(S)-N-(3-(acetimidamidomethyl)benzyl)-2-amino-4-methylpentanamide dihydrochloride

ID: ALA4169004

PubChem CID: 145955529

Max Phase: Preclinical

Molecular Formula: C16H28Cl2N4O

Molecular Weight: 290.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=N)NCc1cccc(CNC(=O)[C@@H](N)CC(C)C)c1.Cl.Cl

Standard InChI:  InChI=1S/C16H26N4O.2ClH/c1-11(2)7-15(18)16(21)20-10-14-6-4-5-13(8-14)9-19-12(3)17;;/h4-6,8,11,15H,7,9-10,18H2,1-3H3,(H2,17,19)(H,20,21);2*1H/t15-;;/m0../s1

Standard InChI Key:  RAENNAICWFYKQO-CKUXDGONSA-N

Molfile:  

     RDKit          2D

 23 21  0  0  0  0  0  0  0  0999 V2000
   31.9098   -2.8580    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   25.4315   -3.1124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4303   -3.9397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1451   -4.3526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8615   -3.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8587   -3.1088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1433   -2.6996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7169   -2.7001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0026   -3.1127    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.5716   -2.6935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2876   -3.1034    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.0005   -2.6882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7165   -3.0980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9974   -1.8632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.4294   -2.6828    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.2880   -2.7004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5737   -3.1131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2878   -1.8754    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.7196   -3.9230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4357   -4.3327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4387   -5.1577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1485   -3.9176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2786   -1.8562    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  2  1  0
  2  8  1  0
  8  9  1  0
  6 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 13 15  1  0
  9 16  1  0
 16 17  1  0
 16 18  2  0
 13 19  1  1
 19 20  1  0
 20 21  1  0
 20 22  1  0
M  END

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 290.41

Molecular Weight (Monoisotopic): 290.2107

AlogP: 1.76

#Rotatable Bonds: 7

Polar Surface Area: 91.00

Molecular Species: BASE

HBA: 3

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 12.16

CX LogP: 0.88

CX LogD: -2.59

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.46

Np Likeness Score: 0.07

References

1. Maccallini C, Di Matteo M, Gallorini M, Montagnani M, Graziani V, Ammazzalorso A, Amoia P, De Filippis B, Di Silvestre S, Fantacuzzi M, Giampietro L, Potenza MA, Re N, Pandolfi A, Cataldi A, Amoroso R..  (2018)  Discovery of N-{3-[(ethanimidoylamino)methyl]benzyl}-l-prolinamide dihydrochloride: A new potent and selective inhibitor of the inducible nitric oxide synthase as a promising agent for the therapy of malignant glioma.,  152  [PMID:29689474] [10.1016/j.ejmech.2018.04.027]

Source

Source(1):

• Scientific Literature