(4-(4-cyano-2,6-dimethylphenoxy)-2-(4-cyanophenylamino)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl isopropyl carbonate

ID: ALA4225783

PubChem CID: 134816819

Max Phase: Preclinical

Molecular Formula: C27H24N6O4

Molecular Weight: 496.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(C#N)cc(C)c1Oc1nc(Nc2ccc(C#N)cc2)nc2c1ccn2COC(=O)OC(C)C

Standard InChI:  InChI=1S/C27H24N6O4/c1-16(2)36-27(34)35-15-33-10-9-22-24(33)31-26(30-21-7-5-19(13-28)6-8-21)32-25(22)37-23-17(3)11-20(14-29)12-18(23)4/h5-12,16H,15H2,1-4H3,(H,30,31,32)

Standard InChI Key:  IWSGUOFMIJYMTD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    5.4722   -6.2009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  2  0
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  6 10  1  0
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 14 21  1  0
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 31 32  1  0
 32 33  1  0
 32 34  2  0
 33 35  1  0
 35 36  1  0
 35 37  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4225783

   ---

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: 496.53

Molecular Weight (Monoisotopic): 496.1859

AlogP: 5.85

#Rotatable Bonds: 7

Polar Surface Area: 135.08

Molecular Species: NEUTRAL

HBA: 10

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.16

CX Basic pKa: 4.00

CX LogP: 6.95

CX LogD: 6.95

Aromatic Rings: 4

Heavy Atoms: 37

QED Weighted: 0.31

Np Likeness Score: -1.01

References

1. Huang B, Liu X, Tian Y, Kang D, Zhou Z, Daelemans D, De Clercq E, Pannecouque C, Zhan P, Liu X..  (2018)  First discovery of a potential carbonate prodrug of NNRTI drug candidate RDEA427 with submicromolar inhibitory activity against HIV-1 K103N/Y181C double mutant strain.,  28  (8): [PMID:29534929] [10.1016/j.bmcl.2018.03.012]

Source

Source(1):

• Scientific Literature