N-((3S,4R)-4-(6-(2,6-dichloro-3,5-dimethoxyphenyl)-8-methyl-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-2-ylamino)tetrahydrofuran-3-yl)acrylamide

ID: ALA4764222

PubChem CID: 90436890

Max Phase: Preclinical

Molecular Formula: C23H23Cl2N5O5

Molecular Weight: 520.37

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C=CC(=O)N[C@@H]1COC[C@@H]1Nc1ncc2cc(-c3c(Cl)c(OC)cc(OC)c3Cl)c(=O)n(C)c2n1

Standard InChI:  InChI=1S/C23H23Cl2N5O5/c1-5-17(31)27-13-9-35-10-14(13)28-23-26-8-11-6-12(22(32)30(2)21(11)29-23)18-19(24)15(33-3)7-16(34-4)20(18)25/h5-8,13-14H,1,9-10H2,2-4H3,(H,27,31)(H,26,28,29)/t13-,14+/m1/s1

Standard InChI Key:  ZIJVLVUPDVUSMA-KGLIPLIRSA-N

Molfile:  

 
     RDKit          2D

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   40.6217   -3.0152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.3339   -3.4283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.0477   -3.0147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.0449   -2.1879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.3321   -1.7827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.9131   -3.4251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   38.4910   -4.2400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4996   -3.4211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7953   -3.0040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0819   -3.4087    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.0772   -4.2307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7822   -4.6400    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   41.3297   -0.9613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   42.0403   -0.5465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.7602   -3.4263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   42.7615   -4.2476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.3337   -4.2496    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   39.9110   -1.7831    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   40.6255   -4.6550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.1989   -5.4726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3632   -4.6355    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.6536   -4.2231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5714   -3.4043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7688   -3.2260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.3564   -3.9356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9000   -4.5499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7249   -5.3522    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.9420   -5.5997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7669   -6.4021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9840   -6.6537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3341   -5.0490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
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  4 19  1  0
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  3 21  1  0
  1 22  1  0
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  9 24  1  0
 15 25  1  0
 26 25  1  6
 26 27  1  0
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 30 26  1  0
 30 31  1  6
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 32 35  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4764222

   N-[(3S,4R)-4-[[6-(2,6-dichloro-3,5-dimethoxyphenyl)-8-methyl-7-oxopyrido[2,3-d]pyrimidin-2-yl]amino]oxolan-3-yl]prop-2-enamide

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: 520.37

Molecular Weight (Monoisotopic): 519.1076

AlogP: 2.80

#Rotatable Bonds: 7

Polar Surface Area: 116.60

Molecular Species: NEUTRAL

HBA: 9

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.52

CX Basic pKa: 3.64

CX LogP: 2.52

CX LogD: 2.52

Aromatic Rings: 3

Heavy Atoms: 35

QED Weighted: 0.46

Np Likeness Score: -0.17

References

1. Liu H,Niu D,Tham Sjin RT,Dubrovskiy A,Zhu Z,McDonald JJ,Fahnoe K,Wang Z,Munson M,Scholte A,Barrague M,Fitzgerald M,Liu J,Kothe M,Sun F,Murtie J,Ge J,Rocnik J,Harvey D,Ospina B,Perron K,Zheng G,Shehu E,D'Agostino LA.  (2020)  Discovery of Selective, Covalent FGFR4 Inhibitors with Antitumor Activity in Models of Hepatocellular Carcinoma.,  11  (10): [PMID:33062171] [10.1021/acsmedchemlett.9b00601]

Source

Source(1):

• Scientific Literature