3-((1S,2S,5R)-4-oxo-6,8-dioxabicyclo[3.2.1]octan-2-yl)benzo[d]oxazol-2(3H)-one

ID: ALA4538920

PubChem CID: 1242619

Max Phase: Preclinical

Molecular Formula: C13H11NO5

Molecular Weight: 261.23

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C1C[C@H](n2c(=O)oc3ccccc32)[C@H]2CO[C@@H]1O2

Standard InChI:  InChI=1S/C13H11NO5/c15-9-5-8(11-6-17-12(9)18-11)14-7-3-1-2-4-10(7)19-13(14)16/h1-4,8,11-12H,5-6H2/t8-,11+,12+/m0/s1

Standard InChI Key:  SDNPWXVGSFCVMZ-XXILOJSOSA-N

Molfile:  

 
     RDKit          2D

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   10.7271   -2.1647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7271   -2.9937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4425   -3.4040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1581   -2.9937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1581   -2.1647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4425   -1.7460    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8754   -3.4093    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9204   -1.2854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8820   -1.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8582   -1.7878    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0069   -1.7502    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0097   -3.4093    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1180   -4.4056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9285   -4.2319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7023   -3.6881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2544   -3.0751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9993   -2.2925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1923   -2.1219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6411   -2.7399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8992   -3.5200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5468   -4.7842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  4  7  2  0
  5  8  1  0
  1  9  1  0
  9  8  1  0
  5 10  1  6
  1 11  1  6
  2 12  1  6
 12 16  1  0
 15 13  1  0
 13 14  1  0
 14 12  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 14 21  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4538920

   3-[(1S,2S,5R)-4-oxo-6,8-dioxabicyclo[3.2.1]octan-2-yl]-1,3-benzoxazol-2-one

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 261.23

Molecular Weight (Monoisotopic): 261.0637

AlogP: 0.85

#Rotatable Bonds: 1

Polar Surface Area: 70.67

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 1.20

CX LogD: 1.20

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.76

Np Likeness Score: 0.04

References

1. Giri GF, Danielli M, Marinelli RA, Spanevello RA..  (2016)  Cytotoxic effect of levoglucosenone and related derivatives against human hepatocarcinoma cell lines.,  26  (16): [PMID:27422336] [10.1016/j.bmcl.2016.07.007]

Source

Source(1):

• Scientific Literature