1-{N-[8-(4-imino-2-oxo-1,3,5-triazacyclotridecan-1-yl)octyl]carbamimidoyl}-3-methylurea

ID: ALA5283183

Max Phase: Preclinical

Molecular Formula: C21H42N8O2

Molecular Weight: 438.62

Names and Identifiers

Canonical SMILES:  CNC(=O)NC(=N)NCCCCCCCCN1CCCCCCCCNC(=N)NC1=O

Standard InChI:  InChI=1S/C21H42N8O2/c1-24-20(30)27-18(22)25-14-10-6-2-4-8-12-16-29-17-13-9-5-3-7-11-15-26-19(23)28-21(29)31/h2-17H2,1H3,(H3,23,26,28,31)(H4,22,24,25,27,30)

Standard InChI Key:  MFPRZYJZMSHFPK-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   -4.2818    2.4644    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5686    2.0499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5709    1.2249    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8577    0.8106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5167   -0.5077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8713   -1.2901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6889   -1.1825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0047   -0.4205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7178   -0.0062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7152    0.8186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9997    1.2289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8544    2.4623    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1435    1.2230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1446   -0.4245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4316   -0.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7163   -0.4205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0032   -0.0062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7121   -0.4165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4253   -0.0023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1407   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8537    0.0016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5693   -0.4086    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2823    0.0056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9977   -0.4046    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0000   -1.2293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7155   -1.6397    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7178   -2.4644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2869   -1.6437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2800    0.8304    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8600   -0.0141    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
  7  6  1  0
  8  7  1  0
  9  8  1  0
 10  9  1  0
 10 11  1  0
  1 12  1  0
 12 11  1  0
  3 13  2  0
  5 14  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 26 29  2  0
 24 30  2  0
 15 31  1  0
  5 31  1  0
  6 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5283183

   ---

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: 438.62

Molecular Weight (Monoisotopic): 438.3431

AlogP: 2.67

#Rotatable Bonds: 9

Polar Surface Area: 145.23

Molecular Species: BASE

HBA: 4

HBD: 7

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.08

CX Basic pKa: 9.83

CX LogP: 2.07

CX LogD: 0.11

Aromatic Rings: ┄

Heavy Atoms: 31

QED Weighted: 0.17

Np Likeness Score: -0.40

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