rac-N-[(1S,2S,4S)-4-(1,1'-Biphenyl-4-yloxy)-2-hydroxycyclopentyl]-2,2-diphenylacetamide

ID: ALA3134477

PubChem CID: 76336679

Max Phase: Preclinical

Molecular Formula: C31H29NO3

Molecular Weight: 463.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(N[C@H]1C[C@H](Oc2ccc(-c3ccccc3)cc2)C[C@@H]1O)C(c1ccccc1)c1ccccc1

Standard InChI:  InChI=1S/C31H29NO3/c33-29-21-27(35-26-18-16-23(17-19-26)22-10-4-1-5-11-22)20-28(29)32-31(34)30(24-12-6-2-7-13-24)25-14-8-3-9-15-25/h1-19,27-30,33H,20-21H2,(H,32,34)/t27-,28-,29-/m0/s1

Standard InChI Key:  ZGOBTWRMVVFSBP-AWCRTANDSA-N

Molfile:  

     RDKit          2D

 35 39  0  0  0  0  0  0  0  0999 V2000
   12.1764   -6.2531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4227   -5.9176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2626   -7.0736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8438   -5.7682    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.3365   -5.0971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0039   -4.6122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9177   -3.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1640   -3.4561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4965   -3.9411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5828   -4.7615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7553   -6.4025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0016   -6.0669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3341   -6.5519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4204   -7.3723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1740   -7.7079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8415   -7.2230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5975   -6.1038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3120   -5.6913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9250   -6.2433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5895   -6.9970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7690   -6.9107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3982   -4.8708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0020   -7.7114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4770   -7.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0645   -8.4259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2395   -8.4259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8270   -7.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2395   -6.9970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0645   -6.9970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3020   -7.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7145   -6.9970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5395   -6.9970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9520   -7.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5395   -8.4259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7145   -8.4259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  2  0
  1  4  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  5 10  2  0
  2  5  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 11 16  2  0
  2 11  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 17 21  1  0
 18 22  1  1
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 24 29  2  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 35  1  0
 30 35  2  0
 24 30  1  0
 23 27  1  0
 20 23  1  1
 17  4  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA3134477

   N-[(1S,2S,4S)-2-hydroxy-4-(4-phenylphenoxy)cyclopentyl]-2,2-diphenylacetamide

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: 463.58

Molecular Weight (Monoisotopic): 463.2147

AlogP: 5.57

#Rotatable Bonds: 7

Polar Surface Area: 58.56

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.99

CX Basic pKa: ┄

CX LogP: 5.43

CX LogD: 5.43

Aromatic Rings: 4

Heavy Atoms: 35

QED Weighted: 0.38

Np Likeness Score: 0.11

References

1. Zohrabi-Kalantari V, Wilde F, Grunert R, Bednarski PJ, Link A.  (2014)  4-Aminocyclopentane-1,3-diols as platforms for diversity: synthesis of a screening library,  5  (2): [10.1039/C3MD00252G]

Source

Source(1):

• Scientific Literature