(5S,6S,7S)-5,7-Dihydroxy-1-azabicyclo[4.2.0]octane-2-one

ID: ALA2409321

PubChem CID: 71747510

Max Phase: Preclinical

Molecular Formula: C7H11NO3

Molecular Weight: 157.17

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1CC[C@H](O)[C@H]2[C@@H](O)CN12

Standard InChI:  InChI=1S/C7H11NO3/c9-4-1-2-6(11)8-3-5(10)7(4)8/h4-5,7,9-10H,1-3H2/t4-,5-,7-/m0/s1

Standard InChI Key:  ZHVIEQKJYARANP-VPLCAKHXSA-N

Molfile:  

     RDKit          2D

 12 13  0  0  0  0  0  0  0  0999 V2000
    8.3865   -7.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3865   -8.2462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7971   -7.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0918   -7.0163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5060   -7.0225    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4997   -7.8335    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7976   -8.2471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0914   -8.6509    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4952   -9.3571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2014   -8.9533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9899   -9.1681    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6793   -8.6557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  4  1  0
  2  8  1  0
  7  3  1  0
  3  4  1  0
  3  5  1  6
  7  6  1  6
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10  7  1  0
 10 11  1  1
  2 12  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2409321

   (5S,6S,7S)-5,7-dihydroxy-1-azabicyclo[4.2.0]octan-2-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: 157.17

Molecular Weight (Monoisotopic): 157.0739

AlogP: -1.29

#Rotatable Bonds: ┄

Polar Surface Area: 60.77

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: -1.73

CX LogD: -1.73

Aromatic Rings: ┄

Heavy Atoms: 11

QED Weighted: 0.46

Np Likeness Score: 1.32

References

1. Martínez RF, Araújo N, Jenkinson SF, Nakagawa S, Kato A, Fleet GW..  (2013)  (3R,4S,5R,6R,7S)-3,4,5,7-Tetrahydroxyconidine, an azetidine analogue of 6,7-diepicastanospermine and a conformationally constrained d-deoxyaltronojirimycin, from l-arabinose.,  21  (16): [PMID:23545138] [10.1016/j.bmc.2013.03.004]

Source

Source(1):

• Scientific Literature