(2R,3R,4S)-2-((1-hydroxy-1,1-diphenylpropan-2-ylamino)methyl)pyrrolidine-3,4-diol

ID: ALA2207393

PubChem CID: 71457830

Max Phase: Preclinical

Molecular Formula: C20H26N2O3

Molecular Weight: 342.44

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C20H26N2O3/c1-14(21-12-17-19(24)18(23)13-22-17)20(25,15-8-4-2-5-9-15)16-10-6-3-7-11-16/h2-11,14,17-19,21-25H,12-13H2,1H3/t14?,17-,18+,19-/m1/s1

Standard InChI Key:  YKDIBSLOOWMSJH-DPGVMXDBSA-N

Molfile:  

     RDKit          2D

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   26.3810   -6.0462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6378   -5.2621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9685   -4.7753    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.3034   -5.2621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0701   -6.7131    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.8651   -6.7143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.4229   -5.0083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0352   -5.5611    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.8202   -5.3073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4326   -5.8602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9929   -4.5005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2600   -6.6670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2176   -5.6064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0146   -6.4421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.8284   -6.1600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6128   -5.9067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7861   -5.0991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1688   -4.5453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3867   -4.8016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4770   -6.9178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3042   -7.7237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9169   -8.2775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7051   -8.0199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8742   -7.2145    0.0000 C   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
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  1  6  1  1
  2  7  1  1
  3  8  1  6
  8  9  1  0
  9 10  1  0
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 10 12  1  0
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 11 14  1  0
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 14 16  2  0
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 20 14  1  0
 13 21  2  0
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 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 13  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2207393

   (2R,3R,4S)-2-[[(1-hydroxy-1,1-diphenylpropan-2-yl)amino]methyl]pyrrolidine-3,4-diol

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: 342.44

Molecular Weight (Monoisotopic): 342.1943

AlogP: 0.59

#Rotatable Bonds: 6

Polar Surface Area: 84.75

Molecular Species: BASE

HBA: 5

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.76

CX Basic pKa: 9.18

CX LogP: 1.09

CX LogD: -0.70

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.53

Np Likeness Score: 0.51

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