(6aR,12bS)-2-Phenyl-5,6,6a,7,8,12b-hexahydro-benzo[a]phenanthridine-10,11-diol

ID: ALA320428

PubChem CID: 10382833

Max Phase: Preclinical

Molecular Formula: C23H21NO2

Molecular Weight: 343.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Oc1cc2c(cc1O)[C@H]1c3cc(-c4ccccc4)ccc3CN[C@@H]1CC2

Standard InChI:  InChI=1S/C23H21NO2/c25-21-11-16-8-9-20-23(19(16)12-22(21)26)18-10-15(6-7-17(18)13-24-20)14-4-2-1-3-5-14/h1-7,10-12,20,23-26H,8-9,13H2/t20-,23-/m1/s1

Standard InChI Key:  RMDMGQSKVJJQEX-NFBKMPQASA-N

Molfile:  

     RDKit          2D

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    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
    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
    1.7542   -1.5292    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
    0.2167   -3.3125    0.0000 C   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
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    0.9792   -4.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2167   -4.1917    0.0000 C   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
    2.5042   -4.6375    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
    3.2917   -0.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.2750   -4.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.5500   -4.6375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0042    0.6833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2375   -0.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5250   -0.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2500    1.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5208    0.6958    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  1  1  0
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 25 22  1  0
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 10 27  1  1
  3 28  1  6
 11 13  1  0
 19 10  1  0
 12 14  1  0
 16  9  1  0
 25 26  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA320428

   (6aR,12bS)-2-Phenyl-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: 343.43

Molecular Weight (Monoisotopic): 343.1572

AlogP: 4.31

#Rotatable Bonds: 1

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: 9.72

CX Basic pKa: 8.97

CX LogP: 4.15

CX LogD: 2.90

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.58

Np Likeness Score: 0.82

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