N-[4-(2-Hydroxy-3-isopropylamino-propoxy)-5,6,7,8,9,9a-hexahydro-4bH-benzo[3,4]cyclobuta[1,2]cyclohepten-1-yl]-butyramide

ID: ALA165043

PubChem CID: 44378947

Max Phase: Preclinical

Molecular Formula: C23H36N2O3

Molecular Weight: 388.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCC(=O)Nc1ccc(OCC(O)CNC(C)C)c2c1[C@H]1CCCCC[C@@H]21

Standard InChI:  InChI=1S/C23H36N2O3/c1-4-8-21(27)25-19-11-12-20(28-14-16(26)13-24-15(2)3)23-18-10-7-5-6-9-17(18)22(19)23/h11-12,15-18,24,26H,4-10,13-14H2,1-3H3,(H,25,27)/t16?,17-,18+/m0/s1

Standard InChI Key:  YLBWVHADZBYSLQ-UQJFVLDMSA-N

Molfile:  

     RDKit          2D

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    2.1750    0.0958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7792   -0.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7792    0.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6542   -0.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6542   -1.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6542    0.3958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1750   -1.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1375   -0.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6542    0.9958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7042   -1.6250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4208    1.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1375    1.2958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1000    1.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.2042   -0.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6125    0.3958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.6542   -2.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4625    1.0083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9375    1.9083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7792    0.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7292   -0.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -3.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0542   -0.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7750   -1.1125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7750    0.6958    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  1  2  0
  6  5  1  0
  7  2  2  0
  8  6  1  0
  9  5  1  0
 10  7  1  0
 11  8  2  0
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 13 16  1  0
 14 15  1  0
 15 10  1  0
 16 14  1  0
 17  4  1  0
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 19 14  1  0
 20 13  1  0
 21  8  1  0
 22 21  1  0
 23 20  1  0
 24 20  1  0
 25 17  1  0
 26 18  1  0
 27 22  1  0
 28 26  1  0
  3 29  1  1
  4 30  1  1
  4  2  1  0
  7 12  1  0
 25 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA165043

   N-[(1S,8R)-6-[2-hydroxy-3-(propan-2-ylamino)propoxy]-3-tricyclo[6.5.0.02,7]trideca-2,4,6-trienyl]butanamide

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: 388.55

Molecular Weight (Monoisotopic): 388.2726

AlogP: 4.31

#Rotatable Bonds: 9

Polar Surface Area: 70.59

Molecular Species: BASE

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 14.00

CX Basic pKa: 9.67

CX LogP: 3.98

CX LogD: 1.76

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.59

Np Likeness Score: -0.39

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