4-[2-((S)-1-Methyl-pyrrolidin-2-yl)-ethylsulfanyl]-phenol

ID: ALA46914

PubChem CID: 10799899

Max Phase: Preclinical

Molecular Formula: C13H19NOS

Molecular Weight: 237.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1CCC[C@H]1CCSc1ccc(O)cc1

Standard InChI:  InChI=1S/C13H19NOS/c1-14-9-2-3-11(14)8-10-16-13-6-4-12(15)5-7-13/h4-7,11,15H,2-3,8-10H2,1H3/t11-/m0/s1

Standard InChI Key:  NVZGJSVPOOILDI-NSHDSACASA-N

Molfile:  

     RDKit          2D

 17 18  0  0  1  0  0  0  0  0999 V2000
    8.7292   -5.0542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9750   -4.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8417   -5.1417    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.1167   -4.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2667   -5.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6917   -3.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5542   -4.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2917   -4.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4042   -5.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1167   -3.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6917   -4.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4042   -3.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9125   -5.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9792   -3.4917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8667   -3.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0542   -3.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2667   -4.3042    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  7  1  0
  4  3  1  0
  2  5  1  6
  6 12  1  0
  7  5  1  0
  8  1  1  0
  9  4  2  0
 10  4  1  0
 11  9  1  0
 12 10  2  0
 13  1  1  0
 14  6  1  0
 15  8  1  0
 16  2  1  0
  2 17  1  1
 15 16  1  0
 11  6  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA46914

   4-[2-((S)-1-Methyl-pyrrolidin-2-yl)-ethylsulfanyl]-phenol

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: 237.37

Molecular Weight (Monoisotopic): 237.1187

AlogP: 2.97

#Rotatable Bonds: 4

Polar Surface Area: 23.47

Molecular Species: BASE

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.19

CX Basic pKa: 9.81

CX LogP: 1.93

CX LogD: 0.58

Aromatic Rings: 1

Heavy Atoms: 16

QED Weighted: 0.81

Np Likeness Score: -0.27

References

1. Vernier JM, El-Abdellaoui H, Holsenback H, Cosford ND, Bleicher L, Barker G, Bontempi B, Chavez-Noriega L, Menzaghi F, Rao TS, Reid R, Sacaan AI, Suto C, Washburn M, Lloyd GK, McDonald IA..  (1999)  4-[[2-(1-Methyl-2-pyrrolidinyl)ethyl]thio]phenol hydrochloride (SIB-1553A): a novel cognitive enhancer with selectivity for neuronal nicotinic acetylcholine receptors.,  42  (10): [PMID:10346920] [10.1021/jm990035d]

2. Jensen AA, Frølund B, Liljefors T, Krogsgaard-Larsen P..  (2005)  Neuronal nicotinic acetylcholine receptors: structural revelations, target identifications, and therapeutic inspirations.,  48  (15): [PMID:16033252] [10.1021/jm040219e]

Source

Source(1):

• Scientific Literature