Ethyl 5-((1H-Pyrrolo-[2,3-b]pyridin-3-yl)methylene)-4-oxo-2-((4-(2,2,2-trifluoroethyl)piperazin-1-yl)amino)-4,5-dihydrofuran-3-carboxylate

ID: ALA4868568

PubChem CID: 136618371

Max Phase: Phase

Molecular Formula: C21H22F3N5O4

Molecular Weight: 465.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)C1=C(NN2CCN(CC(F)(F)F)CC2)O/C(=C\c2c[nH]c3ncccc23)C1=O

Standard InChI:  InChI=1S/C21H22F3N5O4/c1-2-32-20(31)16-17(30)15(10-13-11-26-18-14(13)4-3-5-25-18)33-19(16)27-29-8-6-28(7-9-29)12-21(22,23)24/h3-5,10-11,27H,2,6-9,12H2,1H3,(H,25,26)/b15-10-

Standard InChI Key:  DNTVXDZWVOVLOD-GDNBJRDFSA-N

Molfile:  

     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
   -3.3533    3.7694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0678    3.3569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6553    2.6424    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6389    2.5319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6389    3.3569    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9244    2.1194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2099    2.5318    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2099    3.3568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9244    3.7694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2100    0.8818    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4955    1.2943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4954    2.1193    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0385    0.0749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2180   -0.0114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1176    0.7422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6516   -0.4772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4362   -0.2222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6077    0.5847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2669   -0.6789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4230    0.1609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9381    0.8284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7284   -0.4204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2435    0.2471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2737    1.5821    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1507   -0.6347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7637   -0.0827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4282    0.6710    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5484   -0.3376    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7200   -1.1445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1069   -1.6966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3222   -1.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4803    4.0714    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7823    2.9444    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  4  5  1  0
  1  5  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  4  6  1  0
  5  9  1  0
 10 11  1  0
 11 12  1  0
  7 12  1  0
 13 14  1  0
 14 15  1  0
 10 13  1  0
 11 15  2  0
 16 17  1  0
 17 18  2  0
 13 16  2  0
 20 21  1  0
 14 19  2  0
 15 21  1  0
 22 23  1  0
 20 23  1  0
 21 24  2  0
 25 26  2  0
 26 27  1  0
 17 25  1  0
 18 27  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 25 31  1  0
 26 28  1  0
  2 32  1  0
  2 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4868568

   MONZOSERTIB

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: 465.43

Molecular Weight (Monoisotopic): 465.1624

AlogP: 1.96

#Rotatable Bonds: 6

Polar Surface Area: 99.79

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.25

CX LogP: 2.21

CX LogD: 2.21

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.38

Np Likeness Score: -1.11

References

1. Irie T, Asami T, Sawa A, Uno Y, Taniyama C, Funakoshi Y, Masai H, Sawa M..  (2021)  Discovery of AS-0141, a Potent and Selective Inhibitor of CDC7 Kinase for the Treatment of Solid Cancers.,  64  (19.0): [PMID:34607435] [10.1021/acs.jmedchem.1c01319]

2. International Nonproprietary Names for Pharmaceutical Substances (INN), 

Source

Source(2):

• Scientific Literature
• International Nonproprietary Names