isopropyl 4-[6-(4-{[(2-fluoroethyl)carbamoyl]amino}phenyl)-4-morpholin-4-yl-1Hpyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carboxylate

ID: ALA1094981

PubChem CID: 44605426

Max Phase: Preclinical

Molecular Formula: C27H35FN8O4

Molecular Weight: 554.63

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)OC(=O)N1CCC(n2ncc3c(N4CCOCC4)nc(-c4ccc(NC(=O)NCCF)cc4)nc32)CC1

Standard InChI:  InChI=1S/C27H35FN8O4/c1-18(2)40-27(38)35-11-7-21(8-12-35)36-25-22(17-30-36)24(34-13-15-39-16-14-34)32-23(33-25)19-3-5-20(6-4-19)31-26(37)29-10-9-28/h3-6,17-18,21H,7-16H2,1-2H3,(H2,29,31,37)

Standard InChI Key:  WQJYOLLPRXNMCU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    5.0414   -4.0854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6672   -2.6302    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3826   -2.2193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3845   -1.3943    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.8115   -2.2226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6264   -4.7985    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8664   -4.0883    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.8614   -5.5172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  2 10  1  0
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  3  6  2  0
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  4 14  1  0
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 14 15  1  0
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  1  2  2  0
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  6  7  1  0
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  7  8  1  0
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 14 19  1  0
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 15 16  1  0
 36 40  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1094981

   isopropyl 4-[6-(4-{[(2-fluoroethyl)carbamoyl]amino}phenyl)-4-morpholin-4-yl-1Hpyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carboxylate

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: 554.63

Molecular Weight (Monoisotopic): 554.2765

AlogP: 3.60

#Rotatable Bonds: 7

Polar Surface Area: 126.74

Molecular Species: NEUTRAL

HBA: 9

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 13.01

CX Basic pKa: 4.01

CX LogP: 2.92

CX LogD: 2.92

Aromatic Rings: 3

Heavy Atoms: 40

QED Weighted: 0.45

Np Likeness Score: -2.00

References

1. Verheijen JC, Richard DJ, Curran K, Kaplan J, Lefever M, Nowak P, Malwitz DJ, Brooijmans N, Toral-Barza L, Zhang WG, Lucas J, Hollander I, Ayral-Kaloustian S, Mansour TS, Yu K, Zask A..  (2009)  Discovery of 4-morpholino-6-aryl-1H-pyrazolo[3,4-d]pyrimidines as highly potent and selective ATP-competitive inhibitors of the mammalian target of rapamycin (mTOR): optimization of the 6-aryl substituent.,  52  (24): [PMID:19894727] [10.1021/jm9013828]

Source

Source(1):

• Scientific Literature