5792   -3.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4000   -2.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7542   -2.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1458    0.5458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1458   -0.3042    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 25  1  0
 25 28  1  0
 26 17  1  0
 27 18  1  0
 28 23  1  0
 29 24  1  0
 30 24  1  0
 31 24  1  0
 32 26  1  0
 33 27  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:

   

   ALA195377

   21-[2-(Tert-butylamino)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: 449.51

Molecular Weight (Monoisotopic): 449.1951

AlogP: 3.84

#Rotatable Bonds: 5

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: 9.45

CX LogP: 2.76

CX LogD: 0.74

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.46

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