6-Propyl-5,6,6a,7,8,12b-hexahydro-benzo[a]phenanthridine-10,11-diol

ID: ALA299161

PubChem CID: 9904738

Max Phase: Preclinical

Molecular Formula: C20H23NO2

Molecular Weight: 309.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCN1Cc2ccccc2[C@@H]2c3cc(O)c(O)cc3CC[C@H]21

Standard InChI:  InChI=1S/C20H23NO2/c1-2-9-21-12-14-5-3-4-6-15(14)20-16-11-19(23)18(22)10-13(16)7-8-17(20)21/h3-6,10-11,17,20,22-23H,2,7-9,12H2,1H3/t17-,20-/m1/s1

Standard InChI Key:  VNVHTKVGILYCGH-YLJYHZDGSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  1  0  0  0  0  0999 V2000
    2.1167   -3.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8792   -3.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4125   -3.1917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6417   -3.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875   -2.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1167   -4.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3542   -3.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6542   -1.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4167   -2.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5917   -3.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3542   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5917   -4.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6500   -4.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8792   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1667   -3.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1708   -3.1792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1750   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1292   -1.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6667   -0.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1625   -4.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1292   -0.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9042   -0.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9250   -4.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1167   -2.7292    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4042   -4.0667    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  1  1  0
  7  1  2  0
  8  5  2  0
  9  8  1  0
 10  7  1  0
 11  6  2  0
 12 10  2  0
 13 14  1  0
 14  6  1  0
 15  3  1  0
 16 10  1  0
 17 12  1  0
 18  5  1  0
 19  8  1  0
 20 15  1  0
 21 18  2  0
 22 21  1  0
 23 20  1  0
  2 24  1  6
  4 25  1  1
 12 11  1  0
  4 13  1  0
  9  3  1  0
 22 19  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA299161

   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: 309.41

Molecular Weight (Monoisotopic): 309.1729

AlogP: 3.77

#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: 9.55

CX Basic pKa: 8.22

CX LogP: 4.08

CX LogD: 3.36

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.83

Np Likeness Score: 0.54

References

1. Brewster WK, Nichols DE, Riggs RM, Mottola DM, Lovenberg TW, Lewis MH, Mailman RB..  (1990)  trans-10,11-dihydroxy-5,6,6a,7,8,12b-hexahydrobenzo[a]phenanthridine: a highly potent selective dopamine D1 full agonist.,  33  (6): [PMID:1971308] [10.1021/jm00168a034]

2. Mottola DM, Laiter S, Watts VJ, Tropsha A, Wyrick SD, Nichols DE, Mailman RB..  (1996)  Conformational analysis of D1 dopamine receptor agonists: pharmacophore assessment and receptor mapping.,  39  (1): [PMID:8568818] [10.1021/jm9502100]

3. 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