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

ID: ALA4759172

PubChem CID: 146489226

Max Phase: Preclinical

Molecular Formula: C22H23Cl2N5O6S

Molecular Weight: 556.43

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C22H23Cl2N5O6S/c1-5-36(31,32)28-14-10-35-9-13(14)26-22-25-8-11-6-12(21(30)29(2)20(11)27-22)17-18(23)15(33-3)7-16(34-4)19(17)24/h5-8,13-14,28H,1,9-10H2,2-4H3,(H,25,26,27)/t13-,14+/m1/s1

Standard InChI Key:  IZXXKUVQQOCKPB-KGLIPLIRSA-N

Molfile:  

 
     RDKit          2D

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   18.6303  -14.0326    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   18.4200  -13.2390    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.3150  -10.6276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3139  -11.4512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0260  -11.8643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7398  -11.4508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7370  -10.6240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   23.8980  -11.4457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8945  -13.0873    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.6107  -12.6811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1831  -12.6760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1917  -11.8572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4874  -11.4400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7740  -11.8448    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   22.4743  -13.0761    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   26.7324   -8.9826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4523  -11.8624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.4536  -12.6837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0258  -12.6856    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   24.6031  -10.2191    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   25.3176  -13.0910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.8910  -13.9087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0553  -13.0715    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.3457  -12.6592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2635  -11.8403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4609  -11.6620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0485  -12.3717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5921  -12.9859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4171  -13.7883    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.4591  -14.8381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6761  -15.0898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
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  5 10  1  0
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 17 18  1  0
 18 19  2  0
 19 14  1  0
  9 20  1  0
 20 21  1  0
  7 22  1  0
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  6 24  1  0
  4 25  1  0
 13 26  2  0
 12 27  1  0
 18 28  1  0
 29 28  1  1
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 31 32  1  0
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 33 34  1  1
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  2 35  1  0
 35 36  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4759172

   ---

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: 556.43

Molecular Weight (Monoisotopic): 555.0746

AlogP: 2.56

#Rotatable Bonds: 8

Polar Surface Area: 133.67

Molecular Species: NEUTRAL

HBA: 10

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 9.57

CX Basic pKa: 2.66

CX LogP: 1.99

CX LogD: 1.99

Aromatic Rings: 3

Heavy Atoms: 36

QED Weighted: 0.43

Np Likeness Score: -0.33

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