5-cyclohexyl-N-(((2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-2-yl)methyl)pentanamide

ID: ALA4099259

PubChem CID: 137658800

Max Phase: Preclinical

Molecular Formula: C17H32N2O4

Molecular Weight: 328.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(CCCCC1CCCCC1)NC[C@@H]1N[C@H](CO)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C17H32N2O4/c20-11-14-17(23)16(22)13(19-14)10-18-15(21)9-5-4-8-12-6-2-1-3-7-12/h12-14,16-17,19-20,22-23H,1-11H2,(H,18,21)/t13-,14+,16+,17-/m0/s1

Standard InChI Key:  ZTMUKXWXXQKIQC-ABFRBSLYSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
   23.2457  -10.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0707  -10.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3275   -9.7659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6582   -9.2791    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.9931   -9.7659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2084   -9.5113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0366   -8.7043    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.7599  -11.2168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.5548  -11.2180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.1125   -9.5120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2851   -8.7053    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.0700   -8.4515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2428   -7.6447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.6824   -9.0043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5098   -9.8110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1221  -10.3639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9495  -11.1707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5617  -11.7235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3838  -12.5270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9921  -13.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7788  -12.8291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9535  -12.0218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3417  -11.4645    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
  5  1  1  0
  5  6  1  1
  6  7  1  0
  1  8  1  1
  2  9  1  1
  3 10  1  1
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 23  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4099259

   ---

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: 328.45

Molecular Weight (Monoisotopic): 328.2362

AlogP: 0.30

#Rotatable Bonds: 8

Polar Surface Area: 101.82

Molecular Species: BASE

HBA: 5

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.20

CX Basic pKa: 8.67

CX LogP: 0.46

CX LogD: -0.83

Aromatic Rings: ┄

Heavy Atoms: 23

QED Weighted: 0.41

Np Likeness Score: 0.81

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