1-(3-tert-Butylamino-2-hydroxy-propoxy)-5,6,7,8,9,9a-hexahydro-benzo[3,4]cyclobuta[1,2]cyclohepten-4b-ol

ID: ALA167659

PubChem CID: 44379251

Max Phase: Preclinical

Molecular Formula: C20H31NO3

Molecular Weight: 333.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C)NCC(O)COc1cccc2c1[C@@H]1CCCCC[C@]21O

Standard InChI:  InChI=1S/C20H31NO3/c1-19(2,3)21-12-14(22)13-24-17-10-7-9-16-18(17)15-8-5-4-6-11-20(15,16)23/h7,9-10,14-15,21-23H,4-6,8,11-13H2,1-3H3/t14?,15-,20+/m0/s1

Standard InChI Key:  WXQKLUMSPOGXCW-VSUHRXMYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  1  0  0  0  0  0999 V2000
    1.9167   -1.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3167   -1.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9167   -0.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3167   -0.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7917   -0.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8000    0.3750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2833    0.3833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9167   -1.7250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8000    0.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2458    0.3833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2792    0.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3792   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7917   -1.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7583    0.6833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3792   -0.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2458   -0.2167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2792   -1.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2792   -0.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7958    1.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3208    0.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3833    0.8458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9667   -1.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9667   -0.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2292   -0.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9167    0.0833    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  3  1  0
  5  4  2  0
  6  5  1  0
  7 14  1  0
  1  8  1  1
  9  7  1  0
 10 11  1  0
 11  6  1  0
 12  1  1  0
 13  2  2  0
 14 10  1  0
 15  3  1  0
 16 10  1  0
 17 13  1  0
 18  5  1  0
 19  9  1  0
 20  9  1  0
 21  9  1  0
 22 12  1  0
 23 15  1  0
 24 22  1  0
  3 25  1  1
  4  2  1  0
 23 24  1  0
 18 17  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA167659

   (1R,8S)-6-[3-(tert-butylamino)-2-hydroxypropoxy]tricyclo[6.5.0.02,7]trideca-2(7),3,5-trien-1-ol

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: 333.47

Molecular Weight (Monoisotopic): 333.2304

AlogP: 3.06

#Rotatable Bonds: 5

Polar Surface Area: 61.72

Molecular Species: BASE

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.60

CX Basic pKa: 9.76

CX LogP: 2.80

CX LogD: 0.49

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.77

Np Likeness Score: 0.35

References

1. Carre MC, Youlassani A, Caubere P, Saint-Aubin-Floch A, Blanc M, Advenier C..  (1984)  Synthesis of a novel series of (aryloxy)propanolamines: new selective beta 2-blocking agents.,  27  (6): [PMID:6145801] [10.1021/jm00372a016]

Source

Source(1):

• Scientific Literature