acetylusaramine

ID: ALA2269159

PubChem CID: 76330453

Max Phase: Preclinical

Molecular Formula: C20H27NO7

Molecular Weight: 393.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C/C=C1\C[C@@H](C)[C@](O)(COC(C)=O)C(=O)OCC2=CCN3CC[C@@H](OC1=O)[C@@H]23

Standard InChI:  InChI=1S/C20H27NO7/c1-4-14-9-12(2)20(25,11-27-13(3)22)19(24)26-10-15-5-7-21-8-6-16(17(15)21)28-18(14)23/h4-5,12,16-17,25H,6-11H2,1-3H3/b14-4+/t12-,16-,17-,20-/m1/s1

Standard InChI Key:  KLRFTGKPNAYUMI-QTMWKHJZSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   18.3481  -13.7503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3431  -12.4649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8810  -13.1066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1041  -12.7076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1041  -13.5001    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.8566  -13.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3247  -13.1038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8576  -12.4630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8644  -11.6706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3670  -11.6728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.5548  -11.2803    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.5616  -10.4879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2521  -10.0935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6922  -11.2560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7162  -10.4639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9935  -11.6313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4149  -10.0845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0414  -10.0472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1117  -10.5114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8299  -10.1215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0904  -11.3284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2317   -9.4101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4145   -9.4101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8164   -8.7063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0656   -9.2303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2183   -7.9947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8031   -7.2909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0355   -7.9870    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0
  4  2  1  0
  2  3  1  0
  3  1  1  0
  4  5  1  1
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  4  1  0
  8  9  1  0
  2 10  1  1
  9 11  1  0
 11 12  1  0
 12 13  2  0
 12 20  1  0
 10 14  1  0
 14 15  1  0
 14 16  2  0
 15 17  1  0
 15 18  2  0
 17 19  1  0
 19 20  1  0
 19 21  1  6
 20 22  1  6
 20 23  1  0
 22 24  1  0
 18 25  1  0
 24 26  1  0
 26 27  1  0
 26 28  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2269159

   ACETYLUSARAMINE

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: 393.44

Molecular Weight (Monoisotopic): 393.1788

AlogP: 0.74

#Rotatable Bonds: 2

Polar Surface Area: 102.37

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.41

CX Basic pKa: 8.14

CX LogP: 1.04

CX LogD: 0.23

Aromatic Rings: ┄

Heavy Atoms: 28

QED Weighted: 0.32

Np Likeness Score: 2.75

References

1.  (2008)  36  (3): [10.1016/jbse.2007.08.015]

Source

Source(1):

• Scientific Literature