5-(3-tert-Butylamino-2-hydroxy-propoxy)-1,3,4,8b-tetrahydro-2H-biphenylen-4a-ol

ID: ALA163971

PubChem CID: 44378946

Max Phase: Preclinical

Molecular Formula: C19H29NO3

Molecular Weight: 319.45

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C19H29NO3/c1-18(2,3)20-11-13(21)12-23-16-9-6-7-14-15-8-4-5-10-19(15,22)17(14)16/h6-7,9,13,15,20-22H,4-5,8,10-12H2,1-3H3/t13?,15-,19+/m1/s1

Standard InChI Key:  GGXUJGISHRKINL-NRYXDWBNSA-N

Molfile:  

     RDKit          2D

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   -1.2000    0.6583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -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
   -0.0833    0.9708    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
   -0.0708   -0.2417    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
   -4.8458    2.1708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4500    0.6708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4542    0.0625    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 22  1  0
  4 24  1  1
  2  3  1  0
 15 23  1  0
 18 17  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA163971

   (4aS,8bR)-5-[3-(tert-butylamino)-2-hydroxypropoxy]-2,3,4,8b-tetrahydro-1H-biphenylen-4a-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: 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: 2.36

CX LogD: 0.05

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.78

Np Likeness Score: 0.38

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