N-[8-(11-imino-9-oxo-2,3,4,5,6,7,8,9,10,11,12,13-dodecahydro-1,8,10,12-benzoxatriazacyclopentadecin-8-yl)octyl]guanidine

ID: ALA5276418

Max Phase: Preclinical

Molecular Formula: C24H41N7O2

Molecular Weight: 459.64

Names and Identifiers

Canonical SMILES:  N=C(N)NCCCCCCCCN1CCCCCCOc2ccccc2CNC(=N)NC1=O

Standard InChI:  InChI=1S/C24H41N7O2/c25-22(26)28-15-9-3-1-2-4-10-16-31-17-11-5-6-12-18-33-21-14-8-7-13-20(21)19-29-23(27)30-24(31)32/h7-8,13-14H,1-6,9-12,15-19H2,(H4,25,26,28)(H3,27,29,30,32)

Standard InChI Key:  LATHRAXUSVKHPF-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   -3.9285    1.2372    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2140    1.6497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4996    1.2372    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4996    0.4120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7852   -0.0002    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0709    0.4120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3566   -0.0002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3573    0.4120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0716   -0.0002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7852   -0.8248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0709   -1.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3111   -2.2148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3474   -2.0620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2144   -2.4746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9289   -2.0620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9289   -1.2373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6431   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6429   -0.0002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9285    0.4120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3603    0.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0717   -0.0023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0701   -0.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3557   -1.2353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2138   -0.0002    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2140    2.4746    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7859    0.4120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5002   -0.0002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2145    0.4120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9288   -0.0002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3575   -0.8248    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0717    0.4120    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3575   -0.0002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6432    0.4120    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  0
  4  3  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  5 10  1  0
 10 11  1  0
 11 12  1  0
 13 12  1  0
 14 13  1  0
 15 14  1  0
 16 15  1  0
 17 16  1  0
 17 18  2  0
  1 19  1  0
 19 18  1  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 23 17  1  0
 22 23  2  0
  4 24  2  0
  2 25  2  0
  9 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 32 31  1  0
 32 30  2  0
 33 32  1  0
 29 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5276418

   ---

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: 459.64

Molecular Weight (Monoisotopic): 459.3322

AlogP: 3.50

#Rotatable Bonds: 9

Polar Surface Area: 139.35

Molecular Species: BASE

HBA: 4

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.29

CX Basic pKa: 12.30

CX LogP: 2.76

CX LogD: 0.73

Aromatic Rings: 1

Heavy Atoms: 33

QED Weighted: 0.19

Np Likeness Score: -0.33

References

1. Balestri LJI, Trivisani CI, Orofino F, Fiorucci D, Truglio GI, D'Agostino I, Poggialini F, Botta L, Docquier JD, Dreassi E..  (2023)  Discovery and Optimization of a Novel Macrocyclic Amidinourea Series Active as Acidic Mammalian Chitinase Inhibitors.,  14  (4): [PMID:37077400] [10.1021/acsmedchemlett.2c00472]

Source

Source(1):

• Scientific Literature