(4-(5H-pyrimido[5,4-b]indol-4-yl)piperazin-1-yl)(furan-2-yl)methanone

ID: ALA5280028

Max Phase: Preclinical

Molecular Formula: C19H17N5O2

Molecular Weight: 347.38

Names and Identifiers

Canonical SMILES:  O=C(c1ccco1)N1CCN(c2ncnc3c2[nH]c2ccccc23)CC1

Standard InChI:  InChI=1S/C19H17N5O2/c25-19(15-6-3-11-26-15)24-9-7-23(8-10-24)18-17-16(20-12-21-18)13-4-1-2-5-14(13)22-17/h1-6,11-12,22H,7-10H2

Standard InChI Key:  LVBLJETUJLRUDS-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    2.6156    1.6044    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8067    1.4426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2404    2.0089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4583    1.9009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0808    2.6022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6471    3.1685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3752    2.8179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5640    0.6606    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1033    0.0674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8606   -0.6876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0786   -0.8763    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5123   -0.2561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7820    0.4988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8088   -1.6314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3483   -2.2247    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1056   -3.0067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3235   -3.1685    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2157   -2.5752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0269   -1.7932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6202   -1.3348    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2943   -1.7932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0247   -2.5752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5640   -3.1685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3729   -3.0067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6156   -2.2247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0762   -1.6314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
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  3  4  2  0
  4  5  1  0
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  6  7  1  0
  3  7  1  0
  2  8  1  0
  8  9  1  0
  9 10  1  0
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 11 14  1  0
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 25 26  2  0
 21 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5280028

   ---

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: 347.38

Molecular Weight (Monoisotopic): 347.1382

AlogP: 2.67

#Rotatable Bonds: 2

Polar Surface Area: 78.26

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.32

CX Basic pKa: 2.96

CX LogP: 2.24

CX LogD: 2.24

Aromatic Rings: 4

Heavy Atoms: 26

QED Weighted: 0.60

Np Likeness Score: -1.53

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