Digoxigenin (3R)-N-methoxy-2,6-dideoxy-3-O-methyl-beta-D-glucopyranoside

ID: ALA4091319

PubChem CID: 137654852

Max Phase: Preclinical

Molecular Formula: C31H49NO8

Molecular Weight: 563.73

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CO[C@@H]1C[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/C31H49NO8/c1-17-28(35)24(37-4)15-26(40-17)32(38-5)20-8-10-29(2)19(13-20)6-7-22-23(29)14-25(33)30(3)21(9-11-31(22,30)36)18-12-27(34)39-16-18/h12,17,19-26,28,33,35-36H,6-11,13-16H2,1-5H3/t17-,19-,20-,21-,22-,23+,24-,25-,26-,28-,29+,30+,31+/m1/s1

Standard InChI Key:  LSZKNMIUSAAYDH-QJSBGWEOSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA4091319

   ---

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: 563.73

Molecular Weight (Monoisotopic): 563.3458

AlogP: 2.96

#Rotatable Bonds: 5

Polar Surface Area: 117.92

Molecular Species: NEUTRAL

HBA: 9

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.85

CX Basic pKa: 0.21

CX LogP: 2.34

CX LogD: 2.33

Aromatic Rings: ┄

Heavy Atoms: 40

QED Weighted: 0.34

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