2-chloro-4-(6-(5-((2-(methylsulfonyl)ethylamino)methyl)furan-2-yl)quinazolin-4-ylimino)cyclohexa-2,5-dienone

ID: ALA3526380

PubChem CID: 118753021

Max Phase: Preclinical

Molecular Formula: C22H19ClN4O4S

Molecular Weight: 470.94

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CS(=O)(=O)CCNCc1ccc(-c2ccc3ncnc(/N=C4\C=CC(=O)C(Cl)=C4)c3c2)o1

Standard InChI:  InChI=1S/C22H19ClN4O4S/c1-32(29,30)9-8-24-12-16-4-7-21(31-16)14-2-5-19-17(10-14)22(26-13-25-19)27-15-3-6-20(28)18(23)11-15/h2-7,10-11,13,24H,8-9,12H2,1H3/b27-15+

Standard InChI Key:  IFMCGRMBEHWPHR-JFLMPSFJSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   12.5014   -5.2498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2113   -5.6584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7988   -5.5924    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.3635   -5.6584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6123   -5.3283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7874   -5.6584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9211   -5.2498    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.0775   -5.2498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2768   -6.4756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2113   -6.4839    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0675   -5.9350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3409   -6.8925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4761   -6.6490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6310   -6.4839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5014   -4.4285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2113   -4.0199    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.9211   -4.4285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6159   -5.6791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9211   -6.8925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3409   -7.7138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7988   -6.4137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9774   -5.5924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0775   -4.4285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7874   -4.0199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6310   -8.1224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9211   -7.7138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4645   -4.8412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7674   -6.5169    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2503   -5.8483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9503   -6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0483   -8.1229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6310   -8.9396    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3 18  1  0
  4  8  1  0
  5  4  1  0
  6  1  1  0
  7  2  1  0
  8  6  2  0
  9  4  2  0
 10  2  1  0
 11  5  1  0
 12 14  2  0
 13  9  1  0
 14 19  1  0
 15  1  1  0
 16 15  2  0
 17 16  1  0
 18 30  1  0
 19 10  2  0
 20 25  1  0
 21  3  2  0
 22  3  2  0
 23 24  2  0
 24 15  1  0
 25 26  2  0
 26 19  1  0
 27  3  1  0
 28 29  1  0
 29 11  1  0
 30 28  1  0
  7 17  2  0
 23  8  1  0
 11 13  2  0
 20 12  1  0
 20 31  2  0
 25 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3526380

   ---

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: 470.94

Molecular Weight (Monoisotopic): 470.0816

AlogP: 3.36

#Rotatable Bonds: 7

Polar Surface Area: 114.52

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.26

CX LogP: 2.49

CX LogD: 2.25

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.42

Np Likeness Score: -0.83

References

1. Chan EC, New LS, Chua TB, Yap CW, Ho HK, Nelson SD..  (2012)  Interaction of lapatinib with cytochrome P450 3A5.,  40  (7): [PMID:22511346] [10.1124/dmd.112.044958]

2. Takakusa H, Wahlin MD, Zhao C, Hanson KL, New LS, Chan EC, Nelson SD..  (2011)  Metabolic intermediate complex formation of human cytochrome P450 3A4 by lapatinib.,  39  (6): [PMID:21363997] [10.1124/dmd.110.037531]

3. Hardy KD, Wahlin MD, Papageorgiou I, Unadkat JD, Rettie AE, Nelson SD..  (2013)  Studies on the role of metabolic activation in tyrosine kinase inhibitor-dependent hepatotoxicity: induction of CYP3A4 enhances the cytotoxicity of lapatinib in HepaRG cells.,  42  [PMID:24191259] [10.1124/dmd.113.054817]

Source

Source(2):

• Scientific Literature
• Curated Drug Metabolism Pathways