cyclo(D)-Val-(D)-Leu

ID: ALA447980

PubChem CID: 44566899

Max Phase: Preclinical

Molecular Formula: C11H20N2O2

Molecular Weight: 212.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)C[C@H]1NC(=O)[C@@H](C(C)C)NC1=O

Standard InChI:  InChI=1S/C11H20N2O2/c1-6(2)5-8-10(14)13-9(7(3)4)11(15)12-8/h6-9H,5H2,1-4H3,(H,12,15)(H,13,14)/t8-,9-/m1/s1

Standard InChI Key:  UPOUGDHEEGKEGS-RKDXNWHRSA-N

Molfile:  

     RDKit          2D

 15 15  0  0  0  0  0  0  0  0999 V2000
   -3.8211   -4.8152    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2336   -5.5269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2336   -6.9545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8211   -6.2428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0586   -5.5269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4711   -6.2428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4711   -4.8152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9961   -6.2428    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5836   -5.5269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9961   -4.8152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7586   -5.5269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3461   -6.2428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7586   -6.9545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5211   -6.2428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5836   -4.0994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  8  1  0
 10 15  2  0
  1  2  1  0
  2  4  1  0
  4  3  2  0
  2  5  1  1
  5  6  1  0
  5  7  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  1
 11 12  1  0
 12 13  1  0
 12 14  1  0
  1 10  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA447980

   (3R,6R)-3-(2-methylpropyl)-6-propan-2-ylpiperazine-2,5-dione

Molecule Features

Natural Product: Yes

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: 212.29

Molecular Weight (Monoisotopic): 212.1525

AlogP: 0.67

#Rotatable Bonds: 3

Polar Surface Area: 58.20

Molecular Species: NEUTRAL

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.32

CX Basic pKa: ┄

CX LogP: 1.07

CX LogD: 1.07

Aromatic Rings: ┄

Heavy Atoms: 15

QED Weighted: 0.72

Np Likeness Score: 1.85

References

1. Fdhila F, Vázquez V, Sánchez JL, Riguera R..  (2003)  dd-diketopiperazines: antibiotics active against Vibrio anguillarum isolated from marine bacteria associated with cultures of Pecten maximus.,  66  (10): [PMID:14575426] [10.1021/np030233e]

2. 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