N-(((2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-2-yl)methyl)-2-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyloxy)acetamide

ID: ALA4104370

PubChem CID: 137657899

Max Phase: Preclinical

Molecular Formula: C18H34N2O5

Molecular Weight: 358.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)[C@@H]1CC[C@@H](C)C[C@H]1OCC(=O)NC[C@@H]1N[C@H](CO)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C18H34N2O5/c1-10(2)12-5-4-11(3)6-15(12)25-9-16(22)19-7-13-17(23)18(24)14(8-21)20-13/h10-15,17-18,20-21,23-24H,4-9H2,1-3H3,(H,19,22)/t11-,12+,13+,14-,15-,17-,18+/m1/s1

Standard InChI Key:  QRLQYZCQNHOIKT-PMCTTXHBSA-N

Molfile:  

     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
    8.2981  -11.8309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6271  -11.0829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1443  -10.4287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3359  -10.5150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0069  -11.2630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4863  -11.9248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8536   -9.8553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0411   -9.9432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5587   -9.2836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1573  -12.6728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4734   -9.6807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2857   -9.5916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9900   -9.0217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7611  -11.3623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5783  -11.3623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8326  -10.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1697  -10.1035    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5109  -10.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7336  -10.3334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5634   -9.5341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2799  -12.0228    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0578  -12.0240    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6102  -10.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -9.5350    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7298   -8.4845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  4  7  1  1
  7  8  1  0
  8  9  1  0
  6 10  1  1
  3 11  1  6
 11 12  1  0
 11 13  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 14  1  0
 18 19  1  1
 19 20  1  0
 14 21  1  1
 15 22  1  1
 16 23  1  1
 23 24  1  0
 24  9  1  0
  9 25  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4104370

   ---

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: 358.48

Molecular Weight (Monoisotopic): 358.2468

AlogP: -0.37

#Rotatable Bonds: 7

Polar Surface Area: 111.05

Molecular Species: BASE

HBA: 6

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.20

CX Basic pKa: 8.67

CX LogP: -0.17

CX LogD: -1.45

Aromatic Rings: ┄

Heavy Atoms: 25

QED Weighted: 0.42

Np Likeness Score: 0.94

References

1. Cheng WC, Wang JH, Yun WY, Li HY, Hu JM..  (2017)  Rapid preparation of (3R,4S,5R) polyhydroxylated pyrrolidine-based libraries to discover a pharmacological chaperone for treatment of Fabry disease.,  126  [PMID:27744182] [10.1016/j.ejmech.2016.10.004]

Source

Source(1):

• Scientific Literature