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

ID: ALA4529851

PubChem CID: 155545734

Max Phase: Preclinical

Molecular Formula: C23H24Cl2N4O2

Molecular Weight: 422.92

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cl.N=C(N)c1ccc([C@H]2[C@H]3C(=O)N(Cc4ccc(Cl)cc4)C(=O)[C@H]3[C@@H]3CCCN32)cc1

Standard InChI:  InChI=1S/C23H23ClN4O2.ClH/c24-16-9-3-13(4-10-16)12-28-22(29)18-17-2-1-11-27(17)20(19(18)23(28)30)14-5-7-15(8-6-14)21(25)26;/h3-10,17-20H,1-2,11-12H2,(H3,25,26);1H/t17-,18-,19-,20-;/m0./s1

Standard InChI Key:  JFFJYDFCELTCNC-NAACWRBGSA-N

Molfile:  

     RDKit          2D

 34 37  0  0  0  0  0  0  0  0999 V2000
   10.5012  -30.9335    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.2729  -29.4436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0901  -29.4436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4968  -30.1537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3133  -30.1540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7227  -29.4458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3097  -28.7357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4946  -28.7389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8643  -28.7359    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8643  -30.1514    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5399  -29.4447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7973  -29.8488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0214  -30.1049    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0251  -30.9221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8035  -31.1710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2806  -30.5077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0187  -28.7802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7922  -29.0296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2685  -28.3710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7892  -27.7145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0169  -27.9675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3546  -27.4887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0856  -28.3691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5805  -29.2373    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2239  -28.5645    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0399  -26.9367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8388  -26.7649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3813  -27.3723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1795  -27.2010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4309  -26.4225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8779  -25.8151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0817  -25.9895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6135  -29.8481    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.2296  -26.2497    0.0000 Cl  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
 12 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 33  1  1
 30 34  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: 422.92

Molecular Weight (Monoisotopic): 422.1510

AlogP: 2.94

#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: 2.48

CX LogD: -2.14

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.45

Np Likeness Score: -0.39

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