cyclo(D)-Leu-(D)-His

ID: ALA500065

PubChem CID: 44566905

Max Phase: Preclinical

Molecular Formula: C12H18N4O2

Molecular Weight: 250.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)C[C@H]1NC(=O)[C@@H](Cc2cnc[nH]2)NC1=O

Standard InChI:  InChI=1S/C12H18N4O2/c1-7(2)3-9-11(17)16-10(12(18)15-9)4-8-5-13-6-14-8/h5-7,9-10H,3-4H2,1-2H3,(H,13,14)(H,15,18)(H,16,17)/t9-,10-/m1/s1

Standard InChI Key:  QYFSHTYKVAOVJM-NXEZZACHSA-N

Molfile:  

     RDKit          2D

 18 19  0  0  0  0  0  0  0  0999 V2000
   -2.2617  -16.3249    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9789  -16.7399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6919  -17.9766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9789  -17.5617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6919  -16.3249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4050  -16.7399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4050  -17.5617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1181  -16.3249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2617  -17.9766    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5487  -17.5617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5487  -16.7399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8356  -17.9766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6331  -17.8979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1839  -17.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7730  -16.5708    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0339  -16.7425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1225  -17.5617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8356  -16.3249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  9  1  0
 11 18  2  0
  2  1  1  0
  2  4  1  0
  4  3  2  0
  2  5  1  1
  5  6  1  0
  6  7  1  0
  6  8  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  1
 12 17  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 13  1  0
  1 11  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA500065

   (3R,6R)-3-(1H-imidazol-5-ylmethyl)-6-(2-methylpropyl)piperazine-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: 250.30

Molecular Weight (Monoisotopic): 250.1430

AlogP: -0.02

#Rotatable Bonds: 4

Polar Surface Area: 86.88

Molecular Species: NEUTRAL

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.82

CX Basic pKa: 6.74

CX LogP: -0.59

CX LogD: -0.65

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.70

Np Likeness Score: 0.91

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]

Source

Source(1):

• Scientific Literature