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

ID: ALA106836

PubChem CID: 10356457

Max Phase: Preclinical

Molecular Formula: C17H17NO3

Molecular Weight: 283.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Oc1ccc2c(c1)[C@@H]1c3cc(O)c(O)cc3CC[C@H]1NC2

Standard InChI:  InChI=1S/C17H17NO3/c19-11-3-1-10-8-18-14-4-2-9-5-15(20)16(21)7-13(9)17(14)12(10)6-11/h1,3,5-7,14,17-21H,2,4,8H2/t14-,17-/m1/s1

Standard InChI Key:  CHIBSDMOHJPZGC-RHSMWYFYSA-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
    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
    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
    3.2792   -1.5500    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
    4.0417   -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
    3.2750   -4.1917    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
    1.7625   -0.6542    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
    2.5292   -0.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0000   -0.2042    0.0000 O   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
  5  1  2  0
  6  8  1  0
  7  5  1  0
  8  3  1  0
  9  4  2  0
 10  7  2  0
 11  2  2  0
 12  2  1  0
 13  6  1  0
 14  4  1  0
 15 14  1  0
 16 11  1  0
 17 12  2  0
 18  7  1  0
 19 10  1  0
 20 17  1  0
 21 17  1  0
  8 22  1  1
  3 23  1  6
  9 10  1  0
 15  8  1  0
 11 13  1  0
 16 20  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA106836

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

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: 283.33

Molecular Weight (Monoisotopic): 283.1208

AlogP: 2.35

#Rotatable Bonds: ┄

Polar Surface Area: 72.72

Molecular Species: BASE

HBA: 4

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.39

CX Basic pKa: 8.81

CX LogP: 2.08

CX LogD: 0.99

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.56

Np Likeness Score: 1.39

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