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

ID: ALA363839

PubChem CID: 10411339

Max Phase: Preclinical

Molecular Formula: C25H25N3O5

Molecular Weight: 447.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc2c(=O)n(CCN3CCCC3)c3c4cc5c(cc4ncc3c2cc1OC)OCO5

Standard InChI:  InChI=1S/C25H25N3O5/c1-30-20-9-15-16(10-21(20)31-2)25(29)28(8-7-27-5-3-4-6-27)24-17-11-22-23(33-14-32-22)12-19(17)26-13-18(15)24/h9-13H,3-8,14H2,1-2H3

Standard InChI Key:  RWSTWBVRUZUAHJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    2.9792    1.9458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4667    1.2833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.5250    0.8708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5250   -0.8000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1917   -1.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6542   -2.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2458    0.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2458   -0.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 32 33  1  0
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 24 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA363839

   8,9-Dimethoxy-2,3-methylenedioxy-5-[2-(pyrrolidin-1-yl)ethyl]-5H-dibenzo[c,h]1,6-naphthyridin-6-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: 447.49

Molecular Weight (Monoisotopic): 447.1794

AlogP: 3.54

#Rotatable Bonds: 5

Polar Surface Area: 75.05

Molecular Species: NEUTRAL

HBA: 8

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.39

CX LogP: 2.49

CX LogD: 1.46

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.43

Np Likeness Score: -0.54

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