[2'-(3,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-biphenyl-3-yl]-acetonitrile

ID: ALA2303953

Chembl Id: CHEMBL2303953

PubChem CID: 71720288

Max Phase: Preclinical

Molecular Formula: C20H21NO6

Molecular Weight: 371.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#CCc1cccc(-c2ccccc2O[C@H]2O[C@H](CO)[C@@H](O)[C@@H](O)[C@@H]2O)c1

Standard InChI:  InChI=1S/C20H21NO6/c21-9-8-12-4-3-5-13(10-12)14-6-1-2-7-15(14)26-20-19(25)18(24)17(23)16(11-22)27-20/h1-7,10,16-20,22-25H,8,11H2/t16-,17-,18-,19+,20+/m1/s1

Standard InChI Key:  DPOOHZIGCIUSOW-UEDWAMCQSA-N

Alternative Forms

1. Parent:

   

   ALA2303953

   2-[3-[2-[(2R,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]phenyl]acetonitrile

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: 371.39

Molecular Weight (Monoisotopic): 371.1369

AlogP: 0.60

#Rotatable Bonds: 5

Polar Surface Area: 123.17

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.18

CX Basic pKa: ┄

CX LogP: 0.74

CX LogD: 0.74

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.61

Np Likeness Score: 0.97

References

1. Kogan TP, Dupré B, Keller KM, Scott IL, Bui H, Market RV, Beck PJ, Voytus JA, Revelle BM, Scott D..  (1995)  Rational design and synthesis of small molecule, non-oligosaccharide selectin inhibitors: (alpha-D-mannopyranosyloxy)biphenyl-substituted carboxylic acids.,  38  (26): [PMID:8544173] [10.1021/jm00026a004]

Source

Source(1):

• Scientific Literature