4-(1-Propyl-piperidin-3-yl)-benzene-1,2-diol

ID: ALA1907814

PubChem CID: 53946795

Max Phase: Preclinical

Molecular Formula: C14H21NO2

Molecular Weight: 235.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCN1CCC[C@@H](c2ccc(O)c(O)c2)C1

Standard InChI:  InChI=1S/C14H21NO2/c1-2-7-15-8-3-4-12(10-15)11-5-6-13(16)14(17)9-11/h5-6,9,12,16-17H,2-4,7-8,10H2,1H3/t12-/m1/s1

Standard InChI Key:  JBPMHBLMULBWFU-GFCCVEGCSA-N

Molfile:  

     RDKit          2D

 18 19  0  0  0  0  0  0  0  0999 V2000
    4.4625   -2.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5917   -2.6792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4667   -1.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7542   -1.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1667   -2.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8792   -2.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0375   -1.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7417   -2.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0375   -2.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7542   -0.1917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3167   -1.0167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5875   -3.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3125   -2.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8667   -3.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1625   -3.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0250   -2.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7417   -2.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8852   -1.8995    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  6  1  0
  3  1  2  0
  4  3  1  0
  5  1  1  1
  6  5  1  0
  7  9  1  0
  8  1  1  0
  9  8  2  0
 10  4  1  0
 11  7  1  0
 12 14  1  0
 13  2  1  0
 14 15  1  0
 15  5  1  0
 16 13  1  0
 17 16  1  0
  7  4  2  0
 12  2  1  0
  5 18  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA1907814

   4-[(3S)-1-propylpiperidin-3-yl]benzene-1,2-diol

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: 235.33

Molecular Weight (Monoisotopic): 235.1572

AlogP: 2.69

#Rotatable Bonds: 3

Polar Surface Area: 43.70

Molecular Species: BASE

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.89

CX Basic pKa: 8.85

CX LogP: 2.13

CX LogD: 0.94

Aromatic Rings: 1

Heavy Atoms: 17

QED Weighted: 0.79

Np Likeness Score: -0.21

References

1. Wikström H, Elebring T, Hallnemo G, Andersson B, Svensson K, Carlsson A, Rollema H..  (1988)  Occurrence and pharmacological significance of metabolic ortho-hydroxylation of 5- and 8-hydroxy-2-(di-n-propylamino)tetralin.,  31  (6): [PMID:2967374] [10.1021/jm00401a005]

2. Rollema H, Mastebroek D, Wikström H, Svensson K, Carlsson A, Sundell S..  (1986)  Enantiomers of 3-(3,4-dihydroxyphenyl)- and 3-(3-hydroxyphenyl)-N-n-propylpiperidine: central pre- and postsynaptic dopaminergic effects and pharmacokinetics.,  29  (10): [PMID:3761308] [10.1021/jm00160a016]

3. Liljefors T, Wikström H..  (1986)  A molecular mechanics approach to the understanding of presynaptic selectivity for centrally acting dopamine receptor agonists of the phenylpiperidine series.,  29  (10): [PMID:3761309] [10.1021/jm00160a017]

Source

Source(1):

• Scientific Literature