5,7a-Bis-hydroxymethyl-3-phenylamino-2,4a,5,6,7,7a-hexahydro-cyclopenta[1,4]oxazine-5,6,7-triol

ID: ALA314403

Chembl Id: CHEMBL314403

PubChem CID: 44322883

Max Phase: Preclinical

Molecular Formula: C15H20N2O6

Molecular Weight: 324.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  OCC1(O)C(O)C(O)C2(CO)OCC(Nc3ccccc3)=NC12

Standard InChI:  InChI=1S/C15H20N2O6/c18-7-14(22)11(20)12(21)15(8-19)13(14)17-10(6-23-15)16-9-4-2-1-3-5-9/h1-5,11-13,18-22H,6-8H2,(H,16,17)

Standard InChI Key:  VCQTVMUCIZQHEV-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA314403

   3-Anilino-5,7a-bis(hydroxymethyl)-2,4a,6,7-tetrahydrocyclopenta[b][1,4]oxazine-5,6,7-triol

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: 324.33

Molecular Weight (Monoisotopic): 324.1321

AlogP: -1.91

#Rotatable Bonds: 3

Polar Surface Area: 134.77

Molecular Species: NEUTRAL

HBA: 8

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.97

CX Basic pKa: 5.30

CX LogP: -2.37

CX LogD: -2.38

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.38

Np Likeness Score: 0.90

References

1. Uchida C, Kimura H, Ogawa S.  (1994)  Potent glycosidase inhibitors, N-phenyl cyclic isourea derivatives of 5-amino- and 5-amino-1-C-(hydroxymethyl)-cyclopentane-1,2,3,4-tetraols,  4  (22): [10.1016/S0960-894X(01)80688-0]

Source

Source(1):

• Scientific Literature