Digoxigenin (3S)-N-methoxy-6-deoxy-3-O-methyl-beta-D-glucopyranoside

ID: ALA4087959

PubChem CID: 137643913

Max Phase: Preclinical

Molecular Formula: C31H49NO9

Molecular Weight: 579.73

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CO[C@@H]1[C@@H](O)[C@H](N(OC)[C@H]2CC[C@@]3(C)[C@H](CC[C@@H]4[C@@H]3C[C@@H](O)[C@]3(C)[C@@H](C5=CC(=O)OC5)CC[C@]43O)C2)O[C@H](C)[C@H]1O

Standard InChI:  InChI=1S/C31H49NO9/c1-16-25(35)27(38-4)26(36)28(41-16)32(39-5)19-8-10-29(2)18(13-19)6-7-21-22(29)14-23(33)30(3)20(9-11-31(21,30)37)17-12-24(34)40-15-17/h12,16,18-23,25-28,33,35-37H,6-11,13-15H2,1-5H3/t16-,18-,19+,20-,21-,22+,23-,25-,26-,27+,28-,29+,30+,31+/m1/s1

Standard InChI Key:  UKBSNQQGDWHLLX-FTYGUDPDSA-N

Molfile:  

     RDKit          2D

 45 50  0  0  0  0  0  0  0  0999 V2000
    8.4732  -14.2802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0534  -14.2802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5164  -15.5514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4669  -13.9211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7633  -13.8716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2098  -15.1263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1850  -14.3091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4732  -12.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7633  -13.0503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7983  -15.1634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7735  -14.3462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0534  -15.1015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3436  -15.5060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4421  -13.1040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9279  -15.5101    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6378  -15.1015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4732  -15.1015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3436  -13.8716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7633  -15.5060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6378  -14.2802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1049  -15.5927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0554  -13.9583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4732  -13.4630    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0534  -13.4589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0452  -15.9228    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7633  -14.6888    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2056  -15.9394    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1790  -13.0503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1835  -13.8716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9660  -14.1211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4451  -13.4540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9586  -12.7923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2068  -12.0145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9826  -11.7577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9781  -10.9405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1994  -10.6922    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7229  -11.3561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1748  -12.2331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1790  -14.6847    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4742  -11.8245    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6365  -10.4565    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5387  -16.3683    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9407  -16.3272    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6548  -16.7246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1300  -16.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 29  1  0
  2  5  1  0
  3  6  1  0
  4  7  1  0
  5  9  1  0
  6 15  1  0
  7  6  1  0
  8 28  1  0
  9  8  1  0
 10  3  1  0
 11  4  1  0
 12  2  1  0
 13 12  1  0
  4 14  1  1
 16 15  1  1
 16 13  1  0
 17  1  1  0
 18  2  1  0
 19 17  1  0
 20 18  1  0
 10 21  1  1
 11 22  1  6
  1 23  1  1
  2 24  1  1
 12 25  1  1
  5 26  1  6
  6 27  1  6
  5  1  1  0
 19 12  1  0
 20 16  1  0
 11 10  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 28  1  0
 33 34  2  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 37 33  1  0
 32 33  1  1
 28 38  1  1
 29 39  1  1
  8 40  1  1
 35 41  2  0
  3 42  1  6
 15 43  1  0
 43 44  1  0
 21 45  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4087959

   ---

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: 579.73

Molecular Weight (Monoisotopic): 579.3407

AlogP: 1.93

#Rotatable Bonds: 5

Polar Surface Area: 138.15

Molecular Species: NEUTRAL

HBA: 10

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.85

CX Basic pKa: ┄

CX LogP: 1.43

CX LogD: 1.43

Aromatic Rings: ┄

Heavy Atoms: 41

QED Weighted: 0.28

Np Likeness Score: 2.58

References

1. Wang DD, Li XS, Bao YZ, Liu J, Zhang XK, Yao XS, Sun XL, Tang JS..  (2017)  Synthesis of MeON-neoglycosides of digoxigenin with 6-deoxy- and 2,6-dideoxy-d-glucose derivatives and their anticancer activity.,  27  (15): [PMID:28633895] [10.1016/j.bmcl.2017.06.008]

2. Zhan, Yanyan Y and 22 more authors.  2008-09  Cytosporone B is an agonist for nuclear orphan receptor Nur77.  [PMID:18690216]

Source

Source(1):

• Scientific Literature