sodium 1-(5-(benzo[d][1,3]dioxol-5-ylmethylamino)-6-chloroquinazolin-2-yl)piperidine-4-carboxylate

ID: ALA4552529

PubChem CID: 155556194

Max Phase: Preclinical

Molecular Formula: C22H20ClN4NaO4

Molecular Weight: 440.89

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C([O-])C1CCN(c2ncc3c(NCc4ccc5c(c4)OCO5)c(Cl)ccc3n2)CC1.[Na+]

Standard InChI:  InChI=1S/C22H21ClN4O4.Na/c23-16-2-3-17-15(11-25-22(26-17)27-7-5-14(6-8-27)21(28)29)20(16)24-10-13-1-4-18-19(9-13)31-12-30-18;/h1-4,9,11,14,24H,5-8,10,12H2,(H,28,29);/q;+1/p-1

Standard InChI Key:  XWNFBLFXLFUAST-UHFFFAOYSA-M

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   10.9454   -9.0345    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
    3.4324   -7.1813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4313   -8.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1393   -8.4098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1375   -6.7725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8462   -7.1777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8469   -7.9968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5555   -8.4038    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2637   -7.9930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2590   -7.1709    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5499   -6.7675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7246   -6.7729    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.1351   -5.9553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8416   -5.5446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8392   -4.7274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5475   -4.3212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5454   -3.5047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1327   -4.3276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1271   -3.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8343   -3.1011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6616   -2.3014    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8476   -2.2185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5174   -2.9671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9730   -8.3988    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9719   -9.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6771   -9.6183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3857   -9.2104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3844   -8.3923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6747   -7.9820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0934   -9.6190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0935  -10.4362    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8011   -9.2103    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  7  2  0
  6  5  2  0
  5  2  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
  2 12  1  0
  5 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 20  2  0
 19 18  2  0
 18 15  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 19  1  0
  9 24  1  0
 24 25  1  0
 24 29  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 27 30  1  0
 30 31  2  0
 30 32  1  0
M  CHG  2   1   1  32  -1
M  END

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 440.89

Molecular Weight (Monoisotopic): 440.1251

AlogP: 3.93

#Rotatable Bonds: 5

Polar Surface Area: 96.81

Molecular Species: ACID

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.85

CX Basic pKa: 5.01

CX LogP: 2.15

CX LogD: 0.82

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.62

Np Likeness Score: -1.17

References

1. Pobsuk N, Paracha TU, Chaichamnong N, Salaloy N, Suphakun P, Hannongbua S, Choowongkomon K, Pekthong D, Chootip K, Ingkaninan K, Gleeson MP..  (2019)  Design, synthesis and evaluation of N²,N⁴-diaminoquinazoline based inhibitors of phosphodiesterase type 5.,  29  (2): [PMID:30509781] [10.1016/j.bmcl.2018.11.043]

Source

Source(1):

• Scientific Literature