(6aR,12bS)-4-Methyl-5,6,6a,7,8,12b-hexahydro-benzo[a]phenanthridine-10,11-diol

ID: ALA106116

PubChem CID: 9970963

Max Phase: Preclinical

Molecular Formula: C18H19NO2

Molecular Weight: 281.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cccc2c1CN[C@@H]1CCc3cc(O)c(O)cc3[C@@H]21

Standard InChI:  InChI=1S/C18H19NO2/c1-10-3-2-4-12-14(10)9-19-15-6-5-11-7-16(20)17(21)8-13(11)18(12)15/h2-4,7-8,15,18-21H,5-6,9H2,1H3/t15-,18-/m1/s1

Standard InChI Key:  LYRRSOZNQRVMQC-CRAIPNDOSA-N

Molfile:  

     RDKit          2D

 23 26  0  0  1  0  0  0  0  0999 V2000
    1.7417   -3.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5042   -1.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5042   -2.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2792   -1.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7417   -4.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9792   -2.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0375   -2.8792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0417   -1.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2167   -3.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2667   -3.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9792   -4.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2167   -4.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5042   -4.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2917   -0.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2750   -4.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7542   -1.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5458   -2.8667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5500   -4.6375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7625   -0.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5292   -0.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0667   -0.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0292   -3.7542    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7417   -2.4167    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  1  1  0
  4  2  2  0
  5  1  1  0
  6  1  2  0
  7 10  1  0
  8  7  1  0
  9  6  1  0
 10  3  1  0
 11  5  2  0
 12  9  2  0
 13  5  1  0
 14  4  1  0
 15 13  1  0
 16  2  1  0
 17  9  1  0
 18 12  1  0
 19 16  2  0
 20 19  1  0
 21 14  1  0
 10 22  1  1
  3 23  1  6
 11 12  1  0
 15 10  1  0
  4  8  1  0
 14 20  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA106116

   (6aR,12bS)-4-Methyl-5,6,6a,7,8,12b-hexahydro-benzo[a]phenanthridine-10,11-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: 281.36

Molecular Weight (Monoisotopic): 281.1416

AlogP: 2.96

#Rotatable Bonds: ┄

Polar Surface Area: 52.49

Molecular Species: BASE

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.76

CX Basic pKa: 9.04

CX LogP: 2.94

CX LogD: 1.66

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.65

Np Likeness Score: 1.04

References

1. Knoerzer TA, Watts VJ, Nichols DE, Mailman RB..  (1995)  Synthesis and biological evaluation of a series of substituted benzo[a]phenanthridines as agonists at D1 and D2 dopamine receptors.,  38  (16): [PMID:7636869] [10.1021/jm00016a009]

Source

Source(1):

• Scientific Literature