cyclo(L)-Pro-(D)-Leu

ID: ALA463718

Cas Number: 36238-67-2

PubChem CID: 927565

Max Phase: Preclinical

Molecular Formula: C11H18N2O2

Molecular Weight: 210.28

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C11H18N2O2/c1-7(2)6-8-11(15)13-5-3-4-9(13)10(14)12-8/h7-9H,3-6H2,1-2H3,(H,12,14)/t8-,9+/m1/s1

Standard InChI Key:  SZJNCZMRZAUNQT-BDAKNGLRSA-N

Molfile:  

     RDKit          2D

 16 17  0  0  0  0  0  0  0  0999 V2000
   10.6143  -10.6880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6692   -9.3529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1598  -10.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4449   -9.6414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4086  -10.4703    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1045  -10.9136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8409  -10.5329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8771   -9.7040    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1769   -9.2559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5361  -10.9771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0673  -11.7378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2118   -8.4316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2152   -8.8454    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.2684  -10.5972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9636  -11.0415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3056   -9.7731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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
 14 15  1  0
  4  9  1  0
 14 16  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA463718

   Cyclo(D-Leu-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: 210.28

Molecular Weight (Monoisotopic): 210.1368

AlogP: 0.52

#Rotatable Bonds: 2

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: 11.47

CX Basic pKa: ┄

CX LogP: 0.45

CX LogD: 0.45

Aromatic Rings: ┄

Heavy Atoms: 15

QED Weighted: 0.72

Np Likeness Score: 1.04

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]

3. Li X, Zhao C, Jing S, Sun J, Li X, Man S, Wang Y, Gao W..  (2017)  Novel phenanthrene and isocoumarin from the rhizomes of Dioscorea nipponica Makino subsp. rosthornii (Prain et Burkill) C. T. Ting (Dioscoreaceae).,  27  (15): [PMID:28606759] [10.1016/j.bmcl.2017.03.095]

4. Kemkuignou BM, Moussa AY, Decock C, Stadler M..  (2022)  Terpenoids and Meroterpenoids from Cultures of Two Grass-Associated Species of Amylosporus (Basidiomycota).,  85  (4.0): [PMID:35175766] [10.1021/acs.jnatprod.1c00975]

Source

Source(1):

• Scientific Literature