(2S,4R)-N-[(1S,2R)-2-hydroxy-1-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl]propyl]-1-methyl-4-propylpyrrolidine-2-carboxamide

ID: ALA3392932

PubChem CID: 92272361

Max Phase: Preclinical

Molecular Formula: C18H34N2O6S

Molecular Weight: 406.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC[C@@H]1C[C@@H](C(=O)N[C@H]([C@@H]2O[C@H](SC)[C@H](O)[C@@H](O)[C@H]2O)[C@@H](C)O)N(C)C1

Standard InChI:  InChI=1S/C18H34N2O6S/c1-5-6-10-7-11(20(3)8-10)17(25)19-12(9(2)21)16-14(23)13(22)15(24)18(26-16)27-4/h9-16,18,21-24H,5-8H2,1-4H3,(H,19,25)/t9-,10-,11+,12+,13+,14-,15-,16+,18-/m1/s1

Standard InChI Key:  OJMMVQQUTAEWLP-UKGOLDLVSA-N

Molfile:  

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    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.2969   -4.9508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3363   -3.1512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3383   -1.3500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3383    1.3500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.7000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6003    1.4978    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.6387    0.8963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8655   -2.0009    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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  9 19  2  0
  7 20  1  0
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  5 23  1  6
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  3 25  1  1
  2 26  1  1
 26 27  1  0
  6 28  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA3392932

   (2S,4R)-N-[(1S,2R)-2-hydroxy-1-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl]propyl]-1-methyl-4-propylpyrrolidine-2-carboxamide

Molecule Features

Natural Product: Yes

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: 406.55

Molecular Weight (Monoisotopic): 406.2138

AlogP: -0.86

#Rotatable Bonds: 7

Polar Surface Area: 122.49

Molecular Species: NEUTRAL

HBA: 8

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.37

CX Basic pKa: 7.97

CX LogP: -0.32

CX LogD: -0.99

Aromatic Rings: ┄

Heavy Atoms: 27

QED Weighted: 0.37

Np Likeness Score: 0.64

References

1. Kaiser M, Mäser P, Tadoori LP, Ioset JR, Brun R.. Antiprotozoal Activity Profiling of Approved Drugs: A Starting Point toward Drug Repositioning,  [10.6019/CHEMBL3392926]

Source

Source(1):

• Drugs for Neglected Diseases Initiative (DNDi)