(1'S)-1',5'-Anhydro-D-glucitol-spiro-[1',5]-2-phenyl-imidazolin-4-one

ID: ALA4514550

PubChem CID: 138753252

Max Phase: Preclinical

Molecular Formula: C14H16N2O6

Molecular Weight: 308.29

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C1N=C(c2ccccc2)N[C@@]12O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O

Standard InChI:  InChI=1S/C14H16N2O6/c17-6-8-9(18)10(19)11(20)14(22-8)13(21)15-12(16-14)7-4-2-1-3-5-7/h1-5,8-11,17-20H,6H2,(H,15,16,21)/t8-,9-,10+,11-,14+/m1/s1

Standard InChI Key:  BCSCGCOVRJYILO-QEGBUVANSA-N

Molfile:  

 
     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   17.2889  -20.2565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9951  -21.4832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5747  -22.3030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1583  -21.4833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5705  -19.8439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2849  -21.0755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5705  -21.4833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8645  -21.0756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8645  -20.2559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1583  -19.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1620  -19.0268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1061  -20.2565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3605  -19.4798    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.6975  -18.9976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0388  -19.4798    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.6963  -18.1804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5857  -20.9182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4050  -17.7715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4041  -16.9551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6953  -16.5467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9858  -16.9608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9902  -17.7759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  9  5  1  0
  5  1  1  0
  1  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  1
  6  2  1  6
  7  3  1  1
  8  4  1  6
 10 11  1  0
  1 12  1  6
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15  1  1  0
 14 16  1  0
 12 17  2  0
 16 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 16  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4514550

   ---

Molecule Features

Natural Product: No

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: 308.29

Molecular Weight (Monoisotopic): 308.1008

AlogP: -2.27

#Rotatable Bonds: 2

Polar Surface Area: 131.61

Molecular Species: NEUTRAL

HBA: 7

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.20

CX Basic pKa: ┄

CX LogP: -1.47

CX LogD: -1.47

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.42

Np Likeness Score: 1.08

References

1. Szabó KE, Kyriakis E, Psarra AG, Karra AG, Sipos Á, Docsa T, Stravodimos GA, Katsidou E, Skamnaki VT, Liggri PGV, Zographos SE, Mándi A, Király SB, Kurtán T, Leonidas DD, Somsák L..  (2019)  Glucopyranosylidene-spiro-imidazolinones, a New Ring System: Synthesis and Evaluation as Glycogen Phosphorylase Inhibitors by Enzyme Kinetics and X-ray Crystallography.,  62  (13): [PMID:31251604] [10.1021/acs.jmedchem.9b00356]

Source

Source(1):

• Scientific Literature