(4-hydroxypiperidin-1-yl)((trans)-4-(4-(4-(3-(methylsulfonyl)propoxy)-1H-indol-1-yl)pyrimidin-2-ylamino)cyclohexyl)methanone

ID: ALA2425628

PubChem CID: 58017084

Max Phase: Preclinical

Molecular Formula: C28H37N5O5S

Molecular Weight: 555.70

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CS(=O)(=O)CCCOc1cccc2c1ccn2-c1ccnc(N[C@H]2CC[C@H](C(=O)N3CCC(O)CC3)CC2)n1

Standard InChI:  InChI=1S/C28H37N5O5S/c1-39(36,37)19-3-18-38-25-5-2-4-24-23(25)13-17-33(24)26-10-14-29-28(31-26)30-21-8-6-20(7-9-21)27(35)32-15-11-22(34)12-16-32/h2,4-5,10,13-14,17,20-22,34H,3,6-9,11-12,15-16,18-19H2,1H3,(H,29,30,31)/t20-,21-

Standard InChI Key:  NXWXUDHOUKWAQU-MEMLXQNLSA-N

Molfile:  

     RDKit          2D

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   12.9996   -8.0292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4053   -4.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3979   -3.5266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6939   -4.7647    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    3.9805   -4.3503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  3  2  2  0
  2  4  2  0
  5  6  2  0
  6  7  1  0
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  9 10  2  0
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 14 24  1  0
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  9 25  1  0
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  8 27  1  0
 21 28  1  6
 28 29  2  0
 28 30  1  0
 27 31  1  0
 31 32  1  0
 32 33  1  0
 33  2  1  0
  2 34  1  0
 30 35  1  0
 30 38  1  0
 35 36  1  0
 36  1  1  0
  1 37  1  0
 37 38  1  0
  1 39  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2425628

   (4-Hydroxy-piperidin-1-yl)-(4-{4-[4-(3-methanesulfonyl-propoxy)-indol-1-yl]-pyrimidin-2-ylamino}-cyclohexyl)-methanone

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: 555.70

Molecular Weight (Monoisotopic): 555.2515

AlogP: 3.19

#Rotatable Bonds: 9

Polar Surface Area: 126.65

Molecular Species: NEUTRAL

HBA: 9

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 6.04

CX LogP: 1.34

CX LogD: 1.32

Aromatic Rings: 3

Heavy Atoms: 39

QED Weighted: 0.39

Np Likeness Score: -1.22

References

1. Palmer WS, Alam M, Arzeno HB, Chang KC, Dunn JP, Goldstein DM, Gong L, Goyal B, Hermann JC, Hogg JH, Hsieh G, Jahangir A, Janson C, Jin S, Ursula Kammlott R, Kuglstatter A, Lukacs C, Michoud C, Niu L, Reuter DC, Shao A, Silva T, Trejo-Martin TA, Stein K, Tan YC, Tivitmahaisoon P, Tran P, Wagner P, Weller P, Wu SY..  (2013)  Development of amino-pyrimidine inhibitors of c-Jun N-terminal kinase (JNK): kinase profiling guided optimization of a 1,2,3-benzotriazole lead.,  23  (5): [PMID:23352510] [10.1016/j.bmcl.2012.12.047]

2. Klaeger, Susan S and 47 more authors.  2017-12-01  The target landscape of clinical kinase drugs.  [PMID:29191878]

Source

Source(1):

• Scientific Literature