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

ID: ALA167336

PubChem CID: 44379253

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@]1(O)CCCCC[C@H]21

Standard InChI:  InChI=1S/C20H31NO3/c1-19(2,3)21-12-14(22)13-24-17-10-7-8-15-16-9-5-4-6-11-20(16,23)18(15)17/h7-8,10,14,16,21-23H,4-6,9,11-13H2,1-3H3/t14?,16-,20+/m1/s1

Standard InChI Key:  MWSAXCYTLJHCHC-CVEXUSBASA-N

Molfile:  

     RDKit          2D

 25 27  0  0  1  0  0  0  0  0999 V2000
   -0.5958    0.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2000    0.6583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2000    0.0583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5958    0.0583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7208    0.9583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7208    1.5583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6000    1.2625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7958    1.5708    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3208    1.8708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1333    1.0333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7583    1.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2375    1.8583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7208   -0.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2750    1.8708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1333   -0.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7625    0.9625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2375    0.0583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2375    0.6583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3125    2.4708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8458    1.5708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9083    2.0333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4542    0.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4542   -0.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7125    0.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6000   -0.5417    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
  1  7  1  1
  8 14  1  0
  9  8  1  0
 10  1  1  0
 11 12  1  0
 12  6  1  0
 13  3  2  0
 14 11  1  0
 15  4  1  0
 16 11  1  0
 17 13  1  0
 18  5  1  0
 19  9  1  0
 20  9  1  0
 21  9  1  0
 22 10  1  0
 23 15  1  0
 24 22  1  0
  4 25  1  1
  2  3  1  0
 24 23  1  0
 18 17  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA167336

   (1S,8R)-3-[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: 13.49

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