(6aR,12bS)-3-Methyl-6-propyl-5,6,6a,7,8,12b-hexahydro-benzo[a]phenanthridine-10,11-diol

ID: ALA318338

PubChem CID: 10448883

Max Phase: Preclinical

Molecular Formula: C21H25NO2

Molecular Weight: 323.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCN1Cc2cc(C)ccc2[C@@H]2c3cc(O)c(O)cc3CC[C@H]21

Standard InChI:  InChI=1S/C21H25NO2/c1-3-8-22-12-15-9-13(2)4-6-16(15)21-17-11-20(24)19(23)10-14(17)5-7-18(21)22/h4,6,9-11,18,21,23-24H,3,5,7-8,12H2,1-2H3/t18-,21-/m1/s1

Standard InChI Key:  IFODQCSLFYJCSE-WIYYLYMNSA-N

Molfile:  

     RDKit          2D

 26 29  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   -2.8625    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
    3.2667   -3.3125    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
    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
    4.0417   -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
    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
    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
    3.2917   -0.6667    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
    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
    4.7917   -3.3292    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
    2.5417    0.6708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875   -4.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5500   -4.6542    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  1  1  0
  3  4  1  0
  4  2  1  0
  5  2  1  0
  6  5  2  0
  7  1  1  0
  8  1  2  0
  9  6  1  0
 10  8  1  0
 11  7  2  0
 12 10  2  0
 13 16  1  0
 14  5  1  0
 15  6  1  0
 16  7  1  0
 17 14  2  0
 18 17  1  0
 19  3  1  0
 20 10  1  0
 21 12  1  0
 22 18  1  0
 23 19  1  0
 24 23  1  0
  4 25  1  1
  2 26  1  6
 11 12  1  0
 13  4  1  0
  3  9  1  0
 15 18  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA318338

   (6aR,12bS)-3-Methyl-6-propyl-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: 323.44

Molecular Weight (Monoisotopic): 323.1885

AlogP: 4.08

#Rotatable Bonds: 2

Polar Surface Area: 43.70

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.56

CX Basic pKa: 8.29

CX LogP: 4.58

CX LogD: 3.81

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.82

Np Likeness Score: 0.61

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