2-amino-1-(4-(3-(3-(trifluoromethyl)phenyl)ureido)phenyl)-1H-pyrrolo[2,3-b]quinoxaline-3-carboxamide

ID: ALA3321822

PubChem CID: 76871916

Max Phase: Preclinical

Molecular Formula: C25H18F3N7O2

Molecular Weight: 505.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(=O)c1c(N)n(-c2ccc(NC(=O)Nc3cccc(C(F)(F)F)c3)cc2)c2nc3ccccc3nc12

Standard InChI:  InChI=1S/C25H18F3N7O2/c26-25(27,28)13-4-3-5-15(12-13)32-24(37)31-14-8-10-16(11-9-14)35-21(29)19(22(30)36)20-23(35)34-18-7-2-1-6-17(18)33-20/h1-12H,29H2,(H2,30,36)(H2,31,32,37)

Standard InChI Key:  RQXYLZHJULSWPX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    6.3434  -10.6299    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2916   -9.6828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  2  0
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 34 37  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3321822

   2-Amino-1-[4-({[3-(Trifluoromethyl)phenyl]carbamoyl}amino)phenyl]-1h-Pyrrolo[2,3-B]quinoxaline-3-Carboxamide

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: 505.46

Molecular Weight (Monoisotopic): 505.1474

AlogP: 4.92

#Rotatable Bonds: 4

Polar Surface Area: 140.95

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.61

CX Basic pKa: 1.01

CX LogP: 4.82

CX LogD: 4.82

Aromatic Rings: 5

Heavy Atoms: 37

QED Weighted: 0.27

Np Likeness Score: -1.67

References

1. Unzue A, Dong J, Lafleur K, Zhao H, Frugier E, Caflisch A, Nevado C..  (2014)  Pyrrolo[3,2-b]quinoxaline derivatives as types I1/2 and II Eph tyrosine kinase inhibitors: structure-based design, synthesis, and in vivo validation.,  57  (15): [PMID:25076195] [10.1021/jm5009242]

2. Unzue, Andrea, Jessen-Trefzer, Claudia, Spiliotopoulos, Dimitrios, Gaudio, Eugenio, Tarantelli, Chiara, Dong, Jing, Zhao, Hongtao, Pachmayr, Johanna, Zahler, Stefan, Bernasconi, Elena, Sartori, Giulio, Cascione, Luciano, Bertoni, Francesco, Sledz, Pawel, Caflisch, Amedeo, Nevado, Cristina.  (2020)  Understanding the mechanism of action of pyrrolo[3,2-b]quinoxaline-derivatives as kinase inhibitors,  11  (6): [PMID:33479666] [10.1039/d0md00049c]

Source

Source(1):

• Scientific Literature