1-((R)-1-(2,4-Dichlorophenyl)ethyl)-6-((3R,4S)-4-((S)-2-(hydroxymethyl)pyrrolidin-1-yl)-3-methylpiperidin-1-yl)-1H-pyrazolo[3,4-b]pyrazine-3-carbonitrile

ID: ALA4558456

PubChem CID: 134325016

Max Phase: Preclinical

Molecular Formula: C25H29Cl2N7O

Molecular Weight: 514.46

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C[C@@H]1CN(c2cnc3c(C#N)nn([C@H](C)c4ccc(Cl)cc4Cl)c3n2)CC[C@@H]1N1CCC[C@H]1CO

Standard InChI:  InChI=1S/C25H29Cl2N7O/c1-15-13-32(9-7-22(15)33-8-3-4-18(33)14-35)23-12-29-24-21(11-28)31-34(25(24)30-23)16(2)19-6-5-17(26)10-20(19)27/h5-6,10,12,15-16,18,22,35H,3-4,7-9,13-14H2,1-2H3/t15-,16-,18+,22+/m1/s1

Standard InChI Key:  MFJMECBECSYCCV-LVOOAJGHSA-N

Molfile:  

 
     RDKit          2D

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   16.5417  -27.3560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2587  -26.9480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2642  -26.1186    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   18.8726  -23.6593    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   17.2634  -24.0006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0952  -23.7364    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   17.2176  -21.8202    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   15.1180  -27.3504    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.5358  -28.1809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3625  -27.0154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8111  -27.6276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   21.6479  -24.6687    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.1905  -26.2086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4057  -25.9542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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  1 26  1  1
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 32 33  3  0
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 28 34  1  1
 34 35  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4558456

   ---

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: 514.46

Molecular Weight (Monoisotopic): 513.1811

AlogP: 4.29

#Rotatable Bonds: 5

Polar Surface Area: 94.10

Molecular Species: BASE

HBA: 8

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 9.85

CX LogP: 4.31

CX LogD: 1.90

Aromatic Rings: 3

Heavy Atoms: 35

QED Weighted: 0.54

Np Likeness Score: -0.94

References

1. Jackson JJ, Ketcham JM, Younai A, Abraham B, Biannic B, Beck HP, Bui MHT, Chian D, Cutler G, Diokno R, Hu DX, Jacobson S, Karbarz E, Kassner PD, Marshall L, McKinnell J, Meleza C, Okal A, Pookot D, Reilly MK, Robles O, Shunatona HP, Talay O, Walker JR, Wadsworth A, Wustrow DJ, Zibinsky M..  (2019)  Discovery of a Potent and Selective CCR4 Antagonist That Inhibits Treg Trafficking into the Tumor Microenvironment.,  62  (13): [PMID:31259550] [10.1021/acs.jmedchem.9b00506]

Source

Source(1):

• Scientific Literature