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

ID: ALA195611

PubChem CID: 11238021

Max Phase: Preclinical

Molecular Formula: C32H33N3O5

Molecular Weight: 539.63

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc2c(=O)n(CCN(Cc3ccccc3)C(C)(C)C)c3c4cc5c(cc4ncc3c2cc1OC)OCO5

Standard InChI:  InChI=1S/C32H33N3O5/c1-32(2,3)34(18-20-9-7-6-8-10-20)11-12-35-30-23-15-28-29(40-19-39-28)16-25(23)33-17-24(30)21-13-26(37-4)27(38-5)14-22(21)31(35)36/h6-10,13-17H,11-12,18-19H2,1-5H3

Standard InChI Key:  JXLPQNBZAHZTEV-UHFFFAOYSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA195611

   21-[2-[Benzyl(tert-butyl)amino]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: 539.63

Molecular Weight (Monoisotopic): 539.2420

AlogP: 5.75

#Rotatable Bonds: 7

Polar Surface Area: 75.05

Molecular Species: BASE

HBA: 8

HBD: ┄

#RO5 Violations: 2

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 8.93

CX LogP: 4.87

CX LogD: 3.33

Aromatic Rings: 5

Heavy Atoms: 40

QED Weighted: 0.24

Np Likeness Score: -0.48

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