2-bromo-N-((R)-2-(((2R,3R,4S)-3,4-dihydroxypyrrolidin-2-yl)methylamino)-2-phenylethyl)benzamide

ID: ALA2206824

PubChem CID: 16104237

Max Phase: Preclinical

Molecular Formula: C20H24BrN3O3

Molecular Weight: 434.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NC[C@H](NC[C@H]1NC[C@H](O)[C@@H]1O)c1ccccc1)c1ccccc1Br

Standard InChI:  InChI=1S/C20H24BrN3O3/c21-15-9-5-4-8-14(15)20(27)24-10-16(13-6-2-1-3-7-13)22-11-17-19(26)18(25)12-23-17/h1-9,16-19,22-23,25-26H,10-12H2,(H,24,27)/t16-,17+,18-,19+/m0/s1

Standard InChI Key:  FSSLVXRVIVHSCK-ZSYWTGECSA-N

Molfile:  

     RDKit          2D

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   11.9838   -2.9663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1666   -2.9770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9225   -3.7569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5917   -4.2303    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2441   -3.7396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4562   -2.2995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6784   -2.3216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0246   -3.9816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6244   -3.4266    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.4050   -3.6685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0048   -3.1135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5857   -4.4655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9861   -5.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1663   -5.8127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9476   -6.0554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5487   -5.4956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3654   -4.7014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7853   -3.3555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.3852   -2.8005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1657   -3.0425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2044   -2.0036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8062   -1.4518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6260   -0.6555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8447   -0.4129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2436   -0.9727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4269   -1.7669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5861   -1.6957    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  1  1  0
  1  6  1  6
  2  7  1  6
  5  8  1  1
  8  9  1  0
 10  9  1  1
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
 11 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 22 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2206824

   2-bromo-N-[(2R)-2-[[(2R,3R,4S)-3,4-dihydroxypyrrolidin-2-yl]methylamino]-2-phenylethyl]benzamide

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: 434.33

Molecular Weight (Monoisotopic): 433.1001

AlogP: 1.20

#Rotatable Bonds: 7

Polar Surface Area: 93.62

Molecular Species: BASE

HBA: 5

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.14

CX Basic pKa: 9.13

CX LogP: 1.50

CX LogD: -0.23

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.45

Np Likeness Score: 0.04

References

1. Moorthy NS, Brás NF, Ramos MJ, Fernandes PA..  (2012)  Virtual screening and QSAR study of some pyrrolidine derivatives as α-mannosidase inhibitors for binding feature analysis.,  20  (24): [PMID:23151473] [10.1016/j.bmc.2012.10.011]

Source

Source(1):

• Scientific Literature