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

ID: ALA4513358

PubChem CID: 155538891

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(Cc4cccc(F)c4F)C(=O)[C@H]3[C@@H]3CCCN32)cc1

Standard InChI:  InChI=1S/C23H22F2N4O2.ClH/c24-15-4-1-3-14(19(15)25)11-29-22(30)17-16-5-2-10-28(16)20(18(17)23(29)31)12-6-8-13(9-7-12)21(26)27;/h1,3-4,6-9,16-18,20H,2,5,10-11H2,(H3,26,27);1H/t16-,17-,18-,20-;/m0./s1

Standard InChI Key:  BCZGWDMLTMVZNZ-CMPKFCAVSA-N

Molfile:  

     RDKit          2D

 35 38  0  0  0  0  0  0  0  0999 V2000
   39.7241  -31.4087    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   39.0395  -29.9018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.8566  -29.9018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.2634  -30.6118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.0798  -30.6121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.4892  -29.9039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.0763  -29.1938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.2612  -29.1970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.6309  -29.1941    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.6309  -30.6095    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   42.3064  -29.9028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.5639  -30.3069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.7879  -30.5631    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   42.7917  -31.3802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.5700  -31.6291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.0472  -30.9658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.7852  -29.2383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.5588  -29.4877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.0350  -28.8291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.5558  -28.1726    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   42.7834  -28.4256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.1212  -27.9468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   44.8522  -28.8272    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   44.3471  -29.6954    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   41.9904  -29.0227    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   43.8065  -27.3948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.6054  -27.2230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.1478  -27.8304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.9461  -27.6591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.1975  -26.8806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.6445  -26.2732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.8483  -26.4477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.3801  -30.3062    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   45.8924  -25.4946    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   44.2964  -25.8450    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
 31 34  1  0
 32 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: -2.40

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.45

Np Likeness Score: -0.61

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