1-(3-((2S,5S)-5-(4-Hydroxybenzyl)-3,6-dioxopiperazin-2-yl)propyl)guanidine

ID: ALA4543375

PubChem CID: 101064669

Max Phase: Preclinical

Molecular Formula: C15H21N5O3

Molecular Weight: 319.37

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  N=C(N)NCCC[C@@H]1NC(=O)[C@H](Cc2ccc(O)cc2)NC1=O

Standard InChI:  InChI=1S/C15H21N5O3/c16-15(17)18-7-1-2-11-13(22)20-12(14(23)19-11)8-9-3-5-10(21)6-4-9/h3-6,11-12,21H,1-2,7-8H2,(H,19,23)(H,20,22)(H4,16,17,18)/t11-,12-/m0/s1

Standard InChI Key:  VFPZSTOWKCRDSF-RYUDHWBXSA-N

Molfile:  

 
     RDKit          2D

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    5.8029  -28.2715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8029  -29.0887    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5082  -29.4932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2134  -29.0887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2134  -28.2715    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5082  -27.8588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5082  -27.0416    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5082  -30.3104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9206  -29.4983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0940  -27.8650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3875  -28.2757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6791  -27.8660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9731  -28.2760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9751  -29.0941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6890  -29.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3921  -29.0881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2691  -29.5057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6289  -29.0908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3360  -29.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0443  -29.0928    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7514  -29.5024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4597  -29.0949    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7502  -30.3196    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  3  8  2  0
  4  9  1  1
  1 10  1  1
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
 14 17  1  0
  9 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4543375

   2-[3-[(2S,5S)-5-[(4-hydroxyphenyl)methyl]-3,6-dioxopiperazin-2-yl]propyl]guanidine

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: 319.37

Molecular Weight (Monoisotopic): 319.1644

AlogP: -0.82

#Rotatable Bonds: 6

Polar Surface Area: 140.33

Molecular Species: BASE

HBA: 4

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.48

CX Basic pKa: 12.49

CX LogP: -1.11

CX LogD: -2.75

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.23

Np Likeness Score: 0.94

References

1. Simon G, Bérubé C, Voyer N, Grenier D..  (2019)  Anti-biofilm and anti-adherence properties of novel cyclic dipeptides against oral pathogens.,  27  (12): [PMID:30528685] [10.1016/j.bmc.2018.11.042]

Source

Source(1):

• Scientific Literature