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

ID: ALA195805

PubChem CID: 11440778

Max Phase: Preclinical

Molecular Formula: C21H19N3O5

Molecular Weight: 393.40

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C21H19N3O5/c1-26-16-5-11-12(6-17(16)27-2)21(25)24(4-3-22)20-13-7-18-19(29-10-28-18)8-15(13)23-9-14(11)20/h5-9H,3-4,10,22H2,1-2H3

Standard InChI Key:  QOVVSZDKEQNEBI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    1.7917    0.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.7792    0.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0917   -1.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2083    0.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2083   -1.1292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7917   -2.3667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0792   -1.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9333    0.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9333   -0.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  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:

   

   ALA195805

   21-(2-Aminoethyl)-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: 393.40

Molecular Weight (Monoisotopic): 393.1325

AlogP: 2.41

#Rotatable Bonds: 4

Polar Surface Area: 97.83

Molecular Species: BASE

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.99

CX LogP: 1.27

CX LogD: -0.32

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.53

Np Likeness Score: -0.25

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