4-(4-(benzo[d][1,3]dioxol-5-ylmethyl)piperazin-1-yl)-5-phenyl-5H-pyrrolo[3,2-d]pyrimidine-7-carbonitrile

ID: ALA5291352

Max Phase: Preclinical

Molecular Formula: C25H22N6O2

Molecular Weight: 438.49

Names and Identifiers

Canonical SMILES:  N#Cc1cn(-c2ccccc2)c2c(N3CCN(Cc4ccc5c(c4)OCO5)CC3)ncnc12

Standard InChI:  InChI=1S/C25H22N6O2/c26-13-19-15-31(20-4-2-1-3-5-20)24-23(19)27-16-28-25(24)30-10-8-29(9-11-30)14-18-6-7-21-22(12-18)33-17-32-21/h1-7,12,15-16H,8-11,14,17H2

Standard InChI Key:  BWQDVZLEAJDKCR-UHFFFAOYSA-N

Molfile:  

 
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    1.0697    3.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8400    3.7499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7843    2.4198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

Alternative Forms

1. Parent:

   

   ALA5291352

   ---

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: 438.49

Molecular Weight (Monoisotopic): 438.1804

AlogP: 3.34

#Rotatable Bonds: 4

Polar Surface Area: 79.44

Molecular Species: NEUTRAL

HBA: 8

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.02

CX LogP: 4.17

CX LogD: 4.02

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.48

Np Likeness Score: -1.38

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]

2. Jedlitschky, G G and 5 more authors.  1997-10-01  ATP-dependent transport of bilirubin glucuronides by the multidrug resistance protein MRP1 and its hepatocyte canalicular isoform MRP2.  [PMID:9355767]

3. Wong, Iris L K ILK and 7 more authors.  2018-11-21  Discovery of Novel Flavonoid Dimers To Reverse Multidrug Resistance Protein 1 (MRP1, ABCC1) Mediated Drug Resistance in Cancers Using a High Throughput Platform with "Click Chemistry".  [PMID:30351934]

4. Zhu, Xuezhen and 8 more authors.  2019-09-26  Triazole Bridged Flavonoid Dimers as Potent, Nontoxic, and Highly Selective Breast Cancer Resistance Protein (BCRP/ABCG2) Inhibitors.  [PMID:31465686]

Source

Source(1):

• Scientific Literature