(R)-2-(((2R,3R,4R)-3,4-dihydroxy-1-methyl-5-oxopyrrolidin-2-yl)methylamino)-2-phenylethyl 4-bromobenzoate

ID: ALA476343

PubChem CID: 25147648

Max Phase: Preclinical

Molecular Formula: C21H23BrN2O5

Molecular Weight: 463.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1C(=O)[C@H](O)[C@H](O)[C@H]1CN[C@@H](COC(=O)c1ccc(Br)cc1)c1ccccc1

Standard InChI:  InChI=1S/C21H23BrN2O5/c1-24-17(18(25)19(26)20(24)27)11-23-16(13-5-3-2-4-6-13)12-29-21(28)14-7-9-15(22)10-8-14/h2-10,16-19,23,25-26H,11-12H2,1H3/t16-,17+,18+,19+/m0/s1

Standard InChI Key:  LKHOPRZQBRZOTI-WJFTUGDTSA-N

Molfile:  

     RDKit          2D

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   18.0904   -3.9002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8738   -4.6960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5637   -5.1481    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.2068   -4.6316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9143   -3.8604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5738   -3.2570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3663   -3.1703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9167   -5.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9164   -5.8667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.6308   -6.2794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6305   -7.1044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3454   -5.8671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0597   -6.2798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.7743   -5.8675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4886   -6.2802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7746   -5.0425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.4845   -7.1052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1980   -7.5179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9136   -7.1055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9112   -6.2763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1971   -5.8674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9131   -7.5135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9125   -8.3378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6274   -8.7513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3444   -8.3346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3414   -7.5117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6285   -7.5173    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   17.1024   -4.9886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6035   -5.9721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  7  1  6
 14 15  1  0
  2  3  1  0
 14 16  2  0
  4  8  1  1
 15 17  2  0
  3  4  1  0
 17 18  1  0
  8  9  1  0
 18 19  2  0
  4  5  1  0
 19 20  1  0
 10  9  1  1
 20 21  2  0
 21 15  1  0
  5  1  1  0
 11 22  2  0
 10 11  1  0
 22 23  1  0
  1  2  1  0
 23 24  2  0
 10 12  1  0
 24 25  1  0
  1  6  1  6
 25 26  2  0
 26 11  1  0
 12 13  1  0
 19 27  1  0
  2 28  2  0
 13 14  1  0
  3 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA476343

   (R)-2-(((2R,3R,4R)-3,4-dihydroxy-1-methyl-5-oxopyrrolidin-2-yl)methylamino)-2-phenylethyl 4-bromobenzoate

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: 463.33

Molecular Weight (Monoisotopic): 462.0790

AlogP: 1.50

#Rotatable Bonds: 7

Polar Surface Area: 99.10

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.12

CX Basic pKa: 7.21

CX LogP: 2.06

CX LogD: 1.85

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.54

Np Likeness Score: 0.06

References

1. Fiaux H, Kuntz DA, Hoffman D, Janzer RC, Gerber-Lemaire S, Rose DR, Juillerat-Jeanneret L..  (2008)  Functionalized pyrrolidine inhibitors of human type II alpha-mannosidases as anti-cancer agents: optimizing the fit to the active site.,  16  (15): [PMID:18599296] [10.1016/j.bmc.2008.06.021]

Source

Source(1):

• Scientific Literature