5-benzyl-4-[(3-phenylpropyl)amino]-5H-pyrrolo[3,2-d]pyrimidine-7-carbonitrile

ID: ALA5283433

Max Phase: Preclinical

Molecular Formula: C23H21N5

Molecular Weight: 367.46

Names and Identifiers

Canonical SMILES:  N#Cc1cn(Cc2ccccc2)c2c(NCCCc3ccccc3)ncnc12

Standard InChI:  InChI=1S/C23H21N5/c24-14-20-16-28(15-19-10-5-2-6-11-19)22-21(20)26-17-27-23(22)25-13-7-12-18-8-3-1-4-9-18/h1-6,8-11,16-17H,7,12-13,15H2,(H,25,26,27)

Standard InChI Key:  SXEQBLZMVHHAJH-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   -2.3527    0.5470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5487    1.6221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0780    0.9686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5700    0.3011    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2181    2.3565    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4168    2.4373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0538    1.7838    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2768    1.0494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1258    0.3521    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0500    1.7745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7473    2.1772    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3616   -0.4765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9309   -1.0459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7228   -1.8237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2909   -2.3908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0688   -2.1824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2777   -1.4089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9309    0.3521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3336   -0.3451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1387   -0.3451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5413   -1.0424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3465   -1.0426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7473   -1.7382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3445   -2.4357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5434   -2.4373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1370   -1.7427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  5 13  1  0
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 15 14  2  0
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 22 23  1  0
 24 23  2  0
 25 24  1  0
 26 25  2  0
 27 26  1  0
 28 27  2  0
 23 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5283433

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 367.46

Molecular Weight (Monoisotopic): 367.1797

AlogP: 4.40

#Rotatable Bonds: 7

Polar Surface Area: 66.53

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.15

CX LogP: 4.86

CX LogD: 4.86

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.49

Np Likeness Score: -1.15

References

1. Stefan K, Schmitt SM, Wiese M..  (2017)  9-Deazapurines as Broad-Spectrum Inhibitors of the ABC Transport Proteins P-Glycoprotein, Multidrug Resistance-Associated Protein 1, and Breast Cancer Resistance Protein.,  60  (21): [PMID:29016119] [10.1021/acs.jmedchem.7b00788]

Source

Source(1):

• Scientific Literature