4-((3aS,4R,8aS,8bR)-2-(2,4-difluorobenzyl)-1,3-dioxodecahydropyrrolo[3,4-a]pyrrolizin-4-yl)benzimidamide hydrochloride

ID: ALA4529907

PubChem CID: 155545696

Max Phase: Preclinical

Molecular Formula: C23H23ClF2N4O2

Molecular Weight: 424.45

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cl.N=C(N)c1ccc([C@H]2[C@H]3C(=O)N(Cc4ccc(F)cc4F)C(=O)[C@H]3[C@@H]3CCCN32)cc1

Standard InChI:  InChI=1S/C23H22F2N4O2.ClH/c24-15-8-7-14(16(25)10-15)11-29-22(30)18-17-2-1-9-28(17)20(19(18)23(29)31)12-3-5-13(6-4-12)21(26)27;/h3-8,10,17-20H,1-2,9,11H2,(H3,26,27);1H/t17-,18-,19-,20-;/m0./s1

Standard InChI Key:  LRALJYUILNELMH-NAACWRBGSA-N

Molfile:  

     RDKit          2D

 35 38  0  0  0  0  0  0  0  0999 V2000
    1.6156   -6.7474    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.2547   -5.3448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0719   -5.3448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4786   -6.0548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2950   -6.0551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7045   -5.3469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2915   -4.6368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4764   -4.6400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8461   -4.6371    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8461   -6.0525    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5216   -5.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7791   -5.7499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0031   -6.0060    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0069   -6.8232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7853   -7.0721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2624   -6.4088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0005   -4.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7740   -4.9307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2502   -4.2721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7710   -3.6156    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9987   -3.8686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3364   -3.3898    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0674   -4.2702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5623   -5.1384    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2056   -4.4657    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0217   -2.8378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8206   -2.6660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3631   -3.2734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1613   -3.1021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4127   -2.3236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8597   -1.7162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0635   -1.8906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5953   -5.7492    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5116   -1.2880    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.2114   -2.1508    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  3  1  0
  2  9  1  0
  2 10  2  0
 11  6  1  1
 11 13  1  0
 12 18  1  0
 17 11  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 17  1  0
 21 22  2  0
 19 23  2  0
 18 24  1  6
 17 25  1  6
 20 26  1  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 27  1  0
 12 16  1  0
 12 33  1  1
 32 34  1  0
 30 35  1  0
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: 424.45

Molecular Weight (Monoisotopic): 424.1711

AlogP: 2.57

#Rotatable Bonds: 4

Polar Surface Area: 90.49

Molecular Species: BASE

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 11.49

CX LogP: 2.16

CX LogD: -2.42

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.45

Np Likeness Score: -0.64

References

1. Meanwell NA..  (2018)  Fluorine and Fluorinated Motifs in the Design and Application of Bioisosteres for Drug Design.,  61  (14): [PMID:29400967] [10.1021/acs.jmedchem.7b01788]

Source

Source(1):

• Scientific Literature