1-[4-(3,4-Dihydroxy-phenyl)-3,6-dihydro-2H-pyridin-1-yl]-ethanone

ID: ALA324880

PubChem CID: 616160

Max Phase: Preclinical

Molecular Formula: C13H15NO3

Molecular Weight: 233.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)N1CC=C(c2ccc(O)c(O)c2)CC1

Standard InChI:  InChI=1S/C13H15NO3/c1-9(15)14-6-4-10(5-7-14)11-2-3-12(16)13(17)8-11/h2-4,8,16-17H,5-7H2,1H3

Standard InChI Key:  UMFUUSYHSYHHNV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 17 18  0  0  0  0  0  0  0  0999 V2000
   -0.9583   -3.0292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9500   -1.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9583   -3.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9500   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4333   -2.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4333   -0.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4333   -0.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4333   -2.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4708   -2.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9500   -0.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4708   -2.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4375   -3.9375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4708   -0.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4708   -0.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0875   -0.0292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9583    0.5708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4750   -3.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2 11  1  0
  3  1  1  0
  4  2  1  0
  5  8  1  0
  6  4  2  0
  7  6  1  0
  8  1  1  0
  9  1  1  0
 10 14  1  0
 11  9  1  0
 12  3  2  0
 13  4  1  0
 14 13  2  0
 15  7  1  0
 16 10  1  0
 17  3  1  0
  5  2  2  0
  7 10  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA324880

   1,2,3,6-Tetrahydropyridine, 1-acetyl-4-[4,5-dihydroxyphenyl]-

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: 233.27

Molecular Weight (Monoisotopic): 233.1052

AlogP: 1.73

#Rotatable Bonds: 1

Polar Surface Area: 60.77

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.24

CX Basic pKa: ┄

CX LogP: 0.97

CX LogD: 0.96

Aromatic Rings: 1

Heavy Atoms: 17

QED Weighted: 0.73

Np Likeness Score: 0.07

References

1. Gessner W, Brossi A, Shen R, Abell CW..  (1985)  Synthesis and dihydropteridine reductase inhibitory effects of potential metabolites of the neurotoxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine.,  28  (3): [PMID:3871859] [10.1021/jm00381a009]

Source

Source(1):

• Scientific Literature