cyclo(D)-Pro-(D)-Phe

ID: ALA462452

PubChem CID: 6992199

Max Phase: Preclinical

Molecular Formula: C14H16N2O2

Molecular Weight: 244.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1N[C@H](Cc2ccccc2)C(=O)N2CCC[C@H]12

Standard InChI:  InChI=1S/C14H16N2O2/c17-13-12-7-4-8-16(12)14(18)11(15-13)9-10-5-2-1-3-6-10/h1-3,5-6,11-12H,4,7-9H2,(H,15,17)/t11-,12-/m1/s1

Standard InChI Key:  QZBUWPVZSXDWSB-VXGBXAGGSA-N

Molfile:  

     RDKit          2D

 19 21  0  0  0  0  0  0  0  0999 V2000
   -5.2482    0.3495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1933    1.6846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7027    1.0367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4176    1.3961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4539    0.5672    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7580    0.1239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0216    0.5046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9854    1.3335    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6856    1.7816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3264    0.0604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3636   -0.7638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0946   -1.1411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1321   -1.9645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4364   -2.4096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7015   -2.0254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6676   -1.2032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7952   -0.7003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6507    2.6059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6473    2.1921    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  0
  1  5  1  0
  7 10  1  6
 10 11  1  0
  4  2  1  0
 11 12  2  0
  2  3  1  0
 12 13  1  0
  3  1  1  0
 13 14  2  0
  4  5  1  0
 14 15  1  0
  4  9  1  0
 15 16  2  0
 16 11  1  0
  5  6  1  0
  6 17  2  0
  6  7  1  0
  9 18  2  0
  7  8  1  0
  4 19  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA462452

   (3R,8aR)-3-benzyl-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-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: 244.29

Molecular Weight (Monoisotopic): 244.1212

AlogP: 0.72

#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: 11.28

CX Basic pKa: ┄

CX LogP: 0.86

CX LogD: 0.86

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.83

Np Likeness Score: 0.71

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