Indirubin-3'-(2-beta-D-glucopyranosylethyl)oxime Ether

ID: ALA4100916

Chembl Id: CHEMBL4100916

PubChem CID: 137658647

Max Phase: Preclinical

Molecular Formula: C24H25N3O8

Molecular Weight: 483.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1Nc2ccccc2/C1=C1/Nc2ccccc2/C1=N\OCCO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

Standard InChI:  InChI=1S/C24H25N3O8/c28-11-16-20(29)21(30)22(31)24(35-16)33-9-10-34-27-18-13-6-2-4-8-15(13)25-19(18)17-12-5-1-3-7-14(12)26-23(17)32/h1-8,16,20-22,24-25,28-31H,9-11H2,(H,26,32)/b19-17-,27-18+/t16-,20-,21+,22-,24-/m1/s1

Standard InChI Key:  WBNOICUDTXIEJB-WRIZEAHVSA-N

Alternative Forms

1. Parent:

   

   ALA4100916

   ---

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: 483.48

Molecular Weight (Monoisotopic): 483.1642

AlogP: 0.01

#Rotatable Bonds: 6

Polar Surface Area: 162.10

Molecular Species: NEUTRAL

HBA: 10

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 10.68

CX Basic pKa: 4.04

CX LogP: -0.29

CX LogD: -0.29

Aromatic Rings: 2

Heavy Atoms: 35

QED Weighted: 0.19

Np Likeness Score: 0.94

References

1. Cheng X, Merz KH, Vatter S, Zeller J, Muehlbeyer S, Thommet A, Christ J, Wölfl S, Eisenbrand G..  (2017)  Identification of a Water-Soluble Indirubin Derivative as Potent Inhibitor of Insulin-like Growth Factor 1 Receptor through Structural Modification of the Parent Natural Molecule.,  60  (12): [PMID:28557430] [10.1021/acs.jmedchem.7b00324]

2. Wang H, Wang Z, Wei C, Wang J, Xu Y, Bai G, Yao Q, Zhang L, Chen Y..  (2021)  Anticancer potential of indirubins in medicinal chemistry: Biological activity, structural modification, and structure-activity relationship.,  223  [PMID:34161865] [10.1016/j.ejmech.2021.113652]

Source

Source(1):

• Scientific Literature