3-(ammoniomethyl)-2,6-difluorobenzenolate

ID: ALA321931

Chembl Id: CHEMBL321931

Cas Number: 252664-91-8

PubChem CID: 10351955

Max Phase: Preclinical

Molecular Formula: C7H7F2NO

Molecular Weight: 159.13

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NCc1ccc(F)c(O)c1F

Standard InChI:  InChI=1S/C7H7F2NO/c8-5-2-1-4(3-10)6(9)7(5)11/h1-2,11H,3,10H2

Standard InChI Key:  ARLSXSJLCYMMDM-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA321931

   3-(Aminomethyl)-2,6-difluorophenol

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: 159.13

Molecular Weight (Monoisotopic): 159.0496

AlogP: 1.13

#Rotatable Bonds: 1

Polar Surface Area: 46.25

Molecular Species: BASE

HBA: 2

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 2

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 7.20

CX Basic pKa: 8.66

CX LogP: 0.30

CX LogD: 0.21

Aromatic Rings: 1

Heavy Atoms: 11

QED Weighted: 0.64

Np Likeness Score: -0.50

References

1. Chebib M, Johnston GA, Mattsson JP, Rydström K, Nilsson K, Qiu J, Stevenson SH, Silverman RB..  (1999)  Aminomethyl-2,6-difluorophenols as a novel class of increased lipophilicity GABA(C) receptor antagonists.,  9  (21): [PMID:10560731] [10.1016/s0960-894x(99)00542-9]

2. Qiu J, Stevenson SH, O'Beirne MJ, Silverman RB..  (1999)  2,6-Difluorophenol as a bioisostere of a carboxylic acid: bioisosteric analogues of gamma-aminobutyric acid.,  42  (2): [PMID:9925739] [10.1021/jm980435l]

3. Meanwell NA..  (2011)  Synopsis of some recent tactical application of bioisosteres in drug design.,  54  (8): [PMID:21413808] [10.1021/jm1013693]

4. Gillis EP, Eastman KJ, Hill MD, Donnelly DJ, Meanwell NA..  (2015)  Applications of Fluorine in Medicinal Chemistry.,  58  (21): [PMID:26200936] [10.1021/acs.jmedchem.5b00258]

5. Meanwell NA..  (2018)  Fluorine and Fluorinated Motifs in the Design and Application of Bioisosteres for Drug Design.,  61  (14): [PMID:29400967] [10.1021/acs.jmedchem.7b01788]

Source

Source(1):

• Scientific Literature