cyclo(D)-trans-4-OH-Pro-(D)-Phe

ID: ALA460332

PubChem CID: 44566898

Max Phase: Preclinical

Molecular Formula: C14H16N2O3

Molecular Weight: 260.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1N[C@H](Cc2ccccc2)C(=O)N2C[C@H](O)C[C@H]12

Standard InChI:  InChI=1S/C14H16N2O3/c17-10-7-12-13(18)15-11(14(19)16(12)8-10)6-9-4-2-1-3-5-9/h1-5,10-12,17H,6-8H2,(H,15,18)/t10-,11-,12-/m1/s1

Standard InChI Key:  PYQJYHACQOBZLF-IJLUTSLNSA-N

Molfile:  

     RDKit          2D

 20 22  0  0  0  0  0  0  0  0999 V2000
   16.4101    0.6495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4650    1.9846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9557    1.3367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2407    1.6961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2045    0.8672    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.9003    0.4239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6367    0.8046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6730    1.6335    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.9728    2.0816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3319    0.3604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2947   -0.4638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5638   -0.8411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5263   -1.6645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2219   -2.1096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9568   -1.7254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9907   -0.9032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8631   -0.4003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0076    2.9059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0110    2.4921    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.1314    1.3704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  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
  8  9  1  0
  3 20  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA460332

   (3R,7R,8aR)-3-benzyl-7-hydroxy-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: 260.29

Molecular Weight (Monoisotopic): 260.1161

AlogP: -0.31

#Rotatable Bonds: 2

Polar Surface Area: 69.64

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.14

CX Basic pKa: ┄

CX LogP: -0.29

CX LogD: -0.29

Aromatic Rings: 1

Heavy Atoms: 19

QED Weighted: 0.77

Np Likeness Score: 0.89

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