1-tert-Butylamino-3-(5,6,7,8,9,9a-hexahydro-4bH-benzo[3,4]cyclobuta[1,2]cyclohepten-1-yloxy)-propan-2-ol

ID: ALA168023

PubChem CID: 44379038

Max Phase: Preclinical

Molecular Formula: C20H31NO2

Molecular Weight: 317.47

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C20H31NO2/c1-20(2,3)21-12-14(22)13-23-18-11-7-10-17-15-8-5-4-6-9-16(15)19(17)18/h7,10-11,14-16,21-22H,4-6,8-9,12-13H2,1-3H3/t14?,15-,16+/m0/s1

Standard InChI Key:  AASURSKOEDBGHE-MERJSTESSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  1  0  0  0  0  0999 V2000
    0.3167   -0.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3167   -0.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9167   -0.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9250   -0.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2083    0.0208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2000    0.6208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2833    0.6333    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8000    0.9333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2458    0.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7208    0.9208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7583    0.9333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2083   -1.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3917    0.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3917   -1.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2458    0.0250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7208   -0.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7208   -0.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7958    1.5333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3208    0.6333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3208    1.2333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9792   -0.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9875   -1.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2417   -0.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9167   -1.4792    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9167    0.3250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  4  1  0
  4  1  1  0
  5  2  2  0
  6  5  1  0
  7 11  1  0
  8  7  1  0
  9 10  1  0
 10  6  1  0
 11  9  1  0
 12  1  2  0
 13  3  1  0
 14  4  1  0
 15  9  1  0
 16 12  1  0
 17 16  2  0
 18  8  1  0
 19  8  1  0
 20  8  1  0
 21 13  1  0
 22 14  1  0
 23 22  1  0
  4 24  1  1
  3 25  1  1
  2  3  1  0
  5 17  1  0
 21 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA168023

   1-(tert-butylamino)-3-[[(1R,8S)-3-tricyclo[6.5.0.02,7]trideca-2(7),3,5-trienyl]oxy]propan-2-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: 317.47

Molecular Weight (Monoisotopic): 317.2355

AlogP: 3.96

#Rotatable Bonds: 5

Polar Surface Area: 41.49

Molecular Species: BASE

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.76

CX LogP: 3.88

CX LogD: 1.57

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.86

Np Likeness Score: -0.06

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