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

ID: ALA195102

PubChem CID: 22139509

Max Phase: Preclinical

Molecular Formula: C26H28N4O5

Molecular Weight: 476.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc2c(=O)n(CCN3CCN(C)CC3)c3c4cc5c(cc4ncc3c2cc1OC)OCO5

Standard InChI:  InChI=1S/C26H28N4O5/c1-28-4-6-29(7-5-28)8-9-30-25-18-12-23-24(35-15-34-23)13-20(18)27-14-19(25)16-10-21(32-2)22(33-3)11-17(16)26(30)31/h10-14H,4-9,15H2,1-3H3

Standard InChI Key:  RUZDATVGHQQGPD-UHFFFAOYSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA195102

   16,17-Dimethoxy-21-[2-(4-methylpiperazin-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: 476.53

Molecular Weight (Monoisotopic): 476.2060

AlogP: 2.70

#Rotatable Bonds: 5

Polar Surface Area: 78.29

Molecular Species: NEUTRAL

HBA: 9

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.83

CX LogP: 1.93

CX LogD: 1.37

Aromatic Rings: 4

Heavy Atoms: 35

QED Weighted: 0.41

Np Likeness Score: -0.60

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