(R,S)-diethyl 2-(3-oxo-1-(pyridin-3-yl)-4-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)butyl)malonate

ID: ALA562504

PubChem CID: 45268036

Max Phase: Preclinical

Molecular Formula: C22H31NO10

Molecular Weight: 469.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)C(C(=O)OCC)C(CC(=O)C[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)c1cccnc1

Standard InChI:  InChI=1S/C22H31NO10/c1-3-31-21(29)17(22(30)32-4-2)14(12-6-5-7-23-10-12)8-13(25)9-15-18(26)20(28)19(27)16(11-24)33-15/h5-7,10,14-20,24,26-28H,3-4,8-9,11H2,1-2H3/t14?,15-,16+,18-,19+,20+/m0/s1

Standard InChI Key:  XRIRJMUGHZZJMK-PINDGCKHSA-N

Molfile:  

     RDKit          2D

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   12.1570   -5.6573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8729   -5.2448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5846   -5.6573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1570   -6.4823    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   10.7295   -5.6573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7295   -6.4823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4453   -6.8948    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0136   -6.8948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0136   -7.7198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2977   -6.4823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5860   -6.8948    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   10.0136   -5.2448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   15.0146   -5.6579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7294   -5.2460    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0139   -6.4829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4435   -5.6591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1583   -5.2472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3012   -4.4198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0160   -4.0079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5870   -4.0067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7301   -4.4210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4449   -4.0091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8688   -6.8903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8674   -7.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5819   -8.1287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2993   -7.7127    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.2972   -6.8898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  7 15  1  0
  7  1  1  1
  4 18  1  0
  1  2  1  0
  6 19  1  0
  2  3  1  0
 19 20  1  0
  3  4  1  0
 19 21  2  0
  2  5  2  0
 20 22  1  0
  4  6  1  0
 22 23  1  0
  7  8  1  0
  6 24  1  0
  8  9  1  6
 24 25  1  0
  8 10  1  0
 24 26  2  0
 10 11  1  1
 25 27  1  0
 10 12  1  0
 27 28  1  0
 12 13  1  6
 18 29  2  0
 12 14  1  0
 29 30  1  0
 14 15  1  0
 30 31  2  0
 14 16  1  1
 31 32  1  0
 16 17  1  0
 32 33  2  0
 33 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA562504

   diethyl 2-[3-oxo-1-pyridin-3-yl-4-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]butyl]propanedioate

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: 469.49

Molecular Weight (Monoisotopic): 469.1948

AlogP: -0.90

#Rotatable Bonds: 11

Polar Surface Area: 172.71

Molecular Species: NEUTRAL

HBA: 11

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.60

CX Basic pKa: 4.90

CX LogP: -1.25

CX LogD: -1.25

Aromatic Rings: 1

Heavy Atoms: 33

QED Weighted: 0.23

Np Likeness Score: 0.46

References

1. Bisht SS, Fatima S, Tamrakar AK, Rahuja N, Jaiswal N, Srivastava AK, Tripathi RP..  (2009)  Synthetic studies in butenonyl C-glycosides: Preparation of polyfunctional alkanonyl glycosides and their enzyme inhibitory activity.,  19  (10): [PMID:19362832] [10.1016/j.bmcl.2009.03.136]

Source

Source(1):

• Scientific Literature