2,3-Dimethoxy-12-[2-(4-methyl-piperidin-1-yl)-ethyl]-12H-8,10-dioxa-6,12-diaza-cyclopenta[b]chrysen-13-one

ID: ALA191909

PubChem CID: 11751876

Max Phase: Preclinical

Molecular Formula: C27H29N3O5

Molecular Weight: 475.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc2c(=O)n(CCN3CCC(C)CC3)c3c4cc5c(cc4ncc3c2cc1OC)OCO5

Standard InChI:  InChI=1S/C27H29N3O5/c1-16-4-6-29(7-5-16)8-9-30-26-19-12-24-25(35-15-34-24)13-21(19)28-14-20(26)17-10-22(32-2)23(33-3)11-18(17)27(30)31/h10-14,16H,4-9,15H2,1-3H3

Standard InChI Key:  WCCVBYZDMZQENR-UHFFFAOYSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA191909

   16,17-Dimethoxy-21-[2-(4-methylpiperidin-1-yl)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: 475.55

Molecular Weight (Monoisotopic): 475.2107

AlogP: 4.18

#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: 8.46

CX LogP: 3.22

CX LogD: 2.13

Aromatic Rings: 4

Heavy Atoms: 35

QED Weighted: 0.40

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