Ethyl 4-(2-(3-(Dimethylamino)-pyrrolidin-1-yl)-8-fluoro-4-oxoquinazolin-3(4H)-yl)-benzoate

ID: ALA4453424

PubChem CID: 155522804

Max Phase: Preclinical

Molecular Formula: C23H25FN4O3

Molecular Weight: 424.48

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1ccc(-n2c(N3CCC(N(C)C)C3)nc3c(F)cccc3c2=O)cc1

Standard InChI:  InChI=1S/C23H25FN4O3/c1-4-31-22(30)15-8-10-16(11-9-15)28-21(29)18-6-5-7-19(24)20(18)25-23(28)27-13-12-17(14-27)26(2)3/h5-11,17H,4,12-14H2,1-3H3

Standard InChI Key:  WNZMIVQWFAEOQR-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
   20.4696  -15.9765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4685  -16.7960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1765  -17.2050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1747  -15.5676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8834  -15.9729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8868  -16.7981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5991  -17.2055    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.3127  -16.7922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3093  -15.9670    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.5924  -15.5551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5879  -14.7379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.0147  -15.5566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7240  -15.9647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4299  -15.5546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4278  -14.7365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7139  -14.3303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0108  -14.7427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0215  -17.1989    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.1751  -18.0222    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   26.1363  -14.3222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8458  -14.7276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.1327  -13.5050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.5517  -14.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2612  -14.7214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1098  -18.0101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9096  -18.1778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3163  -17.4689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7678  -16.8632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1288  -17.3812    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.6109  -18.0410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4590  -16.6338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  5 10  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
  9 12  1  0
  8 18  1  0
  3 19  1  0
 20 21  1  0
 20 22  2  0
 15 20  1  0
 21 23  1  0
 23 24  1  0
 18 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 18  1  0
 27 29  1  0
 29 30  1  0
 29 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4453424

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 424.48

Molecular Weight (Monoisotopic): 424.1911

AlogP: 2.84

#Rotatable Bonds: 5

Polar Surface Area: 67.67

Molecular Species: BASE

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.51

CX LogP: 3.39

CX LogD: 2.24

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.59

Np Likeness Score: -1.42

References

1. Atobe M, Nagami T, Muramatsu S, Ohno T, Kitagawa M, Suzuki H, Ishiguro M, Watanabe A, Kawanishi M..  (2019)  Discovery of Novel Transient Receptor Potential Vanilloid 4 (TRPV4) Agonists as Regulators of Chondrogenic Differentiation: Identification of Quinazolin-4(3 H)-ones and in Vivo Studies on a Surgically Induced Rat Model of Osteoarthritis.,  62  (3): [PMID:30629441] [10.1021/acs.jmedchem.8b01615]

Source

Source(1):

• Scientific Literature