(1R,5S,7R)-3-benzyl-7-(morpholine-4-carbonyl)-6,8-dioxa-3-azabicyclo[3.2.1]octan-2-one

ID: ALA601830

PubChem CID: 46229299

Max Phase: Preclinical

Molecular Formula: C17H20N2O5

Molecular Weight: 332.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C([C@@H]1O[C@H]2CN(Cc3ccccc3)C(=O)[C@@H]1O2)N1CCOCC1

Standard InChI:  InChI=1S/C17H20N2O5/c20-16(18-6-8-22-9-7-18)14-15-17(21)19(11-13(23-14)24-15)10-12-4-2-1-3-5-12/h1-5,13-15H,6-11H2/t13-,14-,15-/m1/s1

Standard InChI Key:  ZKVMEJZZTZTCKC-RBSFLKMASA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
    6.7832   -2.9112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5792   -2.7093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2395   -3.2070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4442   -3.6654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2651   -4.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8231   -4.3998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6336   -4.5592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9871   -4.4350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9977   -5.2599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6962   -4.0134    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2375   -3.6042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6195   -3.6877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2264   -4.4130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4011   -4.4311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0081   -5.1556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4398   -5.8596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2686   -5.8346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6579   -5.1096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3276   -5.0594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5750   -1.8833    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6292   -5.3833    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4187   -4.4210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1257   -4.0029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1194   -3.1775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3998   -2.7721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6866   -3.1919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
 12 13  1  0
  5  7  1  0
 13 14  2  0
  6  7  1  0
 14 15  1  0
  1  4  1  0
 15 16  2  0
 16 17  1  0
  3  5  1  0
 17 18  2  0
 18 13  1  0
  8  9  2  0
  6 19  2  0
  8 10  1  0
  2 20  1  1
  5  8  1  1
  7 21  1  1
 10 22  1  0
  2  3  1  0
  7 11  1  0
  2 11  1  0
  4  6  1  0
  4 12  1  0
 10 26  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA601830

   (1S,5R,6R)-3-benzyl-6-(morpholine-4-carbonyl)-7,8-dioxa-3-azabicyclo[3.2.1]octan-4-one

Molecule Features

Natural Product: No

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: 332.36

Molecular Weight (Monoisotopic): 332.1372

AlogP: 0.00

#Rotatable Bonds: 3

Polar Surface Area: 68.31

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.06

CX Basic pKa: ┄

CX LogP: 0.23

CX LogD: 0.23

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.78

Np Likeness Score: -0.73

References

1. Trabocchi A, Mannino C, Machetti F, De Bernardis F, Arancia S, Cauda R, Cassone A, Guarna A..  (2010)  Identification of inhibitors of drug-resistant Candida albicans strains from a library of bicyclic peptidomimetic compounds.,  53  (6): [PMID:20184325] [10.1021/jm901734u]

Source

Source(1):

• Scientific Literature