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

ID: ALA166047

PubChem CID: 44379254

Max Phase: Preclinical

Molecular Formula: C19H29NO3

Molecular Weight: 319.45

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C19H29NO3/c1-13(2)20-11-14(21)12-23-17-9-6-7-15-16-8-4-3-5-10-19(16,22)18(15)17/h6-7,9,13-14,16,20-22H,3-5,8,10-12H2,1-2H3/t14?,16-,19+/m1/s1

Standard InChI Key:  UGHUCCDBYPSHON-NBMIWUGMSA-N

Molfile:  

     RDKit          2D

 24 26  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
   -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
   -4.3208    1.8708    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
    0.4542    0.9000    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
    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 13  1  0
  9  1  1  0
 10 11  1  0
 11  6  1  0
 12  3  2  0
 13 10  1  0
 14  4  1  0
 15 10  1  0
 16 12  1  0
 17  8  1  0
 18  5  1  0
 19  9  1  0
 20 17  1  0
 21 17  1  0
 22 14  1  0
 23 19  1  0
  4 24  1  1
  2  3  1  0
 23 22  1  0
 18 16  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA166047

   (1S,8R)-3-[2-hydroxy-3-(propan-2-ylamino)propoxy]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: 319.45

Molecular Weight (Monoisotopic): 319.2147

AlogP: 2.67

#Rotatable Bonds: 6

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: 9.67

CX LogP: 2.52

CX LogD: 0.29

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.75

Np Likeness Score: 0.44

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