7-Methoxy-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-h]isoquinoline

ID: ALA71486

PubChem CID: 10219887

Max Phase: Preclinical

Molecular Formula: C12H16N2O

Molecular Weight: 204.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc2c(cn1)C1NCCC1CC2

Standard InChI:  InChI=1S/C12H16N2O/c1-15-11-6-9-3-2-8-4-5-13-12(8)10(9)7-14-11/h6-8,12-13H,2-5H2,1H3

Standard InChI Key:  PXBSPNGMNRTLCH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 15 17  0  0  0  0  0  0  0  0999 V2000
    4.7125   -3.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2250   -3.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1917   -3.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7125   -4.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1917   -4.6792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7917   -3.6542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6750   -4.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6750   -3.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2250   -2.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1875   -2.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7042   -2.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1417   -3.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1542   -4.6792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7917   -2.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6292   -4.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  2  0
  4  1  1  0
  5  4  2  0
  6  2  1  0
  7  5  1  0
  8  3  1  0
  9  2  1  0
 10  3  1  0
 11 10  1  0
 12  6  1  0
 13  7  1  0
 14  9  1  0
 15 13  1  0
  7  8  2  0
 11  9  1  0
 14 12  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA71486

   7-Methoxy-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-h]isoquinoline

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: 204.27

Molecular Weight (Monoisotopic): 204.1263

AlogP: 1.69

#Rotatable Bonds: 1

Polar Surface Area: 34.15

Molecular Species: BASE

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 10.01

CX LogP: 1.63

CX LogD: -0.89

Aromatic Rings: 1

Heavy Atoms: 15

QED Weighted: 0.76

Np Likeness Score: 0.09

References

1. Vernier JM, Holsenback H, Cosford ND, Whitten JP, Menzaghi F, Reid R, Rao TS, Sacaan AI, Lloyd GK, Suto CM, Chavez-Noriega LE, Washburn MS, Urrutia A, McDonald IA..  (1998)  Conformationally restricted analogues of nicotine and anabasine.,  8  (16): [PMID:9873508] [10.1016/s0960-894x(98)00394-1]

2. Dukat M, Taroua M, Dahdouh A, Siripurapu U, Damaj MI, Martin BR, Glennon RA..  (2004)  (+/-)8-Amino-5,6,7,8-tetrahydroisoquinolines as novel antinociceptive agents.,  14  (14): [PMID:15203136] [10.1016/j.bmcl.2004.05.020]

3. 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