6-(3-(2-((2,3-dihydro-1H-inden-2-yl)amino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-3-oxopropyl)benzo[d]oxazol-2(3H)-one

ID: ALA4476558

PubChem CID: 155538462

Max Phase: Preclinical

Molecular Formula: C26H25N5O3

Molecular Weight: 455.52

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(CCc1ccc2[nH]c(=O)oc2c1)N1CCc2nc(NC3Cc4ccccc4C3)ncc2C1

Standard InChI:  InChI=1S/C26H25N5O3/c32-24(8-6-16-5-7-22-23(11-16)34-26(33)30-22)31-10-9-21-19(15-31)14-27-25(29-21)28-20-12-17-3-1-2-4-18(17)13-20/h1-5,7,11,14,20H,6,8-10,12-13,15H2,(H,30,33)(H,27,28,29)

Standard InChI Key:  RXQRKTRNQXXVJE-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   39.8737   -9.4405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.6074   -9.8005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.9913   -8.6330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.7951   -8.4904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.1765   -9.2148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.9927   -9.2457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.4285   -8.5529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.0421   -7.8276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.2271   -7.8002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.1508   -9.8215    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.4594   -9.3859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4958   -8.5688    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.8052   -8.1333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7435   -9.7670    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.0522   -9.3352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0800   -8.5169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   35.6660   -8.4690    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.6383   -9.2872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   34.9732   -8.0357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2515   -8.4190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5587   -7.9857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8370   -8.3691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1456   -7.9374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0929   -9.5710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8112   -9.1858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3951   -9.1377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4203   -8.3197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6501   -8.0428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.1488   -8.6898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6093   -9.3664    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.3320   -8.6646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.0020   -7.2190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  5  1  0
  4  3  1  0
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  4  5  2  0
  5  6  1  0
  6  7  2  0
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  9  4  1  0
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 19 20  1  0
 18 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 29  2  0
 28 26  2  0
 26 27  1  0
 27 24  2  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 28  1  0
 31 33  2  0
 21 34  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4476558

   ---

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: 455.52

Molecular Weight (Monoisotopic): 455.1957

AlogP: 3.01

#Rotatable Bonds: 5

Polar Surface Area: 104.12

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.48

CX Basic pKa: 2.77

CX LogP: 3.19

CX LogD: 3.19

Aromatic Rings: 4

Heavy Atoms: 34

QED Weighted: 0.48

Np Likeness Score: -1.07

References

1. Jones SB, Pfeifer LA, Bleisch TJ, Beauchamp TJ, Durbin JD, Klimkowski VJ, Hughes NE, Rito CJ, Dao Y, Gruber JM, Bui H, Chambers MG, Chandrasekhar S, Lin C, McCann DJ, Mudra DR, Oskins JL, Swearingen CA, Thirunavukkarasu K, Norman BH..  (2016)  Novel Autotaxin Inhibitors for the Treatment of Osteoarthritis Pain: Lead Optimization via Structure-Based Drug Design.,  7  (9): [PMID:27660691] [10.1021/acsmedchemlett.6b00207]

Source

Source(1):

• Scientific Literature