cyclo(L)-Pro-(D)-Val

ID: ALA460676

Cas Number: 27483-18-7

PubChem CID: 927560

Max Phase: Preclinical

Molecular Formula: C10H16N2O2

Molecular Weight: 196.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)[C@H]1NC(=O)[C@@H]2CCCN2C1=O

Standard InChI:  InChI=1S/C10H16N2O2/c1-6(2)8-10(14)12-5-3-4-7(12)9(13)11-8/h6-8H,3-5H2,1-2H3,(H,11,13)/t7-,8+/m0/s1

Standard InChI Key:  XLUAWXQORJEMBD-JGVFFNPUSA-N

Molfile:  

     RDKit          2D

 15 16  0  0  0  0  0  0  0  0999 V2000
    0.9726  -11.8588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0275  -10.5238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5182  -11.1717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8032  -10.8122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7670  -11.6411    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4628  -12.0844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1992  -11.7037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2355  -10.8748    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5353  -10.4267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8944  -12.1480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4256  -12.9086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5701   -9.6024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5735  -10.0163    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6267  -11.7681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8572  -12.9721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  9  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  1  5  1  0
  7 10  1  6
  6 11  2  0
  4  2  1  0
  9 12  2  0
  2  3  1  0
  4 13  1  6
  3  1  1  0
 10 14  1  0
  4  5  1  0
 10 15  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA460676

   Cyclo(D-Val-L-Pro)

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: 196.25

Molecular Weight (Monoisotopic): 196.1212

AlogP: 0.13

#Rotatable Bonds: 1

Polar Surface Area: 49.41

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.37

CX Basic pKa: ┄

CX LogP: 0.09

CX LogD: 0.09

Aromatic Rings: ┄

Heavy Atoms: 14

QED Weighted: 0.65

Np Likeness Score: 1.27

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. Kang H, Ku SK, Choi H, Bae JS..  (2016)  Three diketopiperazines from marine-derived bacteria inhibit LPS-induced endothelial inflammatory responses.,  26  (8): [PMID:26988307] [10.1016/j.bmcl.2016.03.030]

Source

Source(1):

• Scientific Literature