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

ID: ALA194932

PubChem CID: 11295832

Max Phase: Preclinical

Molecular Formula: C32H32N4O5

Molecular Weight: 552.63

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc2c(=O)n(CCN3CCN(Cc4ccccc4)CC3)c3c4cc5c(cc4ncc3c2cc1OC)OCO5

Standard InChI:  InChI=1S/C32H32N4O5/c1-38-27-14-22-23(15-28(27)39-2)32(37)36(13-12-34-8-10-35(11-9-34)19-21-6-4-3-5-7-21)31-24-16-29-30(41-20-40-29)17-26(24)33-18-25(22)31/h3-7,14-18H,8-13,19-20H2,1-2H3

Standard InChI Key:  ODDIQIDHCJJRSO-UHFFFAOYSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA194932

   21-[2-(4-Benzylpiperazin-1-yl)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: 552.63

Molecular Weight (Monoisotopic): 552.2373

AlogP: 4.27

#Rotatable Bonds: 7

Polar Surface Area: 78.29

Molecular Species: NEUTRAL

HBA: 9

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 7.76

CX LogP: 3.66

CX LogD: 3.14

Aromatic Rings: 5

Heavy Atoms: 41

QED Weighted: 0.28

Np Likeness Score: -0.66

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